Drug/Small Molecule:
doxycycline

2D structure

Overview

Generic Names: Doxcycline anhydrous; Doxycycline Hyclate; Doxycycline Monohydrate; Doxytetracycline
Trade Names: Alti-Doxycycline; Apo-Doxy; Atridox; Doryx; Doxy 100; Doxy-Caps; Doxy-Lemmon; Doxychel; Doxychel Hyclate; Doxycin; Doxylin; Doxytec; Jenacyclin; Monodox; Novo-Doxylin; Nu-Doxycycline; Oracea; Periostat; Supracyclin; Vibra-Tabs; Vibramycin
PharmGKB Accession Id: PA449415

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 (source: Drug Bank)

Indication

For the treatment of infections caused by susceptible organisms. (source: Drug Bank)

ATC Therapeutic Categories

  • A01AB:Antiinfectives and antiseptics for local oral treatment
  • J01AA:Tetracyclines

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Doxycycline, like minocycline, is lipophilic and can pass through the lipid bilayer of bacteria. Doxycycline reversibly binds to the 30 S ribosomal subunits and possibly the 50S ribosomal subunit(s), blocking the binding of aminoacyl tRNA to the mRNA and inhibiting bacterial protein synthesis. (source: Drug Bank)

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. (source: Drug Bank)

Food Interactions

Avoid alcohol.
Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
Take with a full glass of water Do not take calcium, aluminum, magnesium or Iron supplements within 2 hours of taking this medication. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (source: Drug Bank)

Protein Binding

>90% (source: Drug Bank)

Absorption

Completely absorbed following oral administration. (source: Drug Bank)

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. LD<sub>50</sub>=262 mg/kg (I.P. in rat). (source: Drug Bank)

Isomeric SMILES Code:

C[C@H]1c2cccc(c2C(=O)C3=C([C@]4([C@@H]([C@H]([C@H]13)O)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O.O (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
ABCB1
  •   
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  • PK
  • FA
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Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
  •   
  •   
  •   
  • FA
  •   
Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
HTR1A
  •   
  •   
  •   
  • FA
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
NR1I2
  •   
  •   
  •   
  • FA
  •   
Publications

A list of non-curated publications that mention this drug along with other genes is available.

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation The tetracycline increases the anticoagulant effect (source: Drug Bank)
acitretin Uncurated Annotation Increased risk of intracranial hypertension (source: Drug Bank)
amobarbital Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
amoxicillin Uncurated Annotation Possible antagonism of action (source: Drug Bank)
ampicillin Uncurated Annotation Possible antagonism of action (source: Drug Bank)
aztreonam Uncurated Annotation Possible antagonism of action (source: Drug Bank)
butalbital Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
calcium Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
carbamazepine Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
carbenicillin Uncurated Annotation Possible antagonism of action (source: Drug Bank)
cloxacillin Uncurated Annotation Possible antagonism of action (source: Drug Bank)
dicumarol Uncurated Annotation The tetracycline increases the anticoagulant effect (source: Drug Bank)
digoxin Uncurated Annotation The tetracycline increases the effect of digoxin in 10% of patients (source: Drug Bank)
ethinyl estradiol Uncurated Annotation This anti-infectious agent could decrease the effect of the oral contraceptive (source: Drug Bank)
etretinate Uncurated Annotation Increased risk of intracranial hypertension (source: Drug Bank)
hexobarbital Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
insulin-glargine Uncurated Annotation Tetracycline increases the risk of hypoglycemia (source: Drug Bank)
iron Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
isotretinoin Uncurated Annotation Increased risk of intracranial hypertension (source: Drug Bank)
magnesium Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
magnesium oxide Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)
mephenytoin Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
mestranol Uncurated Annotation This anti-infectious agent could decrease the effect of the oral contraceptive (source: Drug Bank)
methotrexate Uncurated Annotation The tetracycline increases methotrexate toxicity (source: Drug Bank)
methylphenobarbital Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
nafcillin Uncurated Annotation Possible antagonism of action (source: Drug Bank)
oxacillin Uncurated Annotation Possible antagonism of action (source: Drug Bank)
penicillin g Uncurated Annotation Possible antagonism of action (source: Drug Bank)
pentobarbital Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
phenobarbital Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
phenytoin Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
piperacillin Uncurated Annotation Possible antagonism of action (source: Drug Bank)
primidone Uncurated Annotation The anticonvulsant decreases the effect of doxycycline (source: Drug Bank)
rifabutin Uncurated Annotation The rifamycin decreases the effect of doxycycline (source: Drug Bank)
rifampin Uncurated Annotation The rifamycin decreases the effect of doxycycline (source: Drug Bank)
ticarcillin Uncurated Annotation Possible antagonism of action (source: Drug Bank)
warfarin Uncurated Annotation The tetracycline increases the anticoagulant effect (source: Drug Bank)
zinc Uncurated Annotation Formation of non-absorbable complexes (source: Drug Bank)

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00254
KEGG Compound ID:
C06973
PubChem Compound ID:
5281011
PubChem Substance ID:
154560

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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