methyl (7S,11R,12R,13R,14R,15R,16R,17R,18R)-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[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1,3,5(35),9,19,21,25(36),26(34),28,30,32-undecaene-13-carboxylate

• ChemBase ID: 153978
• Molecular Formular: C43H51N3O11
• Molecular Mass: 785.87854
• Monoisotopic Mass: 785.35235947
• SMILES: Cc1ccn2c(c1)nc1c2c2c(c3c1c1c(c(c3O)C)O[C@@](C1=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)N2)\C)C)O)C)O)C)C(=O)OC)C)OC)C)O
• 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)C(=O)OC)C)O)C)O)C)/C
• InChI: InChI=1S/C43H51N3O11/c1-19-14-16-46-27(18-19)44-32-29-30-37(49)25(7)39-31(29)40(51)43(8,57-39)56-17-15-26(54-9)22(4)28(42(53)55-10)23(5)36(48)24(6)35(47)20(2)12-11-13-21(3)41(52)45-33(34(32)46)38(30)50/h11-18,20,22-24,26,28,35-36,47-50H,1-10H3,(H,45,52)/t20-,22+,23-,24-,26+,28+,35-,36-,43+/m1/s1
• InChIKey: HIYLTQREEOINNF-NVXPVAIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (7S,11R,12R,13R,14R,15R,16R,17R,18R)-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[23.10.1.1^4,^7.0^5,^3^5.0^2^6,^3^4.0^2^7,^3^2]heptatriaconta-1,3,5(35),9,19,21,25(36),26(34),28,30,32-undecaene-13-carboxylate
• IUPAC Traditional name: methyl (7S,11R,12R,13R,14R,15R,16R,17R,18R)-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[23.10.1.1^4,^7.0^5,^3^5.0^2^6,^3^4.0^2^7,^3^2]heptatriaconta-1,3,5(35),9,19,21,25(36),26(34),28,30,32-undecaene-13-carboxylate
• Synonyms: 4-Deoxy-4′-methylpyrido[1′,2′-1,2]imidazo[5,4-c]rifamycin SV; Rifacol; Rifaximin; 4-脱氧-4′-甲基吡啶并[1′,2′-1,2]咪唑并[5,4-c]利福霉素 SV; 利福昔明; 利福西亚胺

Database IDs

• CAS Number: 80621-81-4
• MDL Number: MFCD00864973
• PubChem SID: 24860754; 162248117
• PubChem CID: 71311771

CALCULATED PROPERTIES

• Acid pKa: 6.0116086
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 4.4017706
• LogD (pH = 7.4): 4.109534
• Log P: 4.603209
• Molar Refractivity: 217.0782 cm^3
• Polarizability: 84.08042 Å^3
• Polar Surface Area: 198.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: KD1576000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C43H51N3O11

DETAILS

Sigma Aldrich - R9904

Application
Rifaximin is a semisynthetic analog of rifamycin with poor absorptivity. It selectively inhibits (E. coli, B subtilis) bacterial DNA-dependent RNA polymerase by a mechanism similar to rifabutin, β subunit binding. It is effective against aerobic and anaerobic Gram-positive and Gram-negative bacteria. It is active against species of Staphylococcus, Streptococcus and Enterococcus. It is less active against species of Enterobacteriaceae. Rifaximin is a non-systemic, gastrointestinal site-specific antibiotic. It has a pyridoimidazole ring, making it non-absorbable. Rifaximin is a pregnane X receptor (PXR) activator1.
Biochem/physiol Actions
Rifaximin is a semisynthetic antibiotic used to treat diarrhea caused by E. coli. It is also used to treat hepatic encephalopathy by reducing blood ammonia concentrations. Rifaximin is a potential treatment for inflammatory bowel disease1.

Sigma Aldrich - 33999

Legal Information
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