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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24N2O8.C7H8O5S
Molecular Weight 648.635
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXYCYCLINE 4-GUAIACOLSULFONATE

SMILES

COC1=C(O)C=CC(=C1)S(O)(=O)=O.[H][C@@]23[C@@H](C)C4=C(C(O)=CC=C4)C(=O)C2=C(O)[C@]5(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]5([H])[C@H]3O

InChI

InChIKey=FDMODUJZMAVDCJ-CVHRZJFOSA-N
InChI=1S/C22H24N2O8.C7H8O5S/c1-7-8-5-4-6-9(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;1-12-7-4-5(13(9,10)11)2-3-6(7)8/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);2-4,8H,1H3,(H,9,10,11)/t7-,10+,14+,15-,17-,22-;/m0./s1

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
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
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
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
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
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
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
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
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
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
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: 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: Page: p.86
Disc. AE: Vomiting, Dysphagia...
AEs leading to
discontinuation/dose reduction:
Vomiting (0.5%)
Dysphagia (0.5%)
Hypersensitivity (0.5%)
Sources: 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: 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: Page: p.86
Disc. AE: Headache, Hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Headache (0.5%)
Hypersensitivity (0.5%)
Sources: 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: 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: 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: 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:
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
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:
50 mg 1 times / day steady, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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:
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
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:
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
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:
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
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:
unhealthy, adults
n = 84
Health Status: unhealthy
Condition: Papulopustular Rosacea
Age Group: adults
Population Size: 84
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
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:
unhealthy
n = 15
Health Status: unhealthy
Condition: Proliferative Diabetic Retinopathy
Population Size: 15
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
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
[Leukocytoclastic vasculitis due to drug allergy presenting as generalized pustular exanthema].
1981 Sep
Screening for new compounds with antiherpes activity.
1984 Oct
Anosmia after doxycycline use.
1990 Apr 16
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
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
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
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
Pharmacodynamics of doxycycline in a murine malaria model.
2007 Dec
Combinatorial computational approaches to identify tetracycline derivatives as flavivirus inhibitors.
2007 May 9
Protection by doxycycline against doxorubicin-induced oxidative stress and apoptosis in mouse testes.
2007 Oct 1
Self-reported adverse events associated with antimalarial chemoprophylaxis in peace corps volunteers.
2007 Sep
Severe drug hypersensitivity reaction in a young woman treated with doxycycline.
2008
Heartworm and Wolbachia: therapeutic implications.
2008 Dec 10
Doxycycline delays aneurysm rupture in a mouse model of Marfan syndrome.
2008 Jan
Doxycycline attenuates isoproterenol- and transverse aortic banding-induced cardiac hypertrophy in mice.
2008 Mar
[Idiopathic intracranial hypertension as a side effect of doxycycline].
2009 Dec
De novo discovery of a gamma-secretase inhibitor response signature using a novel in vivo breast tumor model.
2009 Dec 1
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
Doxycycline-induced dizziness in dental patient. Case report.
2010 Aug-Sep
Original quinazoline derivatives displaying antiplasmodial properties.
2010 Feb
Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression.
2010 Feb 2
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
Angiotensin-(1-7) ameliorates myocardial remodeling and interstitial fibrosis in spontaneous hypertension: role of MMPs/TIMPs.
2010 Nov 30
Azelaic acid gel 15% in the management of papulopustular rosacea: a status report on available efficacy data and clinical application.
2011 Aug
Novel 1-hydroxypiperazine-2,6-diones as new leads in the inhibition of metalloproteinases.
2011 Dec 22
Adverse cutaneous reactions to epidermal growth factor receptor inhibitors: a study of 14 patients.
2011 May-Jun
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
Differential action of monohydroxylated polycyclic aromatic hydrocarbons with estrogen receptors α and β.
2013 Apr
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
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

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
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.
Name Type Language
DOXYCYCLINE 4-GUAIACOLSULFONATE
Common Name English
Code System Code Type Description
FDA UNII
6OTC606JGA
Created by admin on Sat Dec 16 08:18:02 GMT 2023 , Edited by admin on Sat Dec 16 08:18:02 GMT 2023
PRIMARY
CAS
56608-92-5
Created by admin on Sat Dec 16 08:18:02 GMT 2023 , Edited by admin on Sat Dec 16 08:18:02 GMT 2023
PRIMARY
PUBCHEM
86278202
Created by admin on Sat Dec 16 08:18:02 GMT 2023 , Edited by admin on Sat Dec 16 08:18:02 GMT 2023
PRIMARY