Alfuzosin hydrochloride

Alfuzosin hydrochloride Basic information
Product Name:Alfuzosin hydrochloride
Synonyms: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
CAS:81403-68-1
MF:C19H28ClN5O4
MW:425.91
EINECS:620-512-3
Product Categories:Heterocycles;Antihypertensive, Treatment of BPH;Intermediates & Fine Chemicals;Pharmaceuticals;APIs;Antihypertensive;Alfuzosin;Uroxatral;API;Amines;Aromatics
Mol File:81403-68-1.mol
Alfuzosin hydrochloride Structure
Alfuzosin hydrochloride Chemical Properties
Melting point 225°C
storage temp. 2-8°C
solubility DMSO: >10mg/mL
pka8.13(at 25℃)
form solid
color White to Off-White
Merck 14,238
CAS DataBase Reference81403-68-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22
WGK Germany 3
RTECS LT9965475
HS Code 2934990002
MSDS Information
Alfuzosin hydrochloride Usage And Synthesis
DescriptionAlfuzosin (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 PropertiesWhite to Off-White Solid
UsesAntihypertensor;Alpha 1- adrenergic antagonist
Usesa-1- Adrenoceptor antagonist structurally similar to prozosin
Usesα1-Adrenoceptor antagonist structurally similar to Prozosin. Antihypertensive. Alfuzosin hydrochloride is used in treatment of benign prostatic hypertrophy.
Brand nameUroxatral (Sanofi Aventis).
General DescriptionPharmaceutical 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 ActivityFunctionally 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 ActionsAlfuzosin 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 UseAlpha-blocker:
Treatment of benign prostatic hyperplasia
Treatment of acute urinary retention

SynthesisAlthough 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 interactionsPotentially 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.







MetabolismExtensively metabolised in the liver, mainly by the cytochrome P450 isoenzyme CYP3A4, to inactive metabolites that are mainly excreted in faeces via the bile.
Propyl gallate ALFUZOSIN-METHYL-D3, HYDROCHLORIDE Tetrahydro Dimethoxy Aminoacetonitrile hydrochloride Topotecan hydrochloride ISOPROPYLHYDRAZINE HYDROCHLORIDE Sibutramine hydrochloride Tramadol hydrochloride ALTRENOGEST Alfuzosin 1-AdaMantanethylaMine Quinazoline 3-Chloropropyltriethoxysilane AMINO ACIDS Propyl butyrate Alfuzosin hydrochloride 3-Mercaptopropyltriethoxysilane

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