Identification

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

Tamsulosin is a selective antagonist at alpha-1A and alpha-1B-adrenoceptors in the prostate, prostatic capsule, prostatic urethra, and bladder neck. At least three discrete alpha1-adrenoceptor subtypes have been identified: alpha-1A, alpha-1B and alpha-1D; their distribution differs between human organs and tissue. Approximately 70% of the alpha1-receptors in human prostate are of the alpha-1A subtype. Blockage of these receptors causes relaxation of smooth muscles in the bladder neck and prostate.

Structure
Thumb
Synonyms
  • (R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide
  • 5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxy-benzenesulfonamide
  • 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/1OralBoehringer Ingelheim Pharmaceuticals, Inc.1997-09-122014-11-03Us
FlomaxCapsule0.4 mg/1Oralbryant ranch prepack1997-09-12Not applicableUs
FlomaxCapsule0.4 mg/1OralRemedy Repack2009-12-072017-03-07Us
FlomaxCapsule0.4 mg/1OralStat Rx USA1997-09-12Not applicableUs
FlomaxCapsule0.4 mg/1OralBoehringer Ingelheim1997-09-12Not applicableUs
FlomaxCapsule0.4 mg/1OralRemedy Repack2017-05-15Not applicableUs
FlomaxCapsule0.4 mg/1OralA S Medication Solutions1999-06-03Not applicableUs
FlomaxCapsule0.4 mg/1OralCardinal Health1997-09-122012-09-30Us
FlomaxCapsule, extended release0.4 mgOralBoehringer Ingelheim (Canada) Ltd Ltee1998-06-192009-08-27Canada
FlomaxCapsule0.4 mg/1OralPhysicians Total Care, Inc.2001-08-28Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tamsulosin CRTablet, extended release0.4 mgOralApotex Corporation2012-02-09Not applicableCanada
Ava-tamsulosin CRTablet, extended release0.4 mgOralAvanstra Inc2011-09-192014-08-21Canada
Jamp-tamsulosinCapsule, extended release0.4 mgOralJamp Pharma Corporation2010-06-162012-07-05Canada
Mylan-tamsulosinCapsule, extended release0.4 mgOralMylan Pharmaceuticals2007-08-162017-01-09Canada
Ran-tamsulosinCapsule, extended release0.4 mgOralRanbaxy Inc.2007-08-152012-06-13Canada
Ratio-tamsulosinCapsule, extended release0.4 mgOralTeva2007-04-27Not applicableCanada
Tamsulosin HydrochlorideCapsule0.4 mg/1OralAidarex Pharmaceuticals LLC2010-04-27Not applicableUs
Tamsulosin HydrochlorideCapsule0.4 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2010-07-15Not applicableUs
Tamsulosin HydrochlorideCapsule0.4 mg/1OralNucare Pharmaceuticals, Inc.2010-07-15Not applicableUs
Tamsulosin HydrochlorideCapsule0.4 mg/1OralPhysicians Total Care, Inc.2010-03-10Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Dutasteride and Tamsulosin HydrochlorideTamsulosin Hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralPrasco Laboratories2016-07-01Not applicableUs
Dutasteride and Tamsulosin HydrochlorideTamsulosin Hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralPar Pharmaceutical2015-11-18Not 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)CapsuleOralActavis Pharma, Inc.2016-04-13Not applicableUs
Dutasteride and tamsulosin hydrochlorideTamsulosin Hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralCadila Pharnmaceuticals2018-06-04Not applicableUs
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
JalynTamsulosin Hydrochloride (0.4 mg/1) + Dutasteride (0.5 mg/1)CapsuleOralGlaxoSmithKline LLC2010-06-21Not applicableUs00173 0809 61 nlmimage10 d11968cb
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

Used in the treatment of signs and symptoms of benign prostatic hyperplasia (reduction in urinary obstruction and relief of associated manifestations such as hesitancy, terminal dribbling of urine, interrupted or weak stream...etc.)

Associated Conditions
Pharmacodynamics

Tamsulosin, a sulfamoylphenethylamine-derivative alpha-adrenoceptor blocker with enhanced specificity for the alpha-adrenoceptors of the prostate, is commonly used to treat benign prostatic hyperplasia (BPH). The drug is commercially available in a racemic mixture of 2 isomers, and is pharmacologically related to doxazocin, prazosin, and terazosin. However, unlike these drugs, tamsulosin has a higher affinity for the alpha-1A- adrenergic receptors, which are located in vascular smooth muscle. Studies show that tamsulosin has about 12 times greater affinity for alpha-1 adrenergic receptors in the prostate than those in the aorta, which may result in a reduced incidence of adverse cardiovascular effects.

Mechanism of action

Tamsulosin is a selective antagonist at alpha-1A and alpha-1B-adrenoceptors in the prostate, prostatic capsule, prostatic urethra, and bladder neck. At least three discrete alpha1-adrenoceptor subtypes have been identified: alpha-1A, alpha-1B and alpha-1D; their distribution differs between human organs and tissue. Approximately 70% of the alpha1-receptors in human prostate are of the alpha-1A subtype. Blockage of these receptors causes relaxation of smooth muscles in the bladder neck and prostate, and thus decreases urinary outflow resistance in men.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
antagonist
Human
UAlpha-1D adrenergic receptor
antagonist
Human
UAlpha-1B adrenergic receptor
antagonist
Human
Absorption

Absorption of tamsulosin HCI from capsules 0.4 mg is essentially complete (>90%) following oral administration under fasting conditions.

Volume of distribution
  • 16 L [intravenous administration to ten healthy male adults]
Protein binding

94%-99%

Metabolism

Tamsulosin HCI is extensively metabolized by cytochrome P450 enzymes in the liver, however, the pharmacokinetic profile of the metabolites in humans has not been established.

Route of elimination

Tamsulosin hydrochloride is extensively metabolized by cytochrome P450 enzymes in the liver and less than 10% of the dose is excreted in urine unchanged. The metabolites of tamsulosin hydrochloride undergo extensive conjugation to glucuronide or sulfate prior to renal excretion. On administration of the radiolabeled dose of tamsulosin hydrochloride to four healthy volunteers, 97% of the administered radioactivity was recovered, with urine (76%) representing the primary route of excretion compared to feces (21%) over 168 hours.

Half life

5-7 hours

Clearance
  • 2.88 L/h
Toxicity

LD50 = 650 mg/kg (in rats)

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

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Tamsulosin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Tamsulosin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Tamsulosin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Tamsulosin.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Tamsulosin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Tamsulosin.
6-Deoxyerythronolide BThe metabolism of Tamsulosin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Tamsulosin.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Tamsulosin.
AbacavirTamsulosin may decrease the excretion rate of Abacavir which could result in a higher serum level.
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. Lyseng-Williamson KA, Jarvis B, Wagstaff AJ: Tamsulosin: an update of its role in the management of lower urinary tract symptoms. Drugs. 2002;62(1):135-67. [PubMed:11790159]
  3. Wilt TJ, Mac Donald R, Rutks I: Tamsulosin for benign prostatic hyperplasia. Cochrane Database Syst Rev. 2003;(1):CD002081. [PubMed:12535426]
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
IUPHAR
488
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tamsulosin
ATC Codes
G04CA02 — TamsulosinG04CA53 — Tamsulosin and solifenacinG04CA52 — Tamsulosin and dutasteride
AHFS Codes
  • 12:16.04.12 — Selective Alfa-1-adrenergic Blocking Agents
FDA label
Download (248 KB)
MSDS
Download (20.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingPreventionInguinal Hernias / Urinary Retention1
1CompletedNot AvailableBenign Prostatic Hyperplasia (BPH)1
1CompletedNot AvailableCardiovascular / Healthy Volunteers / Pharmacokinetics1
1CompletedNot AvailableHealthy Volunteers2
1CompletedBasic ScienceBenign Prostatic Hyperplasia (BPH) / Healthy Volunteers / Lower Urinary Tract Symptoms (LUTS) / Phase 11
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 Dysfunction (ED)1
1CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Healthy Volunteers1
1CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / LUTS / Urinary Bladder, Overactive1
1CompletedTreatmentErectile Dysfunction (ED)1
1CompletedTreatmentErectile Dysfunction (ED) / Prostatic Hyperplasia2
1CompletedTreatmentHealthy Volunteers5
1CompletedTreatmentHealty Male Volunteers1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
1CompletedTreatmentProstatic Hyperplasia8
1CompletedTreatmentUrination Disorders1
1, 2Not Yet RecruitingTreatmentDiabetic Macular Edema (DME)1
1, 2RecruitingTreatmentUrinary Retention1
1, 2Unknown StatusTreatmentNeurogenic Bladder Dysfunction1
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
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
3Active Not RecruitingPreventionUrinary Retention / Urinary Tract Infections (UTIs)1
3CompletedTreatmentBenign Prostatic Hyperplasia (BPH)6
3CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Erectile Dysfunction (ED) / Prostatic Hyperplasia1
3CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Lower Urinary Tract Symptoms (LUTS)1
3CompletedTreatmentNon-oncological Indication to Ureteral Stenting1
3CompletedTreatmentProstatic Hyperplasia2
3CompletedTreatmentRectal Carcinoma / Urinary Retention1
3CompletedTreatmentUreteral Calculus / Ureterolithiasis1
3CompletedTreatmentUrological Manifestations1
3RecruitingPreventionPostoperative Urinary Retention2
3RecruitingTreatmentBenign Prostatic Hyperplasia (BPH)1
3RecruitingTreatmentBenign Prostatic Hyperplasia (BPH) / Erectile Dysfunction (ED)1
3RecruitingTreatmentBenign Prostatic Hyperplasia (BPH) / Lower Urinary Tract Symptoms (LUTS)1
3TerminatedTreatmentBenign Prostatic Hyperplasia (BPH)1
3TerminatedTreatmentBenign Prostatic Hyperplasia (BPH) / Chronic Prostatitis (CP)1
3TerminatedTreatmentUrinary Retention1
3Unknown StatusTreatmentHyperplasia1
3Unknown StatusTreatmentLower Urinary Tract Symptoms (LUTS)1
3Unknown StatusTreatmentRenal Stones1
3WithdrawnTreatmentRenal Stones1
4Active Not RecruitingTreatmentBenign Prostatic Hyperplasia (BPH)1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH)1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Benign Prostatic Hypertrophy (BPH) / Urinary Bladder, Overactive1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Lower Urinary Tract Symptoms (LUTS) / Urinary Bladder, Overactive1
4CompletedTreatmentBenign Prostatic Hyperplasia (BPH) / Urinary Bladder, Overactive1
4CompletedTreatmentCalcium Nephrolithiasis / Ureterolithiases1
4CompletedTreatmentProstatic Hyperplasia5
4CompletedTreatmentRelieve of Ureteral Stent Symptoms1
4CompletedTreatmentUreteral Obstruction1
4CompletedTreatmentUrinary Bladder, Overactive1
4CompletedTreatmentUrinary Incontinence (UI)1
4Enrolling by InvitationPreventionPostoperative Urinary Retention1
4Enrolling by InvitationTreatmentCalcium Nephrolithiasis1
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
4WithdrawnTreatmentBenign Prostatic Hyperplasia (BPH)1
Not AvailableCompletedNot AvailableProstatic Hyperplasia6
Not AvailableCompletedBasic ScienceUrethral Sphincter Activity1
Not AvailableCompletedTreatmentCalcium Nephrolithiasis / Ureteral Calculus1
Not AvailableCompletedTreatmentRenal Stones1
Not AvailableCompletedTreatmentRenal Stones / Ureteral Stones1
Not AvailableCompletedTreatmentUreteral Calculus1
Not AvailableNot Yet RecruitingTreatmentDisorder of Urinary Stent1
Not AvailableNot Yet RecruitingTreatmentQuality of Life / Ureter Obstruction / Ureter Stone1
Not AvailableRecruitingTreatmentProstate Cancer1
Not AvailableTerminatedPreventionPostoperative Urinary Retention1
Not AvailableTerminatedTreatmentUrolithiasis1
Not AvailableUnknown StatusScreeningRenal 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
Tablet, extended releaseOral0.4 mg
CapsuleOral
Capsule, extended releaseOral
CapsuleOral.4 mg/1
Capsule, extended releaseOral0.4 mg
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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)226-228 °C (HCl salt)Not Available
water solubilitySparingly soluble in waterNot Available
logP2.3Not Available
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
Human
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
Human
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
Human
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
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Kind
Protein
Organism
Human
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 12, 2018 07:07