Identification

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Name
Tamsulosin
Accession Number
DB00706  (APRD00036)
Type
Small Molecule
Groups
Approved, Investigational
Description

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

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Tamsulosin hydrochloride11SV1951MR106463-17-6ZZIZZTHXZRDOFM-XFULWGLBSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FlomaxCapsule0.4 mg/1Oralsanofi-aventis U.S. LLC2019-04-16Not applicableUs
FlomaxCapsule0.4 mg/1OralRemedy Repack2009-12-072017-03-07Us
FlomaxCapsule0.4 mg/1OralREMEDYREPACK INC.2017-09-13Not applicableUs
FlomaxCapsule0.4 mg/1Oralbryant ranch prepack1997-09-12Not applicableUs
FlomaxCapsule0.4 mg/1OralBoehringer Ingelheim Pharmaceuticals, Inc.1997-09-122014-11-03Us
FlomaxCapsule0.4 mg/1OralPhysicians Total Care, Inc.2001-08-28Not applicableUs
FlomaxCapsule0.4 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2010-05-132014-09-10Us
FlomaxCapsule, extended release0.4 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1998-06-192009-08-27Canada
FlomaxCapsule0.4 mg/1OralStat Rx USA1997-09-12Not applicableUs
FlomaxCapsule0.4 mg/1OralBoehringer Ingelheim Pharmaceuticals, Inc.1997-09-122021-04-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tamsulosin CRTablet, extended releaseOralApotex Corporation2012-02-09Not applicableCanada
Ava-tamsulosin CRTablet, extended releaseOralAvanstra Inc2011-09-192014-08-21Canada
Jamp-tamsulosinCapsule, extended releaseOralJamp Pharma Corporation2010-06-162012-07-05Canada
Mylan-tamsulosinCapsule, extended releaseOralMylan Pharmaceuticals2007-08-162017-01-09Canada
Ran-tamsulosinCapsule, extended releaseOralRanbaxy Inc.2007-08-152012-06-13Canada
Ratio-tamsulosinCapsule, extended releaseOralTEVA Canada Limited2007-04-27Not applicableCanada
Sandoz TamsulosinCapsule, extended releaseOralSandoz Canada Incorporated2014-03-19Not applicableCanada
Sandoz TamsulosinCapsule, extended releaseOralSandoz Canada Incorporated2007-05-162017-05-24Canada
Sandoz Tamsulosin CRTablet, extended releaseOralSandoz Canada Incorporated2011-01-04Not applicableCanada
Tamsulosin hydrochlorideCapsule0.4 mg/1OralRed Pharm Drug, Inc.2010-04-27Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Dutasteride and tamsulosin hydrochlorideTamsulosin hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralActavis Pharma, Inc.2016-04-13Not applicableUs
Dutasteride and tamsulosin hydrochlorideTamsulosin hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralZydus Pharmaceuticals Usa, Inc.2018-06-04Not applicableUs
Dutasteride and Tamsulosin HydrochlorideTamsulosin hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralPar Pharmaceutical, Inc.2015-11-18Not applicableUs
Dutasteride and tamsulosin hydrochlorideTamsulosin hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralCadila Pharnmaceuticals2018-06-04Not applicableUs
Dutasteride and Tamsulosin HydrochlorideTamsulosin hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralPrasco Laboratories2016-07-01Not applicableUs
JalynTamsulosin hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralGlaxoSmithKline LLC2010-06-21Not applicableUs00173 0809 61 nlmimage10 d11968cb
JalynTamsulosin hydrochloride (0.4 mg) + Dutasteride (0.5 mg)Capsule, extended releaseOralGlaxosmithkline Inc2011-11-17Not applicableCanada
JalynTamsulosin hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralPhysicians Total Care, Inc.2012-05-02Not applicableUs54868 632820180907 15195 11okuzb
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)
Categories
UNII
G3P28OML5I
CAS number
106133-20-4
Weight
Average: 408.512
Monoisotopic: 408.171892706
Chemical Formula
C20H28N2O5S
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

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

Associated Conditions
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

TargetActionsOrganism
AAlpha-1A adrenergic receptor
antagonist
Humans
UAlpha-1D adrenergic receptor
antagonist
Humans
UAlpha-1B adrenergic receptor
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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 can deacetylate tamsulosin to the M-1 metabolite or perform oxidative deamination to the AM-1 metabolite.2,3 CYP2D6 can hydroxylate tamsulosin to the M-3 metabolite or demethylate tamsulosin to the M-4 metabolite.2 Finally, an unknown enzyme can hydroxylate tamsulosin at a different position to form the M-2 metabolite.2 The M-1, M-2, M-3, and M-4 metabolites can be glucuronidated or the M-1 and M-3 metabolites can undergo sulfate conjugation to form other metabolites before excretion.3

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

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Tamsulosin can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Tamsulosin.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Tamsulosin can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Tamsulosin can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of Tamsulosin can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Tamsulosin.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Tamsulosin.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Tamsulosin.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Tamsulosin.
AbacavirTamsulosin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take 30 minutes after a meal (always after the same meal). Taking the drug with food minimizes plasma levels variations.

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
  1. 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. [PubMed:11950378]
  2. 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. [PubMed:9492387]
  3. 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. [PubMed:8810034]
  4. Rivard R: Tamsulosin: ureteral stones (distal). Hosp Pharm. 2015 Jan;50(1):31-3. doi: 10.1310/hjp5001-031. [PubMed:25684798]
  5. Lepor H, Roehrborn C: Historical Overview of Medical Therapy for Benign Prostatic Hyperplasia Reviews in Urology.
  6. FDA Approved Drug Products: Flomax [Link]
  7. 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
ChEBI
9398
ChEMBL
CHEMBL836
Therapeutic Targets Database
DAP000086
PharmGKB
PA451583
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tamsulosin
ATC Codes
G04CA52 — Tamsulosin and dutasterideG04CA02 — TamsulosinG01AE10 — Combinations of sulfonamidesG04CA53 — Tamsulosin and solifenacin
AHFS Codes
  • 12:16.04.12 — Selective Alfa-1-adrenergic Blocking Agents
FDA label
Download (570 KB)
MSDS
Download (20.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingPreventionInguinal Hernias / Urinary Retention1
0Not Yet RecruitingTreatmentUreteric Stone1
1CompletedNot AvailableBenign Prostatic Hyperplasia (BPH)1
1CompletedNot AvailableCardiovascular / Healthy Volunteers / Pharmacokinetics1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of Tamsulosin Hydrochloride1
1CompletedBasic ScienceBenign Prostatic Hyperplasia (BPH) / Healthy Volunteers / Lower Urinary Tract Symptoms (LUTS) / Phase 11
1CompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers1
1CompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers / Pharmacokinetics1
1CompletedBasic ScienceEC905 / Healthy Volunteers / Multiple Dose / Pharmacokinetics1
1CompletedBasic ScienceEC905 / Healthy Volunteers / Pharmacokinetics1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedOtherUrologic Diseases2
1CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Erectile Dysfunction1
1CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Healthy Volunteers1
1CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / LUTS(Lower Urinary Tract Symptoms) / Urinary Bladder, Overactive1
1CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / LUTS / Urinary Bladder, Overactive1
1CompletedTreatmentBenign Prostatic Hypertrophy1
1CompletedTreatmentErectile Dysfunction1
1CompletedTreatmentErectile Dysfunction / Prostatic Hyperplasia2
1CompletedTreatmentHealthy Volunteers6
1CompletedTreatmentHealty Male Volunteers1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentProstatic Hyperplasia8
1CompletedTreatmentUrination Disorders1
1RecruitingTreatmentBenign Prostatic Hyperplasia (BPH)2
1, 2Not Yet RecruitingPreventionInguinal Hernias / Urinary Retention1
1, 2RecruitingTreatmentUrinary Retention1
1, 2Unknown StatusTreatmentNeurogenic Bladder Dysfunction1
1, 2WithdrawnTreatmentDiabetic Macular Edema (DME)1
2CompletedTreatmentBenign Prostatic Hyperplasia (BPH)2
2CompletedTreatmentBladder Outlet Obstruction / Lower Urinary Tract Symptoms (LUTS)1
2CompletedTreatmentLower Urinary Tract Symptoms (LUTS)2
2CompletedTreatmentLower Urinary Tract Symptoms (LUTS) / Prostatic Hyperplasia1
2CompletedTreatmentNeurogenic Bladder Dysfunction1
2CompletedTreatmentProstate Hyperplasia1
2CompletedTreatmentProstatic Hyperplasia1
2RecruitingPreventionUrinary Retention1
2RecruitingTreatmentBenign Prostatic Hyperplasia (BPH) / Lower Urinary Track Symptoms1
2RecruitingTreatmentProstate Cancer1
2Unknown StatusTreatmentUpper Tract Ureterolithiasis1
2, 3CompletedTreatmentLower Urinary Tract Symptoms (LUTS) / Urinary Bladder, Overactive1
2, 3CompletedTreatmentNeurogenic Bladder Dysfunction1
2, 3RecruitingTreatmentLower Urinary Tract Symptoms (LUTS) / Pelvic Organ Prolapse (POP) / Stress Urinary Incontinence (SUI) / Urinary Retention1
3CompletedPreventionUrinary Retention / Urinary Tract Infection1
3CompletedTreatmentBenign Prostatic Hyperplasia (BPH)6
3CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Erectile Dysfunction / Prostatic Hyperplasia1
3CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Lower Urinary Tract Symptoms (LUTS)3
3CompletedTreatmentNon-oncological Indication to Ureteral Stenting1
3CompletedTreatmentProstate Cancer1
3CompletedTreatmentProstatic Hyperplasia2
3CompletedTreatmentRectal Carcinoma / Urinary Retention1
3CompletedTreatmentUreteral Calculus / Ureterolithiasis1
3CompletedTreatmentUrological Manifestations1
3Not Yet RecruitingTreatmentPremature Ejaculation1
3RecruitingPreventionPostoperative Urinary Retention1
3RecruitingTreatmentBenign Prostatic Hyperplasia (BPH)1
3RecruitingTreatmentBenign Prostatic Hyperplasia (BPH) / Erectile Dysfunction1
3TerminatedPreventionPostoperative Urinary Retention1
3TerminatedTreatmentBenign Prostatic Hyperplasia (BPH)1
3TerminatedTreatmentBenign Prostatic Hyperplasia (BPH) / Chronic Prostatitis (CP)1
3TerminatedTreatmentUrinary Retention1
3Unknown StatusTreatmentHyperplasia1
3Unknown StatusTreatmentKidney Stones1
3Unknown StatusTreatmentLower Urinary Tract Symptoms (LUTS)1
3WithdrawnTreatmentKidney Stones1
4Active Not RecruitingTreatmentBenign Prostatic Hyperplasia (BPH)1
4CompletedBasic ScienceBenign Prostatic Hyperplasia (BPH)1
4CompletedPreventionPostoperative Urinary Retention1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH)4
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Benign Prostatic Hypertrophy / Urinary Bladder, Overactive1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Ischaemic Heart Disease (IHD) / Lower Urinary Tract Symptoms (LUTS)1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Lower Urinary Tract Symptoms (LUTS) / Urinary Bladder, Overactive1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Urinary Bladder, Overactive1
4CompletedTreatmentCalcium Nephrolithiasis / Ureterolithiases1
4CompletedTreatmentLower Urinary Tract Symptoms (LUTS) Associated With Benign Prostatic Hyperplasia (BPH)1
4CompletedTreatmentProstatic Hyperplasia6
4CompletedTreatmentRelieve of Ureteral Stent Symptoms1
4CompletedTreatmentUreteral Obstruction1
4CompletedTreatmentUrinary Bladder, Overactive3
4CompletedTreatmentUrinary Incontinence (UI)2
4Enrolling by InvitationSupportive CareUreteral Diseases1
4Enrolling by InvitationTreatmentCalcium Nephrolithiasis1
4Not Yet RecruitingPreventionArthropathy of Hip / Arthropathy of Knee / Postoperative Urinary Retention1
4Not Yet RecruitingTreatmentBenign Prostatic Hyperplasia (BPH) / Urinary Bladder, Overactive1
4RecruitingPreventionHernia / Urinary Retention1
4RecruitingPreventionPostoperative Urinary Retention1
4RecruitingTreatmentBladder Cancers1
4RecruitingTreatmentCalcium Nephrolithiasis1
4RecruitingTreatmentLower Urinary Tract Symptoms (LUTS)1
4RecruitingTreatmentUreteral Calculus / Ureterolithiasis / Urolithiasis1
4TerminatedTreatmentProstatic Hyperplasia1
4TerminatedTreatmentUreteral Calculus / Ureteral Stones / Ureterolithiasis1
4Unknown StatusTreatmentNeurogenic Lower Urinary Tract Dysfunction1
4Unknown StatusTreatmentNocturia1
4Unknown StatusTreatmentRenal Colic1
4Unknown StatusTreatmentUreteral Calculus1
4Unknown StatusTreatmentUrinary Tract Stones1
4WithdrawnTreatmentBenign Prostatic Hyperplasia (BPH)1
Not AvailableActive Not RecruitingTreatmentProstate Cancer1
Not AvailableCompletedNot AvailableBenign Prostatic Hyperplasia (BPH)1
Not AvailableCompletedNot AvailableProstatic Hyperplasia8
Not AvailableCompletedBasic ScienceUrethral Sphincter Activity1
Not AvailableCompletedTreatmentCalcium Nephrolithiasis / Ureteral Calculus1
Not AvailableCompletedTreatmentKidney Stones1
Not AvailableCompletedTreatmentKidney Stones / Ureteral Stones1
Not AvailableCompletedTreatmentLower Urinary Tract Symptoms (LUTS)1
Not AvailableCompletedTreatmentUreteral Calculus1
Not AvailableNot Yet RecruitingTreatmentDisorder of Urinary Stent1
Not AvailableRecruitingTreatmentQuality of Life / Ureter Obstruction / Ureter Stone1
Not AvailableTerminatedPreventionPostoperative Urinary Retention1
Not AvailableTerminatedTreatmentUrolithiasis1
Not AvailableUnknown StatusScreeningKidney Stones1
Not AvailableUnknown StatusTreatmentBenign Prostatic Hyperplasia (BPH)2
Not AvailableUnknown StatusTreatmentChronic Renal Failure (CRF) / Prostatic Hyperplasia1
Not AvailableUnknown StatusTreatmentProstatic Neoplasms, Prostatectomy1
Not AvailableUnknown StatusTreatmentProstatitis1

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
FormRouteStrength
CapsuleOral0.4 mg/1
Capsule, extended releaseOral0.4 mg
Tablet, extended releaseOral
CapsuleOral
Capsule, extended releaseOral
CapsuleOral.4 mg/1
Capsule, extended releaseOral
Prices
Unit descriptionCostUnit
Flomax 0.4 mg capsule4.71USD capsule
Tamsulosin hcl 0.4 mg capsule4.3USD capsule
Flomax Cr 0.4 mg Extended-Release Tablet0.63USD tablet
Mylan-Tamsulosin 0.4 mg Sustained-Release Capsule0.63USD capsule
Novo-Tamsulosin 0.4 mg Sustained-Release Capsule0.57USD capsule
Ran-Tamsulosin 0.4 mg Sustained-Release Capsule0.57USD capsule
Ratio-Tamsulosin 0.4 mg Sustained-Release Capsule0.57USD capsule
Sandoz Tamsulosin 0.4 mg Sustained-Release Capsule0.57USD capsule
Tamsulosin 0.4 mg Sustained-Release Capsule0.57USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4703063No1987-10-272010-04-27Us
CA2490299No2008-08-262023-12-24Canada
CA2144077No2005-05-242013-09-10Canada
US5565467No1996-10-152015-11-20Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)230FDA Label
water solubilitySparingly soluble in waterFDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.00655 mg/mLALOGPS
logP3.05ALOGPS
logP2.04ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)9.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.88 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity108.86 m3·mol-1ChemAxon
Polarizability43.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.5915
Caco-2 permeable-0.6473
P-glycoprotein substrateSubstrate0.5911
P-glycoprotein inhibitor INon-inhibitor0.5734
P-glycoprotein inhibitor IINon-inhibitor0.5522
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.6012
CYP450 1A2 substrateNon-inhibitor0.7876
CYP450 2C9 inhibitorInhibitor0.5916
CYP450 2D6 inhibitorNon-inhibitor0.8614
CYP450 2C19 inhibitorNon-inhibitor0.5056
CYP450 3A4 inhibitorInhibitor0.718
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6146
Ames testNon AMES toxic0.6245
CarcinogenicityNon-carcinogens0.6419
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4091 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8367
hERG inhibition (predictor II)Non-inhibitor0.6971
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Benzenesulfonamides / Phenylpropanes / Benzenesulfonyl compounds / Phenoxy compounds / Methoxybenzenes / Anisoles / Aralkylamines / Alkyl aryl ethers / Organosulfonamides / Aminosulfonyl compounds
show 4 more
Substituents
Amphetamine or derivatives / Benzenesulfonamide / Benzenesulfonyl group / Phenylpropane / Phenoxy compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / Aralkylamine
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
sulfonamide (CHEBI:9398)

Targets

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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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. [PubMed:9352698]
  3. 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. [PubMed:10503165]
  4. 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. [PubMed:9352700]
  5. 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. [PubMed:8647141]
  6. 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. [PubMed:8647140]
  7. 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. [PubMed:19427736]
  8. 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. [PubMed:14680444]
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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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. [PubMed:9117115]
  3. Lowe FC: Summary of clinical experiences with tamsulosin for the treatment of benign prostatic hyperplasia. Rev Urol. 2005;7 Suppl 4:S13-21. [PubMed:16986050]
  4. 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. [PubMed:16518087]
  5. 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. [PubMed:12270758]
  6. 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. [PubMed:8996174]
  7. 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. [PubMed:14680444]
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
  1. 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. [PubMed:12270758]
  2. 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. [PubMed:7911719]
  3. 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. [PubMed:8996174]
  4. 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. [PubMed:9294627]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. 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. [PubMed:14680444]

Enzymes

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
  1. 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 . [PubMed:9849639]
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
  1. 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 . [PubMed:9849639]

Carriers

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
  1. 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. [PubMed:10737910]
  2. 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. [PubMed:17666829]
  3. 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. [PubMed:8973992]

Drug created on June 13, 2005 07:24 / Updated on December 06, 2019 11:48