CAS No.13292-46-1,Rifampicin Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	13292-46-1
Name:	Rifampicin
Article Data:	14

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

Synthetic route

: 6928-85-4
N-amino-N'-methylpiperazine

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

: 13292-46-1
rifampicin

Conditions

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;

: 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

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃; for 24h;	18 mg

: 123-75-1
pyrrolidine

: 6928-85-4
N-amino-N'-methylpiperazine

: di(isobutoxymethyl)-methylamine

: 62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2
rifamycin S

: 13292-46-1
rifampicin

Conditions

Conditions	Yield
With acetic acid In water; dimethyl sulfoxide; acetone

...Expand

: 123-75-1
pyrrolidine

: 64-19-7
acetic acid

: 62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2
rifamycin S

: 13292-46-1
rifampicin

Conditions

Conditions	Yield
In N-methyl-acetamide; water

...Expand

: 6928-85-4
N-amino-N'-methylpiperazine

: 62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2
rifamycin S

: 10560-39-1
1,3,5-tri-tert-butyl-1,3,5-triazacyclohexane

: 13292-46-1
rifampicin

Conditions

Conditions	Yield
With acetic acid In N-methyl-acetamide

...Expand

: 6928-85-4
N-amino-N'-methylpiperazine

: 70935-97-6
1,3,5-tris[2-(morpholin-4-yl)ethyl][1,3,5]triazinane

: 62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2
rifamycin S

: 13292-46-1
rifampicin

Conditions

Conditions	Yield
With nitrogen; oxalic acid In N-methyl-acetamide; dichloromethane
oxalic acid In ISOPROPYLAMIDE

...Expand

: 62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2
rifamycin S

: 13292-46-1
rifampicin

Conditions

Conditions	Yield
With oxalic acid; paraformaldehyde In N-methyl-acetamide

: 62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2
rifamycin S

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

Conditions	Yield
With oxalic acid; paraformaldehyde In N-methyl-acetamide

: 62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2
rifamycin S

: 10560-39-1
1,3,5-tri-tert-butyl-1,3,5-triazacyclohexane

: 13292-46-1
rifampicin

Conditions

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

: C59H66Cl4N5O16Pol

A: C17H9Cl4F3NO4Pol

B: 13292-46-1
rifampicin

Conditions

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

Raw Materials

64-19-7

10560-39-1

70935-97-6

6928-85-4

123-75-1

Downstream Products

13292-22-3

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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: Harmful Xn, Irritant 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.