RFP

RIFAMPICIN

Created: 2001-03-16
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count117
Chiral Atom Count9
Bond Count121
Aromatic Bond Count11
2D diagram of RFP
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Chemical Component Summary

NameRIFAMPICIN
Systematic Name (OpenEye OEToolkits)n/a
FormulaC43 H58 N4 O12
Molecular Weight822.94
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C4c5c2c(O)c(\C=N\N1CCN(C)CC1)c3c(O)c2c(O)c(c5OC4(OC=CC(OC)C(C(OC(=O)C)C(C)C(O)C(C)C(O)C(C=CC=C(C(=O)N3)C)C)C)C)C
SMILESCACTVS3.341CO[CH]1C=CO[C]2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=CC=C[CH](C)[CH](O)[CH](C)[CH](O)[CH](C)[CH](OC(C)=O)[CH]1C)C)c(C=NN5CCN(C)CC5)c(O)c4c3C2=O
SMILESOpenEye OEToolkits1.5.0Cc1c(c2c3c4c1OC(C4=O)(OC=CC(C(C(C(C(C(C(C(C=CC=C(C(=O)Nc(c2O)c(c3O)C=NN5CCN(CC5)C)C)C)O)C)O)C)OC(=O)C)C)OC)C)O
Canonical SMILESCACTVS3.341 CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)\C(=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C)c(\C=N\N5CCN(C)CC5)c(O)c4c3C2=O
Canonical SMILESOpenEye OEToolkits1.5.0 Cc1c(c2c3c4c1O[C@@](C4=O)(O\C=C\[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](C=C\C=C(/C(=O)Nc(c2O)c(c3O)\C=N\N5CCN(CC5)C)\C)C)O)C)O)C)OC(=O)C)C)OC)C)O
InChIInChI1.03 InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1
InChIKeyInChI1.03 JQXXHWHPUNPDRT-WLSIYKJHSA-N

Drug Info: DrugBank

DrugBank IDDB01045 
NameRifampin
Groups approved
DescriptionRifampin, also known as rifampicin, is a broad-spectrum antimicrobial [A263748] that was first discovered in 1965 [A263753] and clinically used in 1968.[A263768] Rifampin is used to treat tuberculosis and works by inhibiting the microbial DNA-dependent RNA polymerase (RNAP).[A263768]
Synonyms
  • Rifampicinum
  • Rifampicin
  • Rifampicina
  • 5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-[N-(4-methyl-1-piperazinyl)formimidoyl]-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione 21-acetate
  • Rifampicin sodium
Brand Names
  • Rifadin
  • Rifater
  • Rifamate
  • Rifampin
  • Rifadin Cap 300mg
IndicationRifampin is indicated for the treatment of tuberculosis and asymptomatic carriers of _Neisseria meningitidis_ to eliminate meningococci from the nasopharynx.[L45374, L50718] In combination with [pyrazinamide] and [isoniazid], it is used in the initial phase of the short-course treatment of pulmonary tuberculosis.[L45369]
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics, Antitubercular
  • Antiinfectives for Systemic Use
ATC-Code
  • J04BA50
  • J04AM02
  • J04BA51
  • J04AB02
  • J04AM06
CAS number13292-46-1

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA-directed RNA polymerase subunit betaMLEGCILADSRQSKTAASPSPSRPQSSSNNSVPGAPNRVSFAKLREPLEV...unknowninhibitor
Nuclear receptor subfamily 1 group I member 2MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...unknownagonist
UDP-glucuronosyltransferase 1A1MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...unknowninducer
UDP-glucuronosyltransferase 1A9MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...unknowninhibitor
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknowninducer
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

Related Resource References

Resource NameReference
Pharos CHEMBL374478
PubChem 135398735, 136262914
ChEMBL CHEMBL374478
ChEBI CHEBI:28077, CHEBI:71365