Product Name

  • Name

    Alfuzosin hydrochloride

  • EINECS 620-512-3
  • CAS No. 81403-68-1
  • Article Data16
  • CAS DataBase
  • Density 1.272 g/cm3
  • Solubility
  • Melting Point 225 °C
  • Formula C19H27N5O4.HCl
  • Boiling Point 687.7 °C at 760 mmHg
  • Molecular Weight 425.915
  • Flash Point 369.7 °C
  • Transport Information
  • Appearance White to off-white solid
  • Safety
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 81403-68-1 (Alfuzosin hydrochloride)
  • Hazard Symbols HarmfulXn
  • 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;
  • PSA 111.83000
  • LogP 3.12480

Synthetic route

alfuzosin
81403-80-7

alfuzosin

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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%
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

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

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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%
N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide
81403-67-0

N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide

2-chloro-6,7-dimethoxyquinazolin-4-amine
23680-84-4

2-chloro-6,7-dimethoxyquinazolin-4-amine

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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%
tetrahydro-2-furancarboxylic acid
16874-33-2

tetrahydro-2-furancarboxylic acid

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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
tetrahydro-N-(3-cyanopropyl)-N-methylfurancarboxamide
72104-44-0

tetrahydro-N-(3-cyanopropyl)-N-methylfurancarboxamide

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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
C8H12O5
167391-50-6

C8H12O5

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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
N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine
76362-29-3

N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine

1-(tetrahydrofuran-2-ylcarbonyl)-1H-imidazole
1005197-73-8

1-(tetrahydrofuran-2-ylcarbonyl)-1H-imidazole

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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
(R,S)-N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide acetate
1100050-87-0

(R,S)-N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide acetate

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol Product distribution / selectivity; Heating / reflux;
tetrahydrofuran-2-carbonyl chloride
52449-98-6

tetrahydrofuran-2-carbonyl chloride

N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine
76362-29-3

N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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;
tetrahydrofuran-2-carbonyl chloride
52449-98-6

tetrahydrofuran-2-carbonyl chloride

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
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
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

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

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

Conditions
ConditionsYield
Stage #1: alfuzosin hydrochloride With sodium hydroxide In dichloromethane; water
Stage #2: 10-camphorsufonic acid In dichloromethane at 20 - 40℃; Product distribution / selectivity;		84%
alfuzosin hydrochloride
81403-68-1

alfuzosin hydrochloride

alfuzosin
81403-80-7

alfuzosin

Conditions
ConditionsYield
With potassium carbonate In water
With sodium hydroxide In dichloromethane; water at 20 - 25℃; for 0.25h; pH=12; Product distribution / selectivity;

Alfuzosin hydrochloride 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%.

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.

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