DOXYCYCLINE CALCIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H24N2O8.2Ca
Molecular Weight	524.591
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	4

SHOW SMILES / InChI

Structure Search

SMILES

[Ca++].[Ca++].C[C@@H]1[C@H]2[C@H](O)[C@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C2C(=O)C4=C1C=CC=C4O

InChI

InChIKey=IYECPECUTCOMMD-QFWOMMJSSA-N

InChI=1S/C22H24N2O8.2Ca/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);;/q;2*+2/t7-,10+,14+,15-,17-,22-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula	C22H20N2O8
Molecular Weight	440.4028
Charge	-4
Count

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

Molecular Formula	Ca
Molecular Weight	40.078
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Doxycycline hyclate (Vibramycin, Periostat, Vibra-Tabs) is salt of tetracycline antibiotic Doxycycline, that used to treat many kinds of infections, like dental, skin, respiratory, and urinary tract infections. It also treats acne, Lyme disease, malaria, and certain sexually transmitted diseases. Doxycycline hyclate is a light-yellow crystalline powder which is soluble in water, while doxycycline monohydrate is very slightly soluble in water. Doxycycline is bacteriostatic, inhibiting bacterial protein synthesis due to disruption of transfer RNA and messenger RNA at ribosomal sites. Doxycycline hyclate is indicated for use in the treatment of chronic adult periodontitis for a gain in clinical attachment, reduction in probing depth, and reduction in bleeding on probing.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
30S ribosomal protein S12 20 Target ID: CHEMBL1641336 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15156014	Inhibitor 8504
30S ribosomal protein S12 20 Target ID: CHEMBL1641336 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15156014	Inhibitor 8504

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 8583	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 8583	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 8583	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 8583	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 8583	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 8583	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 8583	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 8583	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT2 153 OAT3 747 OAT4 150	OAT1 395	P-gp 301 CYP1B1 71 UGT1A8 8 UGT1A10 9

Drug as perpetrator

Target	Modality	Activity
OAT2 155	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/jjp/88/1/88_1_69/_pdf/-char/en#page=1 Page: 1.0	no
OAT3 749	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/jjp/88/1/88_1_69/_pdf/-char/en#page=1 Page: 1.0	no
OAT4 150	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/jjp/88/1/88_1_69/_pdf/-char/en#page=1 Page: 1.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10716067/ Page: 1.0	strong [Ki 1.1 uM]
CYP1B1 93	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/22273977/ Page: 7.0	yes
P-gp 1932	inducer 1966 Sources: https://core.ac.uk/download/pdf/232288318.pdf#page=1 Page: 1.0	yes
UGT1A10 46	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/22273977/ Page: 7.0	yes
UGT1A8 49	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/22273977/ Page: 7.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 395	substrate 4014 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
eMolecules	4775684	https://www.emolecules.com/cgi-bin/more?vid=4775684
MolPort	MolPort-002-507-423	https://www.molport.com/shop/molecule-link/MolPort-002-507-423
ZINC	ZINC000016052277	http://zinc15.docking.org/substances/ZINC000016052277

PubMed

Title	Date	PubMed
Evaluation of a new antibacterial agent. Doxycycline monohydrate and doxycycline hyclate (Vibramycin).	1969 Jul 28	5819422
[Vibravenös in infections of the biliary and respiratory tracts (author's transl)].	1977 Feb 22	138789
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
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
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
Treatment of endocarditis due to vancomycin-resistant Enterococcus faecium with quinupristin/dalfopristin, doxycycline, and rifampin: a synergistic drug combination.	1998 Dec	9868693
[Clinical use of tetracyclines in the treatment of periodontal diseases].	2000 May-Jun	11089368
Antiprotozoals effective in vitro against the scuticociliate fish pathogen Philasterides dicentrarchi.	2002 Jun 3	12113305
Serious adverse events among participants in the Centers for Disease Control and Prevention's Anthrax Vaccine and Antimicrobial Availability Program for persons at risk for bioterrorism-related inhalational anthrax.	2003 Oct 1	13130401
Molecular interactions between matrilysin and the matrix metalloproteinase inhibitor doxycycline investigated by deuterium exchange mass spectrometry.	2005 Apr	15665254
Caffeine inhibits human immunodeficiency virus type 1 transduction of nondividing cells.	2005 Feb	15681408
Chemically modified tetracycline (CMT)-3 inhibits histamine release and cytokine production in mast cells: possible involvement of protein kinase C.	2005 Jul	16134060
Effect of doxycycline on sulfur mustard-induced respiratory lesions in guinea pigs.	2005 Jul	15778244
Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial.	2005 Jun 18-24	15964448
Doxycycline may reduce the incidence of aneurysms in haemodialysis vascular accesses.	2005 May	15741211
Combination therapy with adapalene gel 0.1% and doxycycline for severe acne vulgaris: a multicenter, investigator-blind, randomized, controlled study.	2005 May-Jun	15891249
Safety of doxycycline and minocycline: a systematic review.	2005 Sep	16291409
Doxycycline modulates nitric oxide production in murine lung epithelial cells.	2006 Jan 1	16365451
[Skin signs associated with epidermal growth factor inhibitors].	2006 Mar	16800173
Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum.	2006 Sep	16940111
Doxycycline-induced amnesia: a case report.	2007 Jan	17103211
Sulfated glucosamine inhibits MMP-2 and MMP-9 expressions in human fibrosarcoma cells.	2007 Jul 15	17498959
Combinatorial computational approaches to identify tetracycline derivatives as flavivirus inhibitors.	2007 May 9	17502914
Minocycline toxicity requiring liver transplant.	2007 Nov	17404879
Protection by doxycycline against doxorubicin-induced oxidative stress and apoptosis in mouse testes.	2007 Oct 1	17673183
Self-reported adverse events associated with antimalarial chemoprophylaxis in peace corps volunteers.	2007 Sep	17826578
[Idiopathic intracranial hypertension as a side effect of doxycycline].	2009 Dec	19345447
De novo discovery of a gamma-secretase inhibitor response signature using a novel in vivo breast tumor model.	2009 Dec 1	19903844
Doxycycline-induced pseudotumor cerebri.	2009 Mar	19204639
Chloramphenicol causes mitochondrial stress, decreases ATP biosynthesis, induces matrix metalloproteinase-13 expression, and solid-tumor cell invasion.	2010 Jul	20338993
Angiotensin-(1-7) ameliorates myocardial remodeling and interstitial fibrosis in spontaneous hypertension: role of MMPs/TIMPs.	2010 Nov 30	20837116
Molecular effects of doxycycline treatment on pterygium as revealed by massive transcriptome sequencing.	2012	22724003
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

Patents

Sample Use Guides

In Vivo Use Guide

The usual dose of oral doxycycline is 200 mg on the first day of treatment (administered 100 mg every 12 hours) followed by a maintenance dose of 100 mg/day. In the management of more severe infections (particularly chronic infections of the urinary tract), 100 mg every 12 hours is recommended.

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 `Mon Mar 31 18:25:08 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:08 GMT 2025`
Record UNII	8ZL07I20SB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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-(4A,4AA,5A,5AA,6A,12AA))-, CALCIUM SALT (2:1)

Preferred Name

English

DOXYCYCLINE CALCIUM

Common Name

English

DOXYCYCLINE CALCIUM [ORANGE BOOK]

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 calcium salt (2:1)

Common Name

English

DOXYCYCLINE CALCIUM [USP IMPURITY]

Common Name

English

DOXYCYCLINE CALCIUM [MART.]

Common Name

English

Doxycycline calcium [WHO-DD]

Common Name

English

DOXYCYCLINE CALCIUM [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1595