Abramycin;Abricycline;Achromycin;Achromycin V;Actisite;Agromicina;Ambramicina;Ambramycin;Amycin;Bio-Tetra;Biocycline;Bristaciclin;Bristaciclina;Bristacycline;Cefracycline;Ciclibion;Copharlan;Criseociclina;Cyclopar;Cytome;Democracin;Deschlorobiomycin;Dumocyclin;Enterocycline;Hostacyclin;Lexacycline;Limecycline;Liquamycin;Medocycline;Mericycline;Micycline;Neocycline;Oletetrin;Omegamycin;Orlycycline;Panmycin;Polycycline;Polyotic;Purocyclina;Resteclin;Retet;Robitet;Roviciclina;SK-Tetracycline;Solvocin;Sumycin;TAC;Tetra-CO;Tetrabon;Tetrachel;Tetracycl;Tetracycline II;Tetracyn;Tetradecin;Tetrafil;Tetramed;Tetraverine;Tetrex;Topicycline;Tsiklomistsin;Tsiklomitsin;Veracin;Vetacyclinum;

Anhydrotetracycline;TC;Tetracycline HCl;

Tetracycline is a broad spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria. It exerts a bacteriostatic effect on bacteria by binding reversible to the bacterial 30S ribosomal subunit and blocking incoming aminoacyl tRNA from binding to the ribosome acceptor site. It also binds to some extent to the bacterial 50S ribosomal subunit and may alter the cytoplasmic membrane causing intracellular components to leak from bacterial cells.

• Angus chemical co
• Apothecon inc div bristol myers squibb
• Bristol laboratories inc div bristol myers co
• Heritage pharmaceuticals inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Lederle laboratories div american cyanamid co
• On site therapeutics inc
• Par pharmaceutical
• Par pharmaceutical inc
• Pfipharmecs div pfizer inc
• Pfizer laboratories div pfizer inc
• Pharmacia and upjohn co
• Shire development inc
• Solvay pharmaceuticals
• Storz ophthalmics inc sub american cyanamid co
• Warner chilcott div warner lambert co
• Wyeth ayerst laboratories

• Advanced Pharmaceutical Services Inc.
• Aidarex Pharmacuticals LLC
• Apotheca Inc.
• A-S Medication Solutions LLC
• Axcan Pharma Inc.
• Barr Pharmaceuticals
• Belgomex Sprl
• Blenheim Pharmacal
• Bryant Ranch Prepack
• C.O. Truxton Inc.
• Central Texas Community Health Centers
• Comprehensive Consultant Services Inc.
• Coupler Enterprises Inc.
• Direct Dispensing Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Draxis Specialty Pharmaceuticals Inc.
• E.R. Squibb and Sons LLC
• Gallipot
• Global Pharmaceuticals
• Golden State Medical Supply Inc.
• Goldline Laboratories Inc.
• Group Health Cooperative
• H and H Laboratories
• H.J. Harkins Co. Inc.
• Heartland Repack Services LLC
• Ivax Pharmaceuticals
• Kaiser Foundation Hospital
• Laboratorios Atral Sarl
• Liberty Pharmaceuticals
• Major Pharmaceuticals
• Medisca Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Nucare Pharmaceuticals Inc.
• Palmetto Pharmaceuticals Inc.
• Par Pharmaceuticals
• Patient First Corp.
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Pharmedix
• Physicians Total Care Inc.
• Preferred Pharmaceuticals Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Prometheus Laboratories Inc.
• Proter SPA
• Qualitest
• Rebel Distributors Corp.
• Remedy Repack
• Sandhills Packaging Inc.
• Sino American Shanghai Squibb Pharmaceutical Ltd.
• Southwood Pharmaceuticals
• Talbert Medical Management Corp.
• Tya Pharmaceuticals
• Veratex Corp.
• Warner Chilcott Co. Inc.
• Watson Pharmaceuticals

Synthesis Reference	Not Available
General Reference	Link Griffin MO, Fricovsky E, Ceballos G, Villarreal F: Tetracyclines: a pleitropic family of compounds with promising therapeutic properties. Review of the literature. Am J Physiol Cell Physiol. 2010 Sep;299(3):C539-48. Epub 2010 Jun 30. Pubmed

Type	small molecule

Classes

Tetracyclines

Substructures

Tetracyclines Hydroxy Compounds Benzyl Alcohols and Derivatives Naphthalenes Phenols and Derivatives Amino Ketones Phenylpropenes Benzene and Derivatives Aliphatic and Aryl Amines Alcohols and Polyols Aromatic compounds Cinnamaldehydes Ketenes and Derivatives Phenyl Esters Enols Ketones

antibacterials 抗细菌;

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.
Pharmacodynamics	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.
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.
Volume of distribution	Not Available
Protein binding	20 - 67% protein bound
Metabolism	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
Clearance	Not Available
Toxicity	LD50=808mg/kg (orally in mice)
Affected organisms	Enteric bacteria and other eubacteria
Pathways	Pathway Name SMPDB ID Tetracycline Pathway SMP00294

Properties
State	solid
Experimental Properties	Property Value Source melting point 172.5 dec °C PhysProp water solubility 231 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -1.30 HANSCH,C ET AL. (1995) logS -3.12 ADME Research, USCD pKa 3.3 (at 25 °C) SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties	Property Value Source water solubility 1.33e+00 g/l ALOGPS logP -0.56 ALOGPS logP -3.5 ChemAxon logS -2.5 ALOGPS pKa (strongest acidic) -2.2 ChemAxon pKa (strongest basic) 8.24 ChemAxon physiological charge -1 ChemAxon hydrogen acceptor count 9 ChemAxon hydrogen donor count 6 ChemAxon polar surface area 181.62 ChemAxon rotatable bond count 2 ChemAxon refractivity 114.19 ChemAxon polarizability 43.03 ChemAxon

Drug	Interaction
Acenocoumarol	Tetracycline may increase the anticoagulant effect of acenocoumarol.
Acitretin	Increased risk of intracranial hypertension
Aluminium	Formation of non-absorbable complexes
Amoxicillin	Possible antagonism of action
Ampicillin	Possible antagonism of action
Anisindione	Tetracycline may increase the anticoagulant effect of anisindione.
Atovaquone	Tetracycline may decrease the effect of atovaquone.
Attapulgite	Formation of non-absorbable complexes
Azlocillin	Possible antagonism of action
Aztreonam	Possible antagonism of action
Bacampicillin	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).
Bismuth Subsalicylate	Formation of non-absorbable complexes
Calcium	Formation of non-absorbable complexes
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.
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.
Carbenicillin	Possible antagonism of action
Clavulanate	Possible antagonism of action
Cloxacillin	Possible antagonism of action
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.
Cyclacillin	Possible antagonism of action
Dicloxacillin	Possible antagonism of action
Dicumarol	Tetracycline may increase the anticoagulant effect of dicumarol.
Dihydroxyaluminium	Formation of non-absorbable complexes
Ethinyl Estradiol	This anti-infectious agent could decrease the effect of the oral contraceptive
Etretinate	Increased risk of intracranial hypertension
Flucloxacillin	Possible antagonism of action
Hetacillin	Possible antagonism of action
Iron	Formation of non-absorbable complexes
Iron Dextran	Formation of non-absorbable complexes
Isotretinoin	Increased risk of intracranial hypertension
Magnesium	Formation of non-absorbable complexes
Magnesium salicylate	Formation of non-absorbable complexes
Mestranol	This anti-infectious agent could decrease the effect of the oral contraceptive
Methicillin Acyl-Serine	Possible antagonism of action
Methotrexate	Tetracycline may increase methotrexate toxicity.
Methoxyflurane	Tetracycline may increase the renal toxicity of methoxyflurane.
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
Piperacillin	Possible antagonism of action
Pivampicillin	Possible antagonism of action
Pivmecillinam	Possible antagonism of action
Quinapril	Quinapril may decrease the absorption of tetracycline.
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.
Tazobactam	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.
Tolterodine	Tetracycline may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Tramadol	Tetracycline may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
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.
Tretinoin	Demeclocycline may increase the adverse effects of oral Tretinoin. Increase risk of pseudotumour cerebri. Concurrent therapy should be avoided.
Trisalicylate-choline	Formation of non-absorbable complexes
Warfarin	Tetracycline may increase the anticoagulant effect of warfarin.
Zinc	Formation of non-absorbable complexes

• 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.