QuickView for tetracycline (compound)

Summary
General Info

PubChem

PubChem Compound 1548931

Name:	Tetracycline
PubChem Compound ID:	1548931
Description:	A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.
Molecular formula:	C₂₂H₂₅N₂O₈⁺
Molecular weight:	445.443 g/mol
Synonyms:	ZINC01530482

DrugBank

Identification

Name:	Tetracycline
Name (isomeric):	DB00759
Drug Type:	small molecule
Description:	A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.
Synonyms:	Tetracycline HCl; Anhydrotetracycline; TC
Brand:	Deschlorobiomycin, Panmycin, Dumocyclin, Roviciclina, Lexacycline, Tetramed, Abramycin, Tetrex, Tetrachel, Criseociclina, Ambramycin, Tetra-CO, Tetraverine, Tetrafil, Tetradecin, Mericycline, Achromycin, Micycline, Ciclibion, Purocyclina, Cefracycline, Tetracycl, Topicycline, Enterocycline, Copharlan, Retet, SK-Tetracycline, Biocycline, Medocycline, Orlycycline, Bristaciclina, Tsiklomitsin, Bio-Tetra, Oletetrin, TAC, Amycin, Abricycline, Achromycin V, Cyclopar, Tetracycline II, Cytome, Polyotic, Resteclin, Vetacyclinum, Limecycline, Neocycline, Ambramicina, Polycycline, Robitet, Tetrabon, Tsiklomistsin, Solvocin, Democracin, Omegamycin, Liquamycin, Bristaciclin, Bristacycline, Sumycin, Hostacyclin, Veracin, Actisite, Agromicina, Tetracyn
Brand name mixture:	Helidac(Metronidazole + Bismuth subsalicylate + tetracycline hydrochloride), Neotetramed PWR(Neomycin sulfate + Tetracycline hydrochloride), Delta-Albaplex tablets(Novobiocin sodium + Prednisolone + Tetracycline hydrochloride), Neo-Chlor(Neomycin sulfate + Tetracycline hydrochloride), Neo Chlor PWR(Neomycin sulfate + Tetracycline hydrochloride),... show more » Helidac(Metronidazole + Bismuth subsalicylate + tetracycline hydrochloride), Neotetramed PWR(Neomycin sulfate + Tetracycline hydrochloride), Delta-Albaplex tablets(Novobiocin sodium + Prednisolone + Tetracycline hydrochloride), Neo-Chlor(Neomycin sulfate + Tetracycline hydrochloride), Neo Chlor PWR(Neomycin sulfate + Tetracycline hydrochloride), P Onytricin P(Calcium D-pantothenate + Menadione sodium bisulfite + Nicotinamide + Tetracycline hydrochloride + Vitamin A + Vitamin B12 + Vitamin B2 + Vitamin B6 + Vitamin D3 + Vitamin E) show less «
Category:	Protein Synthesis Inhibitors, Anti-Bacterial Agents, Antiprotozoals, Tetracyclines
CAS number:	60-54-8

Pharmacology

Indication:	Used to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever, rickettsialpox and Brill-Zinsser disease. May be used to treat infections caused by Chlamydiae spp., B. burgdorferi (Lyme disease), and upper respiratory infections caused by typical (S. pneumoniae, H. influenzae, and M. catarrhalis) and atypical organisms (C. pneumoniae, M. pneumoniae, L. pneumophila). May also be used to treat acne. Tetracycline may be an alternative drug for people who are allergic to penicillin.
Pharmacology:	Tetracycline is a short-acting antibiotic that inhibits bacterial growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. It also binds to some extent to the 50S ribosomal subunit. This binding is reversible in nature. Additionally tetracycline may alter t... show more » Tetracycline is a short-acting antibiotic that inhibits bacterial growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. It also binds to some extent to the 50S ribosomal subunit. This binding is reversible in nature. Additionally tetracycline may alter the cytoplasmic membrane of bacteria causing leakage of intracellular contents, such as nucleotides, from the cell. show less «
Mechanism of Action:	Tetracycline passively diffuses through porin channels in the bacterial membrane and reversibly binds to the 30S ribosomal subunit, preventing binding of tRNA to the mRNA-ribosome complex, and thus interfering with protein synthesis.
Absorption:	Bioavailability is less than 40% when administered via intramuscular injection, 100% intravenously, and 60-80% orally (fasting adults). Food and/or milk reduce GI absorption of oral preparations of tetracycline by 50% or more.
Protein binding:	20 - 67% protein bound
Biotransformation:	Not metabolized
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:	6-12 hours
Toxicity:	LD₅₀=808mg/kg (orally in mice)
Affected organisms:	Enteric bacteria and other eubacteria

Interactions

Food interaction:

Avoid milk, calcium containing dairy products, iron, antacids, or aluminium salts 2 hours before or 6 hours after using antacids while on this medication.

Take on empty stomach: 1 hour before or 2 hours after meals.

Take with a full glass of water.

Drug interaction:

Bismuth Subsalicylate	Formation of non-absorbable complexes
Tazobactam	Possible antagonism of action
Isotretinoin	Increased risk of intracranial hypertension
Dicumarol	Tetracycline may increase the anticoagulant effect of dicumarol.
Acenocoumarol	Tetracycline may increase the anticoagulant effect of acenocoumarol.

Bismuth Subsalicylate	Formation of non-absorbable complexes
Tazobactam	Possible antagonism of action
Isotretinoin	Increased risk of intracranial hypertension
Dicumarol	Tetracycline may increase the anticoagulant effect of dicumarol.
Acenocoumarol	Tetracycline may increase the anticoagulant effect of acenocoumarol.
Calcium	Formation of non-absorbable complexes
Magnesium salicylate	Formation of non-absorbable complexes
Methotrexate	Tetracycline may increase methotrexate toxicity.
Oxacillin	Possible antagonism of action
Etretinate	Increased risk of intracranial hypertension
Trazodone	The CYP3A4 inhibitor, Tetracycline, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Tetracycline is initiated, discontinued or dose changed.
Mezlocillin	Possible antagonism of action
Nafcillin	Possible antagonism of action
Penicillin V	Possible antagonism of action
Cloxacillin	Possible antagonism of action
Methoxyflurane	Tetracycline may increase the renal toxicity of methoxyflurane.
Calcium Acetate	Calcium salts such as calcium acetate may decrease the serum concentration of tetracycline derivatives such as tetracycline. 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.
Carbenicillin	Possible antagonism of action
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	Demeclocycline may increase the adverse effects of oral Tretinoin. Increase risk of pseudotumour cerebri. Concurrent therapy should be avoided.
Calcium Chloride	Calcium salts such as calcium chloride may decrease the serum concentration of tetracycline derivatives such as tetracycline. 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.
Dicloxacillin	Possible antagonism of action
Trisalicylate-choline	Formation of non-absorbable complexes
Warfarin	Tetracycline may increase the anticoagulant effect of warfarin.
Tramadol	Tetracycline may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
Clavulanate	Possible antagonism of action
Flucloxacillin	Possible antagonism of action
Hetacillin	Possible antagonism of action
Iron	Formation of non-absorbable complexes
Tolterodine	Tetracycline may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Anisindione	Tetracycline may increase the anticoagulant effect of anisindione.
Dihydroxyaluminium	Formation of non-absorbable complexes
Penicillin G	Possible antagonism of action
Zinc	Formation of non-absorbable complexes
Piperacillin	Possible antagonism of action
Bexarotene	Tetracycline 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).
Magnesium	Formation of non-absorbable complexes
Pivampicillin	Possible antagonism of action
Atovaquone	Tetracycline may decrease the effect of atovaquone.
Bacampicillin	Possible antagonism of action
Ethinyl Estradiol	This anti-infectious agent could decrease the effect of the oral contraceptive
Aluminium	Formation of non-absorbable complexes
Attapulgite	Formation of non-absorbable complexes
Quinapril	Quinapril may decrease the absorption of tetracycline.
Cyclacillin	Possible antagonism of action
Aztreonam	Possible antagonism of action
Iron Dextran	Formation of non-absorbable complexes
Tamsulosin	Tetracycline, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Tetracycline is initiated, discontinued, or dose changed.
Azlocillin	Possible antagonism of action
Ticarcillin	Tetracycline 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 Tetracycline.
Methicillin Acyl-Serine	Possible antagonism of action

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Targets

30S ribosomal protein S7

30S ribosomal protein S14

30S ribosomal protein S3

30S ribosomal protein S8

30S ribosomal protein S19

16S rRNA

Major prion protein

Enzymes

Cytochrome P450 3A4

Transporters

Solute carrier family 22 member 6

Solute carrier family 22 member 8

Solute carrier family 22 member 11

Solute carrier family 22 member 7

Carriers

Serum albumin