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R9904

Sigma-Aldrich

Rifaximin

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C43H51N3O11
Numéro CAS:
80621-81-4
Poids moléculaire :
785.88
Numéro MDL:
MFCD00864973
Code UNSPSC :
51283604
ID de substance PubChem :
329824049
Nomenclature NACRES :
NA.85

Forme

powder

Conditions de stockage

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

Couleur

red to orange

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

protein synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

HIYLTQREEOINNF-HTEWPBCCSA-N

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Catégories apparentées

Description générale

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.

Actions biochimiques/physiologiques

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.†

Notes préparatoires

Practically insoluble in water, soluble in acetone and methanol.

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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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
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
Vishesh Kothary et al.
Antimicrobial agents and chemotherapy, 57(2), 811-817 (2012-11-28)
Escherichia coli is implicated in the pathogenesis of inflammatory bowel disease (IBD). Rifaximin, a nonabsorbable derivative of rifampin effective against E. coli, improves symptoms in mild-to-moderate IBD. However, rifaximin resistance can develop in a single step in vitro. We examined
P Meyrat et al.
Alimentary pharmacology & therapeutics, 36(11-12), 1084-1093 (2012-10-17)
While rifaximin was able to improve symptoms in patients with irritable bowel syndrome (IBS) in phase III trials, these results are yet to be repeated in phase IV studies. To evaluate the treatment response to rifaximin in IBS patients in
E Mattila et al.
Alimentary pharmacology & therapeutics, 37(1), 122-128 (2012-10-26)
Clostridium difficile can cause severe antibiotic-associated colitis. Conventional treatments with metronidazole and vancomycin improve symptoms, but after discontinuation of treatment, C. difficile infection (CDI) recurs in a number of patients. Rifaximin is a rifamycin-based non-systemic antibiotic that has effect against
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