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R9904

Sigma-Aldrich

Rifaximin

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C43H51N3O11
Numero CAS:
80621-81-4
Peso molecolare:
785.88
Numero MDL:
MFCD00864973
Codice UNSPSC:
51283604
ID PubChem:
329824049
NACRES:
NA.85

Forma fisica

powder

Condizioni di stoccaggio

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

Colore

red to orange

Spettro attività antibiotica

Gram-negative bacteria
Gram-positive bacteria

Modalità d’azione

protein synthesis | interferes

Temperatura di conservazione

2-8°C

Stringa SMILE

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
HIYLTQREEOINNF-HTEWPBCCSA-N

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Descrizione generale

Chemical structure: macrolide

Applicazioni

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.

Azioni biochim/fisiol

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.†

Nota sulla preparazione

Practically insoluble in water, soluble in acetone and methanol.

Altre note

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (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
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
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
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
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