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MedKoo Cat#: 330103 | Name: Rifamycin S
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rifamycin S is a potent inhibitor of DNA-dependent RNA polymerase.

Chemical Structure

Rifamycin S
Rifamycin S
CAS#13553-79-2

Theoretical Analysis

MedKoo Cat#: 330103

Name: Rifamycin S

CAS#: 13553-79-2

Chemical Formula: C37H45NO12

Exact Mass: 695.2942

Molecular Weight: 695.76

Elemental Analysis: C, 63.87; H, 6.52; N, 2.01; O, 27.59

Price and Availability

Size Price Availability Quantity
1g USD 450.00
2g USD 750.00
5g USD 1,250.00
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Related CAS #
No Data
Synonym
Rifamycin S; NSC 144130; NSC-144130; NSC144130; NCI 144-130.
IUPAC/Chemical Name
2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,6,9,11(2H)-tetrone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate
InChi Key
BTVYFIMKUHNOBZ-URFUDWCHSA-N
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
SMILES Code
N1C(C(=CC=C[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H](OC)C=CO[C@@]2(C(c3c4C(C=C1C(c4c(O)c(c3O2)C)=O)=O)=O)C)C)OC(C)=O)C)O)C)O)C)C)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
The rifamycins are a group of antibiotics that are synthesized either naturally by the bacterium Amycolatopsis rifamycinica or artificially. They are a subclass of the larger family of ansamycins. Rifamycins are particularly effective against mycobacteria, and are therefore used to treat tuberculosis, leprosy, and mycobacterium avium complex (MAC) infections. The rifamycin group includes the "classic" rifamycin drugs as well as the rifamycin derivatives rifampicin (or rifampin), rifabutin, rifapentine, rifalazil and rifaximin.

Preparing Stock Solutions

The following data is based on the product molecular weight 695.76 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Chen M, Roush WR. Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S. J Org Chem. 2013 Jan 4;78(1):3-8. doi: 10.1021/jo3008226. Epub 2012 Jun 15. PubMed PMID: 22703288; PubMed Central PMCID: PMC3465507. 2: Jin Y, Gill SK, Kirchhoff PD, Wan B, Franzblau SG, Garcia GA, Showalter HD. Synthesis and structure-activity relationships of novel substituted 8-amino, 8-thio, and 1,8-pyrazole congeners of antitubercular rifamycin S and rifampin. Bioorg Med Chem Lett. 2011 Oct 15;21(20):6094-9. doi: 10.1016/j.bmcl.2011.08.054. Epub 2011 Aug 19. PubMed PMID: 21903392. 3: Huang H, Wu X, Yi S, Zhou Z, Zhu J, Fang Z, Yue J, Bao S. Rifamycin S and its geometric isomer produced by a newly found actinomycete, Micromonospora rifamycinica. Antonie Van Leeuwenhoek. 2009 Feb;95(2):143-8. doi: 10.1007/s10482-008-9297-0. Epub 2009 Jan 6. PubMed PMID: 19125348. 4: Turks M, Huang X, Vogel P. Expeditious asymmetric synthesis of a stereoheptad corresponding to the C(19)-C(27)-ansa chain of rifamycins: formal total synthesis of Rifamycin S. Chemistry. 2005 Jan 7;11(2):465-76. PubMed PMID: 15551311. 5: BouzBouz S, Cossy J. Efficient strategy for the synthesis of stereopentad subunits of scytophycin, rifamycin S, and discodermolide. Org Lett. 2001 Dec 13;3(25):3995-8. PubMed PMID: 11735568. 6: Hunt KW, Grieco PA. Oxabicyclo[3.2.1]octenes in organic synthesis--direct ring opening of oxabicyclo[3.2.1] systems employing silyl ketene acetals in concentrated solutions of lithium perchlorate-diethyl ether: application to the synthesis of the C(19)-C(27) fragment of rifamycin S. Org Lett. 2001 Feb 8;3(3):481-4. PubMed PMID: 11428044. 7: Chênevert R, Rose YS. Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S. J Org Chem. 2000 Mar 24;65(6):1707-9. PubMed PMID: 10750492. 8: Spisani S, Traniello S, Onori AM, Rizzuti O, Martuccio C, Cellai L. 3-(Carboxyalkylthio) rifamycin S and SV derivatives inhibit human neutrophil functions. Inflammation. 1998 Oct;22(5):459-69. PubMed PMID: 9793793. 9: Rao DN, Cederbaum AI. A comparative study of the redox-cycling of a quinone (rifamycin S) and a quinonimine (rifabutin) antibiotic by rat liver microsomes. Free Radic Biol Med. 1997;22(3):439-46. PubMed PMID: 8981035. 10: Bartolucci C, Cellai L, Marzano M, Segre A, Brufani M, Filocamo L, Bianco AD, Guiso M, Brizzi V, Benedetto A, et al. Structure-activity relationships in open ansa-chain rifamycin S derivatives as inhibitors of HIV-1 reverse transcriptase. Farmaco. 1995 Sep;50(9):587-93. PubMed PMID: 7495468. 11: Arora SK, Arjunan P. Molecular structure and conformation of rifamycin S, a potent inhibitor of DNA-dependent RNA polymerase. J Antibiot (Tokyo). 1992 Mar;45(3):428-31. PubMed PMID: 1577671. 12: O'Brien RJ, Lyle MA, Snider DE Jr. 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. Review. PubMed PMID: 3037676. 13: Brufani M, Cellai L, Cozzella L, Federici M, Guiso M, Segre A. Chemical modifications of the aliphatic bridge of ansamycins. 3. Synthesis and activity of 21-epi-rifamycin S. J Antibiot (Tokyo). 1985 Oct;38(10):1359-62. PubMed PMID: 4066489. 14: Arora SK. Correlation of structure and activity in ansamycins: structure, conformation, and interactions of antibiotic rifamycin S. J Med Chem. 1985 Aug;28(8):1099-102. PubMed PMID: 4020831. 15: Taguchi M, Tsukamoto G. Chemical modification of the amide group of rifamycin S. Chem Pharm Bull (Tokyo). 1985 May;33(5):2133-6. PubMed PMID: 4053236. 16: Brufani M, Cellai L, Cerrini S, Fedeli W, Marchi E, Segre A, Vaciago A. X-ray crystal structure of 4-deoxy-3'-bromopyrido[1',2'-1,2]imidazo[5,4-c]rifamycin S. J Antibiot (Tokyo). 1984 Dec;37(12):1623-7. PubMed PMID: 6549316. 17: Marsili L, Franceschi G, Galliani C, Sanfilippo A, Vigevani A. New rifamycins. II. Synthesis and biological activity of oximes, hydrazones, and semicarbazones of 3-N-(piperidin-4-one)rifamycin S. Farmaco Sci. 1982 Dec;37(12):781-6. PubMed PMID: 7152013. 18: Kono Y. Aerobic oxidation of rifamycin SV to rifamycin S catalyzed by horseradish peroxidase. J Biochem. 1982 May;91(5):1789-94. PubMed PMID: 7096316. 19: Brufani M, Cellai L, Cerrini S, Fedeli W, Segre A, Vaciago A. Structure-activity relationships in the ansamycins. Molecular structure and activity of 3-carbomethoxy rifamycin S. Mol Pharmacol. 1982 Mar;21(2):394-9. PubMed PMID: 7048060. 20: Ghisalba O, Roos R, Schupp T, Nüesch J. Transformation of rifamycin S into rifamycins B and L. A revision of the current biosynthetic hypothesis. J Antibiot (Tokyo). 1982 Jan;35(1):74-80. PubMed PMID: 7200089.

View History

Peptide 399

Peptide 399

Mon 0856

Mon 0856

Perflisopent

Perflisopent

Perafensine

Perafensine

Perazine fendizoate

Perazine fendizoate