General
Preferred name
tamsulosin
Synonyms
TAMSULOSIN HYDROCHLORIDE ()
Flomax hydrochloride ()
Flomax ()
Tamsulosina hydrochloride, Tamsulosinum hydrochloride ()
Tamsulosin (hydrochloride) ()
(R)-(-)-YM12617 (free base) ()
LY253351 (free base) ()
(R)-(-)-YM12617 ()
LY253351 ()
Tamsulon ()
HIP1402 ()
HGP-0412 ()
HIP-1402 ()
YM-12617-1 ()
LY-253351 ()
Tamurex ()
Alphacard MR ()
Flomax MR ()
Stronazon ()
Tabphyn MR ()
Pinexel PR ()
Tamsulosin hcl ()
R-(-)-YM-12617 ()
Galebon ()
Harnal ()
Morvesin XL ()
Omnic MR ()
Diffundox ()
Tamfrex XL ()
Flomaxtra XL ()
Maxtron ()
Losinate MR ()
Pamsvax XL ()
Petyme ()
YM617 ()
YM-617 ()
Cositam XL ()
Bazetham MR ()
Contiflo XL ()
Prosurin XL ()
Flomax Relief MR ()
Flectone XL ()
Faramsil ()
Tamsulosin-d4 (hydrochloride) ()
P&D ID
PD010069
CAS
106133-20-4
106463-17-6
1231943-97-7
Tags
available
natural product
drug
Approved by
FDA
First approval
1997
Drug Status
investigational
approved
Drug indication
Benign Prostatic Hyperplasia Therapy Agent
Benign prostatic hyperplasia
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
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.[A1078] The final subtype, alpha-1B, are most common in the aorta and spleen.[A1078] Tamsulosin binds to alpha-1A receptors 3.9-38 times more selectively than alpha-1B and 3-20 times more selectively than alpha-1D.[A1078] This selectivity allows for a significant effect on urinary flow with a reduced incidence of adverse reactions like orthostatic hypotension.[A1078]
MOA Tamsulosin is a blocker of alpha-1A and alpha-1D adrenoceptors.[Label,A1078] 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.[A1078] The specificity of tamsulosin focuses the effects to the target area while minimizing effects in other areas.[Label]
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.[A178339,L6259]
ROE 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,A1078]
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]
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]
METABOLISM Tamsulosin is mostly metabolized in the liver by cytochrome P450 (CYP) 3A4 and 2D6, with some metabolism by other CYPs.[Label,A1078] CYP3A4 can deacetylate tamsulosin to the M-1 metabolite or perform oxidative deamination to the AM-1 metabolite.[A178276,A178321] CYP2D6 can hydroxylate tamsulosin to the M-3 metabolite or demethylate tamsulosin to the M-4 metabolite.[A178276] Finally, an unknown enzyme can hydroxylate tamsulosin at a different position to form the M-2 metabolite.[A178276] 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.[A178321]
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]
DESCRIPTION Tamsulosin is a selective α1A-adrenoceptor antagonist drug. (GtoPdb)
DESCRIPTION Dopamine receptor antagonist; antipsychotic (Tocris Bioactive Compound Library)
DESCRIPTION Selective alpha1A antagonist (Tocriscreen Plus)
Cell lines
0
Organisms
2
Compound Sets
27
AdooQ Bioactive Compound Library
A14936
Cayman Chemical Bioactives
24020
28486
ChEMBL Approved Drugs
CHEMBL836
CHEMBL1200914
ChEMBL Drugs
CHEMBL836
CHEMBL1200914
Concise Guide to Pharmacology 2017/18
488
Concise Guide to Pharmacology 2019/20
488
Concise Guide to Pharmacology 2021/22
488
Concise Guide to Pharmacology 2023/24
488
Drug Repurposing Hub
DrugBank
DB00706
DrugBank Approved Drugs
DB00706
DrugCentral
2562
DrugCentral Approved Drugs
2562
DrugMAP
DM5QF9V
DrugMAP Approved Drugs
DM5QF9V
EU-OPENSCREEN Bioactive Compound Library
EOS102165
Guide to Pharmacology
488
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL836
Mcule NIBR MoA Box Subset
MCULE-2390447399
MedChem Express Bioactive Compound Library
HY-B0661
HY-B0661A
NCATS Inxight Approved Drugs
G3P28OML5I
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Selleckchem Bioactive Compound Library
Tamsulosin-hydrochloride
TargetMol Bioactive Compound Library
T0210
Tocris Bioactive Compound Library
3050
Tocriscreen Plus
3050
External IDs
69
Properties
(calculated by RDKit )
Molecular Weight
408.17
Hydrogen Bond Acceptors
6
Hydrogen Bond Donors
2
Rotatable Bonds
11
Ring Count
2
Aromatic Ring Count
2
cLogP
2.34
TPSA
99.88
Fraction CSP3
0.4
Chiral centers
1.0
Largest ring
6.0
QED
0.55
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
7-TM Receptors
Pathway
GPCR/G protein
Metabolic Enzyme/Protease
Neuronal Signaling
Target
??1A-adrenergic receptor
??1B-adrenergic receptor
??1D-adrenergic receptor
ADRA1A, ADRA1B, ADRA1D
Adrenergic Receptor
Endogenous Metabolite
Primary Target
Adrenergic ?1 Receptors
MOA
Antagonist
alpha1-Adrenoceptor Antagonists
Adrenergic Receptor antagonist
Member status
member
Indication
benign prostatic hyperplasia (BPH)
Therapeutic Class
Anticancer Agents
Source data