Rifaximin

Names

[ Name ]:
Rifaximin

[Synonym ]:
Normix
acétate de (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,36-tétrahydroxy-11-méthoxy-3,7,12,14,16,18,22,30-octaméthyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.1.0.0.0]heptatriaconta-1(35),1(36),2,4,9,19,21,25,28,30,32,34-dodécaén-13-yle
rifaxidin
Xifaxan
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-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[23.10.1.1.0.0.0]heptatriaconta-1(35),1(36),2,4,9,19,21,25,28,30,32,34-dodecaen-13-yl acetate
RIFAMIXIN
Rifacol
2,7-(Epoxy[1,11,13]pentadecatrienoimino)furo[2'',3'':7',8']naphth[1',2':4,5]imidazo[1,2-a]pyridine-1,15(2H)-dione, 25-(acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-, (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-
l105sv
Rifaximin
l105
MFCD00864973
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-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[23.10.1.1.0.0.0]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl acetate
fatroximin
28e))-27r

Biological Activity

[Description]:

Rifaximin(Xifaxan) is an orally administered, semi-synthetic, nonsystemic antibiotic derived from rifamycin SV with antibacterial activity.IC50 Value:Target: RNA polymerase; antibacterialRifaximin is a semisynthetic, rifamycin-based non-systemic antibiotic, meaning that very little of the drug will pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It is used in the treatment of traveler's diarrhea and hepatic encephalopathy, for which it received orphan drug status from the U.S. Food and Drug Administration in 1998. Rifaximin interferes with transcription by binding to the β-subunit of bacterial RNA polymerase. This results in the blockage of the translocation step that normally follows the formation of the first phosphodiester bond, which occurs in the transcription process. From Wikipedia.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Cruciani F, Brigidi P, Calanni F et al. Efficacy of rifaximin vaginal tablets in treatment of bacterial vaginosis: a molecular characterization of the vaginal microbiota. Antimicrob Agents Chemother. 2012 Aug;56(8):4062-70.

[2]. Cremonini F, Lembo A. Rifaximin for the treatment of irritable bowel syndrome. Expert Opin Pharmacother. 2012 Feb;13(3):433-40.

[3]. Rivkin A, Gim S. Rifaximin: new therapeutic indication and future directions. Clin Ther. 2011 Jul;33(7):812-27.

[4]. Cottreau J, Baker SF, DuPont HL, Garey KW. Rifaximin: a nonsystemic rifamycin antibiotic for gastrointestinal infections. Expert Rev Anti Infect Ther. 2010 Jul;8(7):747-60.

[5]. Koo HL, DuPont HL. Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases. Curr Opin Gastroenterol. 2010 Jan;26(1):17-25.

[6]. Ojetti V, Lauritano EC, Barbaro F et al. Rifaximin pharmacology and clinical implications. Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):675-82.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
200-205ºC(dec)

[ Molecular Formula ]:
C₄₃H₅₁N₃O₁₁

[ Molecular Weight ]:
785.878

[ Exact Mass ]:
785.352356

[ PSA ]:
198.38000

[ LogP ]:
3.22

[ Index of Refraction ]:
1.634

[ Storage condition ]:
0-6°C

[ Water Solubility ]:
ethanol: soluble1mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2.0

[ RTECS ]:
KD1576000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Methane biogenesis during sodium azide-induced chemical hypoxia in rats.

Am. J. Physiol. Cell Physiol. 304(2) , C207-14, (2013)

Previous studies demonstrated methane generation in aerobic cells. Our aims were to investigate the methanogenic features of sodium azide (NaN(3))-induced chemical hypoxia in the whole animal and to s...

Effectiveness of different therapeutic strategies in preventing diverticulitis recurrence.

Eur. Rev. Med. Pharmacol. Sci. 17(3) , 342-8, (2013)

Colonic diverticulitis shows a high recurrence rate.To assess the efficacy of three different therapeutic strategies in preventing diverticulitis recurrence.One hundred thirty patients suffering from ...

Combination therapy for the treatment and prevention of hepatic encephalopathy.

Ann. Pharmacother. 46(11) , 1559-63, (2012)

To evaluate the efficacy and safety of combination therapy for the treatment and prevention of hepatic encephalopathy (HE).A PubMed MEDLINE search was conducted (1947-June 2012) using the key terms la...