ChemicalBook > CAS DataBase List > Alfuzosin hydrochloride

Alfuzosin hydrochloride

Product Name
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
Formula Weight
425.91
MOL File
81403-68-1.mol
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Alfuzosin hydrochloride Property

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)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
LT9965475
HS Code 
2934990002
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

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

a-1- Adrenoceptor antagonist structurally similar to prozosin

Uses

Antihypertensor;Alpha 1- adrenergic antagonist

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.

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.

Alfuzosin hydrochloride Preparation Products And Raw materials

Raw materials

3-Aminopropionitrile Alfuzosin Quinazoline

Preparation Products

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Alfuzosin hydrochloride Suppliers

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View Lastest Price from Alfuzosin hydrochloride manufacturers

Wuhan Circle Star Chem-medical Technology Co.,Ltd
Product
Alfuzosin hydrochloride 81403-68-1
Price
US $0.00-0.00/g
Min. Order
1g
Purity
98
Supply Ability
1000
Release date
2025-01-16
Hebei Mujin Biotechnology Co.,Ltd
Product
Alfuzosin hydrochloride 81403-68-1
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-07-04
Hebei Zhuanglai Chemical Trading Co Ltd
Product
Alfuzosin hydrochloride 81403-68-1
Price
US $50.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-12-09

81403-68-1, Alfuzosin hydrochlorideRelated Search:

Glycine Propyl gallate 3-Mercaptopropyltriethoxysilane Propyl butyrate 3-Aminopropyltriethoxysilane 1-AdaMantanethylaMine ALTRENOGEST AMINOGUANIDINE HYDROCHLORIDE Lithium diisopropylamide Alfuzosin Topotecan hydrochloride N,N-Dimethylformamide Aminoacetonitrile hydrochloride D-Glucosamine hydrochloride ISOPROPYLHYDRAZINE HYDROCHLORIDE 3-Chloropropyltriethoxysilane Tramadol hydrochloride Sibutramine hydrochloride

  • Alfuzosin-d7 HCl
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  • 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
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  • n-[3-[(4-amino-6,7-dimethoxy-2-quinazolynyl)methylamino]propyl]tetrahydro-2-furancarboxamide hydrochloride
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  • Alfoten
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  • TIANFU Alfuzosin hydrochloride
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  • SL 77499-10|||Alfuzosin HCl
  • Alfuzosin hydrochloride, 10 mM in DMSO
  • 81403-68-1
  • C19H27N5O4ClH
  • C19H27N5O4HCl
  • H19H27N5O4HCl
  • Uroxatral
  • API
  • Amines
  • Aromatics
  • Heterocycles
  • Antihypertensive, Treatment of BPH
  • Intermediates & Fine Chemicals