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Rifampicin (13292-46-1)

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Chemistry

Empirical Formula: C43H58N4O12
Molecular Weight: 822.9402 
Index of Refraction: 1.613
Density: 1.345 g/cm3
Flash Point: 561.253 °C
Enthalpy of Vaporization: 153.544 kJ/mol
Boiling Point: 1004.42 °C at 760 mmHg
Melting point: 183°C (dec.)
Storage tempreture: 2-8 °C
Appearance: Red to orange crystalline solid
Structure of Rifampicin (CAS NO.13292-46-1):
                    
Product Category of Rifampicin (CAS NO.13292-46-1): Antibiotics;Antitubercular;Antibiotics for Research and Experimental Use;Biochemistry;Antibiotic Explorer;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labeled Compounds;Peptide Synthesis/Antibiotics

History

In 1957, a sample of soil coming from a pine wood on the French Riviera was brought for analysis to the Lepetit Pharmaceuticals research lab in Milan, Italy. There, a research group headed by Prof. Piero Sensi (1920-) discovered a new bacterium. This new species appeared immediately of great scientific interest since it was producing a new class of molecules with antibiotic activity. Rifampicin was introduced in 1967, as a major addition to the cocktail-drug treatment of tuberculosis and inactive meningitis, along with isoniazid, ethambutol, pyrazinamide and streptomycin. Because Prof. Sensi and some of his fellow researchers were particularly fond of the French crime story Rififi (about a jewel heist and rival gangs), they decided to call these compounds "Rifamycins". After two years of attempts in order to obtain more stable semi-synthetic products, in 1959 a new molecule with high efficacy and good tolerability was produced and was named "Rifampicin".

Uses

 Rifampicin(13292-46-1) is used to treat tuberculosis and infections, and should be used in combination with other antibiotics. In combination with fusidic acid, it is used in prophylactic therapy against Neisseria meningitidis (meningococcal) infection.

Toxicity Data With Reference
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 639mg/kg (639mg/kg)   Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970.
human TDLo oral 180mg/kg (180mg/kg) SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE
SENSE ORGANS AND SPECIAL SENSES: IRITIS: EYE
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 British Medical Journal. Vol. 2, Pg. 1189, 1977.
man LDLo oral 857mg/kg (857mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING
GASTROINTESTINAL: OTHER CHANGES
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 JAMA, Journal of the American Medical Association. Vol. 240, Pg. 2283, 1978.
man TDLo oral 13mg/kg/2D (13mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE British Medical Journal. Vol. 1, Pg. 199, 1976.
man TDLo oral 814mg/kg/15W- (814mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
KIDNEY, URETER, AND BLADDER: HEMATURIA		 American Journal of Kidney Diseases. Vol. 32, Pg. 533, 1998.
mouse LD50 intraperitoneal 416mg/kg (416mg/kg)   Chemotherapia. Vol. 12, Pg. 155, 1967.
mouse LD50 intravenous 260mg/kg (260mg/kg)   Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970.
mouse LD50 oral 500mg/kg (500mg/kg)   Comptes Rendus des Seances de l'Academie des Sciences, Serie D: Sciences Naturelles. Vol. 269, Pg. 2147, 1969.
mouse LD50 subcutaneous 621mg/kg (621mg/kg)   Japanese Journal of Antibiotics. Vol. 23, Pg. 242, 1970.
rabbit LD50 oral 2120mg/kg (2120mg/kg)   Antibiotica et Chemotherapia Vol. 16, Pg. 316, 1970.
rat LD50 intraperitoneal 511mg/kg (511mg/kg)   Japanese Journal of Antibiotics. Vol. 23, Pg. 257, 1970.
rat LD50 oral 1570mg/kg (1570mg/kg)   Japanese Journal of Antibiotics. Vol. 23, Pg. 257, 1970.
rat LD50 subcutaneous 534mg/kg (534mg/kg)   Japanese Journal of Antibiotics. Vol. 23, Pg. 242, 1970.
women TDLo oral 315mg/kg/5W-I (315mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Journal of the American Academy of Dermatology. Vol. 17, Pg. 303, 1987.
women TDLo oral 504mg/kg/42D- (504mg/kg) BEHAVIORAL: MUSCLE WEAKNESS
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
BLOOD: APLASTIC ANEMIA		 American Journal of Medicine. Vol. 87, Pg. 459, 1989.
women TDLo oral 744mg/kg/9W-I (744mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"		 American Journal of Kidney Diseases. Vol. 31, Pg. 108, 1998.
Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-36/38
 R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R36/38:Irritating to eyes and skin.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.

Specification

 Rifampicin , its cas register number is 13292-46-1. It also can be called Rifampin ; Rimactane ; Rifadin ; Rimactan ; and 3-[[(4-methyl-1-piperazinyl)imino]methyl]-rifamycin . It is a bactericidal antibiotic drug of the rifamycin group, and is a semisynthetic compound derived from Amycolatopsis rifamycinica. There are various types of rifamycins from which this is derived, but this particular form is by far the most clinically effective. It inhibits DNA-dependent RNA polymerase in bacterial cells by binding its beta-subunit, thus preventing transcription to RNA and subsequent translation to proteins.

Basic information

  • Product Name:

    Rifampicin

  • CAS No:13292-46-1
  • Formula:C43H58N4O12
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