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Rifamycin S (NSC144130; NSC 144130; NSC-144130) is a DNA-dependent RNA polymerase and an impurity of Rifaximin. Rifaximin (L-105SV; BRN-3584528; Normix; Rifacol; Fatroximin; Rifaxidin; Rifaxin; Ritacol; RCIFAX, Rifagut, Xifaxan, Zaxine) is an orally bioavailable and semi-synthetic RNA synthesis inhibitor used to treat traveler's diarrhea caused by certain bacteria.
| ln Vitro |
Rifamycin SV limits bacterial growth due to the redox cycle of intracellular rifamycin SV that generates reactive oxygen species. Aerobic oxidation of rifamycin SV to rifamycin S is stimulated by metal ions such as Mn2+, Cu2+ and Co2+. The most effective metal ion is Mn2+[2].
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|---|---|
| ln Vivo |
Subsequential granules of rat liver produce hydroxyl radicals when NADH and rifamycin S are present. Compound I, or NADH dehydrogenase, is the primary enzyme responsible for reducing rifamycin S. When compared to NADPH, NADH is nearly as effective as rifamycin S at catalyzing the interaction of these antibiotics with rat liver microsomes. Fe(II) readily reduces rifamycin S to its equivalent hydroquinone, rifamycin SV. A discernible Fe(II)-(rifamycin S)3 complex is formed by rifamycin S. It is possible to fully prevent Fe:ATP-induced lipid peroxidation with rifamycin S. When iron complexes are present, rifamycin S can interact with rat liver microsomes to cause them to go through a redox cycle and then produce hydroxyl radicals [1].
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| References |
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| Additional Infomation |
Rifamycin S is an organic molecular entity.
Rifamycin S has been reported in Amycolatopsis mediterranei and Streptomyces hygroscopicus with data available. |
| Molecular Formula |
C37H45NO12
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|---|---|
| Molecular Weight |
695.762
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| Exact Mass |
695.294
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| CAS # |
13553-79-2
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| PubChem CID |
6436726
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| Appearance |
Light yellow to orange solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
917.4±65.0 °C at 760 mmHg
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| Melting Point |
179-181ºC (dec.)
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| Flash Point |
508.6±34.3 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
|
| Index of Refraction |
1.605
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| LogP |
2.87
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| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
12
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
50
|
| Complexity |
1480
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| Defined Atom Stereocenter Count |
9
|
| SMILES |
C[C@H]1/C=C/C=C(\C(=O)NC2=CC(=O)C3=C(C2=O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)/C
|
| InChi Key |
BTVYFIMKUHNOBZ-ODRIEIDWSA-N
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| InChi Code |
InChI=1S/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
|
| Chemical Name |
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate
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| Synonyms |
NSC-144130 NSC 144130 Rifamycin S
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~143.73 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (3.59 mM) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4373 mL | 7.1864 mL | 14.3728 mL | |
| 5 mM | 0.2875 mL | 1.4373 mL | 2.8746 mL | |
| 10 mM | 0.1437 mL | 0.7186 mL | 1.4373 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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