ALFUZOSIN HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H27N5O4.ClH
Molecular Weight	425.91
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.COC1=CC2=C(C=C1OC)C(N)=NC(=N2)N(C)CCCNC(=O)C3CCCO3

InChI

InChIKey=YTNKWDJILNVLGX-UHFFFAOYSA-N

InChI=1S/C19H27N5O4.ClH/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19;/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C19H27N5O4
Molecular Weight	389.4488
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf | https://www.drugbank.ca/drugs/DB00346

Alfuzosin is a quinazoline-derivative alpha-adrenergic blocking agent used to treat hypertension and benign prostatic hyperplasia. Alfuzosin is marketed in the United States by Sanofi Aventis under the brand name Uroxatral. UROXATRAL (alfuzosin HCl extended-release tablets) is indicated for the treatment of the signs and symptoms of benign prostatic hyperplasia. UROXATRAL is not indicated for the treatment of hypertension. Alfuzosin is a non-subtype specific alpha(1)-adrenergic blocking agent that exhibits selectivity for alpha(1)-adrenergic receptors in the lower urinary tract. Inhibition of these adrenoreceptors leads to the relaxation of smooth muscle in the bladder neck and prostate, resulting in the improvement in urine flow and a reduction in symptoms in benign prostate hyperplasia. Alfuzosin also inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Alpha-1a adrenergic receptor 67 Target ID: CHEMBL229 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9135028 \| https://www.ncbi.nlm.nih.gov/pubmed/10812954	Antagonist 2849	8.0 null [pKi]
Alpha-1b adrenergic receptor 45 Target ID: CHEMBL232 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9135028 \| https://www.ncbi.nlm.nih.gov/pubmed/10812954	Antagonist 2849	8.0 null [pKi]
Alpha-1d adrenergic receptor 37 Target ID: CHEMBL223 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9135028 \| https://www.ncbi.nlm.nih.gov/pubmed/10812954	Antagonist 2849	8.5 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021287s011lbl.pdf	Primary		Approved 8583	UROXATRAL Approved Use UROXATRAL is indicated for the treatment of signs and symptoms of benign prostatic hyperplasia. UROXATRAL is an alpha adrenergic antagonist, indicated for the treatment of signs and symptoms of benign prostatic hyperplasia. (1) Important Limitations of Use: UROXATRAL is not indicated for treatment of hypertension. (1.1) UROXATRAL is not indicated for use in the pediatric population. (1.1, 8.4, 12.3) 1.1 Important Limitations of Use UROXATRAL is not indicated for the treatment of hypertension. UROXATRAL is not indicated for use in the pediatric population. Launch Date 2003

C_max

Value	Dose	Co-administered	Analyte	Population
13.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021287s013lbl.pdf	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ALFUZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
194 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021287s013lbl.pdf	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ALFUZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
10 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021287s013lbl.pdf	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ALFUZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
14% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021287s013lbl.pdf	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ALFUZOSIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087		inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP2A6 879 CYP1A2 2153	CYP1A2 1197	CYP1A 59 CYP2A6 86

Drug as perpetrator

Target	Modality	Activity
CYP1A 122	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no
CYP2A6 911	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	major		yes (co-administration study) Comment: administration with ketoconazole increased alfuzosin Cmax and AUClast by, 2.3-fold and 3.2 fold, respectively; administration with diltiazem increased Cmax and AUC0-24 of alfuzosin 1.5-fold and 1.3-fold, respectively; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_BioPharmr_P1.pdf#page=34 Page: 34.0	minor

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_Pharmr_P1.pdf#page=27 Page: 27,28

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51141	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51141
ChemicalBook	CB4332422	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4332422
eMolecules	901348	https://www.emolecules.com/cgi-bin/more?vid=901348
MolPort	MolPort-003-666-623	https://www.molport.com/shop/molecule-link/MolPort-003-666-623

PubMed

Title	Date	PubMed
Clinical significance of alpha1-adrenoceptor selectivity in the management of benign prostatic hyperplasia.	2001	12230262
Long-term aspects of medical treatment of BPH.	2001	11786671
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.	2001	11583366
Alfuzosin: overview of pharmacokinetics, safety, and efficacy of a clinically uroselective alpha-blocker.	2001 Dec	11750253
Efficacy and safety of once-daily alfuzosin in the treatment of lower urinary tract symptoms and clinical benign prostatic hyperplasia: a randomized, placebo-controlled trial.	2001 Dec	11744466
Do alpha-blockers prevent the occurrence of acute urinary retention?	2001 Mar	11306896
Worldwide experience with alfuzosin and tamsulosin.	2001 Oct	11597528
Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms.	2002	11950378
Alfuzosin: a review of the therapeutic use of the prolonged-release formulation given once daily in the management of benign prostatic hyperplasia.	2002	11893233
Tamsulosin: an update of its role in the management of lower urinary tract symptoms.	2002	11790159
Alfuzosin: a clinically uroselective alpha1-blocker.	2002 Apr	12022709
Pharmacokinetics and safety of a single oral dose of once-daily alfuzosin, 10 mg, in male subjects with mild to severe renal impairment.	2002 Dec	12463725
Finasteride in the treatment of clinical benign prostatic hyperplasia: a systematic review of randomised trials.	2002 Dec 12	12477383
[Comparative evaluation of the effectiveness and safety of combined drug therapy of patients with benign prostatic hyperplasia with finasteride and alfuzozine].	2002 Jan-Feb	11877966
Alfuzosin, an alpha1-adrenoceptor antagonist for the treatment of benign prostatic hyperplasia: once daily versus 3 times daily dosing in healthy subjects.	2002 Jul	12139205
alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia.	2002 Jul	12037374
[Chiral separation and preparation of three new antagonists of alpha 1-adrenoceptors by chiral mobile phase HPLC].	2002 Jun	12579804
Gateways to clinical trials.	2002 Oct	12500432
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness].	2002 Sep	12426862
[Drug therapy of benign prostatic hyperplasia syndrome with alpha 1-receptor blockers. Basic principles and clinical results].	2002 Sep	12426859
Clinical and pressure-flow changes after long-term treatment with alfuzosin SR.	2003	12845257
Use of alpha-blockers and the risk of hip/femur fractures.	2003 Dec	14641795
Safety and efficacy of alfuzosin 10 mg once-daily in the treatment of lower urinary tract symptoms and clinical benign prostatic hyperplasia: a pooled analysis of three double-blind, placebo-controlled studies.	2003 Dec	14632873
Proceedings of the 99th meeting of the Food and Drug Administration Cardiovascular and Renal Drugs Advisory Committee. May 29th and 30th, 2003.	2003 Jun 17	12814989
First dose efficacy of alfuzosin once daily in men with symptomatic benign prostatic hyperplasia.	2003 Nov	14624914
Alfuzosin for the management of benign prostate hyperplasia.	2003 Nov	14596659
Alfuzosin treatment for chronic prostatitis/chronic pelvic pain syndrome: a prospective, randomized, double-blind, placebo-controlled, pilot study.	2003 Sep	12946740
Priapism as a possible acute side effect of radical radiotherapy for prostate cancer.	2004 Apr	15182410
Drug approval highlights for 2003.	2004 Feb	14872168
Alfuzosin improves penile erection triggered by apomorphine in spontaneous hypertensive rats.	2004 Jan	14667526
Alfuzosin (uroxatral)--another alpha1-blocker for benign prostatic hyperplasia.	2004 Jan 5	14691408
[Can selective alpha-blockers help the spontaneous passage of the stones located in the uretero-bladder junction?].	2004 Jan-Mar	15688769
The role of alpha-blockers in the management of acute urinary retention caused by benign prostatic obstruction.	2004 Mar	15036678
Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia.	2004 Mar	14767264
[The growth inhibition effect of alpha-adrenoceptor antagonists on androgen- independent prostate cancer cell line].	2004 May 22	15265404
New drugs 04. Part III.	2004 Sep	15382384
Prostate size influences the outcome after presenting with acute urinary retention.	2004 Sep	15329112
Alfuzosin-induced acute hepatitis in a patient with chronic liver disease.	2004 Sep	15280514
Clinical assessment of drug-induced QT prolongation in association with heart rate changes.	2005 Apr	15903123
Early symptom improvement of benign prostatic hyperplasia (BPH) treated with once daily alfuzosin.	2005 Aug	16197598
Symptom deterioration during treatment and history of AUR are the strongest predictors for AUR and BPH-related surgery in men with LUTS treated with alfuzosin 10 mg once daily.	2005 Aug	16098361
A pharmacoepidemiological approach to investigating inappropriate physician prescribing in a managed care setting in Israel.	2005 Feb	15726856
Re: Alfuzosin once daily facilitates return to voiding in patients in acute urinary retention.	2005 Jul	15947706
Sexual dysfunction and lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH).	2005 Jun	15925080
Lower urinary tract symptoms suggestive of benign prostatic hyperplasia: latest update on alpha-adrenoceptor antagonists.	2005 Jun	15871733
Alfuzosin 10 mg once daily improves sexual function in men with lower urinary tract symptoms and concomitant sexual dysfunction.	2005 Nov	16217354
Alfuzosin for treatment of lower urinary tract symptoms compatible with benign prostatic hyperplasia: a systematic review of efficacy and adverse effects.	2005 Oct	16230138
The economic impact of using alfuzosin 10 mg once daily in the management of acute urinary retention in the UK: a 6-month analysis.	2005 Sep	16104911
A comparative study on the safety and efficacy of tamsulosin and alfuzosin in the management of symptomatic benign prostatic hyperplasia: a randomized controlled clinical trial.	2005 Sep-Oct	16222890

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Benign Prostatic Hyperplasia Extended-release tablet: 10 mg orally once a day immediately after the same meal each day

Route of Administration: Oral

In Vitro Use Guide

In organ baths, isolated prostatic strips and isolated bladder strips were incubated with vehicle, tadalafil (10⁻⁶ M and 10⁻⁵ M), alfuzosin (3×10⁻⁸ M or 10⁻⁶ M and 10⁻⁵ M) or a combination. Concentration-response curves (CRCs) to norepinephrine were generated on prostatic strips and detrusor strips precontracted with carbachol. Strips were also submitted to electrical field stimulation (EFS). When alfuzosin and tadalafil were combined, the maximal relaxation to norepinephrine on carbachol-precontracted detrusor strips was significantly increased compared with tadalafil alone, and EFS-induced detrusor contractions were better inhibited compared with each compound alone. Tadalafil significantly inhibited norepinephrine-induced prostatic strip contractions by reducing the maximal effect, whereas alfuzosin shifted the CRC of norepinephrine to the right. Combining both tadalafil and alfuzosin resulted in a greater relaxant effect.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:32:30 GMT 2025` Edited by `admin` on `Mon Mar 31 21:32:30 GMT 2025`
Record UNII	75046A1XTN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

UROXATRAL

Preferred Name

English

ALFUZOSIN HYDROCHLORIDE

Official Name

English

ALFUZOSIN HYDROCHLORIDE [JAN]

Common Name

English

ALFUZOSIN HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

SL-77499-10

Code

English

ALFUZOSIN HYDROCHLORIDE [USAN]

Common Name

English

ALFUZOSIN HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

ALFUZOSIN HYDROCHLORIDE [MART.]

Common Name

English

ALFUZOSIN HYDROCHLORIDE [MI]

Common Name

English

ALFUZOSIN HCL

Common Name

English

SL 77 499-10

Code

English

ALFUZOSIN HYDROCHLORIDE [USP-RS]

Common Name

English

ALFUZOSIN HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

Alfuzosin hydrochloride [WHO-DD]

Common Name

English

SL-77-499-10

Code

English

2-FURANCARBOXAMIDE, (±)-N-(3-((4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)METHYLAMINO)PROPYL)TETRAHYDRO-, MONOHYDROCHLORIDE

Common Name

English

(±)-N-(3-((4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)METHYLAMINO)PROPYL)TETRAHYDRO-2-FURAMIDE MONOHYDROCHLORIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713