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Merck
CN

R9904

Sigma-Aldrich

Rifaximin

Synonym(s):

4-Deoxy-4′-methylpyrido[1′,2′-1,2]imidazo[5,4-c]rifamycin SV, Rifacol

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About This Item

Empirical Formula (Hill Notation):
C43H51N3O11
CAS Number:
80621-81-4
Molecular Weight:
785.88
MDL number:
MFCD00864973
UNSPSC Code:
51283604
PubChem Substance ID:
329824049
NACRES:
NA.85

Key Documents

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form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

color

red to orange

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(C)=C\C=C\[C@@H](C)[C@@H](O)[C@@H](C)[C@H](O)[C@H](C)[C@H]([C@H]1C)C(=O)OC)c5c(nc6cc(C)ccn56)c4c3C2=O

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)/b12-11+,17-15+,21-13-/t20-,22+,23-,24-,26+,28+,35-,36-,43+/m1/s1

InChI key

HIYLTQREEOINNF-HTEWPBCCSA-N

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General description

Chemical structure: macrolide

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) activator.

Biochem/physiol Actions

Rifaximin is a semisynthetic analog of rifamycin with poor absorptivity. Mode of action: selectively inhibits (E. coli, B subtilis) bacterial DNA-dependent RNA polymerase by mechanism similar to rifabutin, β subunit binding.
Antimicrobial spectrum: Aerobic and anaerobic Gram-positive and Gram-negative bacteria. Active against species of Staphylococcus, Streptococcus and Enterococcus; less active against species of Enterobacteriaceae.†

Preparation Note

Practically insoluble in water, soluble in acetone and methanol.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000458081
0000458081
0000434327
0000434327
0000389695

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J C Gillis et al.
Drugs, 49(3), 467-484 (1995-03-01)
Rifaximin is a derivative of rifamycin which acts by inhibiting bacterial ribonucleic acid (RNA) synthesis. It is virtually unabsorbed after oral administration; thus it is used primarily to treat local conditions within the gastrointestinal tract. In vitro data indicate rifaximin
Marina Ferrer et al.
International journal of molecular sciences, 22(2) (2021-01-10)
Rifaximin is a broad-spectrum antibiotic that ameliorates symptomatology in inflammatory/functional gastrointestinal disorders. We assessed changes in gut commensal microbiota (GCM) and Toll-like receptors (TLRs) associated to rifaximin treatment in mice. Adult C57BL/6NCrl mice were treated (7/14 days) with rifaximin (50/150
Angel Lanas et al.
Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver, 45(2), 104-109 (2012-10-25)
Evidence supporting appropriate medical therapy to prevent recurrence of colonic diverticulitis is limited. Our goal was to evaluate the potential of rifaximin given periodically in addition to fibre for the prophylaxis of recurrences. We conducted a multicentre, randomized, open controlled
P Layer et al.
Alimentary pharmacology & therapeutics, 31(11), 1155-1164 (2010-03-25)
Travellers' diarrhoea, a common problem worldwide with significant medical impact, is generally treated with anti-diarrhoeal agents and fluid replacement. Systemic antibiotics are also used in selected cases, but these may be associated with adverse effects, bacterial resistance and drug-drug interactions.
Mark Pimentel
Expert opinion on investigational drugs, 18(3), 349-358 (2009-02-27)
Rifaximin is a broad-range, gastrointestinal-specific antibiotic that demonstrates no clinically relevant bacterial resistance. Therefore, rifaximin may be useful in the treatment of gastrointestinal disorders associated with altered bacterial flora, including irritable bowel syndrome (IBS) and small intestinal bacterial overgrowth (SIBO).
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