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Alfuzosin hydrochloride

CAS No.
81403-68-1
Chemical Name:
Alfuzosin hydrochloride
Synonyms
URION;XATRAL;Alfoten;MITTOVAL;Uroxatral;UROXANTRAL;Udon:xatral;SL-77,499-10;ALFUZOSIN HCL;Alfuzosin-d7 HCl
CBNumber:
CB8703590
Molecular Formula:
C19H28ClN5O4
Molecular Weight:
425.91
MDL Number:
MFCD00879135
MOL File:
81403-68-1.mol
MSDS File:
SDS
Last updated:2023-10-08 13:01:37

Alfuzosin hydrochloride Properties

Melting point 225°C
storage temp. 2-8°C
solubility DMSO: >10mg/mL
pka 8.13(at 25℃)
form solid
color White to Off-White
Merck 14,238
CAS DataBase Reference 81403-68-1(CAS DataBase Reference)
FDA UNII 75046A1XTN
NCI Drug Dictionary alfuzosin hydrochloride

Pharmacokinetic data

Protein binding 90%
Excreted unchanged in urine 11%
Volume of distribution 3.2(L/kg)
Biological half-life 3-5; XL: 8-9.1 / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P330-P501
Hazard Codes  Xn
Risk Statements  22
WGK Germany  3
RTECS  LT9965475
HS Code  2934990002
NFPA 704
0
2 0

Alfuzosin hydrochloride price More Price(44)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich BP847 Alfuzosin impurity standard British Pharmacopoeia (BP) Reference Standard 81403-68-1 25MG $266 2024-03-01 Buy
Sigma-Aldrich BP825 Alfuzosin hydrochloride British Pharmacopoeia (BP) Reference Standard 81403-68-1 100MG $257 2024-03-01 Buy
Sigma-Aldrich A0232 Alfuzosin hydrochloride ≥98% (HPLC), solid 81403-68-1 5mg $140 2024-03-01 Buy
Sigma-Aldrich 1012917 Alfuzosin hydrochloride United States Pharmacopeia (USP) Reference Standard 81403-68-1 150mg $358.8 2024-03-01 Buy
TCI Chemical A2591 Alfuzosin Hydrochloride >98.0%(HPLC) 81403-68-1 1g $237 2024-03-01 Buy
Product number Packaging Price Buy
BP847 25MG $266 Buy
BP825 100MG $257 Buy
A0232 5mg $140 Buy
1012917 150mg $358.8 Buy
A2591 1g $237 Buy

Alfuzosin hydrochloride Chemical Properties,Uses,Production

Description

Alfuzosin (SL-77499) (I), a quinazoline derivative which is a uroselective alpha-1 adrenoreceptor antagonist, has been developed and launched worldwide by Sanofi-Synthelabo, for the treatment of benign prostate hyperplasia (BPH). In November 2003, alfuzosin (I) was launched as an extended release formulation in the US as Uroxatral utilizing Skyepharma’s oral controlled release technology.

Chemical Properties

White to Off-White Solid

Uses

Antihypertensor;Alpha 1- adrenergic antagonist

Uses

a-1- Adrenoceptor antagonist structurally similar to prozosin

Uses

α1-Adrenoceptor antagonist structurally similar to Prozosin. Antihypertensive. Alfuzosin hydrochloride is used in treatment of benign prostatic hypertrophy.

brand name

Uroxatral (Sanofi Aventis).

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Biological Activity

Functionally uro-selective α 1 adrenoceptor antagonist that does not discriminate between α 1 subtypes. Inhibits increases in intraurethral pressure caused by phenylephrine-induced contraction by 81% with minor cardiovascular effects. Also relaxes corpus cavernosum tissue (pIC 50 = 7.64) in vitro .

Biochem/physiol Actions

Alfuzosin hydrochloride is an alpha-adrenergic blocker used to treat benign prostatic hyperplasia (BPH). It works by relaxing the muscles in the prostate and bladder neck, making it easier to urinate.

Clinical Use

Alpha-blocker:
Treatment of benign prostatic hyperplasia
Treatment of acute urinary retention

Synthesis

Although syntheses of alfuzosin (I) have appeared in several reports, an optimized route used for the manufacture of the compound does not appear in the literature. The synthesis reported by the Sanofi group for alfuzosin will be described and is shown in the scheme. The commercially available 4- amino-2-chloro-6,7-dimethoxyquinazoline (1) was treated with 3-methylaminopropionitrile (2) in isoamyl alcohol and refluxed for 5 hrs. Filtration of the precipitated product and washing with ethanol gave nitrile 3 in 62% yield. Hydrogenation of the nitrile was done in 15% ammonia solution in ethanol with Raney nickel as catalyst at 70??C and 1000 psi to obtain the corresponding amine free base. Conversion of the free base to the hydrochloride salt was done in ethanol to give the HCl salt 4 in 52% yield. The final acylation of amine 4 was done with the imidazolyl anhydride of furan 5. Thus, 2-carboxyfuran was treated with carbonyldiimidazole in THF at 40??C for 1 hr and then cooled to 10??C. Addition of amine 4 in THF in the presence of triethylamine at 10??C, then refluxing the reaction for 1 hr, and aqueous workup gave the alfuzosin free base. After conversion to the hydrochloride salt and recrystallization from 2-propanol alfuzosin hydrochloride (I) was obtained in 44% yield.

Synthesis_81403-68-1

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Antidepressants: enhanced hypotensive effect with MAOIs.
Antivirals: concentration possibly increased by ritonavir - avoid; avoid with telaprevir.
Avanafil, vardenafil, sildenafil and tadalafil: enhanced hypotensive effect, separate administration by 4-6 hours.
Beta-blockers: enhanced hypotensive effect; increased risk of first dose hypotensive effect.
Calcium-channel blockers: enhanced hypotensive effect; increased risk of first dose hypotensive effect.
Cobicistat: concentration of alfuzosin possibly increased - avoid.
Diuretics: enhanced hypotensive effect; increased risk of first dose hypotensive effect.
Moxisylyte: possibly severe postural hypotension.

Metabolism

Extensively metabolised in the liver, mainly by the cytochrome P450 isoenzyme CYP3A4, to inactive metabolites that are mainly excreted in faeces via the bile.

81403-80-7
81403-68-1
Synthesis of Alfuzosin hydrochloride from Alfuzosin
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View Lastest Price from Alfuzosin hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Alfuzosine Hydrochloride pictures 2023-10-09 Alfuzosine Hydrochloride
81403-68-1
US $0.00 / kg 1kg 0.99 20tons Hebei Yanxi Chemical Co., Ltd.
Alfuzosin hydrochloride pictures 2023-10-08 Alfuzosin hydrochloride
81403-68-1
US $30.00 / KG 1KG 99% 20T Firsky International Trade (Wuhan) Co., Ltd
Alfuzosin hydrochloride pictures 2023-09-12 Alfuzosin hydrochloride
81403-68-1
US $100.00 / bag 1bag 99 5000 Hebei Fengqiang Trading Co., LTD

Alfuzosin hydrochloride Spectrum

Alfuzosin-d7 HCl Alfuzosin hydrochlorid Alfuzosin Hydrochloride (150 mg) Alfuzosin hydrochloride(Uroxatral) Uroxatral Alfuzosin hydrocholoride Uroxatral hydrochloride N-(3-((4-Amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino)-propyl)tetrahydrofuran-2-carboxamid N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolynyl)methylamino]propyl]tetrahydro-2-furancarboxamide, SL-77,499-10, Mittoval, Urion, Xatral 2-Furancarboxamide, N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-, hydrochloride Uroxatral hydrochloride, N-(3-((4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-2-furancarboxamide hydrochloride Udon:xatral alfuzosinehydrochloride SL-77,499-10 MITTOVAL N-[3-[(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLYNYL)METHYLAMINO]PROPYL]TETRAHYDRO-2-FURANCARBOXAMIDE n-[3-[(4-amino-6,7-dimethoxy-2-quinazolynyl)methylamino]propyl]tetrahydro-2-furancarboxamide hydrochloride XATRAL URION UROXANTRAL ALFUZOSIN HCL ALFUZOSIN HYDROCHLORIDE Alfoten N-[3-[(4-Amino-6,7-dimethoxy-2-quimdinyl)methyl-lamino]propyl]tetrahydro-2-furancarboxamide hydrochloride N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamidehydrochloride Alfuzosin hydrochloride (SL 77499-10) (RS)-N-[3-[(4-Amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino]propyl]tetrahydrofuran-2-carboxamide hydrochloride Alfuzosin for peak identification Alfuzosin for system suitability A N-[3-[(4-amino-6,7-dimethoxy-1,4-dihydroquinazolin-2-yl)-methylamino]propyl]-2-oxolanecarboxamide hydrochloride Alfuzosin Hydrochloride > Alfuzosin hydrochloride CRS N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolynyl 4-Amino-6,7-dimethoxy-2-[methyl[3-[(tetrahydro-2-furoyl)amino]propyl]amino]quinazoline Hydrochloride Alfuzosin hydrochloride USP/EP/BP Afzosin hydrochloride impurity 81403-68-1 Alfuzosin Hydrochloride N-(3-((4-Amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino)propyl)tetrahydrofuran-2-carboxamide hydrochloride Alfuzosin HCl (SL 77499-10 HCl) Alfuzosin for peak identification (Y0001883) Alfuzosin for system suitability A (Y0001906) Alfuzosin HydrochlorideQ: What is Alfuzosin Hydrochloride Q: What is the CAS Number of Alfuzosin Hydrochloride Q: What is the storage condition of Alfuzosin Hydrochloride Q: What are the applications of Alfuzosin Hydrochloride TIANFU Alfuzosin hydrochloride Alfuzosin Hydrochloride (1012917) Alfuzosin HCl (RS)-N-[3-[(4-Amino-6,7-dimethoxyquinazolin-2- yl)(methyl)amino]propyl]tetrahydrofuran-2-carboxamide hydrochloride 81403-68-1 C19H27N5O4HCl H19H27N5O4HCl C19H27N5O4ClH Heterocycles Antihypertensive, Treatment of BPH Intermediates & Fine Chemicals Pharmaceuticals APIs Antihypertensive Alfuzosin Uroxatral API