RFP
RIFAMPICIN
Created: | 2001-03-16 |
Last modified: | 2011-06-04 |
Find Related PDB Entry |
---|
Find related ligands: |
---|
Chemical Details | |
---|---|
Formal Charge | 0 |
Atom Count | 117 |
Chiral Atom Count | 9 |
Bond Count | 121 |
Aromatic Bond Count | 11 |
Chemical Component Summary | |
---|---|
Name | RIFAMPICIN |
Systematic Name (OpenEye OEToolkits) | n/a |
Formula | C43 H58 N4 O12 |
Molecular Weight | 822.94 |
Type | NON-POLYMER |
Chemical Descriptors | |||
---|---|---|---|
Type | Program | Version | Descriptor |
SMILES | ACDLabs | 10.04 | O=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 |
SMILES | CACTVS | 3.341 | CO[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 |
SMILES | OpenEye OEToolkits | 1.5.0 | Cc1c(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 SMILES | CACTVS | 3.341 | 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 SMILES | OpenEye OEToolkits | 1.5.0 | 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 |
InChI | InChI | 1.03 | 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 |
InChIKey | InChI | 1.03 | JQXXHWHPUNPDRT-WLSIYKJHSA-N |
Drug Info: DrugBank
DrugBank ID | DB01045 |
---|---|
Name | Rifampicin |
Groups | approved |
Description | A 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 |
|
Brand Names |
|
Indication | Rifampin 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 |
|
ATC-Code |
|
CAS number | 13292-46-1 |
Drug Targets
Name | Target Sequence | Pharmacological Action | Actions |
---|---|---|---|
DNA-directed RNA polymerase subunit beta | MVYSYTEKKRIRKDFGKRPQVLDVPYLLSIQLDSFQKFIEQDPEGQYGLE... | unknown | inhibitor |
Nuclear receptor subfamily 1 group I member 2 | MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG... | unknown | agonist |
Cytochrome P450 2A6 | MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN... | unknown | inducer |
Cytochrome P450 2E1 | MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL... | unknown | inducer |
Cytochrome P450 3A43 | MDLIPNFAMETWVLVATSLVLLYIYGTHSHKLFKKLGIPGPTPLPFLGTI... | unknown | inducer |
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 Name | Reference |
---|---|
Pharos | CHEMBL374478 |
PubChem | 136262914, 135398735 |
ChEMBL | CHEMBL374478 |
ChEBI | CHEBI:28077, CHEBI:71365 |