RFP

RIFAMPICIN


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Chemical Component Summary

NameRIFAMPICIN
Identifiersn/a
FormulaC43 H58 N4 O12
Molecular Weight822.94
TypeNON-POLYMER
Isomeric SMILESCc1c(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
InChIInChI=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
InChIKeyJQXXHWHPUNPDRT-WLSIYKJHSA-N

Chemical Details

Formal Charge0
Atom Count117
Chiral Atom Count9
Bond Count121
Aromatic Bond Count11

Drug Info: DrugBank

DrugBank IDDB01045 
NameRifampicin
Groups approved
DescriptionA semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)
Synonyms
  • Rifampicina
  • Rifampicine
  • 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV
  • RFP
  • Rifampicin sodium
Brand Names
  • Rifampin
  • Rifadin
  • Rifadin Cap 300mg
  • Rifater
  • Rifamate
IndicationRifampin is indicated for the treatment of tuberculosis and tuberculosis-related mycobacterial infections.[L45374] 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 betaMVYSYTEKKRIRKDFGKRPQVLDVPYLLSIQLDSFQKFIEQDPEGQYGLE...unknowninhibitor
Nuclear receptor subfamily 1 group I member 2MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...unknownagonist
Cytochrome P450 2A6MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...unknowninducer
Cytochrome P450 2E1MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...unknowninducer
Cytochrome P450 3A43MDLIPNFAMETWVLVATSLVLLYIYGTHSHKLFKKLGIPGPTPLPFLGTI...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