Drug/Small Molecule:

doxycycline

Overview

Generic Names:	Doxcycline anhydrous; Doxycycline Hyclate; Doxycycline Monohydrate; Doxytetracycline
IUPAC Name:	(2Z,4S,4aR,5S,5aR,6R,12aS)-2-(amino-hydroxymethylidene)-4-dimethylamino-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione
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]

Indication

For the treatment of infections caused by susceptible organisms.

ATC Therapeutic Categories

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

Pharmacology and Interactions

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.

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.

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.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic

Protein Binding

>90%

Absorption

Completely absorbed following oral administration.

Half Life

18-22 hours

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).

Chemical Properties

Chemical Formula:

C₂₂H₂₄N₂O₈

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

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

444.4346 / 444.1533

Curated Information

The following genes are in curated knowledge about this drug.

	Gene	Relationship	Evidence
	ABCB1	FA	Publications
	HTR1A	FA	Publications

Non-Curated Information

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

Metabolizing Enzymes

• CYP3A43

Non-Curated Information

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

Drug Interactions

Non-Curated Information

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

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

1. Physicochemical determinants of human renal clearance
2. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

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