RIFAMPIN

PRODUCT IDENTIFICATION

CAS NO. 13292-46-1

RIFAMPIN

EINECS NO. 236-312-0
FORMULA C43H58N4O12
MOL WT. 822.95

H.S. CODE

3003.20

TOXICITY

 
SYNONYMS Rifampicin; Rifaldazine; Tubocin;
Rimycin; (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-1,2-Dihydro-5,6,9,17,19- pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-(4-methylpiperazin- 1-yliminomethyl)-1,11-dioxo-2,7- (epoxypentadeca[1,11,13]-trienimino)naphtho[2,1-b] furan-21-yl acetate; Rimactan; 3-(((4-Methyl-1-piperazinyl)imino)-methyl) rifamycin; Sinerdol;

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

Orange to red-brown crystalline powder

MELTING POINT

183 - 188 C (Decomposes)

BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER

slightly soluble

pH 4.5 - 6.5
VAPOR DENSITY  

AUTOIGNITION

 

NFPA RATINGS

 

REFRACTIVE INDEX

 

FLASH POINT

 

STABILITY Stable under ordinary conditions

GENERAL DESCRIPTION AND APPLICATIONS

Rifamycin: a family of antibiotics divided into naphthalenic ansamycins. Ansamycins are natural compounds characterized by a macrocyclic structure consisting of an aromatic ring system connected to an aliphatic chain that forms an amide linkage to the amino group of the aromatic moiety. 3-Amino-5-hydroxybenzoic acid (AHBA) is the start unit for the biosynthesis of ansamycins. Based on the structure of the AHBA derived aromatic moiety, this family of compounds can be further subdivided into a benzenic and a naphthalenic sub-group. Geldanamycins, ansatrienins, and ansamitocins are the benzenic ansamycins, which have been isolated from actinomycetes or higher plants. They are mainly cytotoxic agents against eukaryotes. the naphthalenic ansamycins, such as naphthomycins, streptovaricins, rifamycins, and tolypomycins, represent antibacterial activity against gram-positive cocci, some gram-negative bacilli, and Mycobacterium tuberculosis and certain other mycobacterial infections. Rifamycins are biosynthesized by fermentation, and its biosynthesis involves the assembly of a polyketide by addition of acetate and propionate chain extension units to a unique start unit, AHBA. Further downstream processing of the initially generated polyketide, proansamycin X, leads to the various chemically modified rifamycins isolated from the fermentation. Rifamycins are used for the treatment of tuberculosis, leprosy, gonorrhea, and biliary tract and respiratory infections. They have been described as having in vitro activity against Helicobacter pylori. The five components are designated A, B, C, D, and E; rifamycin O, S, and SV are derivatives of the B component, and AG and X are derivatives of the O component. Rifampicin is the international nonproprietary name for rifampin which is derived from rifamycin SV; red-brown crystalline powder slightly soluble in water at neutral pH, freely soluble in chloroform, soluble in ethyl acetate and in methanol. The chemical designation is 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,20,22- heptamethyl-8- [N-(4-methyl-1- piperazinyl) formimidoyl]-2,7 - (epoxypentadeca [1,11,13]trienimino) naphtho [2,1- b ] furan-1,11(2H)-dione 21-acetate. Rifampicin acts by inhibiting the formation of DNA-dependent RNA polymerase in susceptible organisms by binding its beta subunit, thereby preventing the formation of messenger RNA (mRNA) and the subsequent translation to proteins. Other rifamycins include followings:
  • Rifabutin: a semisynthetic antibiotic derivative from rifamycin S, used for the prevention of disseminated Mycobacterium avium complex or tuberculosis; administered orally.
  • Rifamide: a derivative of rifamycin B; used in the treatment of respiratory infections due to gram-positive cocci and in biliary tract infections due to gram-negative and gram-positive organisms.
  • Rifapentine: similar antibiotic to rifampin but has a longer half-life than rifampin.
SALES SPECIFICATION

APPEARANCE

Orange to red-brown crystalline powder

ASSAY

97.0 - 103.0%

RIFAMPIN QUINONE

1.5% max

INDIVIDUAL IMPURITY

1.0% max

TOTAL IMPURITY

3.0% max

HEAVY METALS

10ppm max

SULFATED ASH

0.1% max

LOSS ON DRYING

1.0% max

pH 4.5 - 6.5
TRANSPORTATION
PACKING
 
HAZARD CLASS  
UN NO.  
OTHER INFORMATION
Hazard Symbols: XN, Risk Phrases: 22-36/37/38, Safety Phrases: 26-36
PRICE INFORMATION
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