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
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
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 | ( + / - ) |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9556192
Curator's Comment: Alfuzosin does not penetrate the blood–brain barrier well
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
8.0 null [pKi] | |||
8.0 null [pKi] | |||
8.5 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | UROXATRAL Approved UseUROXATRAL 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 Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.6 ng/mL |
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 |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10 h |
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14% |
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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0 |
no | |||
no | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0 |
no | |||
no | ||||
no | ||||
no | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21287_uroxatral_lbl.pdf#page=5 Page: 5.0 |
no | |||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
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 |
|||
minor |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-287_Uroxatral_Pharmr_P1.pdf#page=27 Page: 27,28 |
PubMed
Title | Date | PubMed |
---|---|---|
Clinical significance of alpha1-adrenoceptor selectivity in the management of benign prostatic hyperplasia. | 2001 |
|
Long-term aspects of medical treatment of BPH. | 2001 |
|
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia. | 2001 |
|
Alfuzosin: overview of pharmacokinetics, safety, and efficacy of a clinically uroselective alpha-blocker. | 2001 Dec |
|
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 |
|
Do alpha-blockers prevent the occurrence of acute urinary retention? | 2001 Mar |
|
Worldwide experience with alfuzosin and tamsulosin. | 2001 Oct |
|
Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms. | 2002 |
|
Alfuzosin: a review of the therapeutic use of the prolonged-release formulation given once daily in the management of benign prostatic hyperplasia. | 2002 |
|
Tamsulosin: an update of its role in the management of lower urinary tract symptoms. | 2002 |
|
Alfuzosin: a clinically uroselective alpha1-blocker. | 2002 Apr |
|
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 |
|
Finasteride in the treatment of clinical benign prostatic hyperplasia: a systematic review of randomised trials. | 2002 Dec 12 |
|
[Comparative evaluation of the effectiveness and safety of combined drug therapy of patients with benign prostatic hyperplasia with finasteride and alfuzozine]. | 2002 Jan-Feb |
|
Alfuzosin, an alpha1-adrenoceptor antagonist for the treatment of benign prostatic hyperplasia: once daily versus 3 times daily dosing in healthy subjects. | 2002 Jul |
|
alpha-Adrenoceptor antagonists in the treatment of benign prostate hyperplasia. | 2002 Jul |
|
[Chiral separation and preparation of three new antagonists of alpha 1-adrenoceptors by chiral mobile phase HPLC]. | 2002 Jun |
|
Gateways to clinical trials. | 2002 Oct |
|
[alpha 1-receptor blockade in therapy of benign prostatic hyperplasia syndrome. Correct dosing for optimal effectiveness]. | 2002 Sep |
|
[Drug therapy of benign prostatic hyperplasia syndrome with alpha 1-receptor blockers. Basic principles and clinical results]. | 2002 Sep |
|
Clinical and pressure-flow changes after long-term treatment with alfuzosin SR. | 2003 |
|
Use of alpha-blockers and the risk of hip/femur fractures. | 2003 Dec |
|
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 |
|
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 |
|
First dose efficacy of alfuzosin once daily in men with symptomatic benign prostatic hyperplasia. | 2003 Nov |
|
Alfuzosin for the management of benign prostate hyperplasia. | 2003 Nov |
|
Alfuzosin treatment for chronic prostatitis/chronic pelvic pain syndrome: a prospective, randomized, double-blind, placebo-controlled, pilot study. | 2003 Sep |
|
Priapism as a possible acute side effect of radical radiotherapy for prostate cancer. | 2004 Apr |
|
Drug approval highlights for 2003. | 2004 Feb |
|
Alfuzosin improves penile erection triggered by apomorphine in spontaneous hypertensive rats. | 2004 Jan |
|
Alfuzosin (uroxatral)--another alpha1-blocker for benign prostatic hyperplasia. | 2004 Jan 5 |
|
[Can selective alpha-blockers help the spontaneous passage of the stones located in the uretero-bladder junction?]. | 2004 Jan-Mar |
|
The role of alpha-blockers in the management of acute urinary retention caused by benign prostatic obstruction. | 2004 Mar |
|
Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia. | 2004 Mar |
|
[The growth inhibition effect of alpha-adrenoceptor antagonists on androgen- independent prostate cancer cell line]. | 2004 May 22 |
|
New drugs 04. Part III. | 2004 Sep |
|
Prostate size influences the outcome after presenting with acute urinary retention. | 2004 Sep |
|
Alfuzosin-induced acute hepatitis in a patient with chronic liver disease. | 2004 Sep |
|
Clinical assessment of drug-induced QT prolongation in association with heart rate changes. | 2005 Apr |
|
Early symptom improvement of benign prostatic hyperplasia (BPH) treated with once daily alfuzosin. | 2005 Aug |
|
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 |
|
A pharmacoepidemiological approach to investigating inappropriate physician prescribing in a managed care setting in Israel. | 2005 Feb |
|
Re: Alfuzosin once daily facilitates return to voiding in patients in acute urinary retention. | 2005 Jul |
|
Sexual dysfunction and lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH). | 2005 Jun |
|
Lower urinary tract symptoms suggestive of benign prostatic hyperplasia: latest update on alpha-adrenoceptor antagonists. | 2005 Jun |
|
Alfuzosin 10 mg once daily improves sexual function in men with lower urinary tract symptoms and concomitant sexual dysfunction. | 2005 Nov |
|
Alfuzosin for treatment of lower urinary tract symptoms compatible with benign prostatic hyperplasia: a systematic review of efficacy and adverse effects. | 2005 Oct |
|
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 |
|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/alfuzosin.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19428174
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
Edited
Mon Mar 31 21:32:30 GMT 2025
by
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on
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Record UNII |
75046A1XTN
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Record Status |
Validated (UNII)
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Record Version |
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C29713
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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