CAS 13553-79-2: Rifamycin S
Description:Rifamycin S is a natural antibiotic belonging to the rifamycin class, primarily derived from the bacterium Amycolatopsis rifamycinica. It is characterized by its complex macrocyclic structure, which includes a naphthalenic core and a characteristic rifamycin chromophore. This compound exhibits potent antibacterial activity, particularly against Mycobacterium tuberculosis, making it significant in the treatment of tuberculosis and other bacterial infections. Rifamycin S functions by inhibiting bacterial RNA synthesis through binding to the DNA-dependent RNA polymerase, thereby preventing transcription. The substance is typically administered in its derivative forms, such as rifampicin, which enhances its pharmacological properties. In addition to its antimicrobial efficacy, Rifamycin S has a relatively low toxicity profile, although it can cause side effects such as liver enzyme elevation and hypersensitivity reactions in some patients. Its solubility characteristics vary, influencing its formulation and delivery methods in clinical settings. Overall, Rifamycin S is a crucial compound in the field of antimicrobial therapy, particularly for resistant bacterial strains.
Formula:C37H45NO12
InChI:InChI=1/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
InChI key:InChIKey=BTVYFIMKUHNOBZ-ODRIEIDWSA-N
SMILES:O=C1C=C2NC(=O)C(=CC=CC(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C(C)C(OC)C=COC3(OC4=C(C3=O)C1=C(C2=O)C(O)=C4C)C)C
- Synonyms:
- (14E,24E)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate
- (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate
- 1,4-Dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
- 1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin
- 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
- 2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan, rifamycin deriv.
- 5,17,19-Trihydroxy-23-Methoxy-2,4,12,16,18,20,22-Heptamethyl-1,6,9,11-Tetraoxo-1,2,6,9-Tetrahydro-2,7-(Epoxypentadeca[1,11,13]Trienoimino)Naphtho[2,1-B]Furan-21-Yl Acetate
- Brn 0604802
- Nci 144-130
- Nsc 144130
- See more synonyms
- Rifamycin, 1,4-dideoxy-1,4-dihydro-1,4-dioxo-
- Rifomycin S
- Unii-Pi53N820Jv