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Merck

R9904

Rifaximin

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C43H51N3O11
Número CAS:
80621-81-4
Peso molecular:
785.88
NACRES:
NA.85
PubChem Substance ID:
329824049
UNSPSC Code:
51283604
MDL number:
MFCD00864973

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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

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 key

HIYLTQREEOINNF-HTEWPBCCSA-N

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

Quality Level

100

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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.†

General description

Chemical structure: macrolide

Other Notes

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

Preparation Note

Practically insoluble in water, soluble in acetone and methanol.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000515763
0000515763
0000458081
0000458081
0000434327

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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
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
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
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
Jiannis Vlachogiannakos et al.
Journal of gastroenterology and hepatology, 28(3), 450-455 (2012-12-12)
Cirrhotic patients are predisposed to intestinal bacterial overgrowth with translocation of bacterial products which may deteriorate liver hemodynamics. Having shown that short-term administration of rifaximin improves liver hemodynamics in decompensated cirrhosis, we conducted this study to investigate the effect of
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