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13292-46-1

Basic Information
CAS No.: 13292-46-1
Name: Rifampicin
Molecular Structure:
Molecular Structure of 13292-46-1 (Rifampicin)
Formula: C43H58N4O12
Molecular Weight: 822.95 .
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: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38-36/38
Safety: 26-36-37/39
Transport Information:
PSA: 220.15000
LogP: 4.34920
Synthetic route
6928-85-4

N-amino-N'-methylpiperazine

N-tert-1,3-oxazine(5,6-c)rifamycin

13292-46-1

rifampicin

Conditions
ConditionsYield
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;
6928-85-4

N-amino-N'-methylpiperazine

(PhCH2)(p-(rifamycin SV-3-yl-CH=NNHCH2)C6H4CH2)N-PEGA 1900 resin

(PhCH2)(p-(rifamycin SV-3-yl-CH=NNHCH2)C6H4CH2)N-PEGA 1900 resin

13292-46-1

rifampicin

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 20℃; for 24h;18 mg
123-75-1

pyrrolidine

6928-85-4

N-amino-N'-methylpiperazine

di(isobutoxymethyl)-methylamine

13292-46-1

rifampicin

Conditions
ConditionsYield
With acetic acid In water; dimethyl sulfoxide; acetone
Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With nitrogen; oxalic acid In N-methyl-acetamide; dichloromethane
oxalic acid In ISOPROPYLAMIDE
Conditions
ConditionsYield
With oxalic acid; paraformaldehyde In N-methyl-acetamide

A

3-(1-ethyl-3-piperidyl)-1,3-oxazino (5,6-c) rifamycin

3-(1-ethyl-3-piperidyl)-1,3-oxazino (5,6-c) rifamycin

B

13292-46-1

rifampicin

Conditions
ConditionsYield
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
ConditionsYield
In N-methyl-acetamide
With paraformaldehyde In dimethyl sulfoxide

C59H66Cl4N5O16Pol

A

C17H9Cl4F3NO4Pol

B

13292-46-1

rifampicin

Conditions
ConditionsYield
With trifluoroacetic acid polystyrene ((aminomethyl)polystyrene); Product distribution / selectivity;

C77H112N4O15

A

C34H56O4

B

13292-46-1

rifampicin

Conditions
ConditionsYield
With water In tetrahydrofuran; aq. phosphate buffer at 4℃; for 192h; pH=7.4; Temperature; Reagent/catalyst;
13292-46-1

rifampicin

13292-22-3

3-formylrifamycin SV

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; water at 20℃; for 96h;88.9%

C54H64N16O24S4(4-)*4Na(1+)

13292-46-1

rifampicin

C43H58N4O12*C54H64N16O24S4(4-)*4Na(1+)

Conditions
ConditionsYield
for 0.5h; Time;66.7%
1033757-04-8

5-bromo(2-nitroso)pyridine

13292-46-1

rifampicin

C48H59BrN6O13

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h;25%
13292-46-1

rifampicin

rifampicin quinone

Conditions
ConditionsYield
With dihydrogen peroxide; horseradish peroxidase In phosphate buffer at 25℃; pH=5.4; Kinetics; Further Variations:; Reagents; concentrations;
13292-46-1

rifampicin

7585-39-9

β‐cyclodextrin

rifampicin β-cyclodextrin complex

Conditions
ConditionsYield
In water at 37℃; for 48h; Darkness;
107-21-1

ethylene glycol

13292-46-1

rifampicin

2.9C2H6O2*C43H58N4O12*2.8H2O

Conditions
ConditionsYield
With water In acetone at 4 - 20℃; for 168h;
13292-46-1

rifampicin

1408300-70-8

C46H58N2O12

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
3: sodium cyanoborohydride / dichloromethane; ethanol / 0.02 h / 20 °C
View Scheme
13292-46-1

rifampicin

1408300-71-9

C46H57FN2O12

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
3: sodium cyanoborohydride / dichloromethane; ethanol / 0.02 h / 20 °C
View Scheme
13292-46-1

rifampicin

1408300-72-0

C46H57FN2O12

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
3: sodium cyanoborohydride / dichloromethane; ethanol / 0.02 h / 20 °C
View Scheme
13292-46-1

rifampicin

1408300-73-1

C46H57FN2O12

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
3: sodium cyanoborohydride / dichloromethane; ethanol / 0.02 h / 20 °C
View Scheme
13292-46-1

rifampicin

55686-24-3

C45H54N2O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
View Scheme
13292-46-1

rifampicin

63624-40-8

3-(benzylamino-methyl)-rifamycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
3: sodium cyanoborohydride / dichloromethane; ethanol / 0.02 h / 20 °C
View Scheme
13292-46-1

rifampicin

C45H53FN2O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
View Scheme
13292-46-1

rifampicin

C45H53FN2O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
View Scheme
13292-46-1

rifampicin

C45H53FN2O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
View Scheme
13292-46-1

rifampicin

C45H53ClN2O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
View Scheme
13292-46-1

rifampicin

C45H53ClN2O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
View Scheme
13292-46-1

rifampicin

C45H53ClN2O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
View Scheme
13292-46-1

rifampicin

C46H56N2O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; diethyl ether / 96 h / 20 °C
2: hydrogenchloride / dichloromethane; ethanol / 0.5 h / 45 °C
View Scheme
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13292-22-3
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    Product name: Rifampicin (Rifampin) CAS No. 13292-46-1 Chemical name: 3-{[(4-Methyl-1-piperazinyl)imino]-methyl}rifamycin Molecular formula: C43H5

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    Rifampicin Basic information Product Name: Rifampicin Synonyms: ,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,1///;2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2-h)-dione,

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    Rifampicin CAS NO 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.