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

Stem definition	Drug id	CAS RN
antihypertensive substances, prazosin derivatives	2562	106133-20-4

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.40	mg	O

ADMET properties:

Property	Value	Reference
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 µM/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:

Date	Agency	Company	Orphan
April 15, 1997	FDA	BOEHRINGER INGELHEIM

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Type	Activity value (-log[M])	Bioact source
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN	Ki	9.10	CHEMBL
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN	Ki	7.87	CHEMBL
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN	Ki	7.89	CHEMBL
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN	Ki	10.24	CHEMBL
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN	Ki	10.54	CHEMBL
Alpha-1B adrenergic receptor	GPCR	P35368	ADA1B_HUMAN	Ki	9.21	CHEMBL
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN	Ki	9.55	CHEMBL
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN	Ki	8.10	CHEMBL
5-hydroxytryptamine receptor 7	GPCR	P34969	5HT7R_HUMAN	Ki	7.08	CHEMBL
Alpha-1B adrenergic receptor	GPCR		ADA1B_MESAU	Ki	9.70	CHEMBL
Alpha-2B adrenergic receptor	GPCR		ADA2B_RAT	Ki	8.17	CHEMBL
Alpha-1D adrenergic receptor	GPCR		ADA1D_RAT	Ki	10.15	CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT	Ki	10.52	CHEMBL
Serotonin 1 (5-HT1) receptor	GPCR		5HT1A_RAT 5HT1B_RAT 5HT1D_RAT 5HT1F_RAT	Ki	6.03	CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_BOVIN	Ki	9.90	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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