Rifamycin sodium
(Synonyms: 利福霉素钠; Rifamycin SV sodium) 目录号 : GC38056
Rifamycin sodium is an antibacterial drug used for treatment of mycobacterium infections.
Cas No.:14897-39-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Rifamycin sodium is an antibacterial drug used for treatment of mycobacterium infections.
| Cas No. | 14897-39-3 | SDF | |
| 别名 | 利福霉素钠; Rifamycin SV sodium | ||
| Canonical SMILES | O=C1C2=C(C([O-])=CC(NC(/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@H]3C)=O)=C4O)C4=C(O)C(C)=C2O[C@@]1(O/C=C/[C@@H]([C@H]([C@@]3([H])OC(C)=O)C)OC)C.[Na+] | ||
| 分子式 | C37H46NNaO12 | 分子量 | 719.75 |
| 溶解度 | DMSO: 250 mg/mL (347.34 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.3894 mL | 6.9469 mL | 13.8937 mL |
| 5 mM | 0.2779 mL | 1.3894 mL | 2.7787 mL |
| 10 mM | 0.1389 mL | 0.6947 mL | 1.3894 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Rifamycin lavage in the treatment of experimental intra-abdominal infection
J Surg Res 2009 Aug;155(2):191-4.PMID:19535094DOI:10.1016/j.jss.2008.03.041.
Hypothesis: Peritoneal lavage with Rifamycin reduces the number of intraperitoneal bacteria and adhesions and improves the outcome of intra-abdominal infection (IAI). Material and methods: Experimental IAI was induced in Wistar rats. After 24 h, the animals underwent relaparotomy. A peritoneal fluid sample was obtained and lavage of the abdominal cavity was performed. Animals were randomly assigned to the three following groups: lavage with 0.9% sodium chloride solution (S group); lavage with Rifamycin at the dose of 25 mg/kg (R25 group); and lavage with Rifamycin at the dose of 12.5 mg/kg (R12.5 group). Mortality was recorded every 8 h for 7 d. All animals that died had a necropsy. Surviving rats were later sacrificed and also underwent a necropsy. At necropsy, intraperitoneal adhesions were noted and a peritoneal fluid sample was obtained for bacterial analysis. Results: Peritoneal lavage with Rifamycin improved survival from 50% in the S group to 91.7 and 100% in the R25 group and R12.5 group, respectively. Adhesion formation was significantly reduced in the R25 group and R12.5 group compared with the S group (P < or = 0.01 and P < 0.01, respectively). There was a greater reduction in bacterial counts in peritoneal fluid in the R25 group compared with the S group (P = 0.003) but there was no significant difference in the reduction of bacterial count between R25 group and R12.5 group. Conclusion: These results suggest that peritoneal lavage with Rifamycin improves the outcome of IAI.
Correlation of structure and activity in ansamycins. Molecular structure of sodium Rifamycin SV
Mol Pharmacol 1983 Jan;23(1):133-40.PMID:6865897doi
The crystal and molecular structure of the sodium salt of Rifamycin SV (clinically known as rifacin) as the monohydrate ethanol solvate has been determined to study the conformation of the ansa chain in unsubstituted rifamycins and also to clarify the metal complexation with rifamycins. The crystals belong to the space group P2(1)2(1)2(1) with cell dimensions (estimated standard deviations in parentheses) of a = 12.061 (2), b = 13.936 (2), and c = 24.731 (4) A. The structure was solved by direct methods and refined to an R factor of 0.069. The conformation of the ansa chain differs from that of other active rifamycins, e.g., rifampcin and Rifamycin B at the joining point of the ansa chain to the naphthohydroquinone chromophore. The conformation of the middle part of the ansa chain, which is essential for activity against DNA-dependent RNA polymerase, remains the same. The sodium ion is penta-coordinated and has a trigonal bipyramidal geometry. The intermolecular hydrogen bonding involves O(9), O(10), O(5), and O(6) through water and ethanol molecules. A two-step mode of action of rifamycins has been postulated, and the conformations of antibiotics suitable for penetration of the membrane barrier and that for antibiotic-enzyme complex formation have been suggested.
Experimental and clinical studies on Rifacinna--the new effective antituberculous drug (review)
Recent Pat Antiinfect Drug Discov 2010 Jan;5(1):76-90.PMID:19929844DOI:10.2174/157489110790112572.
A new Rifamycin derivative 3-(4-cinnamyl-piperazinyl iminomethyl) Rifamycin SV (T9) and its sodium salt (T11, Rifacinna((R))) were in vitro, in vivo, toxicologically and clinically investigated in comparison with rifampicin, rifapentine, rifabutin, rifalazil. Our experiments showed that Rifacinna exhibits excellent in vitro activity against Gram(+), Gram (-) aerobic, anaerobic pathogens and mycobacteria. Rifacinna is active against Staphylococcus, Streptococcus spp. including MRSA, with MIC90- 0.06-0.5 mg/L; against Gram(+), Gram (-) anaerobes with MIC90 0.5 - 1 mg/L; against Mycobacterium tuberculosis (MTB) with MIC90 0.062 mg/L; against MDR resistant MTB (25%-30 %) and Mycobacterium avium complex (MAC) strains with MICs 0.6-1.0 mg/L. It shows high intraphagocytic activity against MAC strains (0.06 0.125mg/L). Single daily dose 10 mg/kg provides complete erradication of mycobacteria in experimental generalized tuberculosis. Pharmacological studies established: excellent pharmacokinetic profile following single oral dose 10mg/kg Tmax 5-6 h, C(max) 5-9 mg/L, T1/2 33-34 h; low toxicity; no teratogenic and embryotoxic effects. The clinical study of Rifacinna shows higher therapeutic efficacy than Rifampicin in patients with infiltrative, disseminated and cavitary form of pulmonary tuberculosis, good tolerability and safety profile. Some of the recent patents related to the treatment of tuberculosis are discussed in this review article.
A mechanism of Rifamycin inhibition and resistance in Pseudomonas aeruginosa
J Antimicrob Chemother 1996 Jul;38(1):133-7.PMID:8858465DOI:10.1093/jac/38.1.133.
We sought to study the nature of rifampicin resistance in Pseudomonas aeruginosa. We hypothesized that the Rifamycin regions of RNA polymerase are conserved in P. aeruginosa and that rifampicin resistance is mediated by a mutation in the rpoB gene encoding the beta subunit of RNA polymerase. Transcription assays showed that 50 nM of rifampicin inhibited transcription > 99% in a clinical isolate (MIC = 32 mg/L) and only < 40% in the rifampicin resistant mutant (MIC = 1000 mg/L). DNA sequencing revealed that the rifampicin regions are conserved in P. aeruginosa and the rifampicin regions of the rifampicin-resistant strain contained a mutation. Sodium hexametaphosphate lowered Rifamycin MIC in a rifamycin-resistant mutant four-fold and in the clinical isolate 32-fold, suggesting that P. aeruginosa has a natural membrane barrier to rifamycins.
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.PMID:10869292DOI:10.1053/jhep.2000.8539.
The antibiotics, Rifamycin SV and rifampicin, are known to interfere with hepatic bile salt and organic anion uptake. The aim of this study was to explore which transport systems are affected. In short-term-cultured rat hepatocytes, low concentrations (10 micromol/L) of both compounds inhibited mainly sodium-independent taurocholate uptake, whereas higher concentrations (100 micromol/L) also inhibited sodium-dependent taurocholate uptake. In Xenopus laevis oocytes expressing the Na(+)/taurocholate cotransporting polypeptide (Ntcp), high Rifamycin SV and rifampicin concentrations were required for inhibition of taurocholate uptake. In contrast, sodium-independent taurocholate uptake mediated by the organic anion transporting polypeptides, Oatp1 and Oatp2, was already substantially inhibited by 10 micromol/L Rifamycin SV. Rifampicin potently inhibited Oatp2-mediated taurocholate uptake, but did not interfere with Oatp1-mediated taurocholate uptake. Similar effects of Rifamycin SV and rifampicin were found for Oatp1- and Oatp2-mediated estradiol-17beta-glucuronide transport. Dixon plot analysis yielded a pattern compatible with competitive inhibition of estradiol-17beta-glucuronide transport with K(i) estimates of 6.6 micromol/L and 7.3 micromol/L for Rifamycin SV-induced inhibition of Oatp1 and Oatp2, respectively, and of 1.4 micromol/L for rifampicin-induced inhibition of Oatp2. These results demonstrate that Rifamycin SV and rifampicin exhibit differential inhibition on Oatp1 and Oatp2, and identify rifampicin as a selective Oatp2 inhibitor. The data indicate that these inhibitors can be used to determine the in vivo relevance of Oatp1 and Oatp2 for the overall bioavailability and disposition of drugs and other Oatp1/2 substrates.