Alfuzosin, 塩酸アルフゾシン

It's only fair to share...Flattr the authorPin on PinterestEmail this to someone
Buffer this pageDigg thisShare on FacebookShare on Google+Tweet about this on TwitterShare on LinkedInShare on YummlyShare on VKShare on RedditShare on StumbleUponPrint this pageShare on Tumblr

Image result for alfuzosinChemSpider 2D Image | Alfuzosin | C19H27N5O4


  • Molecular FormulaC19H27N5O4
  • Average mass389.449 Da
SL 77499-10
2-furancarboxamide, N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-
cas 81403-80-7 [RN]


CAS: 81403-68-1  HCL SALT
Title: Alfuzosin
CAS Registry Number: 81403-80-7
CAS Name: N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide
Additional Names: N1-(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydrofuroyl-2)-propylenediamine
Manufacturers’ Codes: SL-77.499
Molecular Formula: C19H27N5O4
Molecular Weight: 389.45
Percent Composition: C 58.60%, H 6.99%, N 17.98%, O 16.43%
Literature References: a1-Adrenoceptor antagonist structurally similar to prazosin, q.v. Prepn: P. M. J. Manoury, DE 2904445idem, US 4315007 (1979, 1982 both to Synthelabo); and antihypertensive activity in rats: P. M. Manoury et al., J. Med. Chem. 29,19 (1986). Pharmacology: A. G. Ramage, Eur. J. Pharmacol. 129, 307 (1986). HPLC determn in biological fluids: P. Guinebault et al., J. Chromatogr. 353, 361 (1986). Pharmacology in humans: A. H. Deering, Br. J. Clin. Pharmacol. 25, 417 (1988). Clinical evaluation in essential hypertension: S. Leto Di Priolo et al., Eur. J. Clin. Pharmacol. 35, 25 (1988); A. K. Ghosh, S. Ghosh, Ger. Cardiovasc. Med. 1, 81 (1988). Clinical trial in benign prostatic hyperplasia (BPH): C. G. Roehrborn et al., BJU Int. 92, 257 (2003). Review of clinical experience in BPH: D. M. Weiner, F. C. Lowe, Expert Opin. Pharmacother. 4, 2057-2063 (2003).
Alfuzosin hydrochloride: sc-203812...

Alfuzosin hydrochloride (CAS 81403-68-1)

Derivative Type: Hydrochloride
CAS Registry Number: 81403-68-1
Manufacturers’ Codes: SL-77.499-10
Trademarks: Mittoval (Schering AG); Urion (Zambon); UroXatral (Sanofi-Synthelabo); Xatral (Sanofi-Synthelabo)
Molecular Formula: C19H27N5O4.HCl
Molecular Weight: 425.91
Percent Composition: C 53.58%, H 6.63%, N 16.44%, O 15.03%, Cl 8.32%
Properties: Crystals from ethanol + ether, mp 225° (Manoury, 1986), also reported earlier as mp 235° (dec) (Manoury, 1982). pKa 8.13.
Melting point: mp 225° (Manoury, 1986); mp 235° (dec) (Manoury, 1982)
pKa: pKa 8.13
Therap-Cat: Antihypertensive. In treatment of benign prostatic hypertrophy.
Keywords: Antihypertensive; Quinazoline Derivatives; Antiprostatic Hypertrophy; a-Adrenergic Blocker.

Alfuzosin (INN, provided as the hydrochloride salt) is a pharmaceutical drug of the α1 blocker class. As an antagonist of the α1adrenergic receptor, it works by relaxing the muscles in the prostate and bladder neck, making it easier to urinate. It is thus used to treat benign prostatic hyperplasia (BPH).[1]

Alfuzosin is marketed in the United States by Sanofi Aventis under the brand name Uroxatral and elsewhere under the tradenames Xat, Xatral, Prostetrol and Alfural. Alfuzosin was approved by the U.S. FDA for treatment of BPH in June 2003.

Side effects

The most common side effects are dizziness (due to postural hypotension), upper respiratory tract infectionheadachefatigue, and abdominal disturbances. Side effects include stomach pain, heartburn, and congested nose.[2] Adverse effects of alfuzosin are similar to that of tamsulosin with the exception of retrograde ejaculation.[3]


Alfuzosin should be used with caution in patients with severe renal insufficiency, and should not be prescribed to patients with a known history of QT prolongation who are taking medications known to prolong the QT interval.


Alfuzosin contains a stereocenter and is therefore chiral. There are two enantiomeric forms, (R)-alfuzosin and (S)-alfuzosin. The drug is used as a racemate, (RS)-alfuzosin, a 1: 1 mixture of the (R)- and (S)-forms.[4]

Enantiomers of alfuzosin
Strukturformel des (R)-Enantiomers
CAS number: 123739-69-5
Strukturformel des (S)-Enantiomers
CAS number.: 123739-70-8


    • ATC:G04CA01
  • Use:antihypertensive, α1-adrenoceptor antagonist, α-blocker, treatment of benign prostatic hypertrophy (BPH)
  • Chemical name:(±)-N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide
  • Formula:C19H27N5O4
    • MW:389.46 g/mol
    • CAS-RN:81403-80-7



    • Formula:C19H27N5O4 • HCl
    • MW:425.92 g/mol
    • CAS-RN:81403-68-1

    Substance Classes

    Synthesis Path

    Substances Referenced in Synthesis Path

    CAS-RN Formula Chemical Name CAS Index Name
    23680-84-4 C10H10ClN3O2 4-amino-2-chloro-6,7-dimethoxyquinazoline 4-Quinazolinamine, 2-chloro-6,7-dimethoxy-
    5004-88-6 C9H12N2O3 2-amino-4,5-dimethoxybenzamide Benzamide, 2-amino-4,5-dimethoxy-
    541-41-3 C3H5ClO2 chloroformic acid ethyl ester Carbonochloridic acid, ethyl ester
    72104-44-0 C9H14N2O2 2-cyano-N-methyl-N-tetrahydrofuroylethylamine 2-Furancarboxamide, N-(2-cyanoethyl)tetrahydro-N-methyl-
    27631-29-4 C10H8Cl2N2O2 2,4-dichloro-6,7-dimethoxyquinazoline Quinazoline, 2,4-dichloro-6,7-dimethoxy-
    28888-44-0 C10H10N2O4 2,4-dihydroxy-6,7-dimethoxyquinazoline 2,4(1H,3H)-Quinazolinedione, 6,7-dimethoxy-
    20357-25-9 C9H9NO5 4,5-dimethoxy-2-nitrobenzaldehyde Benzaldehyde, 4,5-dimethoxy-2-nitro-
    4959-60-8 C9H10N2O5 4,5-dimethoxy-2-nitrobenzamide Benzamide, 4,5-dimethoxy-2-nitro-
    28888-44-0 C10H10N2O4 6,7-dimethoxyquinazoline-2,4-dione 2,4(1H,3H)-Quinazolinedione, 6,7-dimethoxy-
    541-41-3 C3H5ClO2 ethyl chloroformate Carbonochloridic acid, ethyl ester
    693-05-0 C4H8N2 3-(methylamino)propanenitrile Propanenitrile, 3-(methylamino)-
    81403-67-0 C9H18N2O2 N1-methyl-N2-tetrahydrofuroyltrimethylenediamine 2-Furancarboxamide, tetrahydro-N-[3-(methylamino)propyl]-
    16874-33-2 C5H8O3 (±)-tetrahydrofuran-2-carboxylic acid 2-Furancarboxylic acid, tetrahydro-
    167391-50-6 C8H12O5 tetrahydro-2-furancarboxylic acid anhydride with ethyl hydrogen carbonate 2-Furancarboxylic acid, tetrahydro-, anhydride with ethyl hydrogen carbonate
    57-13-6 CH4N2O urea Urea
    120-14-9 C9H10O3 veratraldehyde Benzaldehyde, 3,4-dimethoxy-

    Trade Names

    Country Trade Name Vendor Annotation
    D Alfunar Apogepha
    Alfusin TAD Pharma
    Urion Sanofi-Aventis
    Uroxatral Sanofi-Aventis
    F Urion Zambon
    Xatral Sanofi-Aventis
    GB Xatral Sanofi-Aventis
    I Mittoval Sanofi-Aventis
    Xatral Sanofi-Aventis


    • film tabl. 2.5 mg; retard tabl. 10 mg (hydrochloride)


      • Manoury, P.M. et al.: J. Med. Chem. (JMCMAR) 29, 19 (1986).
      • US 4 315 007 (Synthelabo; 9.2.1982; F-prior. 6.2.1978, 29.12.1978).
      • DE 2 904 445 (Synthelabo; appl. 16.8.1979; F-prior. 6.2.1978, 29.12.1978).
    • synthesis of 6,7-dimethoxyquinazoline-2,4-dione:

      • Althuis, T.H.; Hess, H.J.: J. Med. Chem. (JMCMAR) 20, 146 (1977).


    Mathias Scheer, “Alfuzosin tablets and synthesis.” U.S. Patent US20060062845, issued March 23, 2006.


    Syn,  DOI: 10.1021/jm00151a003 NB: (WO2009001369)

    Image result for alfuzosin

    Image result for alfuzosin

    FTIR spectrum of alfuzosin hydrochloride 


    Add the following:
    Alfuzosin Hydrochloride
    Click to View Image

    C19H27N5O4·HCl 425.91

    2-Furancarboxamide, N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-, monohydrochloride (±).
    (±)-N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furamide monohydrochloride [81403-68-1].
    » Alfuzosin Hydrochloride contains not less than 99.0 percent and not more than 101.0 percent of C19H27N5O4·HCl, calculated on the anhydrous basis.
    Packaging and storage— Preserve in tight, well-closed containers, protected from light and humidity. Store at room temperature.


    B: It meets the requirements of the test for Chloride 191.

    pH 791between 4.0 and 5.5

    Test solution: 20 mg per mL, in carbon dioxide-free water.

    Optical rotation 7810.10 to +0.10

    Test solution: 20 mg per mL, in carbon dioxide-free water.
    Water, Method I 921not more than 0.5%.
    Residue on ignition 281not more than 0.1%.

    Related compounds—

    Solution A— Dilute 5.0 mL of perchloric acid in 900 mL of water, adjust with 2 M sodium hydroxide solution to a pH of 3.5, and dilute with water to 1000 mL.
    Mobile phase— Prepare a filtered and degassed mixture of Solution A, acetonitrile, and tetrahydrofuran (80:20:1). Make adjustments if necessary (see System Suitability under Chromatography 621).
    System suitability solution— Dissolve an accurately weighed quantity of USP Alfuzosin System Suitability Mixture RS in Mobile phase, and dilute quantitatively with Mobile phase to obtain a solution containing about 0.4 mg per mL.
    Test solution— Dissolve 40.0 mg of Alfuzosin Hydrochloride in Mobile phase, and dilute with Mobile phase to 100.0 mL.
    Reference solution— Quantitatively dilute an accurately measured volume of the Test solution by a factor of 1000 with Mobile phase.

    Chromatographic system (see Chromatography 621) The liquid chromatograph is equipped with a detector set at 254 nm and a 4.6-mm × 15-cm column that contains 5-µm packing L1. The flow rate is about 1.5 mL per minute. Chromatograph the System suitability solution, and record the peak responses as directed for Procedure: the peak-to-valley ratio is at least 5. [NOTE—The peak-to-valley ratio is determined as the ratio of the height above the baseline of the impurity A peak to the height above the baseline of the lowest point of the curve separating this impurity peak from the peak due to alfuzosin.]

    Procedure— Separately inject equal volumes (about 10 µL) of the Reference solution and the Test solution, record the chromatograms, and measure the peak responses. Calculate the percentage of each impurity in the portion of Alfuzosin Hydrochloride taken by the formula:

    100[r/ (1000 rS)]

    in which 100 is the percentage conversion factor; rU is the peak response for any impurity obtained from the Test solution; 1000 is the dilution factor; and rS is the peak response for alfuzosin obtained from the Reference solution: the limits are as shown in the accompanying table. Disregard any peak with an area less than 0.05%.

    Compound Relative 
    Retention Time
    Alfuzosin 1.0
    Impurity A1 1.2 *
    Impurity D2 0.5 0.20
    Any individual unspecified impurity 0.10
    Total impurities 0.30
    1  N-[3-[(4-Amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino]propyl]furan-2-carboxamide.
    2  N-(4-Amino-6,7-dimethoxyquinazolin-2-yl)-N-methylpropane-1,3-diamine.
    *  Impurity A, a component of USP Alfuzosin System Suitability Mixture RS, is not a specified impurity.
    Assay— Dissolve about 300 mg of Alfuzosin Hydrochloride, accurately weighed, in a mixture of 40 mL of anhydrous acetic acid and 40 mL of acetic anhydride. Titrate with 0.1 M perchloric acid, determining the endpoint potentiometrically. Each mL of 0.1 M perchloric acid is equivalent to 42.59 mg of C19H27N5O4·HCl.USP32

    Auxiliary Information— Please check for your question in the FAQs before contacting USP.

    Topic/Question Contact Expert Committee
    Monograph Daniel K. Bempong, Ph.D.
    Senior Scientist
    (MDPS05) Monograph Development-Pulmonary and Steroids
    Reference Standards Lili Wang, Technical Services Scientist
    USP32–NF27 Page 1449

    Pharmacopeial Forum: Volume No. 34(1) Page 69

    Chromatographic Column—

    Chromatographic columns text is not derived from, and not part of, USP 32 or NF 27.


    1. Jump up^ Lepor, Herbert (2016). “Alpha-blockers for the Treatment of Benign Prostatic Hyperplasia”Urologic Clinics of North America43 (3): 311–23. doi:10.1016/j.ucl.2016.04.009PMC 2213889Freely accessiblePMID 27476124.
    2. Jump up^ “Alfuzosin”MedlinePlusUnited States National Library of Medicine. April 15, 2016.
    3. Jump up^ Hills, Robert K; Liu, Chenli; Zeng, Guohua; Kang, Ran; Wu, Wenqi; Li, Jiasheng; Chen, Kang; Wan, Show P. (2015). “Efficacy and Safety of Alfuzosin as Medical Expulsive Therapy for Ureteral Stones: A Systematic Review and Meta-Analysis”PLOS ONE10 (8): e0134589. doi:10.1371/journal.pone.0134589ISSN 1932-6203PMC 4526635Freely accessiblePMID 26244843. This article incorporates text available under the CC BY 4.0 license.
    4. Jump up^ Rote Liste Service GmbH (Hrsg.): Rote Liste 2017 – Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte). Rote Liste Service GmbH, Frankfurt/Main, 2017, Aufl. 57, S. 159, ISBN 978-3-946057-10-9.

    External links

    Clinical data
    Pronunciation /ælˈfjuːzsɪn/ al-FEW-zoh-sin
    Trade names Uroxatral, others
    AHFS/ Monograph
    MedlinePlus a64002
    • AU: B2
    • US: B (No risk in non-human studies)
    Routes of
    By mouth (tablets)
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    Bioavailability 49%
    Protein binding 82–90%
    Metabolism Liver (CYP3A4-mediated)
    Elimination half-life 10 hours
    Excretion Feces (69%) and Urine (24%)
    CAS Number
    PubChem CID
    ECHA InfoCard 100.108.671 Edit this at Wikidata
    Chemical and physical data
    Formula C19H27N5O4
    Molar mass 389.46 g·mol−1
    3D model (JSmol)

    /////////////////塩酸アルフゾシン, Uroxatral, alfuzosin


    It's only fair to share...Flattr the authorPin on PinterestEmail this to someone
    Buffer this pageDigg thisShare on FacebookShare on Google+Tweet about this on TwitterShare on LinkedInShare on YummlyShare on VKShare on RedditShare on StumbleUponPrint this pageShare on Tumblr

    Leave a Reply

    Your email address will not be published. Required fields are marked *