Tamsulosin

Identification

Summary

Tamsulosin is an alpha-1A and alpha-1B adrenergic receptor antagonist used to treat benign prostatic hyperplasia, ureteral stones, prostatitis, and female voiding dysfunction.

Brand Names

Flomax, Jalyn

Generic Name

Tamsulosin

DrugBank Accession Number

DB00706

Background

Tamsulosin is a selective alpha-1A and alpha-1B adrenoceptor antagonist that exerts its greatest effect in the prostate and bladder, where these receptors are most common.^Label It is indicated for the treatment of signs and symptoms of benign prostatic hypertrophy.^Label Antagonism of these receptors leads to relaxation of smooth muscle in the prostate and detrusor muscles in the bladder, allowing for better urinary flow.^Label Other alpha-1 adrenoceptor antagonists developed in the 1980s were less selective and more likely to act on the smooth muscle of blood vessels, resulting in hypotension.⁵

Tamsulosin was first approved by the FDA on April 15, 1997.⁶

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 408.512
Monoisotopic: 408.171892706
Chemical Formula: C₂₀H₂₈N₂O₅S

Synonyms

(−)-tamsulosin
(R)-(−)-tamsulosin
(R)-5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide
Tamsulosin
Tamsulosina
Tamsulosine
Tamsulosinum

External IDs

HGP-0412
HIP-1402
HIP1402
LY 253351
Y 617
YM 12617-1
YM-617

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Pharmacology

Indication

Tamsulosin is indicated for the treatment of signs and symptoms of benign prostatic hyperplasia.^Label

Tamsulosin is also used off label for the treatment of ureteral stones, prostatitis, and female voiding dysfunction.^4,7

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level
Symptomatic treatment of	Benign prostatic hyperplasia		••••••••••••
Used in combination to treat	Benign prostatic hypertrophy	Combination Product in combination with: Dutasteride (DB01126)	••••••••••••
Symptomatic treatment of	Bladder outlet obstruction		••• •••••
Treatment of	Ureteral calculi		••• •••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Tamsulosin is an alpha adrenoceptor blocker with specificity for the alpha-1A and alpha-1D subtypes, which are more common in the prostate and submaxillary tissue.¹ The final subtype, alpha-1B, are most common in the aorta and spleen.¹ Tamsulosin binds to alpha-1A receptors 3.9-38 times more selectively than alpha-1B and 3-20 times more selectively than alpha-1D.¹ This selectivity allows for a significant effect on urinary flow with a reduced incidence of adverse reactions like orthostatic hypotension.¹

Mechanism of action

Tamsulosin is a blocker of alpha-1A and alpha-1D adrenoceptors.^Label,1 About 70% of the alpha-1 adrenoceptors in the prostate are of the alpha-1A subtype.^Label By blocking these adrenoceptors, smooth muscle in the prostate is relaxed and urinary flow is improved.^Label The blocking of alpha-1D adrenoceptors relaxes the detrusor muscles of the bladder which prevents storage symptoms.¹ The specificity of tamsulosin focuses the effects to the target area while minimizing effects in other areas.^Label

Target	Actions	Organism
AAlpha-1A adrenergic receptor	antagonist	Humans
UAlpha-1D adrenergic receptor	antagonist	Humans
UAlpha-1B adrenergic receptor	antagonist	Humans

Absorption

Oral tamsulosin is 90% absorbed in fasted patients.^Label The area under the curve is 151-199ng/mL*hr for a 0.4mg oral dose and 440-557ng/mL*hr for a 0.8mg oral dose.^Label The maximum plasma concentration is 3.1-5.3ng/mL for a 0.4mg oral dose and 2.5-3.6ng/mL for a 0.8mg oral dose.^Label Taking tamsulosin with food increases the time to maximum concentration from 4-5 hours to 6-7 hours but increases bioavailability by 30% and maximum plasma concentration by 40-70%.^Label

Volume of distribution

16L after intravenous administration.^Label

Protein binding

Tamsulosin is 94%-99% protein bound, mostly to alpha-1-acid glycoprotein.^Label

Metabolism

Tamsulosin is mostly metabolized in the liver by cytochrome P450 (CYP) 3A4 and 2D6, with some metabolism by other CYPs.^Label,1 CYP3A4 is responsible for the deethylation of tamsulosin to the M-1 metabolite and the oxidative deamination to the AM-1 metabolite,^2,3 while CYP2D6 is responsible for the hydroxylation of tamsulosin to the M-3 metabolite and the demethylation of tamsulosin to the M-4 metabolite.² In addition, tamsulosin can be hydroxylated at a different position by an unknown enzyme to form the M-2 metabolite.² The M-1, M-2, M-3, and M-4 metabolites can be glucuronidated, and the M-1 and M-3 metabolites can undergo sulfate conjugation to form other metabolites before excretion.³

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Tamsulosin

Route of elimination

97% of an orally administered does is recovered in studies, which 76% in the urine and 21% in the feces after 168 hours.^Label 8.7% of the dose is excreted as unmetabolized tamsulosin.^Label,1

Half-life

The half life in fasted patients is 14.9±3.9 hours.^Label The elimination half life is 5-7 hours and the apparent half life is 9 to 13 hours in healthy subjects.^Label In patients who require tamsulosin, the apparent half life is 14-15 hours.^Label

Clearance

2.88L/h.^Label

Adverse Effects

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Toxicity

In the event of overdose, patients may experience hypotension and should lie down in a supine position to maintain blood pressure and heart rate.^Label If further measures are required intravenous fluids should be considered.^Label If further progression is required, vasopressors may be used and renal function should be monitored.^Label Dialysis is unlikely to assist in treating overdose because tamsulosin is extensively protein bound.^Label

The oral LD50 in rats is 650mg/kg.^MSDS

Tamsulosin is not indicated for use in women and no studies have been performed in pregnancy, though animal studies have not shown fetal harm.^Label Tamsulosin is excreted in the milk of rats but there is no available data on what the effect of this tamsulosin exposure may be.^Label Animal studies have shown male and female rat fertility is affected by tamsulosin due to impairment of ejaculation and fertilization.^Label In men, tamsulosin is associated with abnormal ejaculation.^Label Tamsulosin is not mutagenic but may be carcinogenic at levels above the maximum recommended human dose.^Label Female rats experience a slight increase in the rates of mammary gland fibroadenomas and adenocarcinomas.^Label

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Tamsulosin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abaloparatide	The risk or severity of adverse effects can be increased when Tamsulosin is combined with Abaloparatide.
Abametapir	The serum concentration of Tamsulosin can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Tamsulosin can be increased when combined with Abatacept.
Abiraterone	The metabolism of Tamsulosin can be decreased when combined with Abiraterone.

Food Interactions

Take after a meal. Take 30 minutes after the same meal each day to reduce plasma level variations.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Tamsulosin hydrochloride	11SV1951MR	106463-17-6	ZZIZZTHXZRDOFM-XFULWGLBSA-N

Product Images

International/Other Brands

Betamsal (Hemofarm) / Contiflo XL (Ranbaxy) / Flomaxtra (Astellas) / Harnal D (Astellas) / Maxrin (Square) / Mecir (Boehringer Ingelheim) / Omexel (Astellas) / Omipro (Jelfa) / Omix (Astellas) / Omnic (Astellas Pharma Europe) / Pradif (Boehringer Ingelheim) / Ranomax (Ranbaxy) / Salover (Aversi) / Secotex (Boehringer Ingelheim) / Stronazon (Actavis) / Tamsact (Actavis) / Tamsol (Apex) / Tamsul (Aspen Pharmacare) / Urimax (Celeris)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Flomax	Capsule	0.4 mg/1	Oral	Cardinal Health	1997-09-12	2012-09-30
Flomax	Capsule	0.4 mg/1	Oral	Physicians Total Care, Inc.	2001-08-28	Not applicable
Flomax	Capsule, extended release	0.4 mg	Oral	Boehringer Ingelheim (Canada) Ltd Ltee	1998-06-19	2009-08-27
Flomax	Capsule	0.4 mg/1	Oral	REMEDYREPACK INC.	2017-09-13	2020-04-06
Flomax	Capsule	0.4 mg/1	Oral	Boehringer Ingelheim Pharmaceuticals, Inc.	1997-09-12	2014-11-03

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-tamsulosin CR	Tablet, extended release	0.4 mg	Oral	Apotex Corporation	2012-02-09	Not applicable
Ava-tamsulosin CR	Tablet, extended release	0.4 mg	Oral	Avanstra Inc	2011-09-19	2014-08-21
Jamp Tamsulosin	Capsule, extended release	0.4 mg	Oral	Jamp Pharma Corporation	2010-06-16	Not applicable
Mylan-tamsulosin	Capsule, extended release	0.4 mg	Oral	Mylan Pharmaceuticals	2007-08-16	2017-01-09
Ran-tamsulosin	Capsule, extended release	0.4 mg	Oral	Ranbaxy Inc.	2007-08-15	2012-06-13

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Aglandin comp. 0,5 mg/0,4 mg-Hartkapseln	Tamsulosin hydrochloride (0.4 mg) + Dutasteride (0.5 mg)	Capsule	Oral	G.L. Pharma Gmb H	2019-01-16	Not applicable
DUODART	Tamsulosin (0.4 MG) + Dutasteride (0.5 MG)	Capsule	Oral	บริษัท แกล็กโซสมิทไคล์น (ประเทศไทย) จำกัด	2018-09-24	Not applicable
DUODART 0,5 MG/0,4 MG KAPSÜL,30 KAPSÜL	Tamsulosin hydrochloride (0.4 mg) + Dutasteride (0.5 mg)	Capsule	Oral	GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.	2020-08-14	2020-05-22
DUODART 0,5 MG/0,4 MG KAPSÜL,7 KAPSÜL	Tamsulosin hydrochloride (0.4 mg) + Dutasteride (0.5 mg)	Capsule	Oral	GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.	2020-08-14	2020-05-22
DUODART 0,5 MG/0,4 MG KAPSÜL,90 KAPSÜL	Tamsulosin hydrochloride (0.4 mg) + Dutasteride (0.5 mg)	Capsule	Oral	GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.	2020-08-14	2020-05-22

Chemical Identifiers

UNII: G3P28OML5I
CAS number: 106133-20-4
InChI Key: DRHKJLXJIQTDTD-OAHLLOKOSA-N
InChI: InChI=1S/C20H28N2O5S/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24)/t15-/m1/s1
IUPAC Name: 5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide
SMILES: CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC(=C(OC)C=C1)S(N)(=O)=O

References

Synthesis Reference

Hun Wang, Jun Park, Min Kwon, Ji Shim, Bong Lee, Hong Jeon, "Controlled release formulation of tamsulosin hydrochloride and preparation process thereof." U.S. Patent US20050100606, issued May 12, 2005.

US20050100606

General References

Dunn CJ, Matheson A, Faulds DM: Tamsulosin: a review of its pharmacology and therapeutic efficacy in the management of lower urinary tract symptoms. Drugs Aging. 2002;19(2):135-61. [Article]
Matsushima H, Kamimura H, Soeishi Y, Watanabe T, Higuchi S, Tsunoo M: Pharmacokinetics and plasma protein binding of tamsulosin hydrochloride in rats, dogs, and humans. Drug Metab Dispos. 1998 Mar;26(3):240-5. [Article]
Soeishi Y, Matsushima H, Watanabe T, Higuchi S, Cornelissen K, Ward J: Absorption, metabolism and excretion of tamsulosin hydrochloride in man. Xenobiotica. 1996 Jun;26(6):637-45. [Article]
Rivard R: Tamsulosin: ureteral stones (distal). Hosp Pharm. 2015 Jan;50(1):31-3. doi: 10.1310/hjp5001-031. [Article]
Lepor H, Roehrborn C: Historical Overview of Medical Therapy for Benign Prostatic Hyperplasia Reviews in Urology. [Article]
FDA Approved Drug Products: Flomax [Link]
Urology Times: Urologists no longer primary initiator of tamsulosin [Link]

External Links

Human Metabolome Database: HMDB0014844
KEGG Compound: C07124
PubChem Compound: 129211
PubChem Substance: 46507763
ChemSpider: 114457
BindingDB: 50060964
RxNav: 77492
ChEBI: 9398
ChEMBL: CHEMBL836
ZINC: ZINC000001530694
Therapeutic Targets Database: DAP000086
PharmGKB: PA451583
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: JGX
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Tamsulosin

PDB Entries

7ymj

FDA label

Download (570 KB)

MSDS

Download (20.3 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Benign Prostatic Hyperplasia (BPH) / Lower Urinary Tract Symptoms (LUTS)	1
4	Active Not Recruiting	Treatment	Benign Prostatic Hyperplasia (BPH) / Overactive Bladder Syndrome (OABS)	1
4	Active Not Recruiting	Treatment	Lower Ureteric Stones	1
4	Completed	Basic Science	Benign Prostatic Hyperplasia (BPH)	1
4	Completed	Prevention	Postoperative Urinary Retention (POUR)	2

Pharmacoeconomics

Manufacturers

Boehringer ingelheim pharmaceuticals inc
Impax laboratories inc
Mylan pharmaceuticals inc
Sandoz inc
Sun pharmaceutical industries ltd
Synthon pharmaceuticals inc
Teva pharmaceuticals usa
Wockhardt ltd
Zydus pharmaceuticals usa inc

Packagers

Actavis Group
AQ Pharmaceuticals Inc.
A-S Medication Solutions LLC
Astellas Pharma Inc.
Atlantic Biologicals Corporation
Boehringer Ingelheim Ltd.
Bryant Ranch Prepack
Cadila Healthcare Ltd.
Cardinal Health
Diversified Healthcare Services Inc.
GlaxoSmithKline Inc.
Global Pharmaceuticals
Kaiser Foundation Hospital
Major Pharmaceuticals
Mylan
Pharmacy Service Center
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Redpharm Drug
Resource Optimization and Innovation LLC
Sandoz
Stat Rx Usa
Synthon Pharmaceuticals Inc.
Teva Pharmaceutical Industries Ltd.
UDL Laboratories
Vangard Labs Inc.
Wockhardt Ltd.
Zydus Pharmaceuticals

Dosage Forms

Form	Route	Strength
Capsule	Oral	5.000 mg
Capsule	Oral
Capsule	Oral	0.400 mg
Capsule, coated	Oral	0.22 mg
Capsule, extended release	Oral	0.4 mg
Capsule	Oral	0.4 mg/1
Tablet	Oral	0.4 mg
Tablet, soluble	Oral
Tablet	Oral	0.2 mg
Tablet, film coated	Oral	0.4 mg
Tablet, film coated	Oral
Tablet, film coated, extended release	Oral	0.4 mg
Capsule	Oral
Capsule, extended release	Oral
Capsule, delayed release	Oral
Capsule	Oral	0.4 MG
Capsule	Oral	200.000 mg
Capsule	Oral	333.0000 mg
Capsule, extended release	Oral	0.4 mg / cap
Tablet	Oral	0.400 mg
Capsule, delayed release	Oral	0.4 MG
Capsule, delayed release pellets	Oral
Capsule, coated	Oral
Capsule	Oral	.4 mg/1
Capsule	Oral	0.4 mg/0.4mg
Tablet, extended release	Oral
Tablet, film coated, extended release	Oral	0.40 mg
Capsule, extended release	Oral
Capsule, extended release	Oral	400 MICROGRAMMI
Capsule	Oral	0.4 MG
Tablet	Oral
Tablet, extended release	Oral	0.4 mg
Capsule, gelatin coated		0.4 mg
Tablet, delayed release	Oral
Capsule	Oral	0.500 mg

Prices

Unit description	Cost	Unit
Flomax 0.4 mg capsule	4.71USD	capsule
Tamsulosin hcl 0.4 mg capsule	4.3USD	capsule
Flomax Cr 0.4 mg Extended-Release Tablet	0.63USD	tablet
Mylan-Tamsulosin 0.4 mg Sustained-Release Capsule	0.63USD	capsule
Novo-Tamsulosin 0.4 mg Sustained-Release Capsule	0.57USD	capsule
Ran-Tamsulosin 0.4 mg Sustained-Release Capsule	0.57USD	capsule
Ratio-Tamsulosin 0.4 mg Sustained-Release Capsule	0.57USD	capsule
Sandoz Tamsulosin 0.4 mg Sustained-Release Capsule	0.57USD	capsule
Tamsulosin 0.4 mg Sustained-Release Capsule	0.57USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US4703063	No	1987-10-27	2010-04-27
CA2490299	No	2008-08-26	2023-12-24
CA2144077	No	2005-05-24	2013-09-10
US5565467	No	1996-10-15	2015-11-20

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	230	FDA Label
water solubility	Sparingly soluble in water	FDA Label

Predicted Properties

Property	Value	Source
Water Solubility	0.00655 mg/mL	ALOGPS
logP	3.05	ALOGPS
logP	2.04	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.93	Chemaxon
pKa (Strongest Basic)	9.28	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	99.88 Å²	Chemaxon
Rotatable Bond Count	11	Chemaxon
Refractivity	108.86 m³·mol^-1	Chemaxon
Polarizability	43.95 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.997
Blood Brain Barrier	+	0.5915
Caco-2 permeable	-	0.6473
P-glycoprotein substrate	Substrate	0.5911
P-glycoprotein inhibitor I	Non-inhibitor	0.5734
P-glycoprotein inhibitor II	Non-inhibitor	0.5522
Renal organic cation transporter	Non-inhibitor	0.8178
CYP450 2C9 substrate	Non-substrate	0.7898
CYP450 2D6 substrate	Substrate	0.8919
CYP450 3A4 substrate	Substrate	0.6012
CYP450 1A2 substrate	Non-inhibitor	0.7876
CYP450 2C9 inhibitor	Inhibitor	0.5916
CYP450 2D6 inhibitor	Non-inhibitor	0.8614
CYP450 2C19 inhibitor	Non-inhibitor	0.5056
CYP450 3A4 inhibitor	Inhibitor	0.718
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6146
Ames test	Non AMES toxic	0.6245
Carcinogenicity	Non-carcinogens	0.6419
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.4091 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8367
hERG inhibition (predictor II)	Non-inhibitor	0.6971

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0fc0-1696000000-feeed148e3d1a2085e88
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0abi-0090200000-dd7803e5aaaea60d41df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1161900000-79b54b73964ee5987c2d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-05r0-1496100000-799f3938ab8fce9f4f7c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05fr-0091100000-a88e2ac4326a4d8a69b4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052f-7935200000-d739988cd42698037251
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0zfr-2291000000-dbd0c8f638da9e7b308d
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	202.4959786	predicted	DarkChem Lite v0.1.0
[M-H]-	191.92873	predicted	DeepCCS 1.0 (2019)
[M+H]+	203.6285786	predicted	DarkChem Lite v0.1.0
[M+H]+	194.28671	predicted	DeepCCS 1.0 (2019)
[M+Na]+	202.7988786	predicted	DarkChem Lite v0.1.0
[M+Na]+	201.101	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.029	N/A	N/A	A28816
Ki (nM)	0.13	N/A	N/A	A28817
Ki (nM)	0.2	N/A	N/A	A28818
Ki (nM)	0.19	N/A	N/A	A28819 / A28820
Ki (nM)	0.0501	N/A	N/A	A28821

Details1. Alpha-1A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1A
Uniprot ID: P35348
Uniprot Name: Alpha-1A adrenergic receptor
Molecular Weight: 51486.005 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Abrams P, Speakman M, Stott M, Arkell D, Pocock R: A dose-ranging study of the efficacy and safety of tamsulosin, the first prostate-selective alpha 1A-adrenoceptor antagonist, in patients with benign prostatic obstruction (symptomatic benign prostatic hyperplasia). Br J Urol. 1997 Oct;80(4):587-96. [Article]
Na YJ, Guo YL, Gu FL: Clinical comparison of selective and non-selective alpha 1A-adrenoceptor antagonists for bladder outlet obstruction associated with benign prostatic hyperplasia: studies on tamsulosin and terazosin in Chinese patients. The Chinese Tamsulosin Study Group. J Med. 1998;29(5-6):289-304. [Article]
Lee E, Lee C: Clinical comparison of selective and non-selective alpha 1A-adrenoreceptor antagonists in benign prostatic hyperplasia: studies on tamsulosin in a fixed dose and terazosin in increasing doses. Br J Urol. 1997 Oct;80(4):606-11. [Article]
Chapple CR, Wyndaele JJ, Nordling J, Boeminghaus F, Ypma AF, Abrams P: Tamsulosin, the first prostate-selective alpha 1A-adrenoceptor antagonist. A meta-analysis of two randomized, placebo-controlled, multicentre studies in patients with benign prostatic obstruction (symptomatic BPH). European Tamsulosin Study Group. Eur Urol. 1996;29(2):155-67. [Article]
Schulman CC, Cortvriend J, Jonas U, Lock TM, Vaage S, Speakman MJ: Tamsulosin, the first prostate-selective alpha 1A-adrenoceptor antagonist. Analysis of a multinational, multicentre, open-label study assessing the long-term efficacy and safety in patients with benign prostatic obstruction (symptomatic BPH). European Tamsulosin Study Group. Eur Urol. 1996;29(2):145-54. [Article]
Chen Y, Li H, Dong Q, Wang KJ: Blockade of alpha 1A-adrenoceptor: a novel possible strategy for male contraception. Med Hypotheses. 2009 Aug;73(2):140-1. doi: 10.1016/j.mehy.2009.02.022. Epub 2009 May 8. [Article]
Michel MC, de la Rosette JJ: Efficacy and safety of tamsulosin in the treatment of urological diseases. Expert Opin Pharmacother. 2004 Jan;5(1):151-60. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.058	N/A	N/A	A28816
Ki (nM)	0.18	N/A	N/A	A28817
Ki (nM)	0.056	N/A	N/A	A28823
Ki (nM)	0.2	N/A	N/A	A28819 / A28820
Ki (nM)	0.1	N/A	N/A	A28821

Details2. Alpha-1D adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Alpha1-adrenergic receptor activity
Specific Function: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name: ADRA1D
Uniprot ID: P25100
Uniprot Name: Alpha-1D adrenergic receptor
Molecular Weight: 60462.205 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Noble AJ, Chess-Williams R, Couldwell C, Furukawa K, Uchyiuma T, Korstanje C, Chapple CR: The effects of tamsulosin, a high affinity antagonist at functional alpha 1A- and alpha 1D-adrenoceptor subtypes. Br J Pharmacol. 1997 Jan;120(2):231-8. [Article]
Lowe FC: Summary of clinical experiences with tamsulosin for the treatment of benign prostatic hyperplasia. Rev Urol. 2005;7 Suppl 4:S13-21. [Article]
Tomiyama Y, Tatemichi S, Tadachi M, Kobayashi S, Hayashi M, Kobayashi M, Yamazaki Y, Shibata N: [Effect of silodosin on intraurethral pressure increase induced by hypogastric nerve stimulation in dogs with benign prostatic hyperplasia]. Yakugaku Zasshi. 2006 Mar;126 Spec no.:225-30. [Article]
Ishiguro M, Futabayashi Y, Ohnuki T, Ahmed M, Muramatsu I, Nagatomo T: Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. Life Sci. 2002 Oct 11;71(21):2531-41. [Article]
Taguchi K, Saitoh M, Sato S, Asano M, Michel MC: Effects of tamsulosin metabolites at alpha-1 adrenoceptor subtypes. J Pharmacol Exp Ther. 1997 Jan;280(1):1-5. [Article]
Michel MC, de la Rosette JJ: Efficacy and safety of tamsulosin in the treatment of urological diseases. Expert Opin Pharmacother. 2004 Jan;5(1):151-60. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.61	N/A	N/A	A28816
Ki (nM)	0.2	N/A	N/A	A28822
Ki (nM)	1.92	N/A	N/A	A28817
Ki (nM)	0.6	N/A	N/A	A28823
Ki (nM)	2	N/A	N/A	A28819 / A28820
Ki (nM)	0.631	N/A	N/A	A28821

Details3. Alpha-1B adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1B
Uniprot ID: P35368
Uniprot Name: Alpha-1B adrenergic receptor
Molecular Weight: 56835.375 Da

References

Ishiguro M, Futabayashi Y, Ohnuki T, Ahmed M, Muramatsu I, Nagatomo T: Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. Life Sci. 2002 Oct 11;71(21):2531-41. [Article]
Michel MC, Hanft G, Gross G: Functional studies on alpha 1-adrenoceptor subtypes mediating inotropic effects in rat right ventricle. Br J Pharmacol. 1994 Feb;111(2):539-46. [Article]
Taguchi K, Saitoh M, Sato S, Asano M, Michel MC: Effects of tamsulosin metabolites at alpha-1 adrenoceptor subtypes. J Pharmacol Exp Ther. 1997 Jan;280(1):1-5. [Article]
Richardson CD, Donatucci CF, Page SO, Wilson KH, Schwinn DA: Pharmacology of tamsulosin: saturation-binding isotherms and competition analysis using cloned alpha 1-adrenergic receptor subtypes. Prostate. 1997 Sep 15;33(1):55-9. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Michel MC, de la Rosette JJ: Efficacy and safety of tamsulosin in the treatment of urological diseases. Expert Opin Pharmacother. 2004 Jan;5(1):151-60. [Article]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Kamimura H, Oishi S, Matsushima H, Watanabe T, Higuchi S, Hall M, Wood SG, Chasseaud LF: Identification of cytochrome P450 isozymes involved in metabolism of the alpha1-adrenoceptor blocker tamsulosin in human liver microsomes. Xenobiotica. 1998 Oct;28(10):909-22. doi: 10.1080/004982598238985 . [Article]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Kamimura H, Oishi S, Matsushima H, Watanabe T, Higuchi S, Hall M, Wood SG, Chasseaud LF: Identification of cytochrome P450 isozymes involved in metabolism of the alpha1-adrenoceptor blocker tamsulosin in human liver microsomes. Xenobiotica. 1998 Oct;28(10):909-22. doi: 10.1080/004982598238985 . [Article]

Carriers

Details1. Alpha-1-acid glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: No

General Function: Not Available
Specific Function: Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name: ORM1
Uniprot ID: P02763
Uniprot Name: Alpha-1-acid glycoprotein 1
Molecular Weight: 23511.38 Da

References

Matsushima H, Watanabe T, Higuchi S: Effect of alpha(1)-acid glycoprotein on the pharmacokinetics of tamsulosin in rats treated with turpentine oil. J Pharm Sci. 2000 Apr;89(4):490-8. [Article]
Hanada K, Tochikura N, Ogata H: Selective binding of tamsulosin to genetic variants of human alpha1-acid glycoprotein. Biol Pharm Bull. 2007 Aug;30(8):1593-5. [Article]
Koiso K, Akaza H, Kikuchi K, Aoyagi K, Ohba S, Miyazaki M, Ito M, Sueyoshi T, Matsushima H, Kamimura H, Watanabe T, Higuchi S: Pharmacokinetics of tamsulosin hydrochloride in patients with renal impairment: effects of alpha 1-acid glycoprotein. J Clin Pharmacol. 1996 Nov;36(11):1029-38. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Tamsulosin

Identification

Structure for Tamsulosin (DB00706)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

Enzymes

References

References

Carriers

References