QuickView for Doxycycline (compound)

Summary
General Info

PubChem

PubChem Compound 11954377

Name:	Doxycycline
PubChem Compound ID:	11954377
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).
Molecular formula:	C₂₂H₂₀Ca₂N₂O₈
Molecular weight:	520.559 g/mol
Synonyms:	D03903; Doxycycline calcium; Doxycycline calcium (USP); 94088-85-4

DrugBank

Identification

Name:	Doxycycline
Name (isomeric):	DB00254
Drug Type:	small molecule
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).
Synonyms:	Doxytetracycline; Doxcycline anhydrous; Doxycycline Monohydrate; Doxycycline Hyclate
Brand:	Vibramycin, Alti-Doxycycline, Doxytec, Doxylin, Supracyclin, Doryx, Monodox, Vibra-Tabs, Novo-Doxylin, Doxychel Hyclate, Periostat, Oracea, Doxy 100, Doxy-Lemmon, Jenacyclin, Nu-Doxycycline, Atridox, Apo-Doxy, Doxy-Caps, Doxycin, Doxychel
Category:	Antimalarials, Anti-Bacterial Agents, Tetracyclines
CAS number:	564-25-0

Pharmacology

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.
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. Doxycycline prevents the normal function of the apicopl... show more » 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. Doxycycline prevents the normal function of the apicoplast of Plasmodium falciparum, a malaria causing organism. show less «
Absorption:	Completely absorbed following oral administration.
Protein binding:	>90%
Biotransformation:	Hepatic
Route of 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.
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).
Affected organisms:	Enteric bacteria and other eubacteria

Interactions

Food interaction:

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.

Drug interaction:

Tazobactam	Possible antagonism of action
Aprobarbital	The anticonvulsant, aprobarbital, decreases the effect of doxycycline.
Isotretinoin	Increased risk of intracranial hypertension
Tolterodine	Doxycycline may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Rifampin	The rifamycin decreases the effect of doxycycline

Tazobactam	Possible antagonism of action
Aprobarbital	The anticonvulsant, aprobarbital, decreases the effect of doxycycline.
Isotretinoin	Increased risk of intracranial hypertension
Tolterodine	Doxycycline may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Rifampin	The rifamycin decreases the effect of doxycycline
Calcium	Formation of non-absorbable complexes
Oxacillin	Possible antagonism of action
Etretinate	Increased risk of intracranial hypertension
Pentobarbital	The anticonvulsant, pentobarbital, decreases the effect of doxycycline.
Dihydroquinidine barbiturate	The anticonvulsant, dihydroquinidine barbiturate, decreases the effect of doxycycline.
Mezlocillin	Possible antagonism of action
Fosphenytoin	The anticonvulsant, fosphenytoin, decreases the effect of doxycycline.
Nafcillin	Possible antagonism of action
Bexarotene	Tetracycline derivatives like doxycycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Penicillin V	Possible antagonism of action
Cloxacillin	Possible antagonism of action
Ticarcillin	Doxycycline may reduce the effect of Ticarcillin by inhibiting bacterial growth. Ticarcillin exerts its effects on actively growing bacteria. To achieve synergism, Ticarcillin should be administered at least 2 hours prior to using Doxycycline.
Carbenicillin	Possible antagonism of action
Rifabutin	The rifamycin decreases the effect of doxycycline
Ampicillin	Possible antagonism of action
Pivmecillinam	Possible antagonism of action
Mestranol	This anti-infectious agent could decrease the effect of the oral contraceptive
Colesevelam	Bile acid sequestrants such as colesevelam may decrease the absorption of Tetracycline Derivatives. Monitor for decreased therapeutic effects of tetracycline derivatives if coadministered with a bile acid sequestrant. If these agents are used concomitantly, separate doses 2 or more hours to minimize the interaction. The manufacturer of colesevelam suggests that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
Acitretin	Increased risk of intracranial hypertension
Amoxicillin	Possible antagonism of action
Tretinoin	Doxycycline may increase the adverse effects of oral Tretinoin. Increase risk of pseudotumour cerebri. Concurrent therapy should be avoided.
Dicloxacillin	Possible antagonism of action
Ethinyl Estradiol	Doxycycline may decrease the contraceptive effect of ethinyl estradiol.
Thiopental	Thiopental may decrease the serum levels of Doxycycline. A reduction in antimicrobial effects may occur. An alternative antibiotic may be considered.
Clavulanate	Possible antagonism of action
Methylphenobarbital	The anticonvulsant, methylphenobarbital, decreases the effect of doxycycline.
Ethotoin	The anticonvulsant, ethotoin, decreases the effect of doxycycline.
Flucloxacillin	Possible antagonism of action
Hetacillin	Possible antagonism of action
Iron	Formation of non-absorbable complexes
Methotrexate	The tetracycline, doxycycline, may increase methotrexate toxicity.
Warfarin	The tetracycline, doxycycline, may increase the anticoagulant effect of warfarin.
Penicillin G	Possible antagonism of action
Talbutal	The anticonvulsant, talbutal, decreases the effect of doxycycline.
Secobarbital	The anticonvulsant , secobarbital, decreases the effect of doxycycline.
Amobarbital	The anticonvulsant, amobarbital, decreases the effect of doxycycline.
Magnesium oxide	Formation of non-absorbable complexes
Zinc	Formation of non-absorbable complexes
Piperacillin	Possible antagonism of action
Mephenytoin	The anticonvulsant, mephenytoin, decreases the effect of doxycycline.
Methohexital	The anticonvulsant, methohexital, decreases the effect of doxycycline.
Carbamazepine	The anticonvulsant, carbamazepine, may decrease the therapeutic effect of doxycycline.
Pivampicillin	Possible antagonism of action
Magnesium	Formation of non-absorbable complexes
Phenytoin	The anticonvulsant, phenytoin, may decrease the effect of doxycycline.
Tamsulosin	Doxycycline, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Doxycycline is initiated, discontinued, or dose changed.
Bacampicillin	Possible antagonism of action
Quinidine barbiturate	The anticonvulsant, quinidine barbiturate, decreases the effect of doxycycline.
Phenobarbital	The anticonvulsant, phenobarbital, may decrease the therapeutic effect of doxycycline.
Butalbital	The anticonvulsant, butalbital, decreases the effect of doxycycline.
Acenocoumarol	The tetracycline, doxycycline, may increase the anticoagulant effect of acenocoumarol.
Aluminium	Formation of non-absorbable complexes
Attapulgite	Formation of non-absorbable complexes
Butethal	The anticonvulsant, butethal, decreases the effect of doxycycline.
Primidone	The anticonvulsant, primidone, decreases the effect of doxycycline.
Anisindione	The tetracycline, doxycycline, may increase the anticoagulant effect of anisindione.
Dicumarol	The tetracycline, doxycycline, may increase the anticoagulant effect of dicumarol.
Calcium Acetate	Calcium salts such as calcium acetate may decrease the serum concentration of tetracycline derivatives such as doxycycline. In general, the coadministration of oral calcium salts and oral tetracycline derivatives should be avoided. Interactions may be able to be minimized by administering oral calcium preparations several hours before or after the dose of the oral tetracycline derivatives. Even with dose separation, therapy may still be compromised. Monitor for decreased therapeutic effect of oral tetracycline derivatives.
Cyclacillin	Possible antagonism of action
Aztreonam	Possible antagonism of action
Meticillin	Possible antagonism of action
Butabarbital	The anticonvulsant, butabarbital, decreases the effect of doxycycline.
Iron Dextran	Formation of non-absorbable complexes
Calcium Chloride	Calcium salts such as calcium chloride may decrease the serum concentration of tetracycline derivatives such as doxycycline. In general, the coadministration of oral calcium salts and oral tetracycline derivatives should be avoided. Interactions may be able to be minimized by administering oral calcium preparations several hours before or after the dose of the oral tetracycline derivatives. Even with dose separation, therapy may still be compromised. Monitor for decreased therapeutic effect of oral tetracycline derivatives.
Heptabarbital	The anticonvulsant, heptabarbital, decreases the effect of doxycycline.
Azlocillin	Possible antagonism of action
Hexobarbital	The anticonvulsant, hexobarbital, decreases the effect of doxycycline.

show less «

Targets

30S ribosomal protein S9

30S ribosomal protein S4

16S rRNA

Enzymes

Cytochrome P450 3A4

Transporters

Solute carrier family 22 member 6

Solute carrier family 22 member 8

Solute carrier family 22 member 11