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| CAS No.: | 13292-46-1 |
|---|---|
| Name: | Rifampicin |
| Molecular Structure: | |
|
|
|
| Formula: | C43H58N4O12 |
| Molecular Weight: | 822.953 |
| Synonyms: | 3-[[(4-methyl-1-piperazinyl)imino]methyl]-rifamycin;3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV;5,6,9,17,19,21-Hexahydroxy-23-methoxy-2,4,12,16,18,20,22-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;8-(4-Methylpiperazinyliminomethyl) rifamycin SV; |
| EINECS: | 236-312-0 |
| Density: | 1.34 g/cm3 |
| Melting Point: | 183°C (dec.) |
| Boiling Point: | 1004.42 °C at 760 mmHg |
| Flash Point: | 561.253 °C |
| Solubility: | Soluble in DMSO or methanolSoluble in water, ethyl acetate, chloroform, methanol, tetrahydrofuran and dimethyl sulfoxide. |
| Appearance: | Red to orange crystalline solid |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 22-36/37/38-36/38 |
| Safety: | 26-36-37/39 |
| PSA: | 220.15000 |
| LogP: | 4.34920 |
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| Conditions | Yield |
|---|---|
| With acetic acid In butan-1-ol at 70℃; for 2h; Temperature; Solvent; Large scale; | 97.87% |
| In water; N,N-dimethyl-formamide at 75℃; for 0.333333h; Temperature; Time; | 92% |
| In N,N-dimethyl-formamide at 80℃; for 0.333333h; Concentration; |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In tetrahydrofuran at 20℃; for 24h; | 18 mg |
| Conditions | Yield |
|---|---|
| With acetic acid In water; dimethyl sulfoxide; acetone |
| Conditions | Yield |
|---|---|
| In N-methyl-acetamide; water |
- 6928-85-4
N-amino-N'-methylpiperazine
- 10560-39-1
1,3,5-tri-tert-butyl-1,3,5-triazacyclohexane
- 13292-46-1
rifampicin
| Conditions | Yield |
|---|---|
| With acetic acid In N-methyl-acetamide |
- 6928-85-4
N-amino-N'-methylpiperazine
- 70935-97-6
1,3,5-tris[2-(morpholin-4-yl)ethyl][1,3,5]triazinane
- 13292-46-1
rifampicin
| Conditions | Yield |
|---|---|
| With nitrogen; oxalic acid In N-methyl-acetamide; dichloromethane | |
| oxalic acid In ISOPROPYLAMIDE |
- 13292-46-1
rifampicin
| Conditions | Yield |
|---|---|
| With oxalic acid; paraformaldehyde In N-methyl-acetamide |
B
- 13292-46-1
rifampicin
| Conditions | Yield |
|---|---|
| With oxalic acid; paraformaldehyde In N-methyl-acetamide |
- 10560-39-1
1,3,5-tri-tert-butyl-1,3,5-triazacyclohexane
- 13292-46-1
rifampicin
| Conditions | Yield |
|---|---|
| In N-methyl-acetamide | |
| With paraformaldehyde In dimethyl sulfoxide |
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid polystyrene ((aminomethyl)polystyrene); Product distribution / selectivity; |
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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: 
Xn,
Xi
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.