Identification

Name
Tetracycline
Accession Number
DB00759  (APRD00572)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

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.

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
  • Anhydrotetracycline
  • Deschlorobiomycin
  • Tetracyclin
  • Tétracycline
  • Tetracyclinum
  • Tetrazyklin
  • Tsiklomitsin
Product Ingredients
IngredientUNIICASInChI Key
Tetracycline hydrochlorideP6R62377KV64-75-5YCIHPQHVWDULOY-FMZCEJRJSA-N
Tetracycline phosphateNZ662XY5PP13930-32-0WXDJNRXQVCECPF-IZGCTLQUSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Achromycin Ont Oph 1%Ointment1 %OphthalmicLederle Cyanamid Canada Inc.1955-12-311997-08-14Canada
Achromycin VCapsule500 mg/1OralHeritage2013-10-18Not applicableUs
Achromycin VCapsule250 mg/1OralHeritage2013-10-18Not applicableUs
Achromycin V Cap 250mgCapsule250 mgOralLederle Cyanamid Canada Inc.1957-12-311997-08-14Canada
ActisiteFiber, extended release12.7 mgDentalProcter And GambleNot 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 250mgTablet250 mgOralNovopharm Limited1967-12-312008-08-20Canada
Novo-tetra 250mgCapsule250 mgOralNovopharm Limited1967-12-312008-08-20Canada
Novo-tetra Sus 125mg/5mlLiquid125 mgOralNovopharm Limited1967-12-312005-08-10Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Tetra Tabs 250mgTablet250 mgOralApotex Corporation1984-12-312008-08-21Canada
SumycinTablet, film coated250 mg/1OralPar Pharmaceutical2017-04-04Not applicableUs
SumycinTablet, film coated500 mg/1OralPar Pharmaceutical2017-04-04Not applicableUs
Tetracycline HydrochlorideCapsule250 mg/1OralLiberty Pharmaceuticals, Inc.2000-01-31Not applicableUs00172 2416 80 nlmimage10 a00ed066
Tetracycline HydrochlorideCapsule250 mg/1OralChartwell Rx, Llc2015-12-14Not applicableUs
Tetracycline HydrochlorideCapsule500 mg/1OralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
Tetracycline HydrochlorideCapsule500 mg/1Oralbryant ranch prepack2010-12-19Not applicableUs00591 2235 01 nlmimage10 6a34b515
Tetracycline HydrochlorideCapsule500 mg/1OralStat Rx USA2010-03-23Not applicableUs
Tetracycline HydrochlorideCapsule500 mg/1OralAlvogen, Inc.2016-12-19Not applicableUs
Tetracycline HydrochlorideCapsule250 mg/1Oralbryant ranch prepack2010-03-23Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcnecyclineOintment.03 mg/mLTopicalPhillips Company2011-02-15Not applicableUs
DermaclineOintment30 mg/mLTopicalInventus, Llc2016-11-08Not 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
TetraNextOintment30 mg/mLTopicalSaxet Pharmaceuticals2016-08-01Not applicableUs
TetraStemOintment30 mg/gTopicalPhillips Company2014-02-25Not applicableUs
TetraStemOintment30 mg/gTopicalViaderma Ii, Inc.2014-05-282015-12-29Us
International/Other Brands
Achromycin / Liquamycin
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FIRST Marys Mouthwash CompoundingTetracycline hydrochloride + Diphenhydramine hydrochloride + Hydrocortisone + NystatinKitOralCutis Pharma, Inc.2010-12-152017-10-04Us
PyleraTetracycline hydrochloride (125 mg/1) + Bismuth subcitrate potassium (140 mg/1) + Metronidazole (125 mg/1)CapsuleOralPhysicians Total Care, Inc.2010-08-18Not applicableUs
PyleraTetracycline hydrochloride (125 mg/1) + Bismuth subcitrate potassium (140 mg/1) + Metronidazole (125 mg/1)CapsuleOralAllergan2013-08-01Not applicableUs
PyleraTetracycline hydrochloride (125 mg) + Bismuth subcitrate potassium monohydrate (40 mg) + Metronidazole (125 mg)CapsuleOralAptalis Pharma Inc.Not applicableNot applicableCanada
Categories
UNII
F8VB5M810T
CAS number
60-54-8
Weight
Average: 444.4346
Monoisotopic: 444.153265754
Chemical Formula
C22H24N2O8
InChI Key
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)[C@H]2N(C)C)C(=O)C1=C(O)C=CC=C1[C@@]3(C)O

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.

Structured Indications
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.

TargetActionsOrganism
A30S ribosomal protein S7
inhibitor
Escherichia coli (strain K12)
A30S ribosomal protein S14
inhibitor
Escherichia coli (strain K12)
A30S ribosomal protein S3
inhibitor
Escherichia coli (strain K12)
A30S ribosomal protein S8
inhibitor
Escherichia coli (strain K12)
A30S ribosomal protein S19
inhibitor
Escherichia coli (strain K12)
A16S rRNA
inhibitor
Enteric bacteria and other eubacteria
UMajor prion protein
inhibitor
Human
UMultidrug translocase MdfANot AvailableEscherichia coli
UProtein-arginine deiminase type-4Not AvailableHuman
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
  • Borrelia burgdorferi
  • Chlamydia trachomatis
  • Mycoplasma pneumoniae
  • Rickettsia rickettsii
  • Vibrio cholerae
  • Escherichia coli
  • Shigella
  • Coxiella
Pathways
PathwayCategory
Tetracycline Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AmiodaroneThe metabolism of Tetracycline can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Tetracycline can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Tetracycline can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Tetracycline can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Tetracycline is combined with Atorvastatin.Approved
AtovaquoneThe serum concentration of Atovaquone can be decreased when it is combined with Tetracycline.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Tetracycline.Investigational
BoceprevirThe metabolism of Tetracycline can be decreased when combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Tetracycline can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Tetracycline can be decreased when it is combined with Bosentan.Approved, Investigational
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Tetracycline.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Tetracycline.Approved
CarbamazepineThe metabolism of Tetracycline can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Tetracycline can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Tetracycline.Withdrawn
ClarithromycinThe metabolism of Tetracycline can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Tetracycline can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Tetracycline can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Tetracycline can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Tetracycline can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Tetracycline can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Tetracycline can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Tetracycline can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Tetracycline can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Tetracycline can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Tetracycline can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Tetracycline can be decreased when combined with Delavirdine.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Tetracycline.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Tetracycline.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Tetracycline.Experimental
DihydroergotamineThe metabolism of Tetracycline can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Tetracycline can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Tetracycline can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Tetracycline can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Tetracycline can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Tetracycline.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Tetracycline.Approved
ErythromycinThe metabolism of Tetracycline can be decreased when combined with Erythromycin.Approved, Vet Approved
FluconazoleThe metabolism of Tetracycline can be decreased when combined with Fluconazole.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Tetracycline.Approved
FluvoxamineThe metabolism of Tetracycline can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Tetracycline can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Tetracycline can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Tetracycline can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Tetracycline can be increased when it is combined with Fusidic Acid.Approved
IdelalisibThe serum concentration of Tetracycline can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Tetracycline can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Tetracycline can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Tetracycline can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Tetracycline can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Tetracycline can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Tetracycline can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Tetracycline can be decreased when combined with Ketoconazole.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Tetracycline.Approved
LopinavirThe metabolism of Tetracycline can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Tetracycline can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Tetracycline can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Tetracycline can be increased when combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tetracycline.Illicit, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Tetracycline.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Tetracycline.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Tetracycline.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Tetracycline.Experimental
MifepristoneThe serum concentration of Tetracycline can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Tetracycline can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Tetracycline can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Tetracycline can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Tetracycline can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Tetracycline can be increased when combined with Nevirapine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Tetracycline.Approved
NilotinibThe metabolism of Tetracycline can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Tetracycline can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Tetracycline can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Tetracycline can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Tetracycline can be increased when combined with Pentobarbital.Approved, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Tetracycline.Approved, Vet Approved, Withdrawn
PhenobarbitalThe metabolism of Tetracycline can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Tetracycline can be increased when combined with Phenytoin.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Tetracycline.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Tetracycline.Approved
PosaconazoleThe metabolism of Tetracycline can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Tetracycline.Approved
PrimidoneThe metabolism of Tetracycline can be increased when combined with Primidone.Approved, Vet Approved
QuinineThe serum concentration of Quinine can be increased when it is combined with Tetracycline.Approved
RanolazineThe metabolism of Tetracycline can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Tetracycline can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Tetracycline can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Tetracycline can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Tetracycline can be decreased when combined with Ritonavir.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Tetracycline.Approved
SaquinavirThe metabolism of Tetracycline can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Tetracycline can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Tetracycline can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Tetracycline can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Tetracycline.Approved
St. John's WortThe serum concentration of Tetracycline can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Tetracycline can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Tetracycline can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Tetracycline can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Tetracycline can be decreased when combined with Telithromycin.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Tetracycline.Experimental
TiclopidineThe metabolism of Tetracycline can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Tetracycline can be decreased when it is combined with Tocilizumab.Approved
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Tetracycline.Experimental
VenlafaxineThe metabolism of Tetracycline can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Tetracycline can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Tetracycline can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Tetracycline can be decreased when combined with Ziprasidone.Approved
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.

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
Human Metabolome Database
HMDB14897
KEGG Drug
D00201
KEGG Compound
C06570
PubChem Compound
54675776
PubChem Substance
46506693
ChemSpider
10257122
ChEBI
27902
ChEMBL
CHEMBL1440
Therapeutic Targets Database
DAP001527
PharmGKB
PA451640
HET
TAC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tetracycline
ATC Codes
S02AA08 — TetracyclineA02BD08 — Bismuth subcitrate, tetracycline and metronidazoleA01AB13 — TetracyclineJ01RA08 — Tetracycline and oleandomycinJ01AA20 — Combinations of tetracyclinesS03AA02 — TetracyclineD06AA04 — TetracyclineS01AA09 — TetracyclineJ01AA07 — TetracyclineA02BD02 — Lansoprazole, tetracycline and metronidazole
AHFS Codes
  • 08:12.24
  • 52:04.04
PDB Entries
1P87
FDA label
Not Available
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0WithdrawnTreatmentChalazia / Chalazion1
1CompletedTreatmentAcute and Chronic Inflammation / Autoimmune Diseases / Disorder of Pleura and Pleural Cavity / Disorder of Synovium / Felty's Syndrome / Rheumatoid Arthritis / Rheumatoid Nodules / Sjögren's Syndrome1
1CompletedTreatmentAutoimmune Diseases / Disseminated or Multiple Sclerosis Nos / Disseminated Sclerosis / Multiple Sclerosis, Acute Relapsing / Multiple Sclerosis, Chronic Progressive / Multiple Sclerosis, Primary Progressive1
2CompletedTreatmentAlzheimer's Disease (AD) / Mild Cognitive Impairment (MCI)1
2CompletedTreatmentMalignant Lymphomas2
2CompletedTreatmentNon-Hodgkin's Lymphoma (NHL)1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentLung Cancers / Skin Rash1
2, 3TerminatedTreatmentMinor burns1
3CompletedTreatmentHelicobacter Infections1
3RecruitingTreatmentDuodenal Ulcer1
3Unknown StatusTreatmentBacterial Vaginosis (BV) / Candidiasis infection1
3WithdrawnTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4CompletedPreventionTrichiasis1
4CompletedTreatmentCoxiella Infection / Fatigue Syndrome, Chronic / Q Fever1
4CompletedTreatmentCure Rate of Helicobacter Pylori Infection1
4CompletedTreatmentFunctional Dyspepsia / Scarred Peptic Ulcer1
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentHelicobacter Infections1
4CompletedTreatmentHelicobacter Pylori Treatment Failure1
4CompletedTreatmentBone destruction1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Triple Therapy1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4RecruitingPreventionTrachoma1
4RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4Unknown StatusTreatmentEpidermolysis Bullosa1
4Unknown StatusTreatmentH. Pylori Infection1
Not AvailableCompletedBasic ScienceCognitive Dysfunctions / Paresis / Paresthesia / Radicular Pain / Tiredness1
Not AvailableCompletedBasic ScienceOpioid Dependence / Pain1
Not AvailableCompletedSupportive CareUnspecified Adult Solid Tumor, Protocol Specific1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableEnrolling by InvitationTreatmentHelicobacter Infection1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)4
Not AvailableRecruitingTreatmentHelicobacter Infection1
Not AvailableUnknown StatusTreatmentAngelman's syndrome1
Not AvailableUnknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableWithdrawnNot AvailableCancer, Breast1

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 %
Fiber, extended releaseDental12.7 mg
OintmentTopical30 mg/g
OintmentTopical30 mg/mL
KitOral
TabletOral250 mg
LiquidOral125 mg
CapsuleOral
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
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)
US6350468No1998-12-142018-12-14Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)172.5 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01sc-1900000000-7b792268aeb0a63c32c5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01p9-1900000000-da0b69e206bb0369723c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-3900000000-299e4496b1f8e2f213cc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ta-0000900000-e5ca6594fe72eb2bcd1f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ik9-0402900000-9ef4a0d08180ce9b2a1c

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Tetracyclines
Sub Class
Not Available
Direct Parent
Tetracyclines
Alternative Parents
Naphthacenes / Anthracenecarboxylic acids and derivatives / Tetralins / Aryl ketones / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Aralkylamines / Cyclohexenones / Tertiary alcohols / Vinylogous acids
show 8 more
Substituents
Tetracycline / Naphthacene / Tetracene / Anthracene carboxylic acid or derivatives / Tetralin / Aryl ketone / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Cyclohexenone / Aralkylamine
show 23 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
tetracyclines (CHEBI:27902) / tetracyclines, Linear tetracyclines (C06570)

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 ...
Gene Name
rpsG
Uniprot ID
P02359
Uniprot Name
30S ribosomal protein S7
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
Uniprot Name
30S ribosomal protein S14
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...
Gene Name
rpsC
Uniprot ID
P0A7V3
Uniprot Name
30S ribosomal protein S3
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 ...
Gene Name
rpsH
Uniprot ID
P0A7W7
Uniprot Name
30S ribosomal protein S8
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 wi...
Gene Name
rpsS
Uniprot ID
P0A7U3
Uniprot Name
30S ribosomal protein S19
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 requir...
Gene Name
PRNP
Uniprot ID
P04156
Uniprot Name
Major prion protein
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
Uniprot Name
Multidrug translocase MdfA
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...
Gene Name
PADI4
Uniprot ID
Q9UM07
Uniprot Name
Protein-arginine deiminase type-4
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
Substrate
Inhibitor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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 ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
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, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
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
Uniprot Name
Solute carrier family 22 member 11
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 sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
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]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:44