Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C19H27N5O4 |
| Molecular Weight | 389.4488 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1OC)C(N)=NC(=N2)N(C)CCCNC(=O)C3CCCO3
InChI
InChIKey=WNMJYKCGWZFFKR-UHFFFAOYSA-N
InChI=1S/C19H27N5O4/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)
| 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.
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 |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| 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 |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Alfuzosin 10 mg once daily improves sexual function in men with lower urinary tract symptoms and concomitant sexual dysfunction. | 2005-11 |
|
| 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. | 2005-10-15 |
|
| Alfuzosin for treatment of lower urinary tract symptoms compatible with benign prostatic hyperplasia: a systematic review of efficacy and adverse effects. | 2005-10 |
|
| The economic impact of using alfuzosin 10 mg once daily in the management of acute urinary retention in the UK: a 6-month analysis. | 2005-09 |
|
| Early symptom improvement of benign prostatic hyperplasia (BPH) treated with once daily alfuzosin. | 2005-08 |
|
| 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. | 2005-08 |
|
| Re: Alfuzosin once daily facilitates return to voiding in patients in acute urinary retention. | 2005-07 |
|
| Sexual dysfunction and lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH). | 2005-06 |
|
| Lower urinary tract symptoms suggestive of benign prostatic hyperplasia: latest update on alpha-adrenoceptor antagonists. | 2005-06 |
|
| Efficacy and safety of two doses (10 and 15 mg) of alfuzosin or tamsulosin (0.4 mg) once daily for treating symptomatic benign prostatic hyperplasia. | 2005-05 |
|
| Clinical assessment of drug-induced QT prolongation in association with heart rate changes. | 2005-04 |
|
| [The role of alpha1-adrenoblocker alfuzosine in diagnostic-therapeutic algorithm of hyperactive urinary bladder management in women and selection of patients for treatment with M-cholinergic antagonists]. | 2005-03-22 |
|
| The vasodilatory effect of alfuzosin and tamsulosin in passive orthostasis: a randomised, double-blind, placebo-controlled study. | 2005-03 |
|
| Re: alfuzosin once daily facilitates return to voiding in patients in acute urinary retention. | 2005-03 |
|
| Alfuzosin 10 mg once daily improves sexual function in men with lower urinary tract symptoms and concomitant sexual dysfunction. | 2005-03 |
|
| The clinical efficacy and tolerability of doxazosin standard and gastrointestinal therapeutic system for benign prostatic hyperplasia. | 2005-03 |
|
| [Can selective alpha-blockers help the spontaneous passage of the stones located in the uretero-bladder junction?]. | 2005-02-04 |
|
| A pharmacoepidemiological approach to investigating inappropriate physician prescribing in a managed care setting in Israel. | 2005-02 |
|
| Evaluation of tamsulosin and alfuzosin activity in the rat vas deferens: relevance to ejaculation delays. | 2005-02 |
|
| Alfuzosin 10 mg once daily in the management of acute urinary retention: results of a double-blind placebo-controlled study. | 2005-01 |
|
| Role of the newer alpha, -adrenergic-receptor antagonists in the treatment of benign prostatic hyperplasia-related lower urinary tract symptoms. | 2004-11 |
|
| Delayed complications of discontinuation of intrathecal baclofen therapy: resurgence of dyssynergic voiding, which triggered off autonomic dysreflexia and hydronephrosis. | 2004-10 |
|
| New drugs 04. Part III. | 2004-09 |
|
| Prostate size influences the outcome after presenting with acute urinary retention. | 2004-09 |
|
| Alfuzosin-induced acute hepatitis in a patient with chronic liver disease. | 2004-09 |
|
| Ejaculatory dysfunction and alpha-adrenoceptor antagonists. | 2004-08 |
|
| [A suggested treatment algorithm in nocturnal enuresis with emphasis on partial responders]. | 2004-07 |
|
| On call. My doctor gave me a prescription for Uroxatral to treat my enlarged prostate. I tried to look up this medicine in your Harvard Medical School Guide to Men's Health, but I couldn't find it. What can you tell me about Uroxatral? | 2004-06 |
|
| Alfuzosin once daily facilitates return to voiding in patients in acute urinary retention. | 2004-06 |
|
| [The growth inhibition effect of alpha-adrenoceptor antagonists on androgen- independent prostate cancer cell line]. | 2004-05-22 |
|
| New drugs of 2003. | 2004-04-22 |
|
| Priapism as a possible acute side effect of radical radiotherapy for prostate cancer. | 2004-04 |
|
| Comparative efficacy of two alpha-adrenoreceptor antagonists, doxazosin and alfuzosin, in patients with lower urinary tract symptoms from benign prostatic enlargement. | 2004-04 |
|
| Extended-release alfuzosin hydrochloride: a new alpha-adrenergic receptor antagonist for symptomatic benign prostatic hyperplasia. | 2004-03 |
|
| Patients with bladder outlet obstruction who refuse treatment show no clinical and urodynamic change after long-term follow-up. | 2004-03 |
|
| The role of alpha-blockers in the management of acute urinary retention caused by benign prostatic obstruction. | 2004-03 |
|
| A comparison of the effects of tamsulosin and alfuzosin on neurally evoked increases in bladder neck and seminal vesicle pressure in rats. | 2004-03 |
|
| Alpha1-adrenergic receptors and their inhibitors in lower urinary tract symptoms and benign prostatic hyperplasia. | 2004-03 |
|
| A current review of medical therapy for benign prostatic hyperplasia. | 2004-02 |
|
| Drug approval highlights for 2003. | 2004-02 |
|
| Alfuzosin (uroxatral)--another alpha1-blocker for benign prostatic hyperplasia. | 2004-01-05 |
|
| Real life practice in the management of benign prostatic hyperplasia. | 2004-01 |
|
| Alfuzosin improves penile erection triggered by apomorphine in spontaneous hypertensive rats. | 2004-01 |
|
| A comparison of four different alpha1-blockers in benign prostatic hyperplasia patients with and without diabetes. | 2004 |
|
| Use of alpha-blockers and the risk of hip/femur fractures. | 2003-12 |
|
| 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. | 2003-12 |
|
| First dose efficacy of alfuzosin once daily in men with symptomatic benign prostatic hyperplasia. | 2003-11 |
|
| Alfuzosin for the management of benign prostate hyperplasia. | 2003-11 |
|
| [Pharmacologic treatment of benign prostatic hyperplasia]. | 2003-09-14 |
|
| Estimated costs of treatment of benign prostate hyperplasia in Brazil. | 2002-10-24 |
Patents
Sample Use Guides
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 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
Wed Apr 02 08:56:13 GMT 2025
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| Record UNII |
90347YTW5F
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| Record Status |
Validated (UNII)
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WHO-ATC |
G04CA51
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WHO-VATC |
QG04CA51
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WHO-VATC |
QG04CA01
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NBK548748
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NDF-RT |
N0000175553
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N0000000099
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C29713
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WHO-ATC |
G04CA01
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760065
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C047638
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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TARGET -> INHIBITOR |
| Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
in vitro
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
FECAL
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
FECAL
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
FECAL
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METABOLITE INACTIVE -> PARENT |
URINE
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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| Tmax | PHARMACOKINETIC |
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| Volume of Distribution | PHARMACOKINETIC |
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