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Doxycycline

Catalog No. DB00254 Name DrugBank
CAS Number 564-25-0 Website http://www.ualberta.ca/
M. F. C22H24N2O8 Telephone (780) 492-3111
M. W. 444.43456 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 139

SYNONYMS

IUPAC name
(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
IUPAC Traditional name
vibramycin
Brand Name
Doxylin
Vibra-Tabs
Supracyclin
Apo-Doxy
Doryx
Doxy-Lemmon
Jenacyclin
Monodox
Nu-Doxycycline
Periostat
Oracea
Alti-Doxycycline
Atridox
Doxy 100
Doxy-Caps
Doxychel
Doxychel Hyclate
Doxycin
Doxytec
Novo-Doxylin
Vibramycin
Synonyms
Doxycycline Monohydrate
Doxcycline anhydrous
Doxycycline Hyclate
Doxytetracycline

DATABASE IDS

PubChem CID 5281011
CAS Number 564-25-0
PubChem SID 46506491

PROPERTIES

Hydrophobicity(logP) -0.2
Solubility 630 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved; investigational
Description A synthetic tetracycline derivative with similar antimicrobial activity. Animal studies suggest that it may cause less tooth staining than other tetracyclines. It is used in some areas for the treatment of chloroquine-resistant falciparum malaria (malaria, falciparum). [PubChem]
Indication Doxycycline is indicated for use in respiratory tract infections caused by Mycoplasma pneumoniae, Haemophilus influenzae, Streptococcus pneumoniae, Legionella spp., or Klebsiella spp. It is also used for prophylaxis of malaria. Doxycycline is indicated for a variety of bacterial infections, from Mycobacterium fortuitum and M. marinum, to susceptible E. coli and Brucella spp. It can be used as an alternative to treating plague, tetanus, Campylobacter fetus
Pharmacology Doxycycline, a long-acting tetracycline derived from oxytetracycline, is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with COPD, and adult periodontitis.
Toxicity Symptoms of overdose include anorexia, nausea, diarrhoea, glossitis, dysphagia, enterocolitis and inflammatory lesions (with monilial overgrowth) in the anogenital region, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia. LD50=262 mg/kg (I.P. in rat).
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic
Absorption Completely absorbed following oral administration.
Half Life 18-22 hours
Protein Binding >90%
Elimination They are concentrated by the liver in the bile and excreted in the urine and feces at high concentrations in a biologically active form.
References
Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. [Pubmed]
Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. Epub 2003 Mar 5. [Pubmed]
Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. [Pubmed]
External Links
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REFERENCES

  • Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. Pubmed
  • Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. Epub 2003 Mar 5. Pubmed
  • Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. Pubmed