Tamsulosin (CHEM022163)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:22:24 UTC
Update Date2016-11-09 01:17:26 UTC
Accession NumberCHEM022163
Identification
Common NameTamsulosin
ClassSmall Molecule
DescriptionTamsulosin 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. It is indicated for the treatment of signs and symptoms of benign prostatic hypertrophy. Antagonism of these receptors leads to relaxation of smooth muscle in the prostate and detrusor muscles in the bladder, allowing for better urinary flow. 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. Tamsulosin was first approved by the FDA on April 15, 1997.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-TamsulosinChEBI
(R)-(-)-TamsulosinChEBI
(R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamideChEBI
TamsulosinaChEBI
TamsulosineChEBI
TamsulosinumChEBI
FlomaxKegg
TamsulonKegg
(R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulphonamideGenerator
5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxy-benzenesulfonamideHMDB
5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxy-benzenesulphonamideHMDB
YM-617HMDB
5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamideHMDB
Tamsulosin hydrochlorideHMDB
Chemical FormulaC20H28N2O5S
Average Molecular Mass408.512 g/mol
Monoisotopic Mass408.172 g/mol
CAS Registry Number106133-20-4
IUPAC Name5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonamide
Traditional Nametamsulosin
SMILESCCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC(=C(OC)C=C1)S(N)(=O)=O
InChI IdentifierInChI=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
InChI KeyDRHKJLXJIQTDTD-OAHLLOKOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Phenylpropane
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Aralkylamine
  • Organosulfonic acid amide
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0066 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity108.86 m³·mol⁻¹ChemAxon
Polarizability43.95 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fc0-1696000000-feeed148e3d1a2085e88Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0234900000-bc2e2b9eaaaeda3fce7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i0-1593100000-b0b9b35ee520544357c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-5931000000-a01082b9fcdb3d11e596Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2322900000-a47a51f53354ebc1348dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0550-3907200000-6c1b7cdc5c84f0dccbf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vj-9513000000-b91e35440806c5c374f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0090500000-1c851350cf0ebcbae96bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i1-0090100000-b587f2fee8a0ea015942Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-0190000000-e302ff6e9ab7b1839d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0011900000-843109d3cddf29aa626dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-3496200000-c3ebf3e04317201646fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7975000000-15eea5b5d8ae22b42b13Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00706
HMDB IDHMDB0014844
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTamsulosin
Chemspider ID114457
ChEBI ID9398
PubChem Compound ID129211
Kegg Compound IDC07124
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. Wilt TJ, Mac Donald R, Rutks I: Tamsulosin for benign prostatic hyperplasia. Cochrane Database Syst Rev. 2003;(1):CD002081.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2891044
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=29728928
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=29737501
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=29913020
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=29971698
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=29974124
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=30174141
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=30360332