tamsulosin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antihypertensive substances, prazosin derivatives 2562 106133-20-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tamsulosin
  • tamsulosin hydrochloride
  • tamsulosin HCl
  • LY-253352
A sulfonamide derivative and adrenergic alpha-1 receptor antagonist that is used to relieve symptoms of urinary obstruction caused by BENIGN PROSTATIC HYPERPLASIA.
  • Molecular weight: 408.51
  • Formula: C20H28N2O5S
  • CLOGP: 2.17
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 99.88
  • ALOGS: -4.79
  • ROTB: 11

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 8.70 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.03 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.21 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.62 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.01 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6.80 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 15, 1997 FDA BOEHRINGER INGELHEIM

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Product use issue 70.56 37.24 18 177 12151 2345739
Residual urine volume increased 67.95 37.24 7 188 7 2357883
Completed suicide 60.80 37.24 18 177 21016 2336874
Off label use 48.54 37.24 21 174 73577 2284313
Orthostatic hypotension 47.48 37.24 10 185 2869 2355021
Disorganised speech 43.66 37.24 6 189 130 2357760
Presyncope 39.27 37.24 9 186 3794 2354096

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Iris disorder 1344.61 32.47 199 3748 30 1742804
Orthostatic hypotension 681.94 32.47 174 3773 3257 1739577
Procedural complication 674.27 32.47 140 3807 976 1741858
Syncope 584.19 32.47 214 3733 13955 1728879
Dizziness 549.93 32.47 264 3683 34097 1708737
Cataract operation complication 484.02 32.47 74 3873 30 1742804
Hypotension 425.77 32.47 212 3735 29442 1713392
Miosis 393.73 32.47 95 3852 1383 1741451
Iridocele 376.86 32.47 56 3891 9 1742825
Floppy iris syndrome 338.07 32.47 56 3891 74 1742760
Urinary retention 291.60 32.47 100 3847 5295 1737539
Fall 277.06 32.47 155 3792 27059 1715775
Loss of consciousness 244.29 32.47 117 3830 14758 1728076
Drug ineffective 240.97 32.47 196 3751 63605 1679229
Completed suicide 196.30 32.47 104 3843 16208 1726626
Dysuria 182.48 32.47 64 3883 3608 1739226
Drug interaction 177.75 32.47 118 3829 27840 1714994
Pollakiuria 176.22 32.47 59 3888 2887 1739947
Pupillary disorder 175.94 32.47 31 3916 72 1742762
Product substitution issue 162.21 32.47 57 3890 3229 1739605
Dyspnoea 147.22 32.47 136 3811 51923 1690911
Malaise 139.39 32.47 104 3843 29461 1713373
Nocturia 131.79 32.47 38 3909 1123 1741711
Urine flow decreased 116.50 32.47 26 3921 260 1742574
Dysphagia 111.35 32.47 61 3886 10107 1732727
Confusional state 107.21 32.47 78 3869 21200 1721634
Retrograde ejaculation 104.42 32.47 21 3926 120 1742714
Erectile dysfunction 94.22 32.47 42 3905 4455 1738379
Vision blurred 93.48 32.47 51 3896 8372 1734462
Lip swelling 91.91 32.47 36 3911 2759 1740075
Ocular procedural complication 86.30 32.47 15 3932 31 1742803
Palpitations 86.13 32.47 45 3902 6769 1736065
Presyncope 86.07 32.47 34 3913 2664 1740170
Urinary incontinence 82.14 32.47 33 3914 2703 1740131
Pruritus 79.88 32.47 68 3879 23154 1719680
Benign prostatic hyperplasia 79.58 32.47 27 3920 1371 1741463
Somnolence 78.91 32.47 59 3888 16680 1726154
Hypertension 77.41 32.47 62 3885 19386 1723448
Fatigue 76.14 32.47 95 3852 50686 1692148
Oedema peripheral 75.96 32.47 56 3891 15494 1727340
Cataract 75.86 32.47 32 3915 2966 1739868
Priapism 74.49 32.47 26 3921 1438 1741396
Micturition urgency 73.56 32.47 22 3925 739 1742095
Ejaculation failure 73.38 32.47 19 3928 370 1742464
Atrial fibrillation 70.62 32.47 53 3894 15058 1727776
Interstitial lung disease 68.85 32.47 44 3903 9652 1733182
Hyperhidrosis 67.88 32.47 48 3899 12440 1730394
Nausea 67.65 32.47 90 3857 51106 1691728
Asthenia 67.10 32.47 74 3873 34596 1708238
Vertigo 67.00 32.47 33 3914 4380 1738454
Memory impairment 64.77 32.47 37 3910 6626 1736208
Headache 64.16 32.47 72 3875 34304 1708530
Haematuria 63.01 32.47 38 3909 7522 1735312
Product use in unapproved indication 62.56 32.47 41 3906 9381 1733453
Nasal congestion 58.63 32.47 27 3920 3084 1739750
Dry mouth 58.61 32.47 29 3918 3884 1738950
Bradycardia 58.41 32.47 41 3906 10493 1732341
Angioedema 56.83 32.47 39 3908 9625 1733209
Prostatic disorder 54.62 32.47 16 3931 499 1742335
Condition aggravated 53.19 32.47 52 3895 21098 1721736
Circulatory collapse 52.83 32.47 26 3921 3441 1739393
Urinary tract infection 52.78 32.47 38 3909 10115 1732719
Oestrogen receptor positive breast cancer 52.43 32.47 8 3939 3 1742831
Bladder cancer 52.18 32.47 22 3925 2034 1740800
Gynaecomastia 51.41 32.47 22 3925 2110 1740724
Drug hypersensitivity 51.31 32.47 44 3903 15091 1727743
Prostate cancer 51.24 32.47 28 3919 4598 1738236
Rash 50.98 32.47 68 3879 38625 1704209
Angle closure glaucoma 50.26 32.47 13 3934 252 1742582
Visual impairment 48.58 32.47 30 3917 6188 1736646
Diarrhoea 48.37 32.47 79 3868 53773 1689061
Toxicity to various agents 47.54 32.47 57 3890 29084 1713750
Acute kidney injury 46.92 32.47 62 3885 34882 1707952
Dizziness postural 46.73 32.47 16 3931 834 1742000
Iris atrophy 45.26 32.47 8 3939 19 1742815
Pupillary reflex impaired 44.99 32.47 13 3934 386 1742448
Testicular swelling 44.49 32.47 12 3935 275 1742559
Choroidal detachment 44.43 32.47 10 3937 104 1742730
Prostatism 43.68 32.47 9 3938 59 1742775
Hallucination 43.42 32.47 31 3916 8139 1734695
Vitreous loss 43.26 32.47 7 3940 7 1742827
Cataract operation 43.01 32.47 12 3935 313 1742521
Oral mucosal blistering 42.97 32.47 12 3935 314 1742520
Blood pressure decreased 42.92 32.47 30 3917 7616 1735218
Red blood cell sedimentation rate increased 42.80 32.47 16 3931 1077 1741757
Post procedural complication 42.80 32.47 20 3927 2360 1740474
Dacryocystitis 42.78 32.47 7 3940 8 1742826
Swollen tongue 42.61 32.47 21 3926 2787 1740047
Back pain 42.03 32.47 41 3906 16572 1726262
Asthma 41.75 32.47 25 3922 4879 1737955
Abdominal pain 41.71 32.47 46 3901 21444 1721390
Diabetic neuropathy 41.66 32.47 13 3934 504 1742330
Testicular pain 41.43 32.47 14 3933 701 1742133
Muscular weakness 41.40 32.47 33 3914 10216 1732618
Gamma-glutamyltransferase increased 40.85 32.47 25 3922 5073 1737761
Hyperglycaemia 40.55 32.47 25 3922 5140 1737694
Post micturition dribble 40.31 32.47 6 3941 1 1742833
Tremor 40.12 32.47 36 3911 13095 1729739
Hyperkalaemia 39.92 32.47 30 3917 8517 1734317
Nipple pain 38.45 32.47 10 3937 198 1742636
Epistaxis 38.45 32.47 29 3918 8277 1734557
Myalgia 38.41 32.47 38 3909 15620 1727214
Lower urinary tract symptoms 38.00 32.47 8 3939 59 1742775
Blood pressure increased 37.93 32.47 32 3915 10721 1732113
Tachycardia 37.36 32.47 34 3913 12594 1730240
Blindness unilateral 37.31 32.47 14 3933 952 1741882
Insomnia 37.17 32.47 38 3909 16238 1726596
Oesophageal rupture 36.95 32.47 9 3938 135 1742699
Paraplegia 36.93 32.47 12 3935 531 1742303
Bradyarrhythmia 36.72 32.47 11 3936 371 1742463
Overdose 36.35 32.47 38 3909 16663 1726171
Conduction disorder 36.28 32.47 11 3936 387 1742447
Visual acuity reduced 36.18 32.47 21 3926 3867 1738967
Lichenoid keratosis 36.17 32.47 11 3936 391 1742443
Swelling face 35.95 32.47 22 3925 4461 1738373
Obesity 35.81 32.47 14 3933 1065 1741769
Gastrointestinal disorder 34.79 32.47 22 3925 4726 1738108
Guillain-Barre syndrome 34.42 32.47 13 3934 900 1741934
Eye pain 34.08 32.47 17 3930 2314 1740520
Mobility decreased 32.93 32.47 20 3927 4000 1738834
Cerebral infarction 32.93 32.47 22 3925 5187 1737647
Blood pressure systolic increased 32.75 32.47 15 3932 1690 1741144
Depressed level of consciousness 32.71 32.47 24 3923 6568 1736266
Penis disorder 32.62 32.47 10 3937 365 1742469

Pharmacologic Action:

SourceCodeDescription
ATC G04CA02 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
DRUGS USED IN BENIGN PROSTATIC HYPERTROPHY
Alpha-adrenoreceptor antagonists
ATC G04CA52 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
DRUGS USED IN BENIGN PROSTATIC HYPERTROPHY
Alpha-adrenoreceptor antagonists
ATC G04CA53 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
DRUGS USED IN BENIGN PROSTATIC HYPERTROPHY
Alpha-adrenoreceptor antagonists
ATC G04CA54 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
DRUGS USED IN BENIGN PROSTATIC HYPERTROPHY
Alpha-adrenoreceptor antagonists
MeSH PA D018663 Adrenergic Agents
MeSH PA D058668 Adrenergic alpha-1 Receptor Antagonists
FDA EPC N0000175553 alpha-Adrenergic Blocker
MeSH PA D000317 Adrenergic alpha-Antagonists
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D018377 Neurotransmitter Agents
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:37890 alpha-adrenergic antagonist
MeSH PA D064804 Urological Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Benign prostatic hyperplasia indication 266569009
Priapism contraindication 6273006 DOID:9286
Orthostatic hypotension contraindication 28651003
Oligozoospermia contraindication 88311004
Cataract surgery contraindication 110473004
Disease of liver contraindication 235856003 DOID:409
Syncope contraindication 271594007
Pregnancy, function contraindication 289908002
Dizziness contraindication 404640003
Breastfeeding (mother) contraindication 413712001
Intraoperative floppy iris syndrome contraindication 418801006
High-Grade Prostate Cancer contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.71 acidic
pKa2 8.16 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 1A GPCR Ki 9.10 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 7.87 CHEMBL
D(2) dopamine receptor GPCR Ki 7.89 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 10.24 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 10.54 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 9.21 CHEMBL
D(3) dopamine receptor GPCR Ki 9.55 CHEMBL
Alpha-2C adrenergic receptor GPCR Ki 8.10 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 7.08 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 9.70 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 8.17 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 10.15 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 10.52 CHEMBL
Serotonin 1 (5-HT1) receptor GPCR Ki 6.03 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 9.90 CHEMBL

External reference:

IDSource
D000077409 MESH_DESCRIPTOR_UI
4024076 VUID
N0000022081 NUI
C0257343 UMLSCUI
D01024 KEGG_DRUG
11SV1951MR UNII
106463-17-6 SECONDARY_CAS_RN
108559004 SNOMEDCT_US
4024076 VANDF
006115 NDDF
d04121 MMSL
5541 MMSL
77492 RXNORM
372509005 SNOMEDCT_US
CHEMBL836 ChEMBL_ID
DB00706 DRUGBANK_ID
6750 INN_ID
CHEBI:9398 CHEBI
CHEMBL1200914 ChEMBL_ID
129211 PUBCHEM_CID
488 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
FLOMAX HUMAN PRESCRIPTION DRUG LABEL 1 0024-5837 CAPSULE 0.40 mg ORAL NDA 18 sections
JALYN HUMAN PRESCRIPTION DRUG LABEL 2 0173-0809 CAPSULE 0.40 mg ORAL NDA 17 sections
Tamsulosin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0228-2996 CAPSULE 0.40 mg ORAL ANDA 18 sections
Dutasteride and tamsulosin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0591-3771 CAPSULE 0.40 mg ORAL ANDA 17 sections
Flomax HUMAN PRESCRIPTION DRUG LABEL 1 0597-0058 CAPSULE 0.40 mg ORAL NDA 18 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7995 CAPSULE 0.40 mg ORAL ANDA 19 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-8055 CAPSULE 0.40 mg ORAL ANDA 18 sections
tamsulosin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-2076 CAPSULE 0.40 mg ORAL ANDA 17 sections
tamsulosin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6401 CAPSULE 0.40 mg ORAL ANDA 17 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10370-169 CAPSULE 0.40 mg ORAL ANDA 17 sections
Dutasteride and Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 10370-280 CAPSULE 0.40 mg ORAL ANDA 16 sections
Tamsulosin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-280 CAPSULE 0.40 mg ORAL ANDA 18 sections
TAMSULOSIN HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 10544-550 CAPSULE 0.40 mg ORAL ANDA 17 sections
TAMSULOSIN HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-298 CAPSULE 0.40 mg ORAL ANDA 17 sections
FLOMAX HUMAN PRESCRIPTION DRUG LABEL 1 16590-489 CAPSULE 0.40 mg ORAL NDA 19 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-713 CAPSULE 0.40 mg ORAL ANDA 17 sections
TAMSULOSIN HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 33261-839 CAPSULE 0.40 mg ORAL ANDA 16 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33342-159 CAPSULE 0.40 mg ORAL ANDA 17 sections
TAMSULOSIN HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42254-012 CAPSULE 0.40 mg ORAL ANDA 17 sections
Tamsulosin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-264 CAPSULE 0.40 mg ORAL ANDA 18 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-725 CAPSULE 0.40 mg ORAL ANDA 17 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-947 CAPSULE 0.40 mg ORAL ANDA 17 sections
tamsulosin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-013 CAPSULE 0.40 mg ORAL ANDA 19 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-019 CAPSULE 0.40 mg ORAL ANDA 18 sections
Tamsulosin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-663 CAPSULE 0.40 mg ORAL ANDA 19 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-1846 CAPSULE 0.40 mg ORAL ANDA 17 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-3646 CAPSULE 0.40 mg ORAL ANDA 20 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-740 CAPSULE 0.40 mg ORAL ANDA 19 sections
Tamsulosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50436-0598 CAPSULE 0.40 mg ORAL ANDA 18 sections
TAMSULOSIN HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51655-677 CAPSULE 0.40 mg ORAL ANDA 14 sections