3-formyl Rifamycin
目录号 : GC42272
3-formyl Rifamycin is an intermediate of rifampicin that has been used to develop several rifamycin derivatives with antibiotic activity that targets RNA synthesis.
Cas No.:13292-22-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-formyl Rifamycin is an intermediate of rifampicin that has been used to develop several rifamycin derivatives with antibiotic activity that targets RNA synthesis.
| Cas No. | 13292-22-3 | SDF | |
| Canonical SMILES | O=C1C2=C(C3=C(C(C)=C2O[C@]1(C)O/C=C/[C@H](OC)[C@@H](C)[C@]4(OC(C)=O)[H])O)C(O)=C(C(NC(/C(C)=C\C=C\[C@@H]([C@@H]([C@H]([C@@H](O)[C@H]4C)C)O)C)=O)=C3O)C=O | ||
| 分子式 | C38H47NO13 | 分子量 | 725.8 |
| 溶解度 | DMSO : 62.5 mg/mL (86.11 mM; Need ultrasonic) | 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 | 1.3778 mL | 6.889 mL | 13.7779 mL |
| 5 mM | 0.2756 mL | 1.3778 mL | 2.7556 mL |
| 10 mM | 0.1378 mL | 0.6889 mL | 1.3778 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 rifampicin in dissolution medium in presence of isoniazid
Int J Pharm 1999 Nov 10;190(1):109-23.PMID:10528103DOI:10.1016/s0378-5173(99)00286-0.
Rifampicin (RIF) hydrolyzes in acidic medium to form insoluble and poorly absorbed 3-formyl Rifamycin SV (3-FRSV). This study describes development of two principally different methods, Dual Wavelength UV-Vis. spectrophotometry (DW spectrophotometry) and HPTLC, to determine 3-FRSV in presence of RIF. Using DW spectrophotometry, RIF was estimated by using wavelengths 475.0 and 507.0 nm and 3-FRSV was estimated using 457.0 and 492.0 nm. In HPTLC method, a mixture of chloroform:methanol:water (80:20:2.5 v/v) was used as the mobile phase to resolve 3-FRSV from RIF and 3-FRSV was quantified at 333 nm. The linearity range for 3-FRSV was 2-10 microg/ml and 50-250 ng/spot for DW spectrophotometric method and HPTLC method, respectively, and 5-50 microg/ml for RIF using DW spectrophotometric method. Both the methods were found to be specific, accurate and reproducible. The proposed methods were successfully applied to determine the rate of degradation of RIF to 3-FRSV in dissolution medium (0.1 N HCl) and also in presence of isoniazid (INH). The rate of degradation of RIF in presence of INH was almost two times more than that of RIF alone. These methods were utilized to study the stability of RIF in market formulations of RIF and RIF with INH in dissolution medium. It has been observed that RIF degrades by 12.4% to form 3-FRSV (RIF formulations) while in presence of INH the degradation is catalyzed to about 21.5% (RIF+INH formulations), in 45 min. Thus, lower concentration of RIF may be available for absorption leading to poor bioavailability of RIF from combination dosage forms (RIF+INH) as compared to formulations containing only RIF. It is proposed that specific analytical method should be used to measure RIF in presence of 3-FRSV in a dissolution study.
Effect of rifampicin derivatives on the ion compartmentation of biological membranes
J Antibiot (Tokyo) 1977 Jun;30(6):494-9.PMID:885810DOI:10.7164/antibiotics.30.494.
Based on the experimental results that 3-formyl Rifamycin SV acts as an uncoupler in vitro on rat liver mitochondria, the effect of some rifampicin derivatives on the K+ and H+ compartmentation of biological membranes was examined to obtain a chemiosmotic hypothesis for oxidative phosphorylation. The K+ release from mitochondria was remarkably stimulated by 3-formyl Rifamycin SV in accordance with uncoupling of the oxidative phosphorylation. 3-formyl Rifamycin SV also stimulated the K+ release from red blood cells, though its action was not as effective as in mitochondria. It can be suggested that 3-formyl Rifamycin SV interacts with biological membranes, causing a change in permeability to ions, especially of K+ and H+ through the mitochondrial membrane, resulting in uncoupling of the oxidative phosphorylation.
Improved Stability of Rifampicin in the Presence of Gastric-Resistant Isoniazid Microspheres in Acidic Media
Pharmaceutics 2020 Mar 5;12(3):234.PMID:32151053DOI:10.3390/pharmaceutics12030234.
The degradation of rifampicin (RIF) in an acidic medium to form 3-formyl Rifamycin SV, a poorly absorbed compound, is accelerated in the presence of isoniazid, contributing to the poor bioavailability of rifampicin. This manuscript presents a novel approach in which isoniazid is formulated into gastric-resistant sustained-release microspheres and RIF into microporous floating sustained-release microspheres to reduce the potential for interaction between RIF and isoniazid (INH) in an acidic environment. Hydroxypropyl methylcellulose acetate succinate and Eudragit® L100 polymers were used for the manufacture of isoniazid-loaded gastric-resistant sustained-release microspheres using an o/o solvent emulsification evaporation approach. Microporous floating sustained-release microspheres for the delivery of rifampicin in the stomach were manufactured using emulsification and a diffusion/evaporation process. The design of experiments was used to evaluate the impact of input variables on predefined responses or quality attributes of the microspheres. The percent degradation of rifampicin following 12 h dissolution testing in 0.1 M HCl pH 1.2 in the presence of isoniazid gastric-resistant sustained-release microspheres was only 4.44%. These results indicate that the degradation of rifampicin in the presence of isoniazid in acidic media can be reduced by encapsulation of both active pharmaceutical ingredients to ensure release in different segments of the gastrointestinal tract, potentially improving the bioavailability of rifampicin.
Similar effect of rifampin and other rifamycin derivatives on vaccinia virus morphogenesis
J Virol 1971 Aug;8(2):225-31.PMID:4107245DOI:10.1128/JVI.8.2.225-231.1971.
Membrane-limited structures, resembling virus envelope precursors previously shown to form during the interruption of poxvirus assembly by rifampin, were now observed by electron microscopy in vaccinia-infected HeLa cells treated with a series of rifamycin derivatives. The active compounds N-demethyl rifampin, AF/DMI, and 3-formyl Rifamycin SV lacked, respectively, a methyl group, the piperazine ring, and the hydrazone portion of rifampin. A vaccinia mutant selected only for resistance to rifampin was also resistant to the effect on morphogenesis produced by all of the rifamycin derivatives. We concluded that this antiviral effect was specific and was a property associated with the macrocyclic ring rather than the hydrazone-containing side chain of rifampin. In addition to their effects on vaccinia morphogenesis, 3-formyl Rifamycin SV and AF/DMI had unusual cytotoxic effects.
Inhibition of poxvirus maturation by rifamycin derivatives and related compounds
J Virol 1971 Jun;7(6):821-9.PMID:4105118DOI:10.1128/JVI.7.6.821-829.1971.
The effect of a number of rifamycin derivatives and related compounds on the reversibility of the rifampin-induced virus maturation block was studied by using BHK-21 cells infected with vaccinia virus. All of the derivatives of 3-formyl Rifamycin SV maintained this block, the required concentration varying from 100 to 1,000 mug/ml. These compounds vary only in the nature of the side-chain attached to the 3C atom on the naphthohydroquinone moiety; no obvious correlation between the nature of this side-chain and antiviral activity was found. Streptovaricin complex and tolypomycin R also maintained the maturation block; tolypomycin also produced marked alterations in the appearance of the viroplasm contained in rifampin-induced inclusions and immature virus particles.