Rifampicin , 97% , 13292-46-1

Synonym(s):
Rifampicin;Rifampin;microtubes;polypropylene tubes;Rifampin, 3-(4-Methylpiperazinyliminomethyl)rifamycin SV

CAS NO.：13292-46-1

Empirical Formula: C43H58N4O12

Molecular Weight: 822.94

MDL number: MFCD00151389

EINECS: 236-312-0

PRODUCT Properties

• Melting point: 183°C (dec.)
• Boiling point: 761.02°C (rough estimate)
• Density: 1.1782 (rough estimate)
• refractive index: 1.6000 (estimate)
• storage temp.: 2-8°C
• solubility: chloroform: soluble50mg/mL, clear
• pka: 1.7, 7.9(at 25℃)
• form: crystalline
• color: faint red to very dark red
• Water Solubility: Soluble in DMSO or methanolSoluble in water, ethyl acetate, chloroform, methanol, tetrahydrofuran and dimethyl sulfoxide.
• Merck: 14,8216
• BRN: 5723476
• BCS Class: 2
• Stability: Hygroscopic, Light Sensitive

Description and Uses

Rifampicin is a semisynthetic derivative of rifamicin B, a macrolactam antibiotic and one of more than five antibiotics from a mixture of rifamicins A, B, C, D, and E, which is called a rifamicin complex, which is produced by actinomycetes Streptomyces mediteranei (Nocardia mediteranei). It was introduced into medical practice in 1968. Synthesis of rifampicin begins with an aqueous solution of rifamicin, which under the reaction conditions is oxidized to a new derivative of rifamicin S (32.7.4), with the intermediate formation of rifamicin O (32.7.3). Reducing the quinone structure of this product with hydrogen using a palladium on carbon catalyst gives rifamicin SV (32.7.5). The resulting product undergoes aminomethylation by a mixture of formaldehyde and pyrrolidine, giving 3-pyrrolidinomethylrifamicin SV (32.7.6). Oxidizing the resulting product with lead tetracetate to an enamine and subsequent hydrolysis with an aqueous solution of ascorbic acid gives 3-formylrifamicin SV (32.7.7). Reacting this with 1-amino-4-methylpiperazine gives the desired rifampicin (32.7.8).

Rifampicin is used to treat Tuberculosis and Tuberculosis-related mycobacterial infections. It is widely used as an antipruritic agent in the autoimmune cholestatic liver disease, primary biliary cirrhosis (PBC). It has been shown to cause hepatitis.

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H302-H315-H319-H335-H362
• Precautionary statements: P260-P263-P301+P312-P302+P352-P305+P351+P338-P308+P313
• Hazard Codes: Xn,Xi
• Risk Statements: 22-36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: VJ7000000
• F: 8-10-21
• HS Code: 29419000
• Toxicity: LD50 in mice, rats (mg/kg): 885, 1720 orally; 260, 330 i.v.; 640, 550 i.p. (Fürész)