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72559-06-9

72559-06-9 structure
72559-06-9 structure
  • Name: Rifabutin
  • Chemical Name: Rifabutin
  • CAS Number: 72559-06-9
  • Molecular Formula: C46H62N4O11
  • Molecular Weight: 847.005
  • Catalog: API Antibiotics Rifamycin
  • Create Date: 2018-05-15 08:00:00
  • Modify Date: 2024-01-02 19:26:48
  • Rifabutin (Ansamycin) is a semisynthetic ansamycin antibiotic with potent antimycobacterial properties.
Name Rifabutin
Synonyms Rifabutin
4-deoxo-3,4-[2-spiro(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo]-rifamicin S
Ansamycin
RIFABUTINE
Mycobutin
lm427
Rifabatin
antibioticlm427
1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin
Ansatipine
6,9-dihydro-5,17,19,21-tetrahydroxy-8,9-[2-spiro-(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo]-23-methoxy-2,4,12,16,18,20,22-heptamethyl-6-oxo-2,7-epoxypentadeca-[1,11,13]-trienimine-2H-furo[2',3',7,8]nafto[1,2-d]imidazolo-2,4'-piperidine-5,10,26. (3H,9H)-trione-16-acetate
Description Rifabutin (Ansamycin) is a semisynthetic ansamycin antibiotic with potent antimycobacterial properties.
Related Catalog
Target

Antibacterial

In Vitro Rifabutin is primarily bactericidal antibiotic drug used to treat tuberculosis. Its effect on bacteria is based on the DNA-dependent RNA polymerase blocking drug rifamycin S., a semi-synthetic derivative. It is effective, for example, in highly resistant mycobacteria, Gram-positive bacteria (and some are effective against Gram-negative bacteria), but also against Mycobacterium tuberculosis, M. leprae, and M. avium intracellulare.Rifabutin is an antibiotic; antitumor. Rifabutin interferes with HSP-90 molecular chaperone, enhances ubiquitination and protein degradation, and inactivates bacterial RNA polymerase.
References

[1]. Review Article: Rifabutin in the Treatment of Refractory Helicobacter pylori Infection J. P. Gisbert, X. Calvet Issue Alimentary Pharmacology & Therapeutics Volume 35, Issue 2, pages 209-221, January 2012

[2]. Vourvahis M, Davis J, Wang R, Layton G, Choo HW, Chong CL, Tawadrous M.Effect of rifampin and rifabutin on the pharmacokinetics of lersivirine and effect of lersivirine on the pharmacokinetics of rifabutin and 25-o-desacetyl-rifabutin in healthy subjects.Antimicrob Agents Chemother. 2012 Aug;56(8):4303-9.

[3]. Gisbert JP, Castro-Fernandez M, Perez-Aisa A, Cosme A, Molina-Infante J, Rodrigo L, Modolell I, Cabriada JL, Gisbert JL, Lamas E, Marcos E, Calvet X.Fourth-line rescue therapy with rifabutin in patients with three Helicobacter pylori eradication failures.Aliment Pharmacol Ther. 2012 Apr;35(8):941-7. doi: 10.1111/j.1365-2036.2012.05053.x.

[4]. Gisbert JP, Calvet X.Review article: rifabutin in the treatment of refractory Helicobacter pylori infection.Aliment Pharmacol Ther. 2012 Jan;35(2):209-21. doi: 10.1111/j.1365-2036.2011.04937.x.

[5]. Horne DJ, Spitters C, Narita M.Experience with rifabutin replacing rifampin in the treatment of tuberculosis.Int J Tuberc Lung Dis. 2011 Nov;15(11):1485-9, i.
Density 1.3±0.1 g/cm3
Boiling Point 969.6±65.0 °C at 760 mmHg
Melting Point 169-171ºC
Molecular Formula C46H62N4O11
Molecular Weight 847.005
Flash Point 540.2±34.3 °C
Exact Mass 846.441528
PSA 205.55000
LogP 3.45
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.623
Storage condition Amber Vial, -20°C Freezer, Under Inert Atmosphere
Water Solubility DMSO: >5mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VJ6700000
CHEMICAL NAME :
Rifamycin XIV, 1,4-dihydro-1-deoxy-1',4-didehydro-5'-(2-methylpropyl )-1-oxo-
CAS REGISTRY NUMBER :
72559-06-9
LAST UPDATED :
199709
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C46-H62-N4-O11
MOLECULAR WEIGHT :
847.12

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
60 mg/kg/14D-I
TOXIC EFFECTS :
Blood - agranulocytosis
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 348,685,1996
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
84 mg/kg/14D-I
TOXIC EFFECTS :
Blood - agranulocytosis
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 348,685,1996
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
51 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3322 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
266 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
9100 mg/kg/13W-C
TOXIC EFFECTS :
Liver - other changes Kidney, Ureter, Bladder - other changes Blood - changes in spleen
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
29120 mg/kg/1Y-I
TOXIC EFFECTS :
Blood - normocytic anemia Endocrine - changes in spleen weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
47 mg/kg/1Y-C
TOXIC EFFECTS :
Blood - normocytic anemia Blood - changes in spleen Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 47,1,1995
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR NONH for all modes of transport
RTECS VJ6700000
HS Code 2941903000
HS Code 2941903000

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