CAS 13929-35-6

Rifamycin B

Description:

Rifamycin B is a complex antibiotic belonging to the rifamycin class, primarily known for its efficacy against bacterial infections, particularly those caused by Mycobacterium tuberculosis. It is produced by the fermentation of the bacterium Amycolatopsis rifamycinica. The compound exhibits a distinctive red-orange color and is characterized by its large, polycyclic structure, which includes a naphthalenic core and a sugar moiety. Rifamycin B functions by inhibiting bacterial RNA synthesis, specifically targeting DNA-dependent RNA polymerase, which disrupts the transcription process in susceptible bacteria. This mechanism of action makes it a valuable therapeutic agent in treating tuberculosis and other mycobacterial infections. Additionally, it has been studied for its potential use in treating other bacterial infections and has shown activity against certain Gram-positive bacteria. However, its clinical use is often limited by the development of resistance and the availability of more effective derivatives, such as rifampicin. Overall, Rifamycin B remains an important compound in the field of antimicrobial therapy.

Formula: C₃₉H₄₉NO₁₄

InChI: InChI=1S/C39H49NO14/c1-17-11-10-12-18(2)38(49)40-24-15-26(51-16-27(42)43)28-29(34(24)47)33(46)22(6)36-30(28)37(48)39(8,54-36)52-14-13-25(50-9)19(3)35(53-23(7)41)21(5)32(45)20(4)31(17)44/h10-15,17,19-21,25,31-32,35,44-47H,16H2,1-9H3,(H,40,49)(H,42,43)/b11-10-,14-13-,18-12+/t17-,19+,20+,21+,25-,31-,32+,35+,39-/m0/s1

InChI key: InChIKey=SQTCRTQCPJICLD-WFCYQMJWSA-N

SMILES: O(CC(O)=O)C1=C2C3=C4O[C@@](C)(C3=O)O/C=C\[C@H](OC)[C@@H](C)[C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C/C=C(\C)/C(=O)NC(C(O)=C2C(O)=C4C)=C1

Synonyms:

• 2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan, rifamycin deriv.
• 4-O-(Carboxymethyl)rifamycin
• Acetic acid, [(1,2-dihydro-5,6,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-9-yl)oxy]-, 21-acetate
• NSC 145604
• Nancimycin
• Rifamycin, 4-O-(carboxymethyl)-
• Rifomycin B
• {[(14E,24E)-21-(acetyloxy)-5,6,17,19-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-9-yl]oxy}acetic acid
• {[(24E)-21-(acetyloxy)-5,6,17,19-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-9-yl]oxy}acetic acid
• {[(2S,16S,17S,18R,19R,20S,21S,22S,23S)-21-(acetyloxy)-5,6,17,19-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-9-yl]oxy}acetic acid

RIFAMYCIN B CRS

CAS: 13929-35-6

RIFAMYCIN B CRS

Formula: C₃₉H₄₉NO₁₄

Molecular weight: 755.8047

Ref: 41-R0900000

Rifamycin, 4-O-(carboxymethyl)-

CAS: 13929-35-6

Formula: C₃₉H₄₉NO₁₄

Purity: 95%

Color and Shape: Solid

Molecular weight: 755.8047

Ref: IN-DA001AP7

Rifaximin EP Impurity B (Rifamycin B)

CAS: 13929-35-6

Formula: C₃₉H₄₉NO₁₄

Molecular weight: 755.81

Ref: 4Z-R-3511

Rifamycin B

Controlled Product

CAS: 13929-35-6

Impurity Rifaximin EP Impurity B
Stability Unstable in solution
Applications Rifamycin B (Rifaximin EP Impurity B) is a Rifamycin (R508200) derivative as antibacterial agent.
References Cellai, L., et al.: Eur. J. Med. Chem., 24, 105 (1989), Bartolucci, C., et al.: Pharm. Pharmacol. Lett., 3, 1 (1993), Lounis, N., et al.: Curr. Pharm. Des., 10, 3229 (2004),

Formula: C₃₉H₄₉NO₁₄

Color and Shape: Yellow-Orange

Molecular weight: 755.8

Ref: TR-R508170

Rifaximin EP Impurity B

CAS: 13929-35-6

Formula: C₃₉H₄₉NO₁₄

Molecular weight: 755.8

Ref: ST-EA-CP-R42007

Rifamycin B

CAS: 13929-35-6

Rifamycin B is a rifamycin antibiotic that inhibits the bacterial enzyme DNA-dependent RNA polymerase. It is used to treat infectious diseases, such as tuberculosis and staphylococcal infections. Rifamycin B has been shown to be active against methicillin-resistant Staphylococcus aureus (MRSA) and penicillin-resistant Streptococcus pneumoniae. The process optimization of rifamycin B was performed by reacting the compound with inorganic acid, p-hydroxybenzoic acid, and metal hydroxides in order to improve its antimicrobial activity profile. Rifamycin B has also been shown to be an effective agent against resistant mutants of bacteria through surface methodology experiments.

Formula: C₃₉H₄₉NO₁₄

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 755.8 g/mol

Ref: 3D-FR178810