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Identification
NameTetracycline
Accession NumberDB00759  (APRD00572)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionTetracycline 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.
Structure
Thumb
Synonyms
(4S,4AS,5as,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
Abramycin
Achromycin
Anhydrotetracycline
Deschlorobiomycin
Liquamycin
Tetracyclin
Tétracycline
Tetracyclinum
Tetrazyklin
Tsiklomitsin
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Achromycin Ont Oph 1%ointment1 %ophthalmicLederle Cyanamid Canada Inc.1955-12-311997-08-14Canada
Achromycin Vcapsule250 mg/1oralHeritage Pharmaceuticals Inc.2013-10-18Not applicableUs
Achromycin Vcapsule500 mg/1oralHeritage Pharmaceuticals Inc.2013-10-18Not applicableUs
Achromycin V Cap 250mgcapsule250 mgoralLederle Cyanamid Canada Inc.1957-12-311997-08-14Canada
Actisitemiscellaneous12.7 mgdentalProcter & Gamble IncNot applicableNot applicableCanada
Jaa Tetra Tab 250mgtablet250 mgoralJaapharm Canada Inc.1993-12-312016-08-10Canada
Medicycline Cap 250mgcapsule250 mgoralMedic Laboratory LtÉe1962-12-311996-09-09Canada
Novo-tetra 250mgcapsule250 mgoralNovopharm Limited1967-12-312008-08-20Canada
Novo-tetra 250mgtablet250 mgoralNovopharm Limited1967-12-312008-08-20Canada
Novo-tetra Sus 125mg/5mlliquid125 mgoralNovopharm Limited1967-12-312005-08-10Canada
Nu-tetra Capsules 250mgcapsule250 mgoralNu Pharm Inc1990-12-312012-09-04Canada
Tetracyclinecapsule250 mgoralAa Pharma Inc1983-12-31Not applicableCanada
Tetracycline 1% Onguent Ophthalmicointment10 mgophthalmicLaboratoires Sterigen Inc1988-12-31Not applicableCanada
Tetracycline Cap 250mgcapsule250 mgoralDuchesnay Inc1981-12-312003-07-18Canada
Tetracycline Cap 250mgcapsule250 mgoralPro Doc Limitee1962-12-312012-07-23Canada
Tetracycline Hydrochloridecapsule250 mg/1oralHeritage Pharmaceuticals Inc.2013-10-18Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralHeritage Pharmaceuticals Inc.2013-10-18Not applicableUs
Tetracyn Cap 250mgcapsule250 mgoralPfizer Canada Inc1952-12-312000-07-26Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Tetra Tabs 250mgtablet250 mgoralApotex Inc1984-12-312008-08-21Canada
Tetracycline Hydrochloridecapsule500 mg/1oralRebel Distributors Corp2010-03-23Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralLiberty Pharmaceuticals, Inc.2000-01-31Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralContract Pharmacy Services Pa2010-03-15Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralPhysicians Total Care, Inc.1988-03-01Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralSTAT Rx USA LLC2010-03-23Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralREMEDYREPACK INC.2011-05-16Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralWatson Laboratories, Inc.2011-08-15Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralREMEDYREPACK INC.2011-12-132015-12-29Us
Tetracycline Hydrochloridecapsule500 mg/1oralPhysicians Total Care, Inc.1996-10-09Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralSTAT Rx USA LLC2010-03-23Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralH.J. Harkins Company, Inc.2010-03-23Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralWatson Laboratories, Inc.2011-08-15Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralChartwell Rx, Llc2015-12-14Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralbryant ranch prepack2010-03-23Not applicableUs
Tetracycline Hydrochloridecapsule250 mg/1oralRebel Distributors Corp2010-03-23Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralBlenheim Pharmacal, Inc.2010-03-03Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralChartwell Rx, Llc2015-12-14Not applicableUs
Tetracycline Hydrochloridecapsule500 mg/1oralbryant ranch prepack2010-12-19Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acnecyclineointment.03 mg/mLtopicalPhillips Company2011-02-15Not applicableUs
Diabeclineointment30 mg/mLtopicalThru Pharma, Llc2013-05-23Not applicableUs
Diabeclineointment30 mg/gtopicalPhillips Company2013-06-10Not applicableUs
Dyabetexointment.03 mg/mLtopicalPhillips Company2010-08-24Not applicableUs
Tetra-abcointment.03 mg/mLtopicalPhillips Company2010-08-24Not applicableUs
Tetracycline-abcointment.03 mg/mLtopicalPhillips Company2011-02-15Not applicableUs
Tetrastemointment30 mg/gtopicalViaderma Ii, Inc.2014-05-282015-12-29Us
Tetrastemointment30 mg/gtopicalPhillips Company2014-02-25Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
AchromycinNot Available
Brand mixtures
NameLabellerIngredients
First Marys Mouthwash CompoundingCutis Pharma, Inc.
PyleraPhysicians Total Care, Inc.
Salts
Name/CASStructureProperties
Tetracycline hydrochloride
64-75-5
Thumb
  • InChI Key: YCIHPQHVWDULOY-FMZCEJRJSA-N
  • Monoisotopic Mass: 480.129943493
  • Average Mass: 480.896
DBSALT000361
Tetracycline phosphate
ThumbNot applicableDBSALT001631
Categories
UNIIF8VB5M810T
CAS number60-54-8
WeightAverage: 444.4346
Monoisotopic: 444.153265754
Chemical FormulaC22H24N2O8
InChI KeyInChIKey=OFVLGDICTFRJMM-WESIUVDSSA-N
InChI
InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
IUPAC Name
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
SMILES
[H][C@@]12C[C@@]3([H])C(=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[[email protected]]2N(C)C)C(=O)C1=C(O)C=CC=C1[C@@]3(C)O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTetracyclines
Sub ClassNot Available
Direct ParentTetracyclines
Alternative Parents
Substituents
  • Tetracycline
  • Tetracene
  • Naphthacene
  • Anthracene carboxylic acid or derivatives
  • Tetralin
  • Aryl ketone
  • Aralkylamine
  • Benzenoid
  • Vinylogous acid
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Primary carboxylic acid amide
  • Polyol
  • Ketone
  • Carboxamide group
  • Enol
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed 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.
PharmacodynamicsTetracycline 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 actionTetracycline 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.
Related Articles
AbsorptionBioavailability 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 distributionNot Available
Protein binding20 - 67% protein bound
Metabolism

Not metabolized

Route of eliminationThey are concentrated by the liver in the bile and excreted in the urine and feces at high concentrations in a biologically active form.
Half life6-12 hours
ClearanceNot Available
ToxicityLD50=808mg/kg (orally in mice)
Affected organisms
  • Enteric bacteria and other eubacteria
  • Borrelia burgdorferi
  • Chlamydia trachomatis
  • Mycoplasma pneumoniae
  • Rickettsia rickettsii
  • Vibrio cholerae
  • Escherichia coli
  • Shigella
  • Coxiella
Pathways
PathwayCategorySMPDB ID
Tetracycline Action PathwayDrug actionSMP00294
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8006
Blood Brain Barrier-0.9841
Caco-2 permeable+0.7439
P-glycoprotein substrateSubstrate0.791
P-glycoprotein inhibitor INon-inhibitor0.8025
P-glycoprotein inhibitor IINon-inhibitor0.7562
Renal organic cation transporterNon-inhibitor0.9437
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateSubstrate0.6758
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9089
CYP450 3A4 inhibitorNon-inhibitor0.8686
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.781
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9314
BiodegradationNot ready biodegradable0.9906
Rat acute toxicity2.7095 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.7201
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Heritage pharmaceuticals inc
  • Bristol laboratories inc div bristol myers co
  • Warner chilcott div warner lambert co
  • Pharmacia and upjohn co
  • Solvay pharmaceuticals
  • Wyeth ayerst laboratories
  • Apothecon inc div bristol myers squibb
  • Angus chemical co
  • Pfipharmecs div pfizer inc
  • On site therapeutics inc
  • Shire development inc
  • Lederle laboratories div american cyanamid co
  • Pfizer laboratories div pfizer inc
  • Storz ophthalmics inc sub american cyanamid co
  • Par pharmaceutical
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Par pharmaceutical inc
Packagers
Dosage forms
FormRouteStrength
Ointmentophthalmic1 %
Miscellaneousdental12.7 mg
Ointmenttopical30 mg/mL
Ointmenttopical30 mg/g
Kitoral
Tabletoral250 mg
Liquidoral125 mg
Capsuleoral
Ointmenttopical.03 mg/mL
Capsuleoral250 mg
Ointmentophthalmic10 mg
Capsuleoral250 mg/1
Capsuleoral500 mg/1
Prices
Unit descriptionCostUnit
Tetracycline hcl powder2.14USD g
Tetracycline powder1.37USD g
Tetracycline HCl 500 mg capsule0.2USD capsule
Tetracycline HCl 250 mg capsule0.15USD capsule
Apo-Tetra 250 mg Capsule0.07USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6350468 No1998-12-142018-12-14Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point172.5 dec °CPhysProp
water solubility231 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.30HANSCH,C ET AL. (1995)
logS-3.12ADME Research, USCD
pKa3.3 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility1.33 mg/mLALOGPS
logP-0.56ALOGPS
logP-3.5ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)-2.2ChemAxon
pKa (Strongest Basic)8.24ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area181.62 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity114.19 m3·mol-1ChemAxon
Polarizability43.03 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Thomas F. McNamara, Nungavaram S. Ramamurthy, Lorne M. Golub, “Non-antibacterial tetracycline compositions possessing anti-collagenolytic properties and methods of preparing and using same.” U.S. Patent US4704383, issued May, 1963.

US4704383
General References
  1. 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. doi: 10.1152/ajpcell.00047.2010. Epub 2010 Jun 30. [PubMed:20592239 ]
  2. Link [Link]
External Links
ATC CodesA02BD08S02AA08J01RA08A01AB13S03AA02D06AA04S01AA09J01AA07A02BD02
AHFS Codes
  • 08:12.24
  • 52:04.04
PDB Entries
FDA labelNot Available
MSDSDownload (73.8 KB)
Interactions
Drug Interactions
Drug
AmiodaroneThe metabolism of Tetracycline can be decreased when combined with Amiodarone.
AprepitantThe serum concentration of Tetracycline can be increased when it is combined with Aprepitant.
AtazanavirThe metabolism of Tetracycline can be decreased when combined with Atazanavir.
AtomoxetineThe metabolism of Tetracycline can be decreased when combined with Atomoxetine.
AtovaquoneThe serum concentration of Atovaquone can be decreased when it is combined with Tetracycline.
BexaroteneThe serum concentration of Tetracycline can be decreased when it is combined with Bexarotene.
BoceprevirThe metabolism of Tetracycline can be decreased when combined with Boceprevir.
BortezomibThe metabolism of Tetracycline can be decreased when combined with Bortezomib.
BosentanThe serum concentration of Tetracycline can be decreased when it is combined with Bosentan.
CarbamazepineThe metabolism of Tetracycline can be increased when combined with Carbamazepine.
CeritinibThe serum concentration of Tetracycline can be increased when it is combined with Ceritinib.
ClarithromycinThe metabolism of Tetracycline can be decreased when combined with Clarithromycin.
ClemastineThe metabolism of Tetracycline can be decreased when combined with Clemastine.
ClotrimazoleThe metabolism of Tetracycline can be decreased when combined with Clotrimazole.
CobicistatThe metabolism of Tetracycline can be decreased when combined with Cobicistat.
ConivaptanThe serum concentration of Tetracycline can be increased when it is combined with Conivaptan.
CrizotinibThe metabolism of Tetracycline can be decreased when combined with Crizotinib.
CyclosporineThe metabolism of Tetracycline can be decreased when combined with Cyclosporine.
DabrafenibThe serum concentration of Tetracycline can be decreased when it is combined with Dabrafenib.
DarunavirThe metabolism of Tetracycline can be decreased when combined with Darunavir.
DasatinibThe serum concentration of Tetracycline can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Tetracycline can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Tetracycline can be decreased when combined with Delavirdine.
DexamethasoneThe serum concentration of Tetracycline can be decreased when it is combined with Dexamethasone.
DihydroergotamineThe metabolism of Tetracycline can be decreased when combined with Dihydroergotamine.
DiltiazemThe metabolism of Tetracycline can be decreased when combined with Diltiazem.
DoxycyclineThe metabolism of Tetracycline can be decreased when combined with Doxycycline.
DronedaroneThe metabolism of Tetracycline can be decreased when combined with Dronedarone.
EfavirenzThe serum concentration of Tetracycline can be decreased when it is combined with Efavirenz.
EnzalutamideThe serum concentration of Tetracycline can be decreased when it is combined with Enzalutamide.
ErythromycinThe metabolism of Tetracycline can be decreased when combined with Erythromycin.
Eslicarbazepine acetateThe serum concentration of Tetracycline can be decreased when it is combined with Eslicarbazepine acetate.
EtravirineThe serum concentration of Tetracycline can be decreased when it is combined with Etravirine.
FluconazoleThe metabolism of Tetracycline can be decreased when combined with Fluconazole.
FluvoxamineThe metabolism of Tetracycline can be decreased when combined with Fluvoxamine.
FosamprenavirThe metabolism of Tetracycline can be decreased when combined with Fosamprenavir.
FosaprepitantThe serum concentration of Tetracycline can be increased when it is combined with Fosaprepitant.
FosphenytoinThe metabolism of Tetracycline can be increased when combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Tetracycline can be increased when it is combined with Fusidic Acid.
IdelalisibThe serum concentration of Tetracycline can be increased when it is combined with Idelalisib.
ImatinibThe metabolism of Tetracycline can be decreased when combined with Imatinib.
IndinavirThe metabolism of Tetracycline can be decreased when combined with Indinavir.
IsavuconazoniumThe metabolism of Tetracycline can be decreased when combined with Isavuconazonium.
IsradipineThe metabolism of Tetracycline can be decreased when combined with Isradipine.
ItraconazoleThe metabolism of Tetracycline can be decreased when combined with Itraconazole.
IvacaftorThe serum concentration of Tetracycline can be increased when it is combined with Ivacaftor.
KetoconazoleThe metabolism of Tetracycline can be decreased when combined with Ketoconazole.
LopinavirThe metabolism of Tetracycline can be decreased when combined with Lopinavir.
LovastatinThe metabolism of Tetracycline can be decreased when combined with Lovastatin.
LuliconazoleThe serum concentration of Tetracycline can be increased when it is combined with Luliconazole.
MifepristoneThe metabolism of Tetracycline can be decreased when combined with Mifepristone.
MitotaneThe serum concentration of Tetracycline can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Tetracycline can be decreased when it is combined with Modafinil.
NafcillinThe serum concentration of Tetracycline can be decreased when it is combined with Nafcillin.
NefazodoneThe metabolism of Tetracycline can be decreased when combined with Nefazodone.
NelfinavirThe metabolism of Tetracycline can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Tetracycline can be increased when it is combined with Netupitant.
NevirapineThe metabolism of Tetracycline can be decreased when combined with Nevirapine.
NilotinibThe metabolism of Tetracycline can be decreased when combined with Nilotinib.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Tetracycline.
OlaparibThe metabolism of Tetracycline can be decreased when combined with Olaparib.
OsimertinibThe serum concentration of Tetracycline can be increased when it is combined with Osimertinib.
PalbociclibThe serum concentration of Tetracycline can be increased when it is combined with Palbociclib.
PentobarbitalThe metabolism of Tetracycline can be increased when combined with Pentobarbital.
PhenobarbitalThe metabolism of Tetracycline can be increased when combined with Phenobarbital.
PhenytoinThe metabolism of Tetracycline can be increased when combined with Phenytoin.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Tetracycline.
PosaconazoleThe metabolism of Tetracycline can be decreased when combined with Posaconazole.
PrimidoneThe metabolism of Tetracycline can be increased when combined with Primidone.
QuinineThe serum concentration of Quinine can be increased when it is combined with Tetracycline.
RanolazineThe metabolism of Tetracycline can be decreased when combined with Ranolazine.
RifabutinThe metabolism of Tetracycline can be increased when combined with Rifabutin.
RifampicinThe metabolism of Tetracycline can be increased when combined with Rifampicin.
RifapentineThe metabolism of Tetracycline can be increased when combined with Rifapentine.
RitonavirThe metabolism of Tetracycline can be decreased when combined with Ritonavir.
SaquinavirThe metabolism of Tetracycline can be decreased when combined with Saquinavir.
SildenafilThe metabolism of Tetracycline can be decreased when combined with Sildenafil.
SiltuximabThe serum concentration of Tetracycline can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Tetracycline can be increased when it is combined with Simeprevir.
St. John's WortThe serum concentration of Tetracycline can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Tetracycline can be increased when it is combined with Stiripentol.
SulfisoxazoleThe metabolism of Tetracycline can be decreased when combined with Sulfisoxazole.
TelaprevirThe metabolism of Tetracycline can be decreased when combined with Telaprevir.
TelithromycinThe metabolism of Tetracycline can be decreased when combined with Telithromycin.
TiclopidineThe metabolism of Tetracycline can be decreased when combined with Ticlopidine.
TocilizumabThe serum concentration of Tetracycline can be decreased when it is combined with Tocilizumab.
VenlafaxineThe metabolism of Tetracycline can be decreased when combined with Venlafaxine.
VerapamilThe metabolism of Tetracycline can be decreased when combined with Verapamil.
VoriconazoleThe metabolism of Tetracycline can be decreased when combined with Voriconazole.
ZiprasidoneThe metabolism of Tetracycline can be decreased when combined with Ziprasidone.
Food Interactions
  • 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.

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Trna binding
Specific Function:
One of the primary rRNA binding proteins, it binds directly to 16S rRNA where it nucleates assembly of the head domain of the 30S subunit. Is located at the subunit interface close to the decoding center, where it has been shown to contact mRNA. Has been shown to contact tRNA in both the P and E sites; it probably blocks exit of the E site tRNA.Protein S7 is also a translational repressor prote...
Gene Name:
rpsG
Uniprot ID:
P02359
Molecular Weight:
20018.91 Da
References
  1. Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [PubMed:2200507 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of ribosome
Specific Function:
Binds 16S rRNA, required for the assembly of 30S particles and may also be responsible for determining the conformation of the 16S rRNA at the A site.
Gene Name:
rpsN
Uniprot ID:
P0AG59
Molecular Weight:
11580.36 Da
References
  1. Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [PubMed:2200507 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of ribosome
Specific Function:
Binds the lower part of the 30S subunit head. Binds mRNA in the 70S ribosome, positioning it for translation (By similarity).Plays a role in mRNA unwinding by the ribosome, possibly by forming part of a processivity clamp.
Gene Name:
rpsC
Uniprot ID:
P0A7V3
Molecular Weight:
25983.07 Da
References
  1. Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [PubMed:2200507 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of ribosome
Specific Function:
One of the primary rRNA binding proteins, it binds directly to 16S rRNA central domain where it helps coordinate assembly of the platform of the 30S subunit.Protein S8 is a translational repressor protein, it controls the translation of the spc operon by binding to its mRNA.
Gene Name:
rpsH
Uniprot ID:
P0A7W7
Molecular Weight:
14126.435 Da
References
  1. Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [PubMed:2200507 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Trna binding
Specific Function:
In the E.coli 70S ribosome in the initiation state (PubMed:12809609) it has been modeled to contact the 23S rRNA of the 50S subunit forming part of bridge B1a; this bridge is broken in the model with bound EF-G. The 23S rRNA contact site in bridge B1a is modeled to differ in different ribosomal states (PubMed:12859903), contacting alternately S13 or S19. In the 3.5 angstroms resolved ribosome s...
Gene Name:
rpsS
Uniprot ID:
P0A7U3
Molecular Weight:
10430.235 Da
References
  1. Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [PubMed:2200507 ]
6. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
Actions
inhibitor
References
  1. Nawaz M, Sung K, Khan SA, Khan AA, Steele R: Biochemical and molecular characterization of tetracycline-resistant Aeromonas veronii isolates from catfish. Appl Environ Microbiol. 2006 Oct;72(10):6461-6. [PubMed:17021193 ]
  2. Domingue GJ Sr: Cryptic bacterial infection in chronic prostatitis: diagnostic and therapeutic implications. Curr Opin Urol. 1998 Jan;8(1):45-9. [PubMed:17035842 ]
  3. Pringle M, Fellstrom C, Johansson KE: Decreased susceptibility to doxycycline associated with a 16S rRNA gene mutation in Brachyspira hyodysenteriae. Vet Microbiol. 2007 Jul 20;123(1-3):245-8. Epub 2007 Feb 25. [PubMed:17428623 ]
  4. Rasmussen B, Noller HF, Daubresse G, Oliva B, Misulovin Z, Rothstein DM, Ellestad GA, Gluzman Y, Tally FP, Chopra I: Molecular basis of tetracycline action: identification of analogs whose primary target is not the bacterial ribosome. Antimicrob Agents Chemother. 1991 Nov;35(11):2306-11. [PubMed:1725100 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Tubulin binding
Specific Function:
Its primary physiological function is unclear. Has cytoprotective activity against internal or environmental stresses. May play a role in neuronal development and synaptic plasticity. May be required for neuronal myelin sheath maintenance. May play a role in iron uptake and iron homeostasis. Soluble oligomers are toxic to cultured neuroblastoma cells and induce apoptosis (in vitro) (PubMed:1273...
Gene Name:
PRNP
Uniprot ID:
P04156
Molecular Weight:
27661.21 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. De Luigi A, Colombo L, Diomede L, Capobianco R, Mangieri M, Miccolo C, Limido L, Forloni G, Tagliavini F, Salmona M: The efficacy of tetracyclines in peripheral and intracerebral prion infection. PLoS One. 2008 Mar 26;3(3):e1888. doi: 10.1371/journal.pone.0001888. [PubMed:18365024 ]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
unknown
General Function:
Transporter activity
Specific Function:
Not Available
Gene Name:
mdfA
Uniprot ID:
C9EH48
Molecular Weight:
10133.045 Da
References
  1. Nelson ML, Park BH, Andrews JS, Georgian VA, Thomas RC, Levy SB: Inhibition of the tetracycline efflux antiport protein by 13-thio-substituted 5-hydroxy-6-deoxytetracyclines. J Med Chem. 1993 Feb 5;36(3):370-7. [PubMed:8426364 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein-arginine deiminase activity
Specific Function:
Catalyzes the citrullination/deimination of arginine residues of proteins such as histones, thereby playing a key role in histone code and regulation of stem cell maintenance. Citrullinates histone H1 at 'Arg-54' (to form H1R54ci), histone H3 at 'Arg-2', 'Arg-8', 'Arg-17' and/or 'Arg-26' (to form H3R2ci, H3R8ci, H3R17ci, H3R26ci, respectively) and histone H4 at 'Arg-3' (to form H4R3ci). Acts as...
Gene Name:
PADI4
Uniprot ID:
Q9UM07
Molecular Weight:
74078.65 Da
References
  1. Knuckley B, Luo Y, Thompson PR: Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors. Bioorg Med Chem. 2008 Jan 15;16(2):739-45. Epub 2007 Oct 13. [PubMed:17964793 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. [PubMed:11855680 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. [PubMed:11855680 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular Weight:
59970.945 Da
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. [PubMed:11855680 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular Weight:
60025.025 Da
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. [PubMed:11855680 ]
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Drug created on June 13, 2005 07:24 / Updated on September 25, 2016 02:16