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CAS No.: | 72559-06-9 |
---|---|
Name: | Rifabutin |
Molecular Structure: | |
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 |
1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin
Conditions | Yield |
---|---|
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% |
1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin
acetyl chloride
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.0833333h; | 95% |
1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin
acetic anhydride
Conditions | Yield |
---|---|
With pyridine at 20℃; for 72h; | 80% |
1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin
Conditions | Yield |
---|---|
With Oxone; sodium hydrogencarbonate; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water; acetone at 20℃; for 26.5h; pH=7.0; | 51% |
1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin
Conditions | Yield |
---|---|
With sodium tetrahydroborate; platinum(IV) oxide In tetrahydrofuran; ethanol at 20℃; for 4.08333h; | 47.6% |
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. |