DOXYCYCLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H24N2O8.H2O
Molecular Weight	462.4498
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[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

InChI

InChIKey=XQTWDDCIUJNLTR-CVHRZJFOSA-N

InChI=1S/C22H24N2O8.H2O/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;/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);1H2/t7-,10+,14+,15-,17-,22-;/m0./s1

HIDE SMILES / InChI

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	C22H24N2O8
Molecular Weight	444.4346
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/50744lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050006s088,050007s031,050442s019,050480s055,050533s044lbl.pdf

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

Targets

Primary Target	Pharmacology	Condition	Potency
30S ribosomal protein S12 19 Target ID: CHEMBL1641336 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15156014	Inhibitor 8297
30S ribosomal protein S12 19 Target ID: CHEMBL1641336 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15156014	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Rocky Mountain spotted fever 11 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050006s088,050007s031,050442s019,050480s055,050533s044lbl.pdf	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
Typhus fever 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050006s088,050007s031,050442s019,050480s055,050533s044lbl.pdf	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
Granuloma inguinale 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050006s088,050007s031,050442s019,050480s055,050533s044lbl.pdf	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
Bartonellosis 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050006s088,050007s031,050442s019,050480s055,050533s044lbl.pdf	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
Campylobacter fetus infections 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050006s088,050007s031,050442s019,050480s055,050533s044lbl.pdf	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
Periodontitis 23 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/50744lbl.pdf	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
Campylobacter fetus infections 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050006s088,050007s031,050442s019,050480s055,050533s044lbl.pdf	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
Bartonellosis 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050006s088,050007s031,050442s019,050480s055,050533s044lbl.pdf	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT2 145 OAT3 642 OAT4 146	OAT1 326	P-gp 257 CYP1B1 51 UGT1A8 8 UGT1A10 9

Drug as perpetrator

Target	Modality	Activity
OAT2 147	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/jjp/88/1/88_1_69/_pdf/-char/en#page=1 Page: 1.0	no
OAT3 644	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/jjp/88/1/88_1_69/_pdf/-char/en#page=1 Page: 1.0	no
OAT4 146	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/jjp/88/1/88_1_69/_pdf/-char/en#page=1 Page: 1.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10716067/ Page: 1.0	strong [Ki 1.1 uM]
CYP1B1 67	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/22273977/ Page: 7.0	yes
P-gp 1650	inducer 1573 Sources: https://core.ac.uk/download/pdf/232288318.pdf#page=1 Page: 1.0	yes
UGT1A10 41	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/22273977/ Page: 7.0	yes
UGT1A8 48	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/22273977/ Page: 7.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 326	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/jjp/88/1/88_1_69/_pdf/-char/en#page=1 Page: 1.0	likely

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Evaluation of a new antibacterial agent. Doxycycline monohydrate and doxycycline hyclate (Vibramycin).	1969 Jul 28	5819422
Phototoxic potential of minocycline and doxycycline.	1972 May	5026677
The absorption and sputum penetration of doxycycline.	1978 Nov	30746
Pharmacokinetics and tolerability of a single oral 600-mg dose of doxycycline.	1979 Jun 16	38382
[Leukocytoclastic vasculitis due to drug allergy presenting as generalized pustular exanthema].	1981 Sep	6268571
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Tetracycline-induced renal hypophosphatemia in a patient with a syndrome of inappropriate secretion of antidiuretic hormone.	1988	3277077
Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs.	1988 Feb	2452149
Anosmia after doxycycline use.	1990 Apr 16	2139490
Protective activity of tetracycline analogs against the cytopathic effect of the human immunodeficiency viruses in CEM cells.	1990 Jan-Feb	2326552
In vitro and in vivo effects of doxycycline on Toxoplasma gondii.	1990 May	2360817
Asymptomatic neurosyphilis after doxycycline therapy for early latent syphilis.	1993 Nov-Dec	8108759
Quinine toxicity when given with doxycycline and mefloquine.	1994 Jun	7855666
In vitro model to assess effect of antimicrobial agents on Encephalitozoon cuniculi.	1994 Oct	7840584
Carbamazepine-induced hyponatremia resolved with doxycycline.	1995 Aug	7635859
Human neutrophil collagenase (MMP-8), identified in bronchiectasis BAL fluid, correlates with severity of disease.	1995 Jun	7781360
[The influence of selected antibiotics on the central action of aminophyllines--experimental studies].	1996	9190241
Influence of antimicrobial agents on replication and stage conversion of Toxoplasma gondii.	1996	8791704
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996 Dec	9039272
Short report: severe hiccups secondary to doxycycline-induced esophagitis during treatment of malaria.	1996 Feb	8619448
Histologic effect of doxycycline sclerotherapy on rat femoral nerve.	1996 Nov-Dec	8902563
Atypical pneumonia in the Nordic countries: aetiology and clinical results of a trial comparing fleroxacin and doxycycline. Nordic Atypical Pneumonia Study Group.	1997 Apr	9145823
Ataxia following docetaxel infusion.	1997 Aug	9332695
Doxycycline-induced lithium toxicity.	1997 Feb	9004058
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.	1997 May	9145860
Treatment of endocarditis due to vancomycin-resistant Enterococcus faecium with quinupristin/dalfopristin, doxycycline, and rifampin: a synergistic drug combination.	1998 Dec	9868693
Neurotic effects of doxycycline sclerotherapy.	1998 Mar	9527117
De novo discovery of a gamma-secretase inhibitor response signature using a novel in vivo breast tumor model.	2009 Dec 1	19903844
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	19588640
Doxycycline-induced dizziness in dental patient. Case report.	2010 Aug-Sep	21053638
Original quinazoline derivatives displaying antiplasmodial properties.	2010 Feb	19926173
Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression.	2010 Feb 2	20133848
Chloramphenicol causes mitochondrial stress, decreases ATP biosynthesis, induces matrix metalloproteinase-13 expression, and solid-tumor cell invasion.	2010 Jul	20338993
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	20645521
Integrin-linked kinase is involved in cocaine sensitization by regulating PSD-95 and synapsin I expression and GluR1 Ser845 phosphorylation.	2010 Mar	19629758
Angiotensin-(1-7) ameliorates myocardial remodeling and interstitial fibrosis in spontaneous hypertension: role of MMPs/TIMPs.	2010 Nov 30	20837116
Azelaic acid gel 15% in the management of papulopustular rosacea: a status report on available efficacy data and clinical application.	2011 Aug	21916272
Novel 1-hydroxypiperazine-2,6-diones as new leads in the inhibition of metalloproteinases.	2011 Dec 22	22017477
Adverse cutaneous reactions to epidermal growth factor receptor inhibitors: a study of 14 patients.	2011 May-Jun	21738965
Molecular effects of doxycycline treatment on pterygium as revealed by massive transcriptome sequencing.	2012	22724003
Aryl hydrocarbon receptor protects lung adenocarcinoma cells against cigarette sidestream smoke particulates-induced oxidative stress.	2012 Mar 15	22273977
Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs.	2012 May	22331495
Tandem synthesis and in vitro antiplasmodial evaluation of new naphtho[2,1-d]thiazole derivatives.	2012 Sep	22889559
Differential action of monohydroxylated polycyclic aromatic hydrocarbons with estrogen receptors α and β.	2013 Apr	22989670
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	24341604
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903
A simple transcriptomic signature able to predict drug-induced hepatic steatosis.	2014 Apr	24469900
In vitro antiplasmodial activity of some medicinal plants of Burkina Faso.	2014 Jan	24318747
A high-content screen identifies novel compounds that inhibit stress-induced TDP-43 cellular aggregation and associated cytotoxicity.	2014 Jan	24019256
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

Patents

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 15:01:14 GMT 2023` Edited by `admin` on `Fri Dec 15 15:01:14 GMT 2023`
Record UNII	N12000U13O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOXYCYCLINE

Official Name

English

DOXYCYCLINE [MI]

Common Name

English

SUPRACYCLIN

Brand Name

English

DOXYCYCLINE [USAN]

Common Name

English

DOXYCYCLINE [ORANGE BOOK]

Common Name

English

ORACEA

Brand Name

English

DOXYCYCLINE MONOHYDRATE [VANDF]

Common Name

English

DOXYCYCLINE MONOHYDRATE [USP-RS]

Common Name

English

2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-, (4S-(4.ALPHA.,4A.ALPHA.,5.ALPHA.,5A.ALPHA.6.ALPHA.,12A.ALPHA.))-, MONOHYDRATE

Common Name

English

DOXYCYCLINE [VANDF]

Common Name

English

DOXYCYCLINE MONOHYDRATE [MART.]

Common Name

English

DOXIROBE

Brand Name

English

DOXYCYCLINE MONOHYDRATE [EP MONOGRAPH]

Common Name

English

DOXYCYCLINE [USP MONOGRAPH]

Common Name

English

DOXYLIN

Brand Name

English

DOXYCYCLINE MONOHYDRATE [EP IMPURITY]

Common Name

English

DOXYCYCLINE (EMA EPAR: VETERINARY)

Common Name

English

MONODOX

Brand Name

English

GS-3065

Code

English

XYROSA

Brand Name

English

DOXYCYCLINE MONOHYDRATE

Common Name

English

DOXYCHEL

Brand Name

English

Doxycycline monohydrate [WHO-DD]

Common 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 monohydrate

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA01AB22