TAC

TETRACYCLINE

Created: 1999-07-08
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count56
Chiral Atom Count5
Bond Count59
Aromatic Bond Count6
2D diagram of TAC

Chemical Component Summary

NameTETRACYCLINE
Systematic Name (OpenEye OEToolkits)(4aS,5aS,6S,12aS)-4-dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
FormulaC22 H24 N2 O8
Molecular Weight444.435
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C3C2=C(O)C1(O)C(=O)C(=C(O)C(N(C)C)C1CC2C(O)(c4cccc(O)c34)C)C(=O)N
SMILESCACTVS3.341CN(C)[CH]1[CH]2C[CH]3C(=C(O)[C]2(O)C(=O)C(=C1O)C(N)=O)C(=O)c4c(O)cccc4[C]3(C)O
SMILESOpenEye OEToolkits1.5.0CC1(c2cccc(c2C(=O)C3=C(C4(C(CC31)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O
Canonical SMILESCACTVS3.341 CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(=C1O)C(N)=O)C(=O)c4c(O)cccc4[C@@]3(C)O
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@]1(c2cccc(c2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O
InChIInChI1.03 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
InChIKeyInChI1.03 OFVLGDICTFRJMM-WESIUVDSSA-N

Drug Info: DrugBank

DrugBank IDDB00759 
NameTetracycline
Groups
  • approved
  • withdrawn
  • 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. The FDA withdrew its approval for the use of all liquid oral drug products formulated for pediatric use containing tetracycline in a concentration greater than 25 mg/ml.[L43942] Other formulations of tetracycline continue to be used.
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
  • Anhydrotetracycline
  • Abramycin
  • Tetracycline phosphate
  • Deschlorobiomycin
Brand Names
  • Vitastem-tetracycline hydrochloride
  • Bismuth Subcitrate Potassium, Metronidazole, and Tetracycline Hydrochloride
  • Tetracycline Hydrochloride
  • Tetracycline-ABC
  • Achromycin Ont Oph 1%
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.
Categories
  • Agents that produce neuromuscular block (indirect)
  • Alimentary Tract and Metabolism
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-Code
  • S02AA08
  • A02BD02
  • A01AB13
  • J01AA07
  • S01AA09
CAS number60-54-8

Drug Targets

NameTarget SequencePharmacological ActionActions
30S ribosomal protein S7MPRRRVIGQRKILPDPKFGSELLAKFVNILMVDGKKSTAESIVYSALETL...unknowninhibitor
30S ribosomal protein S14MAKQSMKAREVKRVALADKYFAKRAELKAIISDVNASDEDRWNAVLKLQT...unknowninhibitor
30S ribosomal protein S3MGQKVHPNGIRLGIVKPWNSTWFANTKEFADNLDSDFKVRQYLTKELAKA...unknowninhibitor
30S ribosomal protein S8MSMQDPIADMLTRIRNGQAANKAAVTMPSSKLKVAIANVLKEEGFIEDFK...unknowninhibitor
30S ribosomal protein S19MPRSLKKGPFIDLHLLKKVEKAVESGDKKPLRTWSRRSTIFPNMIGLTIA...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682