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Rifabutin

Product Name
Rifabutin
CAS No.
72559-06-9
Chemical Name
Rifabutin
Synonyms
lm427;RIFABUTIN;Mycobutin;Rifabatin;Ansamycin;Ansatipine;RIFABUTINE;72559-06-9;Rifabutin-d7;Rifabutin CRS
CBNumber
CB0702764
Molecular Formula
C46H62N4O11
Formula Weight
847
MOL File
72559-06-9.mol
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Rifabutin Property

Melting point:
169-171°C
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
DMSO: >5mg/mL
form 
powder
Water Solubility 
0.19g/L(temperature not stated)
InChIKey
ATEBXHFBFRCZMA-VXTBVIBXSA-N
CAS DataBase Reference
72559-06-9
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Safety

WGK Germany 
3
RTECS 
VJ6700000
HS Code 
2941906000
Hazardous Substances Data
72559-06-9(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
R3530
Product name
Rifabutin
Purity
>98% (HPLC), powder
Packaging
5mg
Price
$94.3
Updated
2021/03/22
Sigma-Aldrich
Product number
Y0000149
Product name
Rifabutin
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/03/22
Sigma-Aldrich
Product number
PHR2611
Product name
Rifabutin
Packaging
100MG
Price
$199
Updated
2021/03/22
Sigma-Aldrich
Product number
1603800
Product name
Rifabutin
Packaging
50mg
Price
$366
Updated
2021/03/22
TCI Chemical
Product number
R0211
Product name
Rifabutin
Purity
>98.0%(HPLC)
Packaging
100mg
Price
$120
Updated
2021/03/22
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Rifabutin Chemical Properties,Usage,Production

Description

Rifabutin, a rifamycin antibacterial derivative, is the first agent approved and introduced for the prevention of Mycobacterium avium complex (MAC) in AIDS patients. It is also indicated in combination chemotherapy for the prophylaxis and treatment of MAC infections in HIV positive patients and for newly diagnosed and chronic tuberculosis.

Chemical Properties

Red-Brown Powder

Originator

Archifar (Italy)

Uses

Semisynthetic derivative of Rifamycin S that inhibits nucleic acid synthesis. An antibacterial (tuberculostatic).

Uses

Antibiotic;RNA-polymerase inhibitor

Uses

Rifamycins are antibiotics that inhibit DNA-dependent RNA polymerases and are usually bactericidal against Gram-positive bacteria but bacteriostatic against Gram-negative bacteria. Rifamycins are also effective against Mycobacterium species, including M. tuberculosis. Rifabutin is a broad-spectrum rifamycin antibiotic that has applications against tuberculosis, H. pylori, M. avium complex, Chlamydia, and other bacteria. It is also useful in co-infections with human immunodeficiency virus, including tuberculosis.

Indications

Rifabutin (Mycobutin), an antibiotic related to rifampin, shares its mechanism of action, that is, inhibition of RNA polymerase. Rifabutin has significant activity in vitro and in vivo against M. avium-intracellular complex (MAC) isolates from both HIV-infected and non–HIV-infected individuals. It has better activity against MAC organisms than rifampin. Rifabutin is active against M. tuberculosis, including some rifampinresistant strains, such as M.leprae and M.fortuitum. It has a spectrum of activity against gram-positive and gramnegative organisms similar to that of rifampin. The molecular basis for resistance to rifabutin is shared by both rifampin and rifabutin; this explains the virtually complete cross-resistance that occurs between these drugs.

brand name

Mycobutin (Pharmacia & Upjohn).

Antimicrobial activity

The activity is similar to that of rifampicin, but it is more active against the Mycobacterium avium complex (MIC 0.01–2 mg/L) and several other atypical mycobacteria. It inhibits the replication of human immunodeficiency virus 1 (HIV-1) in concentrations (10 mg/L) that are not toxic to lymphoid cells, but no efficacy on HIV infections has been demonstrated.

Acquired resistance

The frequency of spontaneously resistant mutants in several bacterial species, including M. tuberculosis, M. leprae, Staphylococcus aureus and Chlamydia trachomatis, is somewhat lower than with rifampicin.

Pharmaceutical Applications

Rifabutine; ansamycin. Molecular weight: 847.02.
A semisynthetic spiropiperidyl derivative of rifamycin S, available for oral administration. It is slightly soluble in water and soluble in organic solvents.

Pharmacokinetics

Oral absorption:12–20%
Cmax 300 mg oral :0.38 mg/L after 3.3 h
Plasma half-life:16 h
Volume of distribution:9.3 L/kg
Plasma protein binding: 85%
absorption and distribution
Oral absorption is rapid but incomplete, with considerable interpatient variation. It is well distributed, concentrations in many organs being higher than that in plasma. The average concentration in lungs is 6.5 times the simultaneous plasma concentration.
Metabolism and excretion
Rifabutin is mainly metabolized to the active desacetyl derivative, although several other oxidation products have been detected in urine, where some 10% of the dose is eliminated. About 30–50% of the dose can be recovered from the feces. Elimination from plasma is biphasic, with a terminal half-life of 45 h. The drug is a weak inducer of hepatic enzymes. The rate of metabolism increases, and the plasma area under the concentration–time curve (AUC) declines as the treatment continues.

Pharmacology

Rifabutin is well absorbed orally, and peak plasma concentrations are reached in 2 to 3 hours. Because of its lipophilicity, rifabutin achieves a 5- to 10-fold higher concentration in tissues than in plasma. The drug has a half-life range of 16 to 96 hours and is eliminated in urine and bile.
Rifabutin appears as effective as rifampin in the treatment of drug-susceptible tuberculosis and is used in the treatment of latent tuberculosis infection either alone or in combination with pyrazinamide. Clinical use of rifabutin has increased in recent years, especially in the treatment of HIV infection. It is a less potent inducer of cytochrome 450 enzymes pathways than rifampin and results in less drug interaction with the protease inhibitors and nonnucleoside reverse transcriptase inhibitors. Rifabutin is therefore commonly substituted for rifampin in the treatment of tuberculosis in HIV-infected patients. Another important use of rifabutin in the HIV-infected population is prevention and treatment of disseminated MAC.

Clinical Use

Prevention of infections with M. avium complex in AIDS patients
Treatment of non-tuberculous mycobacterial disease (in combination with other agents)
Rifabutin in combination with other agents has been proposed as a rescue therapy after Helicobacter pylori treatment failures.Although some efficacy has been observed in the treatment of tuberculosis, its use for this condition is not recommended.

Clinical Use

Rifabutin, the spiroimidazopiperidyl derivative of rifamycin B was approved in the United States for the prophylaxis of disseminated MAC in AIDS patients on the strength of clinical trials establishing its effectiveness. The activity of rifabutin against MAC organisms greatly exceeds that of rifamycin. This rifamycin derivative is not effective, however, as monotherapy for existing disseminated MAC disease. Rifabutin is a very lipophilic compound with a high affinity for tissues. Its elimination is distribution limited, with a half-life averaging 45 hours (range, 16 69 hours). Approximately 50% of an orally administered dose of rifabutin is absorbed, but the absolute oral bioavailability is only about 20%. Extensive first-pass metabolism and significant biliary excretion of the drug occur, with about 35% and 53% of the orally administered dose excreted, largely as metabolites, in the feces and urine, respectively. Despite its greater potency against M. tuberculosis in vitro, rifabutin is considered inferior to rifampin for the short-term therapy of tuberculosis because of its significantly lower plasma concentrations.
Although rifabutin is believed to cause less hepatotoxicityand induction of cytochrome P450 enzymes than rifampin,these properties should be borne in mind when the drug is usedprophylactically. Rifabutin and its metabolites are highly coloredcompounds that can discolor skin, urine, tears, feces, etc.

Side effects

Rash (4% of patients), gastrointestinal intolerance (3%) and neutropenia (2%) are fairly common and may require discontinuation of treatment. Uveitis and general arthralgia are rare with a 300 mg dosage, but frequent with higher dosages, especially with concomitant use of fluconazole or macrolide antibiotics.

Side effects

The adverse effects that most frequently result in discontinuation of rifabutin include GI intolerance, rash, and neutropenia. Rifabutin levels will be increased with concurrent administration of fluconazole and clarithromycin, resulting in anterior uveitis, polymyalgia syndrome, and a yellowish-tan discoloration of the skin (pseudojaundice). Other adverse reactions are similar to those of rifampin, such as hepatitis, red-orange discoloration of body fluids, and drug interactions due to effects on the hepatic P450 cytochrome enzyme system.

Rifabutin Preparation Products And Raw materials

Raw materials

Preparation Products

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Rifabutin Suppliers

Sichuan Mingxin Pharmaceutical Co., Ltd.
Tel
--
Fax
--
Email
service@scmx.cn
Country
China
ProdList
10
Advantage
58
Hubei Nordina Biotechnology Co., Ltd.
Tel
181-6268-7200
Fax
18162687220
Email
nuodinashengwu@163.com
Country
China
ProdList
628
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5948
Advantage
61
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
9917
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
1938
Advantage
70
Nanjing Chemlin Chemical Co., Ltd
Tel
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
20007
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32358
Advantage
50
XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-2580635- ;0712-2580635
Email
1791901229@qq.com;1791901229@qq.com;
Country
China
ProdList
8934
Advantage
52
China Langchem Inc.
Tel
021-58956006- ;021-58950017-
Fax
021-58956100
Email
sales@langchem.com;sales3@langchem.com
Country
China
ProdList
417
Advantage
57
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View Lastest Price from Rifabutin manufacturers

Baoji Guokang Healthchem co.,ltd
Product
Rifabutin 72559-06-9
Price
US $127.00/g
Min. Order
10g
Purity
99%
Supply Ability
1T
Release date
2021-06-03
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Rifabutin 72559-06-9
Price
US $0.00/Kg/Bag
Min. Order
1g
Purity
95%-102%
Supply Ability
100kgs
Release date
2021-09-29
Shaanxi Dideu Medichem Co. Ltd
Product
Rifabutin 72559-06-9
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-07

72559-06-9, RifabutinRelated Search:


  • 4-Deoxw3,4-[2-spiro(N-isobutyl-4-pipendyl)]-(1H)-imidazo-(2,5-dihydro)rifamycin S
  • 4-N-ISOBUTYLSPIROPIPERIDYLRIFAMYCIN S
  • RIFABUTIN
  • RIFABUTINE
  • 1,4-dihydro-1-deoxy-1’,4-didehydro-5’-(2-methylpropyl)-1-oxo-rifamycinxi
  • (9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-6,16,18,20-Tetrahydroxy-1'-isobutyl-14-methoxy-7,9,15,17,19,21,25-hepta-methyl-spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo-[2',3':7,8]-naphth[1,2-d]imidazol-2,4'-piperidin]-5,10,26-(3H,9H)-trione
  • Ansatipine
  • Mycobutin
  • (9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-6-16,18,20-Tetrahydroxy-1'-isobutyl-14-methoxy-7,9,15,17,19,21,25-heptamethylspiro(9,4-(epoxypentadeca(1,11,13)trienimino)-2H-furo(2',3':7,8)naphth(1,2-d)imidazole-2,4'-piperidine)-5,10,26(3H,9H)-trione,16-acetate
  • 4-Deoxo-3,4-(2-spiro(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo)-rifamycin S
  • Rifamycin XIV, 1,4-dihydro-1-deoxy-1',4-didehydro-5'-(2-methylpropyl)-1-oxo
  • 1',4-Didehydro-1-deoxy-1,4-dihydro-5'-(2-methylpropyl)-1-oxorifamycin XIV
  • Rifabatin
  • Ansamycin (Rifabutin)
  • Rifabutin (50 mg)
  • Collagen proline hydroxylase inhycobutin
  • Rifabutin-d7
  • (9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-16-(acetyloxy)-6,18,20-trihydroxy-14-methoxy-7,9,15,17,19,21,25-heptamethyl-1'-(2-methylpropyl)-spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2',3':7,8]naphth[1,2-d]imidazole-2,4'-piperidine]-5,10,26(3H,9H)-trione
  • 1,4-dihydro-1-deoxy-1’,4-didehydro-5’-(2-methylpropyl)-1-oxorifamycinxiv
  • 1’,4-Didehydro-1-deoxy-1,4-dihydro-5’-(2-methylpropyl)-1-oxo-
  • 4-deoxo-3,4-(2-spiro(n-isobutyl-4-piperidyl)-2,5-dihydro-1h-imidazo)-rifamyc
  • Ansamycin
  • antibioticlm427
  • lm427
  • Ansatipine (Farmitalia)
  • Mycobutin (Farmitalia)
  • 72559-06-9
  • RIFABUTINE(LM-427、ANSAMYCIN、ANSATIPIN、ANSMYCIN、MYCOBUTIN):4-N-ISOBUTYLSPIROPIPERIDYLRIFAMYCIN S
  • Rifamycin XIV, Ansamycin,
  • Rifabutin (Ansamycin)
  • (9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-16-(acetyloxy)-6,18,20-trihydroxy-14-methoxy-7,9,15,17,19,21,25-heptamethyl-1'-(2-methylpropyl)-spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2',3':7,8]naphth[1,2-d]imidaz
  • MYCOBUTIN; ANSAMYCIN; LM 427; ANSATIPINE
  • Rifabutin (Mycobutin)
  • Rifabutin CRS
  • Spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2',3':7,8]naphth[1,2-d]imidazole-2,4'-piperidine]-5,10,26(3H,9H)-trione,16-(acetyloxy)-6,18,20-trihydroxy-14-methoxy-7,9,15,17,19,21,25-heptamethyl-1'-(2-methylpropyl)-,[9S-(9R*,12E,14R*,15S*,16R*,17S*
  • Rifabutin USP/EP/BP
  • Rifabutin Impurity
  • 72559-06-9
  • C46H62N4O11
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Mycobutin
  • API
  • Chiral Reagents
  • Heterocycles
  • Active Pharmaceutical Ingredients