Rifamycin

Rifamycin (Rifamycin SV) is an orally active ansamycin antibiotic. Rifamycin inhibits DNA-dependent RNA synthesis. Rifamycin has antibacterial activity against Mycobacterium tuberculosis. Rifamycin interferes with hepatic bile acid metabolism. Rifamycin has anti-inflammatory effects. Rifamycin can be used in the study of Mycobacterium tuberculosis, Bacteroides fragilis infection, and Lipopolysaccharide (HY-D1056B3) -induced inflammation[1][2][3][4][5][6][7][8][9][10][11].

Product Specifications

CAS Number

[6998-60-3]

Product Name Alternative

Rifamycin SV

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Antibiotic; Bacterial; DNA/RNA Synthesis

Type

Reference compound

Related Pathways

Anti-infection; Cell Cycle/DNA Damage

Applications

COVID-19-immunoregulation

Field of Research

Infection

Assay Protocol

https://www.medchemexpress.com/rifamycin.html

Purity

97.31

Solubility

10 mM in DMSO

Smiles

C[C@H]1/C=C/C=C(C)\C(NC2=CC(O)=C3C(C(O)=C(C)C4=C3C([C@](O/C=C/[C@H](OC)[C@@H](C)[C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@H]1O)(C)O4)=O)=C2O)=O

Molecular Formula

C37H47NO12

Molecular Weight

697.77

Precautions

H302, H315, H319, H335

References & Citations

[1]Floss HG, et al. Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev. 2005 Feb;105 (2) :621-32.|[2]Fattinger K, et al. Rifamycin SV and rifampicin exhibit differential inhibition of the hepatic rat organic anion transporting polypeptides, Oatp1 and Oatp2. Hepatology. 2000 Jul;32 (1) :82-6.|[3]Rosette C, et al. Anti-inflammatory and immunomodulatory activities of rifamycin SV. Int J Antimicrob Agents. 2013 Aug;42 (2) :182-6.|[4]Tsukamura M, et al. Antituberculous Action of Rifamycin SV* In Vitro and In Vivo Studies. The Journal of Antibiotics, Series A, 1962, 15 (5) : 216-224.|[5]Saito K, et al. Rifamycin action on RNA polymerase in antibiotic-tolerant Mycobacterium tuberculosis results in differentially detectable populations. Proc Natl Acad Sci U S A. 2017 Jun 13;114 (24) :E4832-E4840. |[6]Jallouli M, et al. Rifamycin lavage in the treatment of experimental intra-abdominal infection. J Surg Res. 2009 Aug;155 (2) :191-4. |[7]Zhang M, et al. Treatment of tuberculosis with rifamycin-containing regimens in immune-deficient mice. Am J Respir Crit Care Med. 2011 May 1;183 (9) :1254-61.|[8]Omansen TF, et al. High-Dose Rifamycins Enable Shorter Oral Treatment in a Murine Model of Mycobacterium ulcerans Disease. Antimicrob Agents Chemother. 2019 Jan 29;63 (2) :e01478-18.|[9]Özbay C, et al. Ototoxic effect of topical rifamycin SV applied in the middle ear of rats. The Turkish Journal of Ear Nose and Throat, 2017, 27 (1) : 31-38.|[10]Okolicsanyi L, et al. Influence of rifamycin SV on bile acid metabolism in rats. Naunyn Schmiedebergs Arch Pharmacol. 1980 Aug;313 (2) :171-4.|[11]Dijkmans B A C, et al. Efficacy of rifamycin SV and vancomycin against Bacteroides fragilis in vitro and in experimentally infected mice. Current Microbiology, 1985, 12: 53-58.