rifaximin   Click here for help

GtoPdb Ligand ID: 12012

Synonyms: L/105 | Rifamycin L 105 | Xifaxan®
Approved drug PDB Ligand
rifaximin is an approved drug (FDA (2004))
Compound class: Synthetic organic
Comment: Rifaximin is a semisynthetic derivative of rifamycin and belongs to the ansamycin group of antibacterial compounds [1]. It has broad spectrum activity against Gram-positive and Gram-negative bacteria.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 5
Rotatable bonds 3
Topological polar surface area 198.38
Molecular weight 785.35
XLogP 6.08
No. Lipinski's rules broken 1
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Canonical SMILES CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(c(c3C)O)c(O)c(c3c2nc2n3ccc(c2)C)NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C
Isomeric SMILES C[C@H]1/C=C/C=C(\C(=O)Nc2c(c3c(c4c(c(c3O)C)O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)c1c2n2ccc(cc2n1)C)O)/C
InChI InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2004))
IUPAC Name Click here for help
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate
International Nonproprietary Names Click here for help
INN number INN
5244 rifaximin
Synonyms Click here for help
L/105 | Rifamycin L 105 | Xifaxan®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Rifaximin
Other databases
CAS Registry No. 80621-81-4 (source: Scifinder)
ChEMBL Ligand CHEMBL1617
DrugBank Ligand DB01220
GtoPdb PubChem SID 464244153
PubChem CID 6436173
Search Google for chemical match using the InChIKey NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Search Google for chemicals with the same backbone NZCRJKRKKOLAOJ
Search PubMed clinical trials rifaximin
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UniChem Compound Search for chemical match using the InChIKey NZCRJKRKKOLAOJ-XRCRFVBUSA-N
UniChem Connectivity Search for chemical match using the InChIKey NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Wikipedia Rifaximin