Rifamycin S
(Synonyms: 利福霉素S) 目录号 : GC39239
Rifamycin S, a quinone and an antibiotic against Gram-positive bacteria (including MRSA), is a clinical drug used to treat tuberculosis and leprosy. Rifamycin S generates reactive oxygen species (ROS) and inhibits microsomal lipid peroxidation.
Cas No.:13553-79-2
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 S, a quinone and an antibiotic against Gram-positive bacteria (including MRSA), is a clinical drug used to treat tuberculosis and leprosy. Rifamycin S generates reactive oxygen species (ROS) and inhibits microsomal lipid peroxidation.
[1] Huiqin Huang, et al. Antonie Van Leeuwenhoek. 2009 Feb;95(2):143-8. [2] D N Rao, A I Cederbaum. Free Radic Biol Med. 1997;22(3):439-46.
| Cas No. | 13553-79-2 | SDF | |
| 别名 | 利福霉素S | ||
| Canonical SMILES | O=C1C2=C(C(C=C3NC(/C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@H]4C)=O)=O)C(C3=O)=C(O)C(C)=C2O[C@@]1(O/C=C/[C@@H]([C@H]([C@@]4([H])OC(C)=O)C)OC)C | ||
| 分子式 | C37H45NO12 | 分子量 | 695.75 |
| 溶解度 | DMSO: 250 mg/mL (359.32 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 | 1.4373 mL | 7.1865 mL | 14.373 mL |
| 5 mM | 0.2875 mL | 1.4373 mL | 2.8746 mL |
| 10 mM | 0.1437 mL | 0.7186 mL | 1.4373 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。
Stability of Non-Ionic Surfactant Vesicles Loaded with Rifamycin S
Pharmaceutics 2022 Nov 28;14(12):2626.PMID:36559121DOI:10.3390/pharmaceutics14122626.
These days, the eradication of bacterial infections is more difficult due to the mechanism of resistance that bacteria have developed towards traditional antibiotics. One of the medical strategies used against bacteria is the therapy with drug delivery systems. Non-ionic vesicles are nanomaterials with good characteristics for encapsulating drugs, due to their bioavailability and biodegradability, which allow the drugs to reach the specific target and reduce their side effects. In this work, the antibiotic Rifamycin S was encapsulated. The rifamycin antibiotics family has been widely used against Mycobacterium tuberculosis, but recent studies have also shown that Rifamycin S and rifampicin derivatives have bactericidal activity against Staphylococcus epidermidis and Staphylococcus aureus. In this work, a strain of S. aureus was selected to study the antimicrobial activity through Minimum Inhibitory Concentration (MIC) assay. Three formulations of niosomes were prepared using the thin film hydration method by varying the composition of the aqueous phase, which included MilliQ water, glycerol solution, or PEG400 solution. Niosomes with a Rifamycin S concentration of 0.13 μg/g were satisfactorily prepared. Nanovesicles with larger size and higher encapsulation efficiency (EE) were obtained when using glycerol and PEG400 in the aqueous media. Our results showed that niosomes consisting of an aqueous glycerol solution have higher stability and EE across a diversity of temperatures and pHs, and a lower MIC of Rifamycin S against S. aureus.
Study on Dissolution Thermodynamics and Cooling Crystallization of Rifamycin S
ACS Omega 2021 Jan 25;6(5):3752-3762.PMID:33585754DOI:10.1021/acsomega.0c05337.
The solubility data of Rifamycin S were measured in isopropanol, butyl acetate, and their mixed solvents across the temperature range of 283.15-323.15 K by the gravimetric method. The results demonstrate that the solubility of Rifamycin S increases with the increasing temperature in the two pure solvents, and in the mixed solvents, it increases first and then decreases with increasing butyl acetate content. The experimental data of Rifamycin S in the mixed solvents were better correlated using the modified Apelblat equation and ideal model equation. Furthermore, the relevant thermodynamic parameters of the dissolution process were determined based on the van't Hoff equation. The obtained dissolution enthalpy and Gibbs free energy are positive in all cases, which indicate that the dissolving process of Rifamycin S is endothermic and nonspontaneous. The supersolubility data of Rifamycin S were measured by the laser and thermal analytic method. The results demonstrate that the width of the metastable zone of Rifamycin S becomes larger with decreasing cooling rate and increasing butyl acetate content. Furthermore, the crystallization process of Rifamycin S was optimized on the basis of thermodynamic research. The results showed that when V butyl acetate:V mixed solvent was 0.04, the cooling rate was 0.1 K/min, the stirring rate was 150 rpm, the final crystallization temperature was 283.15 K, and the aging time was 8 h, the purity of Rifamycin S crystals could reach 98.5%, and the crystalline yield was 89.6%. After crystallization optimization, the size of Rifamycin S crystals increased, and the dissolution in water was improved.
Rifabutin (ansamycin LM 427): a new rifamycin-S derivative for the treatment of mycobacterial diseases
Rev Infect Dis 1987 May-Jun;9(3):519-30.PMID:3037676DOI:10.1093/clinids/9.3.519.
Rifabutin (ansamycin LM 427), a semisynthetic spiropiperidyl derivative of Rifamycin S, shows good in vitro activity against most mycobacterial species, including Mycobacterium avium complex. In animal models, the drug is more active against both Mycobacterium tuberculosis and Mycobacterium leprae than in rifampin, and studies indicate that rifabutin is active against some rifampin-resistant strains of both species. The drug has a long half-life (16 hr) in humans and a marked tissue tropism, with tissue levels five- to 10-fold higher than that in the serum. In animals rifabutin is no more toxic than rifampin. A large experience from the compassionate use of rifabutin for life-threatening mycobacterial infections in humans, most commonly disseminated M. avium complex disease in patients with AIDS, has also indicated relative drug safety. Although some data suggest that rifabutin is effective, firm conclusions about drug efficacy await results from controlled clinical trials.
Rifamycin S and its geometric isomer produced by a newly found actinomycete, Micromonospora rifamycinica
Antonie Van Leeuwenhoek 2009 Feb;95(2):143-8.PMID:19125348DOI:10.1007/s10482-008-9297-0.
Strain AM105 was separated from mangrove sediment in the South China Sea in this research. The morphological and genomic data showed that the strain merits description as a novel species, proposed as Micromonospora rifamycinica. From the acetate ethyl extract of its fermentation broth, two antibiotics against Gram-positive bacteria (including MRSA), Rifamycin S and its geometric isomer were isolated. Their structures were elucidated on the basis of spectroscopic analyzes. (1)H and (13)C NMR data of the isomer of Rifamycin S were first described in this paper.
Oxygen Enhancement of bactericidal activity of rifamycin SV on Escherichia coli and aerobic oxidation of rifamycin SV to Rifamycin S catalyzed by manganous ions: the role of superoxide
J Biochem 1982 Jan;91(1):381-95.PMID:6279585DOI:10.1093/oxfordjournals.jbchem.a133698.
Oxygen enhanced the bactericidal activity of rifamycin SV to Escherichia coli K12. Anaerobically grown cells, which had a low level of superoxide dismutase, were more susceptible to the bactericidal activity than aerobically grown cells, which contained a high level of superoxide dismutase. Oxygen also enhanced the inhibition of RNA polymerase activity of rifamycin SV, when Mn2+ was used as a cofactor. Rifamycin S was reduced to rifamycin SV by NADPH catalyzed by cell-free extracts of Escherichia coli K12. These results indicate that the inhibition of bacterial growth by rifamycin SV is due to the production of active species of oxygen resulting from the oxidation-reduction cycle of rifamycin SV in the cells. The aerobic oxidation of rifamycin SV to Rifamycin S was induced by metal ions, such as Mn2+, Cu2+, and Co2+. The most effective metal ion was Mn2+. In the presence of Mn2+, accompanying the consumption of 1 mol of oxygen and the oxidation of 1 mol of rifamycin SV, 1 mol of hydrogen peroxide and 1 mol of Rifamycin S were formed. Superoxide was generated during the autoxidation of rifamycin SV. Superoxide dismutase inhibited the formation of Rifamycin S, but scavengers for hydrogen peroxide and the hydroxyl radical did not affect the oxidation. A mechanism of Mn2+-catalyzed oxidation of rifamycin SV is proposed and its relation to bactericidal activity is discussed.