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| CAS No.: | 81403-68-1 |
|---|---|
| Name: | Alfuzosin hydrochloride |
| Article Data: | 16 |
| Molecular Structure: | |
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|
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| Formula: | C19H27N5O4.HCl |
| Molecular Weight: | 425.915 |
| Synonyms: | Xatral;Prestwick_774;Uroxatral;N-[3-[(4-amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]propyl]oxolane-2-carboxamide hydrochloride;Alfuzocin hydrochloride;Uroxatral (TN);2-Furancarboxamide,N-[3-[(4-amino-6,7- dimethoxy-2-quinazolinyl)methylamino]propyl]- tetrahydro-,monohydrochloride;Alfuzosin hydrochloride (JAN/USAN);Alfuzosin HCl; |
| EINECS: | 620-512-3 |
| Density: | 1.272 g/cm3 |
| Melting Point: | 225 °C |
| Boiling Point: | 687.7 °C at 760 mmHg |
| Flash Point: | 369.7 °C |
| Appearance: | White to off-white solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| PSA: | 111.83000 |
| LogP: | 3.12480 |
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- 81403-80-7
alfuzosin
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol at 20 - 25℃; | 88% |
| With hydrogenchloride In methanol; isopropyl alcohol at 20℃; for 0.5h; pH=3 - 4; Product distribution / selectivity; | 85% |
| With hydrogenchloride In isopropyl alcohol at 20℃; for 0.75 - 1h; Product distribution / selectivity; | 82% |
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: N1-(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate With sodium hydroxide In dichloromethane; water at 20℃; for 0.5h; Stage #2: With hydrogenchloride In ethanol; dichloromethane | 87.5% |
- 81403-67-0
N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide
- 23680-84-4
2-chloro-6,7-dimethoxyquinazolin-4-amine
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| In i-Amyl alcohol for 12h; Heating; | 66% |
| In i-Amyl alcohol for 10h; Solvent; Reflux; | 66% |
| In i-Amyl alcohol for 6h; Solvent; Reflux; | 65.5% |
- 16874-33-2
tetrahydro-2-furancarboxylic acid
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: Et3N / tetrahydrofuran / 0.25 h / 5 °C 2: tetrahydrofuran / Ambient temperature 3: 68 percent / H2, 10percent ethanolic NH3 / Rh/C / 80 °C / 43440.4 Torr 4: 66 percent / 3-methyl-butan-1-ol / 12 h / Heating View Scheme | |
| Multi-step reaction with 3 steps 1: thionyl chloride 2: triethylamine / 1,2-dichloro-ethane / 3 h / 5 - 10 °C 3: i-Amyl alcohol / 6 h / Reflux View Scheme | |
| Multi-step reaction with 4 steps 1: thionyl chloride / 3 h / 35 °C 2: triethylamine / 1,2-dichloro-ethane / 3 h / 5 - 35 °C 3: palladium on activated charcoal; ammonium formate / methanol / 2 h / Reflux 4: i-Amyl alcohol / 10 h / Reflux View Scheme |
- 72104-44-0
tetrahydro-N-(3-cyanopropyl)-N-methylfurancarboxamide
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 68 percent / H2, 10percent ethanolic NH3 / Rh/C / 80 °C / 43440.4 Torr 2: 66 percent / 3-methyl-butan-1-ol / 12 h / Heating View Scheme |
- 167391-50-6
C8H12O5
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: tetrahydrofuran / Ambient temperature 2: 68 percent / H2, 10percent ethanolic NH3 / Rh/C / 80 °C / 43440.4 Torr 3: 66 percent / 3-methyl-butan-1-ol / 12 h / Heating View Scheme |
- 76362-29-3
N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine
- 1005197-73-8
1-(tetrahydrofuran-2-ylcarbonyl)-1H-imidazole
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine; 1-(tetrahydrofuran-2-ylcarbonyl)-1H-imidazole In dichloromethane at 38 - 40℃; Stage #2: With hydrogenchloride In ethanol; isopropyl alcohol |
- 1100050-87-0
(R,S)-N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide acetate
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In isopropyl alcohol Product distribution / selectivity; Heating / reflux; |
- 52449-98-6
tetrahydrofuran-2-carbonyl chloride
- 76362-29-3
N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: tetrahydrofuran-2-carbonyl chloride; N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine In toluene at 25 - 30℃; Stage #2: With sodium hydrogencarbonate In dichloromethane; water Stage #3: With hydrogenchloride In methanol; isopropyl alcohol pH=1 - 2; |
- 52449-98-6
tetrahydrofuran-2-carbonyl chloride
- 81403-68-1
alfuzosin hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: triethylamine / 1,2-dichloro-ethane / 3 h / 5 - 35 °C 2: palladium on activated charcoal; ammonium formate / methanol / 2 h / Reflux 3: i-Amyl alcohol / 10 h / Reflux View Scheme |
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Specification
The IUPAC name of Xatral is N-[3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)-methylamino]propyl]oxolane-2-carboxamide hydrochloride. With the CAS registry number 81403-68-1, it is also named as Alfuzosin hydrochloride [USAN]; 2-Furancarboxamide, N-(3-((4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-, monohydrochloride (+-)-. The product's categories are APIs, antihypertensive, treatment of BPH, intermediates & fine chemicals, pharmaceuticals and alfuzosin. It is white to off-white solid which is harmful if swallowed.
The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.43; (4)ACD/LogD (pH 7.4): -2.33; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 9; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Enthalpy of Vaporization: 102.62 kJ/mol; (13)Vapour Pressure: 3.75E-19 mmHg at 25°C; (14)Rotatable Bond Count: 8; (15)Tautomer Count: 6; (16)Exact Mass: 425.182982; (17)MonoIsotopic Mass: 425.182982; (18)Topological Polar Surface Area: 112; (19)Heavy Atom Count: 29.
Preparation of Xatral: It can obtained by 2-chloro-6,7-dimethoxy-quinazolin-4-ylamine and tetrahydro-N-[3-(methylamino)propyl]-furancarboxamide. This reaction needs solvent 3-methyl-butan-1-ol by heating. The reaction time is 12 hours. The yield is 66%.
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Uses of Xatral: It is a-1- Adrenoceptor antagonist structurally similar to prozosin. It is used to treat the signs and symptoms of benign enlargement of the prostate (benign prostatic hyperplasia or BPH).
People can use the following data to convert to the molecule structure.
1. SMILES: O=C(NCCCN(c2nc1cc(OC)c(OC)cc1c(n2)N)C)C3OCCC3.Cl;
2. InChI: InChI=1/C19H27N5O4.ClH/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19;/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23);1H.
The following is the toxicity data which has been tested.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | intravenous | > 200mg/kg (200mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 2569, 2000. | |
| mouse | LD50 | intravenous | 235mg/kg (235mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 2569, 2000. | |
| rat | LD50 | intravenous | 146mg/kg (146mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 2569, 2000. |