rifamycin SV   Click here for help

GtoPdb Ligand ID: 4570

Synonyms: Aemcolo®
Approved drug
rifamycin SV is an approved drug (FDA (2018))
Comment: One of the Ansamycin group of antibiotics. Rifamycin is a natural antibiotic that is produced by Streptomyces mediterranei that exhibits antibiotic and antitubercular properties. Rifamycins are particularly effective against mycobacteria, and are most commonly used to treat tuberculosis, leprosy, and mycobacterium avium complex (MAC) infections.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 3
Topological polar surface area 201.31
Molecular weight 697.31
XLogP 3.97
No. Lipinski's rules broken 1
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Canonical SMILES COC1C=COC2(C)Oc3c(C2=O)c2c(O)cc(c(c2c(c3C)O)O)NC(=O)C(=CC=CC(C(C(C(C(C(C1C)OC(=O)C)C)O)C)O)C)C
Isomeric SMILES CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(O)cc(c(c2c(c3C)O)O)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
InChI InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
1. DuPont HL, Petersen A, Zhao J, Mundt A, Jiang ZD, Miller S, Flores J, Shringarpure R, Moro L, Bagin RG et al.. (2014)
Targeting of rifamycin SV to the colon for treatment of travelers' diarrhea: a randomized, double-blind, placebo-controlled phase 3 study.
J Travel Med, 21 (6): 369-76. [PMID:25345982]
2. Lin SW, Lin CJ, Yang JC. (2017)
Rifamycin SV MMX for the treatment of traveler's diarrhea.
Expert Opin Pharmacother, 18 (12): 1269-1277. [PMID:28697313]
3. Vavricka SR, Van Montfoort J, Ha HR, Meier PJ, Fattinger K. (2002)
Interactions of rifamycin SV and rifampicin with organic anion uptake systems of human liver.
Hepatology, 36 (1): 164-72. [PMID:12085361]