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CAS 6998-60-3

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Rifamycin

Description:
Rifamycin is a complex antibiotic belonging to the rifamycin class, primarily known for its efficacy against bacterial infections, particularly those caused by Mycobacterium tuberculosis, the causative agent of tuberculosis. It is characterized by its large macrocyclic structure, which includes a naphthalenic core and a characteristic rifamycin chromophore. The compound functions by inhibiting bacterial RNA synthesis through binding to the DNA-dependent RNA polymerase, thereby preventing transcription. Rifamycin exhibits broad-spectrum antibacterial activity and is often used in combination therapies to prevent the development of resistance. It is lipophilic, allowing it to penetrate bacterial cell membranes effectively. Additionally, rifamycin is metabolized in the liver and has a relatively short half-life, necessitating careful dosing regimens. Its use is associated with potential side effects, including hepatotoxicity and interactions with other medications due to its influence on liver enzymes. Overall, rifamycin remains a critical agent in the treatment of tuberculosis and other bacterial infections, highlighting its importance in modern medicine.
Formula:C37H47NO12
InChI:InChI=1/C37H47NO12/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/h10-16,18-20,25,29-30,33,40-44H,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=HJYYPODYNSCCOU-ODRIEIDWSA-N
SMILES:O=C1C=2C=3C4=C(O)C(=CC3O)NC(=O)\C(\C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2C(C)=C4O
Synonyms:
  • (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-21-(Acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione
  • 2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan, rifamycin deriv.
  • 2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione, 21-(acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-
  • 2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,11(2H)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate
  • Nsc 133100
  • Rifamicina
  • Rifamicine SV
  • Rifampin SV
  • Rifamycin SV
  • Rifamycin SV MMX
  • See more synonyms
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