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 | |
|---|---|---|---|
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ABCB1 |
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Publications |
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HTR1A |
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Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| acenocoumarol | The tetracycline increases the anticoagulant effect |
| acitretin | Increased risk of intracranial hypertension |
| aluminium | Formation of non-absorbable complexes |
| amobarbital | The anticonvulsant decreases the effect of doxycycline |
| amoxicillin | Possible antagonism of action |
| ampicillin | Possible antagonism of action |
| anisindione | The tetracycline increases the anticoagulant effect |
| aprobarbital | The anticonvulsant decreases the effect of doxycycline |
| attapulgite | Formation of non-absorbable complexes |
| azlocillin | Possible antagonism of action |
| aztreonam | Possible antagonism of action |
| bacampicillin | Possible antagonism of action |
| bismuth | Formation of non-absorbable complexes |
| butabarbital | The anticonvulsant decreases the effect of doxycycline |
| butalbital | The anticonvulsant decreases the effect of doxycycline |
| butethal | The anticonvulsant decreases the effect of doxycycline |
| calcium | Formation of non-absorbable complexes |
| carbamazepine | The anticonvulsant decreases the effect of doxycycline |
| carbenicillin | Possible antagonism of action |
| clavulanate | Possible antagonism of action |
| cloxacillin | Possible antagonism of action |
| cyclacillin | Possible antagonism of action |
| dicloxacillin | Possible antagonism of action |
| dicumarol | The tetracycline increases the anticoagulant effect |
| digoxin | The tetracycline increases the effect of digoxin in 10% of patients |
| dihydroquinidine barbiturate | The anticonvulsant decreases the effect of doxycycline |
| ethinyl estradiol | This anti-infectious agent could decrease the effect of the oral contraceptive |
| ethotoin | The anticonvulsant decreases the effect of doxycycline |
| etretinate | Increased risk of intracranial hypertension |
| flucloxacillin | Possible antagonism of action |
| fosphenytoin | The anticonvulsant decreases the effect of doxycycline |
| heptabarbital | The anticonvulsant decreases the effect of doxycycline |
| hetacillin | Possible antagonism of action |
| hexobarbital | The anticonvulsant decreases the effect of doxycycline |
| insulin | Tetracycline increases the risk of hypoglycemia |
| insulin-aspart | Tetracycline increases the risk of hypoglycemia |
| insulin-detemir | Tetracycline increases the risk of hypoglycemia |
| insulin-glargine | Tetracycline increases the risk of hypoglycemia |
| insulin-glulisine | Tetracycline increases the risk of hypoglycemia |
| insulin-lispro | Tetracycline increases the risk of hypoglycemia |
| iron | Formation of non-absorbable complexes |
| isotretinoin | Increased risk of intracranial hypertension |
| magnesium | Formation of non-absorbable complexes |
| magnesium oxide | Formation of non-absorbable complexes |
| mephenytoin | The anticonvulsant decreases the effect of doxycycline |
| mestranol | This anti-infectious agent could decrease the effect of the oral contraceptive |
| methohexital | The anticonvulsant decreases the effect of doxycycline |
| methotrexate | The tetracycline increases methotrexate toxicity |
| methylphenobarbital | The anticonvulsant decreases the effect of doxycycline |
| meticillin | Possible antagonism of action |
| mezlocillin | Possible antagonism of action |
| nafcillin | Possible antagonism of action |
| oxacillin | Possible antagonism of action |
| penicillin g | Possible antagonism of action |
| penicillin v | Possible antagonism of action |
| pentobarbital | The anticonvulsant decreases the effect of doxycycline |
| phenobarbital | The anticonvulsant decreases the effect of doxycycline |
| phenytoin | The anticonvulsant decreases the effect of doxycycline |
| piperacillin | Possible antagonism of action |
| pivampicillin | Possible antagonism of action |
| pivmecillinam | Possible antagonism of action |
| primidone | The anticonvulsant decreases the effect of doxycycline |
| quinidine barbiturate | The anticonvulsant decreases the effect of doxycycline |
| rifabutin | The rifamycin decreases the effect of doxycycline |
| rifampin | The rifamycin decreases the effect of doxycycline |
| secobarbital | The anticonvulsant decreases the effect of doxycycline |
| talbutal | The anticonvulsant decreases the effect of doxycycline |
| tazobactam | Possible antagonism of action |
| ticarcillin | Possible antagonism of action |
| warfarin | The tetracycline increases the anticoagulant effect |
| zinc | Formation of non-absorbable complexes |
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.
LinkOuts
Common Searches
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.
