CAS 72559-06-9|Rifabutin
| Common Name | Rifabutin | ||
|---|---|---|---|
| CAS Number | 72559-06-9 | Molecular Weight | 847.005 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 969.6±65.0 °C at 760 mmHg |
| Molecular Formula | C46H62N4O11 | Melting Point | 169-171ºC |
| MSDS | ChineseUSA | Flash Point | 540.2±34.3 °C |
Names
| Name | Rifabutin |
|---|---|
| Synonym | More Synonyms |
Rifabutin BiologicalActivity
| Description | Rifabutin (Ansamycin) is a semisynthetic ansamycin antibiotic with potent antimycobacterial properties. |
|---|---|
| Related Catalog | Signaling Pathways >>Anti-infection >>BacterialResearch Areas >>Infection |
| 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. |
Chemical & Physical Properties
| 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
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
Safety Information
| 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 |
Customs
| HS Code | 2941903000 |
|---|
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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 |
