Alfuzosin hydrochloride

Bezeichnung:Alfuzosin hydrochloride

CAS-Nr81403-68-1

Englisch Name:Alfuzosin hydrochloride

CBNumberCB8703590

SummenformelC19H28ClN5O4

Molgewicht425.91

MOL-Datei81403-68-1.mol

Alfuzosin hydrochloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	225°C
storage temp.	2-8°C
Löslichkeit	DMSO: >10mg/mL
pka	8.13(at 25℃)
Aggregatzustand	solid
Farbe	White to Off-White
Merck	14,238
CAS Datenbank	81403-68-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22
WGK Germany	3
RTECS-Nr.	LT9965475
HS Code	2934990002

Gefahreninformationscode (GHS)

Alfuzosin hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
Beschreibung
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.
Chemische Eigenschaften
White to Off-White Solid
Verwenden
α1-Adrenoceptor antagonist structurally similar to Prozosin. Antihypertensive. Alfuzosin hydrochloride is used in treatment of benign prostatic hypertrophy.
Verwenden
Antihypertensor;Alpha 1- adrenergic antagonist
Verwenden
a-1- Adrenoceptor antagonist structurally similar to prozosin
Trademarks
Uroxatral (Sanofi Aventis).
Allgemeine Beschreibung
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.
Biologische Aktivität
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
Synthese
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.
Arzneimittelwechselwirkung
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.
Stoffwechsel
Extensively metabolised in the liver, mainly by the cytochrome P450 isoenzyme CYP3A4, to inactive metabolites that are mainly excreted in faeces via the bile.

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