Rifamycin  (Synonyms: Rifamycin SV)

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]}.

Rifamycin (10 μM; 30 s) mainly inhibits -independent Taurocholate (HY-N0545) uptake in short-term cultured rat hepatocytes^[2].
Rifamycin (10-100 μM; 15 min) effectively inhibits Oatp2-mediated Taurocholate uptake in Xenopus oocytes expressing Na⁺/Ntcp^[2].
Rifamycin (1-100 μM; 24 h) inhibits the synthesis of cytokines and chemokines from lipopolysaccharide-activated monocytes and macrophages^[3].
Rifamycin (0.16 μg/ml; 2 weeks of culture) inhibits the growth of M. tuberculosis and its drug-resistant mutants in TB broth containing 10% serum albumin^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Rifamycin (5 mg/day; s.c.; 3 days a week) is effective in mice infected with M. tuberculosis, significantly reducing the number of viable bacteria in the body^[4].
Rifamycin (12.5-25 mg/kg; peritoneal lavage) can improve the survival rate of rats with experimental intraperitoneal infection and significantly reduce the number of intraperitoneal bacteria and adhesion formation^[6].
Rifamycin (5-40 mg/kg; esophageal gavage; once a day, 5 days a week; 4 weeks) shortens oral treatment duration in a mouse model of Mycobacterium ulcerans disease^[8].
Rifamycin (0.1 mL; intraaural administration; twice daily; 10 days) does not cause hearing loss in adult or weanling rats^[9].
Rifamycin (1 mg i.v. bolus followed by 4 mg i.v. infusion; 70 min) interferes with three major steps of Bile acid metabolism in rats with intravenous Sodium cholate (HY-N0324A) infusion, resulting in a significant decrease in bile acid uptake and excretion^[10].
Rifamycin (10-160 mg/kg; s.c.; single dose) is approximately 11 times less effective than Metronidazole (HY-B0318) in a mouse Bacteroides fragilis thigh infection model^[11].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

697.77

C₃₇H₄₇NO₁₂

6998-60-3

Solid

Light yellow to brown

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

Room temperature in continental US; may vary elsewhere.

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

• [1]. Floss HG, et al. Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev. 2005 Feb;105(2):621-32.  [Content Brief]

  [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.  [Content Brief]

  [3]. Rosette C, et al. Anti-inflammatory and immunomodulatory activities of rifamycin SV. Int J Antimicrob Agents. 2013 Aug;42(2):182-6.  [Content Brief]

  [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.  [Content Brief]

  [6]. Jallouli M, et al. Rifamycin lavage in the treatment of experimental intra-abdominal infection. J Surg Res. 2009 Aug;155(2):191-4.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.