U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C22H24N2O8.C2H6O.2ClH.H2O
Molecular Weight 1025.875
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXYCYCLINE HYCLATE

SMILES

O.Cl.Cl.CCO.[H][C@@]12[C@@H](C)C3=CC=CC(O)=C3C(=O)C1=C(O)[C@]4(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]4([H])[C@H]2O.[H][C@@]56[C@@H](C)C7=CC=CC(O)=C7C(=O)C5=C(O)[C@]8(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]8([H])[C@H]6O

InChI

InChIKey=HALQELOKLVRWRI-VDBOFHIQSA-N
InChI=1S/2C22H24N2O8.C2H6O.2ClH.H2O/c2*1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;1-2-3;;;/h2*4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);3H,2H2,1H3;2*1H;1H2/t2*7-,10+,14+,15-,17-,22-;;;;/m00..../s1

HIDE SMILES / InChI
Molecular Formula C22H24N2O8
Molecular Weight 444.4346
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C2H6O
Molecular Weight 46.0684
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Doxycycline is an antibacterial drug synthetically derived from oxytetracycline and used to treat a wide variety of bacterial infections, including those that cause acne. Doxycycline is used for bacterial pneumonia, acne, chlamydia infections, early Lyme disease, cholera, and syphilis. It is also useful for the treatment of malaria when used with quinine and for the prevention of malaria. Common side effects include diarrhea, nausea, vomiting, a red rash, and an increased risk of a sunburn. If used during pregnancy or in young children may result in permanent problems with the teeth including changes in their color. Its use during breastfeeding is probably safe. Like other tetracycline antibiotics, Doxycycline is protein synthesis inhibitors, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex by binding to the 30S ribosomal subunit in the mRNA translation complex.

CNS Activity

Originator

Approval Year

1967
147
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
VIBRAMYCIN

Approved Use

To reduce the development of drug-resistant bacteria and maintain effectiveness of doxycycline hyclate and other antibacterial drugs, doxycycline hyclate should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment Doxycycline is indicated for the treatment of the following infections: Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae. Respiratory tract infections caused by Mycoplasma pneumoniae. Lymphogranuloma venereum caused by Chlamydia trachomatis. Psittacosis (ornithosis) caused by Chlamydia psittaci. Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence. Inclusion conjunctivitis caused by Chlamydia trachomatis. Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis. Nongonococcal urethritis caused by Ureaplasma urealyticum. Relapsing fever due to Borrelia recurrentis. Doxycycline is also indicated for the treatment of infections caused by the following gram-negative microorganisms: Chancroid caused by Haemophilus ducreyi. Plague due to Yersinia pestis (formerly Pasteurella pestis). Tularemia due to Francisella tularensis (formerly Pasteurella tularensis). Cholera caused by Vibrio cholerae (formerly Vibrio comma). Campylobacter fetus infections caused by Campylobacter fetus (formerly Vibrio fetus). Brucellosis due to Brucella species (in conjunction with streptomycin). Bartonellosis due to Bartonella bacilliformis. Granuloma inguinale caused by Calymmatobacterium granulomatis. Because many strains of the following groups of microorganisms have been shown to be resistant to doxycycline, culture and susceptibility testing are recommended. Doxycycline is indicated for treatment of infections caused by the following gram-negative microorganisms, when bacteriologic testing indicates appropriate susceptibility to the drug: Escherichia coli. Enterobacter aerogenes (formerly Aerobacter aerogenes). Shigella species. Acinetobacter species (formerly Mima species and Herellea species). Respiratory tract infections caused by Haemophilus influenzae. Respiratory tract and urinary tract infections caused by Klebsiella species. Doxycycline is indicated for treatment of infections caused by the following gram-positive microorganisms when bacteriologic testing indicates appropriate susceptibility to the drug: Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae). Anthrax due to Bacillus anthracis, including inhalational anthrax (post-exposure): to reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. When penicillin is contraindicated, doxycycline is an alternative drug in the treatment of the following infections: Uncomplicated gonorrhea caused by Neisseria gonorrhoeae. Syphilis caused by Treponema pallidum. Yaws caused by Treponema pertenue. Listeriosis due to Listeria monocytogenes. Vincent's infection caused by Fusobacterium fusiforme. Actinomycosis caused by Actinomyces israelii. Infections caused by Clostridium species. In acute intestinal amebiasis, doxycycline may be a useful adjunct to amebicides. In severe acne, doxycycline may be useful adjunctive therapy. Prophylaxis Doxycycline is indicated for the prophylaxis of malaria due to Plasmodium falciparum in short-term travelers (< 4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains. See DOSAGE AND ADMINISTRATION section and Information for Patients subsection of the PRECAUTIONS section.

Launch Date

1967
Curative
Approved
8429
VIBRAMYCIN

Approved Use

To reduce the development of drug-resistant bacteria and maintain effectiveness of doxycycline hyclate and other antibacterial drugs, doxycycline hyclate should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment Doxycycline is indicated for the treatment of the following infections: Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae. Respiratory tract infections caused by Mycoplasma pneumoniae. Lymphogranuloma venereum caused by Chlamydia trachomatis. Psittacosis (ornithosis) caused by Chlamydia psittaci. Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence. Inclusion conjunctivitis caused by Chlamydia trachomatis. Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis. Nongonococcal urethritis caused by Ureaplasma urealyticum. Relapsing fever due to Borrelia recurrentis. Doxycycline is also indicated for the treatment of infections caused by the following gram-negative microorganisms: Chancroid caused by Haemophilus ducreyi. Plague due to Yersinia pestis (formerly Pasteurella pestis). Tularemia due to Francisella tularensis (formerly Pasteurella tularensis). Cholera caused by Vibrio cholerae (formerly Vibrio comma). Campylobacter fetus infections caused by Campylobacter fetus (formerly Vibrio fetus). Brucellosis due to Brucella species (in conjunction with streptomycin). Bartonellosis due to Bartonella bacilliformis. Granuloma inguinale caused by Calymmatobacterium granulomatis. Because many strains of the following groups of microorganisms have been shown to be resistant to doxycycline, culture and susceptibility testing are recommended. Doxycycline is indicated for treatment of infections caused by the following gram-negative microorganisms, when bacteriologic testing indicates appropriate susceptibility to the drug: Escherichia coli. Enterobacter aerogenes (formerly Aerobacter aerogenes). Shigella species. Acinetobacter species (formerly Mima species and Herellea species). Respiratory tract infections caused by Haemophilus influenzae. Respiratory tract and urinary tract infections caused by Klebsiella species. Doxycycline is indicated for treatment of infections caused by the following gram-positive microorganisms when bacteriologic testing indicates appropriate susceptibility to the drug: Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae). Anthrax due to Bacillus anthracis, including inhalational anthrax (post-exposure): to reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. When penicillin is contraindicated, doxycycline is an alternative drug in the treatment of the following infections: Uncomplicated gonorrhea caused by Neisseria gonorrhoeae. Syphilis caused by Treponema pallidum. Yaws caused by Treponema pertenue. Listeriosis due to Listeria monocytogenes. Vincent's infection caused by Fusobacterium fusiforme. Actinomycosis caused by Actinomyces israelii. Infections caused by Clostridium species. In acute intestinal amebiasis, doxycycline may be a useful adjunct to amebicides. In severe acne, doxycycline may be useful adjunctive therapy. Prophylaxis Doxycycline is indicated for the prophylaxis of malaria due to Plasmodium falciparum in short-term travelers (< 4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains. See DOSAGE AND ADMINISTRATION section and Information for Patients subsection of the PRECAUTIONS section.

Launch Date

1967
Primary
Approved
8429
VIBRAMYCIN

Approved Use

To reduce the development of drug-resistant bacteria and maintain effectiveness of doxycycline hyclate and other antibacterial drugs, doxycycline hyclate should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment Doxycycline is indicated for the treatment of the following infections: Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae. Respiratory tract infections caused by Mycoplasma pneumoniae. Lymphogranuloma venereum caused by Chlamydia trachomatis. Psittacosis (ornithosis) caused by Chlamydia psittaci. Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence. Inclusion conjunctivitis caused by Chlamydia trachomatis. Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis. Nongonococcal urethritis caused by Ureaplasma urealyticum. Relapsing fever due to Borrelia recurrentis. Doxycycline is also indicated for the treatment of infections caused by the following gram-negative microorganisms: Chancroid caused by Haemophilus ducreyi. Plague due to Yersinia pestis (formerly Pasteurella pestis). Tularemia due to Francisella tularensis (formerly Pasteurella tularensis). Cholera caused by Vibrio cholerae (formerly Vibrio comma). Campylobacter fetus infections caused by Campylobacter fetus (formerly Vibrio fetus). Brucellosis due to Brucella species (in conjunction with streptomycin). Bartonellosis due to Bartonella bacilliformis. Granuloma inguinale caused by Calymmatobacterium granulomatis. Because many strains of the following groups of microorganisms have been shown to be resistant to doxycycline, culture and susceptibility testing are recommended. Doxycycline is indicated for treatment of infections caused by the following gram-negative microorganisms, when bacteriologic testing indicates appropriate susceptibility to the drug: Escherichia coli. Enterobacter aerogenes (formerly Aerobacter aerogenes). Shigella species. Acinetobacter species (formerly Mima species and Herellea species). Respiratory tract infections caused by Haemophilus influenzae. Respiratory tract and urinary tract infections caused by Klebsiella species. Doxycycline is indicated for treatment of infections caused by the following gram-positive microorganisms when bacteriologic testing indicates appropriate susceptibility to the drug: Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae). Anthrax due to Bacillus anthracis, including inhalational anthrax (post-exposure): to reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. When penicillin is contraindicated, doxycycline is an alternative drug in the treatment of the following infections: Uncomplicated gonorrhea caused by Neisseria gonorrhoeae. Syphilis caused by Treponema pallidum. Yaws caused by Treponema pertenue. Listeriosis due to Listeria monocytogenes. Vincent's infection caused by Fusobacterium fusiforme. Actinomycosis caused by Actinomyces israelii. Infections caused by Clostridium species. In acute intestinal amebiasis, doxycycline may be a useful adjunct to amebicides. In severe acne, doxycycline may be useful adjunctive therapy. Prophylaxis Doxycycline is indicated for the prophylaxis of malaria due to Plasmodium falciparum in short-term travelers (< 4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains. See DOSAGE AND ADMINISTRATION section and Information for Patients subsection of the PRECAUTIONS section.

Launch Date

1967
Curative
Approved
8429
VIBRAMYCIN

Approved Use

To reduce the development of drug-resistant bacteria and maintain effectiveness of doxycycline hyclate and other antibacterial drugs, doxycycline hyclate should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment Doxycycline is indicated for the treatment of the following infections: Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae. Respiratory tract infections caused by Mycoplasma pneumoniae. Lymphogranuloma venereum caused by Chlamydia trachomatis. Psittacosis (ornithosis) caused by Chlamydia psittaci. Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence. Inclusion conjunctivitis caused by Chlamydia trachomatis. Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis. Nongonococcal urethritis caused by Ureaplasma urealyticum. Relapsing fever due to Borrelia recurrentis. Doxycycline is also indicated for the treatment of infections caused by the following gram-negative microorganisms: Chancroid caused by Haemophilus ducreyi. Plague due to Yersinia pestis (formerly Pasteurella pestis). Tularemia due to Francisella tularensis (formerly Pasteurella tularensis). Cholera caused by Vibrio cholerae (formerly Vibrio comma). Campylobacter fetus infections caused by Campylobacter fetus (formerly Vibrio fetus). Brucellosis due to Brucella species (in conjunction with streptomycin). Bartonellosis due to Bartonella bacilliformis. Granuloma inguinale caused by Calymmatobacterium granulomatis. Because many strains of the following groups of microorganisms have been shown to be resistant to doxycycline, culture and susceptibility testing are recommended. Doxycycline is indicated for treatment of infections caused by the following gram-negative microorganisms, when bacteriologic testing indicates appropriate susceptibility to the drug: Escherichia coli. Enterobacter aerogenes (formerly Aerobacter aerogenes). Shigella species. Acinetobacter species (formerly Mima species and Herellea species). Respiratory tract infections caused by Haemophilus influenzae. Respiratory tract and urinary tract infections caused by Klebsiella species. Doxycycline is indicated for treatment of infections caused by the following gram-positive microorganisms when bacteriologic testing indicates appropriate susceptibility to the drug: Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae). Anthrax due to Bacillus anthracis, including inhalational anthrax (post-exposure): to reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. When penicillin is contraindicated, doxycycline is an alternative drug in the treatment of the following infections: Uncomplicated gonorrhea caused by Neisseria gonorrhoeae. Syphilis caused by Treponema pallidum. Yaws caused by Treponema pertenue. Listeriosis due to Listeria monocytogenes. Vincent's infection caused by Fusobacterium fusiforme. Actinomycosis caused by Actinomyces israelii. Infections caused by Clostridium species. In acute intestinal amebiasis, doxycycline may be a useful adjunct to amebicides. In severe acne, doxycycline may be useful adjunctive therapy. Prophylaxis Doxycycline is indicated for the prophylaxis of malaria due to Plasmodium falciparum in short-term travelers (< 4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains. See DOSAGE AND ADMINISTRATION section and Information for Patients subsection of the PRECAUTIONS section.

Launch Date

1967
Curative
Approved
8429
VIBRAMYCIN

Approved Use

To reduce the development of drug-resistant bacteria and maintain effectiveness of doxycycline hyclate and other antibacterial drugs, doxycycline hyclate should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment Doxycycline is indicated for the treatment of the following infections: Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae. Respiratory tract infections caused by Mycoplasma pneumoniae. Lymphogranuloma venereum caused by Chlamydia trachomatis. Psittacosis (ornithosis) caused by Chlamydia psittaci. Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence. Inclusion conjunctivitis caused by Chlamydia trachomatis. Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis. Nongonococcal urethritis caused by Ureaplasma urealyticum. Relapsing fever due to Borrelia recurrentis. Doxycycline is also indicated for the treatment of infections caused by the following gram-negative microorganisms: Chancroid caused by Haemophilus ducreyi. Plague due to Yersinia pestis (formerly Pasteurella pestis). Tularemia due to Francisella tularensis (formerly Pasteurella tularensis). Cholera caused by Vibrio cholerae (formerly Vibrio comma). Campylobacter fetus infections caused by Campylobacter fetus (formerly Vibrio fetus). Brucellosis due to Brucella species (in conjunction with streptomycin). Bartonellosis due to Bartonella bacilliformis. Granuloma inguinale caused by Calymmatobacterium granulomatis. Because many strains of the following groups of microorganisms have been shown to be resistant to doxycycline, culture and susceptibility testing are recommended. Doxycycline is indicated for treatment of infections caused by the following gram-negative microorganisms, when bacteriologic testing indicates appropriate susceptibility to the drug: Escherichia coli. Enterobacter aerogenes (formerly Aerobacter aerogenes). Shigella species. Acinetobacter species (formerly Mima species and Herellea species). Respiratory tract infections caused by Haemophilus influenzae. Respiratory tract and urinary tract infections caused by Klebsiella species. Doxycycline is indicated for treatment of infections caused by the following gram-positive microorganisms when bacteriologic testing indicates appropriate susceptibility to the drug: Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae). Anthrax due to Bacillus anthracis, including inhalational anthrax (post-exposure): to reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. When penicillin is contraindicated, doxycycline is an alternative drug in the treatment of the following infections: Uncomplicated gonorrhea caused by Neisseria gonorrhoeae. Syphilis caused by Treponema pallidum. Yaws caused by Treponema pertenue. Listeriosis due to Listeria monocytogenes. Vincent's infection caused by Fusobacterium fusiforme. Actinomycosis caused by Actinomyces israelii. Infections caused by Clostridium species. In acute intestinal amebiasis, doxycycline may be a useful adjunct to amebicides. In severe acne, doxycycline may be useful adjunctive therapy. Prophylaxis Doxycycline is indicated for the prophylaxis of malaria due to Plasmodium falciparum in short-term travelers (< 4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains. See DOSAGE AND ADMINISTRATION section and Information for Patients subsection of the PRECAUTIONS section.

Launch Date

1967
Curative
Approved
8429
Periostat

Approved Use

Uses temporarily relieves the minor aches and pains of muscles and joints associated with simple backache arthritis strains bruises sprains

Launch Date

1967
Curative
Approved
8429
VIBRAMYCIN

Approved Use

To reduce the development of drug-resistant bacteria and maintain effectiveness of doxycycline hyclate and other antibacterial drugs, doxycycline hyclate should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment Doxycycline is indicated for the treatment of the following infections: Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae. Respiratory tract infections caused by Mycoplasma pneumoniae. Lymphogranuloma venereum caused by Chlamydia trachomatis. Psittacosis (ornithosis) caused by Chlamydia psittaci. Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence. Inclusion conjunctivitis caused by Chlamydia trachomatis. Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis. Nongonococcal urethritis caused by Ureaplasma urealyticum. Relapsing fever due to Borrelia recurrentis. Doxycycline is also indicated for the treatment of infections caused by the following gram-negative microorganisms: Chancroid caused by Haemophilus ducreyi. Plague due to Yersinia pestis (formerly Pasteurella pestis). Tularemia due to Francisella tularensis (formerly Pasteurella tularensis). Cholera caused by Vibrio cholerae (formerly Vibrio comma). Campylobacter fetus infections caused by Campylobacter fetus (formerly Vibrio fetus). Brucellosis due to Brucella species (in conjunction with streptomycin). Bartonellosis due to Bartonella bacilliformis. Granuloma inguinale caused by Calymmatobacterium granulomatis. Because many strains of the following groups of microorganisms have been shown to be resistant to doxycycline, culture and susceptibility testing are recommended. Doxycycline is indicated for treatment of infections caused by the following gram-negative microorganisms, when bacteriologic testing indicates appropriate susceptibility to the drug: Escherichia coli. Enterobacter aerogenes (formerly Aerobacter aerogenes). Shigella species. Acinetobacter species (formerly Mima species and Herellea species). Respiratory tract infections caused by Haemophilus influenzae. Respiratory tract and urinary tract infections caused by Klebsiella species. Doxycycline is indicated for treatment of infections caused by the following gram-positive microorganisms when bacteriologic testing indicates appropriate susceptibility to the drug: Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae). Anthrax due to Bacillus anthracis, including inhalational anthrax (post-exposure): to reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. When penicillin is contraindicated, doxycycline is an alternative drug in the treatment of the following infections: Uncomplicated gonorrhea caused by Neisseria gonorrhoeae. Syphilis caused by Treponema pallidum. Yaws caused by Treponema pertenue. Listeriosis due to Listeria monocytogenes. Vincent's infection caused by Fusobacterium fusiforme. Actinomycosis caused by Actinomyces israelii. Infections caused by Clostridium species. In acute intestinal amebiasis, doxycycline may be a useful adjunct to amebicides. In severe acne, doxycycline may be useful adjunctive therapy. Prophylaxis Doxycycline is indicated for the prophylaxis of malaria due to Plasmodium falciparum in short-term travelers (< 4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains. See DOSAGE AND ADMINISTRATION section and Information for Patients subsection of the PRECAUTIONS section.

Launch Date

1967
Curative
Approved
8429
VIBRAMYCIN

Approved Use

To reduce the development of drug-resistant bacteria and maintain effectiveness of doxycycline hyclate and other antibacterial drugs, doxycycline hyclate should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Treatment Doxycycline is indicated for the treatment of the following infections: Rocky Mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae. Respiratory tract infections caused by Mycoplasma pneumoniae. Lymphogranuloma venereum caused by Chlamydia trachomatis. Psittacosis (ornithosis) caused by Chlamydia psittaci. Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence. Inclusion conjunctivitis caused by Chlamydia trachomatis. Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis. Nongonococcal urethritis caused by Ureaplasma urealyticum. Relapsing fever due to Borrelia recurrentis. Doxycycline is also indicated for the treatment of infections caused by the following gram-negative microorganisms: Chancroid caused by Haemophilus ducreyi. Plague due to Yersinia pestis (formerly Pasteurella pestis). Tularemia due to Francisella tularensis (formerly Pasteurella tularensis). Cholera caused by Vibrio cholerae (formerly Vibrio comma). Campylobacter fetus infections caused by Campylobacter fetus (formerly Vibrio fetus). Brucellosis due to Brucella species (in conjunction with streptomycin). Bartonellosis due to Bartonella bacilliformis. Granuloma inguinale caused by Calymmatobacterium granulomatis. Because many strains of the following groups of microorganisms have been shown to be resistant to doxycycline, culture and susceptibility testing are recommended. Doxycycline is indicated for treatment of infections caused by the following gram-negative microorganisms, when bacteriologic testing indicates appropriate susceptibility to the drug: Escherichia coli. Enterobacter aerogenes (formerly Aerobacter aerogenes). Shigella species. Acinetobacter species (formerly Mima species and Herellea species). Respiratory tract infections caused by Haemophilus influenzae. Respiratory tract and urinary tract infections caused by Klebsiella species. Doxycycline is indicated for treatment of infections caused by the following gram-positive microorganisms when bacteriologic testing indicates appropriate susceptibility to the drug: Upper respiratory infections caused by Streptococcus pneumoniae (formerly Diplococcus pneumoniae). Anthrax due to Bacillus anthracis, including inhalational anthrax (post-exposure): to reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. When penicillin is contraindicated, doxycycline is an alternative drug in the treatment of the following infections: Uncomplicated gonorrhea caused by Neisseria gonorrhoeae. Syphilis caused by Treponema pallidum. Yaws caused by Treponema pertenue. Listeriosis due to Listeria monocytogenes. Vincent's infection caused by Fusobacterium fusiforme. Actinomycosis caused by Actinomyces israelii. Infections caused by Clostridium species. In acute intestinal amebiasis, doxycycline may be a useful adjunct to amebicides. In severe acne, doxycycline may be useful adjunctive therapy. Prophylaxis Doxycycline is indicated for the prophylaxis of malaria due to Plasmodium falciparum in short-term travelers (< 4 months) to areas with chloroquine and/or pyrimethamine-sulfadoxine resistant strains. See DOSAGE AND ADMINISTRATION section and Information for Patients subsection of the PRECAUTIONS section.

Launch Date

1967
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.17 μg/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/15793155
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DOXYCYCLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
32 μg × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/15793155
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DOXYCYCLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.5 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/15793155
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DOXYCYCLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
unhealthy, 23.9
n = 190
Health Status: unhealthy
Condition: Urogenital Chlamydia trachomatis infection
Age Group: 23.9
Sex: M+F
Population Size: 190
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
Disc. AE: Vomiting, Dysphagia...
AEs leading to
discontinuation/dose reduction:
Vomiting (0.5%)
Dysphagia (0.5%)
Hypersensitivity (0.5%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
unhealthy, 24.1
n = 188
Health Status: unhealthy
Condition: Urogenital Chlamydia trachomatis infection
Age Group: 24.1
Sex: M+F
Population Size: 188
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
Disc. AE: Headache, Hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Headache (0.5%)
Hypersensitivity (0.5%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
unhealthy, 24.7
n = 223
Health Status: unhealthy
Condition: Chlamydia trachomatis endocervical infection
Age Group: 24.7
Sex: F
Population Size: 223
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
Disc. AE: Dyspepsia, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Dyspepsia (0.45%)
Abdominal pain (0.45%)
Nausea (0.45%)
Vomiting (0.45%)
Chest pain (0.45%)
Dyspnea (0.45%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
40 mg 1 times / day steady, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
Other AEs: Chest pain, Abortion spontaneous...
Other AEs:
Chest pain (serious, 1 patient)
Abortion spontaneous (serious, 1 patient)
Nausea (below serious, 3 patients)
Sinusitis (below serious, 3 patients)
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Other AEs: Pulmonary embolism, Umbilical hernia...
Other AEs:
Pulmonary embolism (serious, 1 patient)
Umbilical hernia (serious, 1 patient)
Vomiting (serious, 1 patient)
Constipation (below serious, 1 patient)
Fatigue (below serious, 1 patient)
Gout (below serious, 1 patient)
Headaches (below serious, 2 patients)
Prostatitis (below serious, 1 patient)
Urinary retention (below serious, 1 patient)
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
AEs

AEs

AESignificanceDosePopulation
Dysphagia 0.5%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
unhealthy, 23.9
n = 190
Health Status: unhealthy
Condition: Urogenital Chlamydia trachomatis infection
Age Group: 23.9
Sex: M+F
Population Size: 190
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
Hypersensitivity 0.5%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
unhealthy, 23.9
n = 190
Health Status: unhealthy
Condition: Urogenital Chlamydia trachomatis infection
Age Group: 23.9
Sex: M+F
Population Size: 190
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
Vomiting 0.5%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
unhealthy, 23.9
n = 190
Health Status: unhealthy
Condition: Urogenital Chlamydia trachomatis infection
Age Group: 23.9
Sex: M+F
Population Size: 190
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
Headache 0.5%
Disc. AE
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
unhealthy, 24.1
n = 188
Health Status: unhealthy
Condition: Urogenital Chlamydia trachomatis infection
Age Group: 24.1
Sex: M+F
Population Size: 188
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
Hypersensitivity 0.5%
Disc. AE
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
unhealthy, 24.1
n = 188
Health Status: unhealthy
Condition: Urogenital Chlamydia trachomatis infection
Age Group: 24.1
Sex: M+F
Population Size: 188
Sources:
https://pubmed.ncbi.nlm.nih.gov/22431798
Page: p.86
Abdominal pain 0.45%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
unhealthy, 24.7
n = 223
Health Status: unhealthy
Condition: Chlamydia trachomatis endocervical infection
Age Group: 24.7
Sex: F
Population Size: 223
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
Chest pain 0.45%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
unhealthy, 24.7
n = 223
Health Status: unhealthy
Condition: Chlamydia trachomatis endocervical infection
Age Group: 24.7
Sex: F
Population Size: 223
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
Dyspepsia 0.45%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
unhealthy, 24.7
n = 223
Health Status: unhealthy
Condition: Chlamydia trachomatis endocervical infection
Age Group: 24.7
Sex: F
Population Size: 223
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
Dyspnea 0.45%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
unhealthy, 24.7
n = 223
Health Status: unhealthy
Condition: Chlamydia trachomatis endocervical infection
Age Group: 24.7
Sex: F
Population Size: 223
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
Nausea 0.45%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
unhealthy, 24.7
n = 223
Health Status: unhealthy
Condition: Chlamydia trachomatis endocervical infection
Age Group: 24.7
Sex: F
Population Size: 223
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
Vomiting 0.45%
Disc. AE
100 mg 2 times / day multiple, oral
Recommended
Dose: 100 mg, 2 times / day
Route: oral
Route: multiple
Dose: 100 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
unhealthy, 24.7
n = 223
Health Status: unhealthy
Condition: Chlamydia trachomatis endocervical infection
Age Group: 24.7
Sex: F
Population Size: 223
Sources:
https://pubmed.ncbi.nlm.nih.gov/9785106
Page: p.114
Nausea below serious, 3 patients
40 mg 1 times / day steady, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
Sinusitis below serious, 3 patients
40 mg 1 times / day steady, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
Abortion spontaneous serious, 1 patient
40 mg 1 times / day steady, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
Chest pain serious, 1 patient
40 mg 1 times / day steady, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
https://clinicaltrials.gov/ct2/show/NCT01308619
Constipation below serious, 1 patient
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Fatigue below serious, 1 patient
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Gout below serious, 1 patient
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Prostatitis below serious, 1 patient
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Urinary retention below serious, 1 patient
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Headaches below serious, 2 patients
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Pulmonary embolism serious, 1 patient
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Umbilical hernia serious, 1 patient
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Vomiting serious, 1 patient
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
https://clinicaltrials.gov/ct2/show/NCT00511875
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT2
145

OAT3
642

OAT4
146
OAT1
326
P-gp
257

CYP1B1
51

UGT1A8
8

UGT1A10
9
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT2
147
 no
OAT3
644
 no
OAT4
146
 no
CYP3A4
1925
 strong [Ki 1.1 uM]
CYP1B1
67
 yes
P-gp
1650
 yes
UGT1A10
41
 yes
UGT1A8
48
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
OAT1
326
 likely
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:50845
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50845
ChemicalBook
CB8663342
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8663342
MolPort
MolPort-002-507-423
https://www.molport.com/shop/molecule-link/MolPort-002-507-423
ZINC
ZINC000016052277
http://zinc15.docking.org/substances/ZINC000016052277
eMolecules
4775684
https://www.emolecules.com/cgi-bin/more?vid=4775684
PubMed

PubMed

TitleDatePubMed
Evaluation of a new antibacterial agent. Doxycycline monohydrate and doxycycline hyclate (Vibramycin).
1969 Jul 28
Phototoxic potential of minocycline and doxycycline.
1972 May
The absorption and sputum penetration of doxycycline.
1978 Nov
Pharmacokinetics and tolerability of a single oral 600-mg dose of doxycycline.
1979 Jun 16
[Leukocytoclastic vasculitis due to drug allergy presenting as generalized pustular exanthema].
1981 Sep
Screening for new compounds with antiherpes activity.
1984 Oct
Tetracycline-induced renal hypophosphatemia in a patient with a syndrome of inappropriate secretion of antidiuretic hormone.
1988
Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs.
1988 Feb
Protective activity of tetracycline analogs against the cytopathic effect of the human immunodeficiency viruses in CEM cells.
1990 Jan-Feb
In vitro and in vivo effects of doxycycline on Toxoplasma gondii.
1990 May
Asymptomatic neurosyphilis after doxycycline therapy for early latent syphilis.
1993 Nov-Dec
Quinine toxicity when given with doxycycline and mefloquine.
1994 Jun
In vitro model to assess effect of antimicrobial agents on Encephalitozoon cuniculi.
1994 Oct
Carbamazepine-induced hyponatremia resolved with doxycycline.
1995 Aug
Human neutrophil collagenase (MMP-8), identified in bronchiectasis BAL fluid, correlates with severity of disease.
1995 Jun
[The influence of selected antibiotics on the central action of aminophyllines--experimental studies].
1996
Influence of antimicrobial agents on replication and stage conversion of Toxoplasma gondii.
1996
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Short report: severe hiccups secondary to doxycycline-induced esophagitis during treatment of malaria.
1996 Feb
Histologic effect of doxycycline sclerotherapy on rat femoral nerve.
1996 Nov-Dec
Atypical pneumonia in the Nordic countries: aetiology and clinical results of a trial comparing fleroxacin and doxycycline. Nordic Atypical Pneumonia Study Group.
1997 Apr
Ataxia following docetaxel infusion.
1997 Aug
Doxycycline-induced lithium toxicity.
1997 Feb
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.
1997 May
Treatment of endocarditis due to vancomycin-resistant Enterococcus faecium with quinupristin/dalfopristin, doxycycline, and rifampin: a synergistic drug combination.
1998 Dec
Neurotic effects of doxycycline sclerotherapy.
1998 Mar
Minocycline toxicity requiring liver transplant.
2007 Nov
Severe drug hypersensitivity reaction in a young woman treated with doxycycline.
2008
Heartworm and Wolbachia: therapeutic implications.
2008 Dec 10
[Idiopathic intracranial hypertension as a side effect of doxycycline].
2009 Dec
A multicenter study of topical azelaic acid 15% gel in combination with oral doxycycline as initial therapy and azelaic acid 15% gel as maintenance monotherapy.
2009 Jul
Doxycycline-induced pseudotumor cerebri.
2009 Mar
Fatal acute hepatitis after sequential treatment with levofloxacin, doxycycline, and naproxen in a patient presenting with acute Mycoplasma pneumoniae infection.
2009 May
Evidence of early involvement of matrix metalloproteinase-2 in lead-induced hypertension.
2009 May
The inhibitory mechanism of a novel cationic glucosamine derivative against MMP-2 and MMP-9 expressions.
2009 May 15
Ocular injuries following sulfur mustard exposure--pathological mechanism and potential therapy.
2009 Sep 1
Chloramphenicol causes mitochondrial stress, decreases ATP biosynthesis, induces matrix metalloproteinase-13 expression, and solid-tumor cell invasion.
2010 Jul
Efficacy of topical azelaic acid (AzA) gel 15% plus oral doxycycline 40 mg versus metronidazole gel 1% plus oral doxycycline 40 mg in mild-to-moderate papulopustular rosacea.
2010 Jun
Integrin-linked kinase is involved in cocaine sensitization by regulating PSD-95 and synapsin I expression and GluR1 Ser845 phosphorylation.
2010 Mar
Molecular effects of doxycycline treatment on pterygium as revealed by massive transcriptome sequencing.
2012
Aryl hydrocarbon receptor protects lung adenocarcinoma cells against cigarette sidestream smoke particulates-induced oxidative stress.
2012 Mar 15
Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs.
2012 May
Tandem synthesis and in vitro antiplasmodial evaluation of new naphtho[2,1-d]thiazole derivatives.
2012 Sep
Differential action of monohydroxylated polycyclic aromatic hydrocarbons with estrogen receptors α and β.
2013 Apr
A SYBR Green 1-based in vitro test of susceptibility of Ghanaian Plasmodium falciparum clinical isolates to a panel of anti-malarial drugs.
2013 Dec 17
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
A simple transcriptomic signature able to predict drug-induced hepatic steatosis.
2014 Apr
In vitro antiplasmodial activity of some medicinal plants of Burkina Faso.
2014 Jan
A high-content screen identifies novel compounds that inhibit stress-induced TDP-43 cellular aggregation and associated cytotoxicity.
2014 Jan
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Patents

04086332
8
04126680
14
04857235
8
04863639
8
04911865
8
07666668
8
08039021
8
08435565
8
08664280
8
CN106492198
8
JP2002511777A
414
JP2009524501A
10
JPH04234313A
14

Sample Use Guides

In Vivo Use Guide
Periostat (Doxycycline hyclate) 20 mg twice daily as an adjunct following scaling and root planing may be administered for up to 9 TM months. Safety beyond 12 months and efficacy beyond 9 months have not been established. Periostat should be administered at least one hour prior to morning and evening meals
Route of Administration: Oral
In Vitro Use Guide
PC3 cells were incubated with LPS (0.5 μg/mL) for 24 h in the presence or absence of doxycycline (5 μg/mL). The effects of LPS and doxycycline on the expressions of MMP-2, MMP-8, MMP-9, MMP-10, NF-κB/p65, IκB-α, p-IκB-α, IKK-β were examined by Western blotting and immunohistochemistry in PC3 cells. LPS increased expression and activity of MMP-9 and expression of MMP-8, MMP-10, NF-κB /p65, p-IκB-α, IKK-β and doxycycline down-regulated its effects with the exception of MMP-10 expression.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:19:34 GMT 2023
Edited
by admin
on Fri Dec 15 15:19:34 GMT 2023
Record UNII
19XTS3T51U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOXYCYCLINE HYCLATE
EP   GREEN BOOK   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
NSC-741421
Code English
ZADORIN
Brand Name English
DOXY
Brand Name English
DURADOXAL
Brand Name English
DOXYCYCLINE HYCLATE [ORANGE BOOK]
Common Name English
VIBRA-TABS
Brand Name English
AZUDOXAT
Brand Name English
SPANOR
Brand Name English
CLINOFUG
Brand Name English
ACTICLATE
Brand Name English
DOXYCYCLINE HYDROCHLORIDE HEMIETHANOLATE HEMIHYDRATE [MI]
Common Name English
DOXYCYCLINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
DOXYCYCLINI HYCLAS [WHO-IP LATIN]
Common Name English
MONODOKS
Common Name English
VIBRAVENOS
Brand Name English
DOXYCYCLINE HYCLATE [VANDF]
Common Name English
DOXYCYCLINE HYCLATE [EP IMPURITY]
Common Name English
DOXYCYCLINE HYCLATE [WHO-IP]
Common Name English
DOXYCYCLINE HYCLATE [EP MONOGRAPH]
Common Name English
DOXYCYCLINE HYCLATE [USP-RS]
Common Name English
MESPAFIN
Brand Name English
DIOCIMEX
Brand Name English
TETRACLEAN
Common Name English
LYMEPAK
Brand Name English
VIBRAMYCIN
Brand Name English
ACTICLATE CAP
Brand Name English
DORYX
Brand Name English
RETENS
Brand Name English
DOXYLAR
Brand Name English
GRANUDOXY
Brand Name English
RONAXAN
Brand Name English
DOXICRISOL
Brand Name English
DOXYCYCLINE HYCLATE [USP MONOGRAPH]
Common Name English
PERIOSTAT
Brand Name English
4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride, compound with ethyl alcohol (2:1), monohydrate
Common Name English
TETRADOX
Brand Name English
DOXYCYCLINE HYDROCHLORIDE HEMIETHANOLATE HEMIHYDRATE
MI  
Common Name English
ATRIDOX
Brand Name English
DOXYCYCLINE HYCLATE [GREEN BOOK]
Common Name English
DOXYPREX
Common Name English
DOXY-LEMMON
Brand Name English
DOXYCHEL HYCLATE
Brand Name English
VIBRAVEINEUSE
Brand Name English
Doxycycline hyclate [WHO-DD]
Common Name English
UNACIL
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1595
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
CFR 21 CFR 522.778
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
EU-Orphan Drug EU/3/12/955
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
Code System Code Type Description
RXCUI
23663
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m4758
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
PRIMARY Merck Index
EVMPD
SUB01830MIG
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
PRIMARY
NCI_THESAURUS
C29007
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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SMS_ID
100000092638
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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DAILYMED
19XTS3T51U
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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CHEBI
50845
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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CHEBI
34730
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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FDA UNII
19XTS3T51U
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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NSC
741421
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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EPA CompTox
DTXSID4041020
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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RS_ITEM_NUM
1226003
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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DRUG BANK
DBSALT000896
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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CAS
24390-14-5
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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ChEMBL
CHEMBL1433
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
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WHO INTERNATIONAL PHARMACOPEIA
DOXYCYCLINE HYCLATE
Created by admin on Fri Dec 15 15:19:34 GMT 2023 , Edited by admin on Fri Dec 15 15:19:34 GMT 2023
PRIMARY Description: A yellow, crystalline powder.Solubility: Soluble in 3 parts of water and in 4 parts of methanol R; practically insoluble in ether R.Category: Antibacterial and antimalarial drug.Storage: Doxycycline hyclate should be kept in a tightly closed container, protected from light.Additional information: Even in the absence of light, Doxycycline hyclate is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures.Requirements: Definition. Doxycycline hyclate contains not less than 95% and not more than 102% of C22H24N2O8,HCl, calculated with reference to the anhydrous and ethanol-free substance.
Related Record Type Details
Structure of DOXYCYCLINE ANHYDROUS
PARENT -> SALT/SOLVATE
Structure of DOXYCYCLINE HYCLATE ANHYDROUS
ANHYDROUS->SOLVATE
Structure of DOXYCYCLINE HYCLATE ANHYDROUS
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Related Record Type Details
Structure of METHACYCLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-ACETYL-2-DECARBAMOYLDOXYCYCLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-EPIDOXYCYCLINE
IMPURITY -> PARENT
Structure of METHACYCLINE
IMPURITY -> PARENT
Structure of 6-EPIDOXYCYCLINE
IMPURITY -> PARENT
Structure of OXYTETRACYCLINE ANHYDROUS
IMPURITY -> PARENT
Structure of 6-EPIDOXYCYCLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-EPI-6-EPIDOXYCYCLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-EPIDOXYCYCLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-EPI-6-EPIDOXYCYCLINE
IMPURITY -> PARENT
Structure of 2-ACETYL-2-DECARBAMOYLDOXYCYCLINE
IMPURITY -> PARENT
Structure of OXYTETRACYCLINE ANHYDROUS
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of DOXYCYCLINE ANHYDROUS
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC SUBGINGIVAL, CONTROLLED-RELEASE: 2 HOURS

ORAL, IMMEDIATE-RELEASE: 2 - 3 HOURS

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