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72559-06-9

Basic Information
CAS No.: 72559-06-9
Name: Rifabutin
Molecular Structure:
Molecular Structure of 72559-06-9 (Rifabutin)
Formula: C46H62N4O11
Molecular Weight: 847.02
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;
EINECS: 615-780-3
Density: 1.339 g/cm3
Melting Point: 169-171oC
Boiling Point: 969.589 °C at 760 mmHg
Flash Point: 540.188 °C
Solubility: 0.19g/L(temperature not stated)
Appearance: Red-brown powder
PSA: 205.55000
LogP: 4.64680
Synthetic route
72559-06-9

1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin

25-hydroxy-rifabutin

Conditions
ConditionsYield
With methanol; sodium hydroxide; water; zinc(II) chloride at 20℃; for 6.5h;99.8%
With sodium hydroxide; water; zinc(II) chloride In methanol at 20℃; for 4h;85.4%
72559-06-9

1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin

75-36-5

acetyl chloride

N'-acetyl-rifabutin

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.0833333h;95%
72559-06-9

1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin

108-24-7

acetic anhydride

21-O-acetyl-rifabutin

Conditions
ConditionsYield
With pyridine at 20℃; for 72h;80%
72559-06-9

1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin

rifabutin N-oxide

Conditions
ConditionsYield
With Oxone; sodium hydrogencarbonate; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water; acetone at 20℃; for 26.5h; pH=7.0;51%
72559-06-9

1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin

rifabutinol

Conditions
ConditionsYield
With sodium tetrahydroborate; platinum(IV) oxide In tetrahydrofuran; ethanol at 20℃; for 4.08333h;47.6%
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History

Scientists at the Italian drug company Achifar discovered rifabutin in 1975. Eventually Archifar became part of Farmitalia Carlo Erba, a unit of the conglomerate Montedison. This company's Adria Laboratories subsidiary filed for Food and Drug Administration (FDA) approval of rifabutin under the brand name Mycobutin in the early 1990s and the drug gained FDA approval in December 1992.

Specification

Rifabutin, with the CAS NO.72559-06-9, has the Synonym of 1',4-Didehydro-1-deoxy-1,4-dihydro-5'-(2-methylpropyl)-1-oxorifamycin XIV; Ansatipine; Ansamycin; Antibiotic LM 427; LM 427; Mycobutin; Rifabutine. Rifabutin's molecular formula is C46H62N4O11 and its molecular weight is 847. It is soluble in Chloroform and Methanol. Rifabutin is a bactericidal antibiotic drug primarily used in the treatment of tuberculosis.

Physical properties about Rifabutin are: (1)ACD/LogP: 3.448; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 0.19; (4)ACD/LogD (pH 7.4): 0.88; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 4.84; (9)#H bond acceptors: 15; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.623; (13)Molar Refractivity: 222.927 cm3; (14)Molar Volume: 632.44 cm3; (15)Polarizability: 88.375 10-24cm3; (16)Surface Tension: 47.2929992675781 dyne/cm; (17)Density: 1.339 g/cm3; (18)Flash Point: 540.188 °C; (19)Enthalpy of Vaporization: 147.962 kJ/mol; (20)Boiling Point: 969.589 °C at 760 mmHg

Uses of Rifabutin:
1、Rifabutin is used in the treatment of mycobacterium avium complex disease, a bacterial infection most commonly encountered in late-stage AIDS patients.
2、Rifabutin is well tolerated in patients with HIV-related tuberculosis (TB).
3、Rifabutin is also used in trials for treating Crohn's Disease as part of the anti-MAP therapy. It has shown significant improvement of the condition in some patients.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14-/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1;
(2)InChIKey=ATEBXHFBFRCZMA-VXTBVIBXSA-N;
(3)SmilesN1C2(N=C3c4c5C(=O)C(NC(C(=CC=C[C@H](C)[C@@H]([C@@H](C)[C@H]([C@@H](C)[C@H](OC(=O)C)[C@@H]([C@H](C=CO[C@@]6(C)Oc(c4C6=O)c(C)c5O)OC)C)O)O)C)=O)=C13)CCN(CC2)CC(C)C;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 2gm/kg (2000mg/kg)   Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
man TDLo unreported 60mg/kg/14D-I (60mg/kg) BLOOD: AGRANULOCYTOSIS Lancet. Vol. 348, Pg. 685, 1996.
monkey LD oral > 4gm/kg (4000mg/kg)   Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
mouse LD50 intravenous 266mg/kg (266mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
mouse LD50 oral 3322mg/kg (3322mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
rat LD50 intravenous 51mg/kg (51mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
rat LD50 oral > 5gm/kg (5000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
women TDLo unreported 84mg/kg/14D-I (84mg/kg) BLOOD: AGRANULOCYTOSIS Lancet. Vol. 348, Pg. 685, 1996.