(+)-Tamsulosin

Details

• Internal ID: fd391d7f-d409-4e22-923f-c987662d9a77
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenethylamines > Amphetamines and derivatives
• IUPAC Name: 5-[(2S)-2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
• SMILES (Canonical): CCOC1=CC=CC=C1OCCNC(C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N
• SMILES (Isomeric): CCOC1=CC=CC=C1OCCN[C@@H](C)CC2=CC(=C(C=C2)OC)S(=O)(=O)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-/m0/s1
• InChI Key: DRHKJLXJIQTDTD-HNNXBMFYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈N₂O₅S
• Molecular Weight: 408.50 g/mol
• Exact Mass: 408.17189317 g/mol
• Topological Polar Surface Area (TPSA): 108.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.34
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 11

Synonyms

• (S)-Tamsulosin
• 106138-88-9
• Tamsulosin, (S)-
• 8KV50K3QKP
• 5-[(2S)-2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
• (S)-5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide
• Benzenesulfonamide, 5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxy-, (S)-
• LY 253352
• ent-tamsulosin
• C20-H28-N2-O5-S
• (S)-Tamulosin
• LY-253352
• (s)-(+)-tamsulosin
• UNII-8KV50K3QKP
• SCHEMBL3343160
• CHEBI:142548
• DTXSID401317377
• AKOS030211725
• (+)-YM-617
• TAMSULOSIN HYDROCHLORIDE IMPURITY G [EP IMPURITY]
• 5-((2S)-2-((2-(2-ETHOXYPHENOXY)ETHYL)AMINO)PROPYL)-2-METHOXYBENZENESULFONAMIDE
• BENZENESULFONAMIDE, 5-((2S)-2-((2-(2-ETHOXYPHENOXY)ETHYL)AMINO)PROPYL)-2-METHOXY-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	-	0.6310	63.10%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.9429	94.29%
Subcellular localzation	Mitochondria	0.4387	43.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9500	95.00%
OATP1B3 inhibitior	+	0.9396	93.96%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6122	61.22%
P-glycoprotein inhibitior	+	0.6764	67.64%
P-glycoprotein substrate	+	0.5652	56.52%
CYP3A4 substrate	+	0.5747	57.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4570	45.70%
CYP3A4 inhibition	+	0.7180	71.80%
CYP2C9 inhibition	+	0.5916	59.16%
CYP2C19 inhibition	-	0.5056	50.56%
CYP2D6 inhibition	-	0.8614	86.14%
CYP1A2 inhibition	-	0.7876	78.76%
CYP2C8 inhibition	+	0.5123	51.23%
CYP inhibitory promiscuity	-	0.6146	61.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5604	56.04%
Carcinogenicity (trinary)	Non-required	0.5936	59.36%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9870	98.70%
Skin irritation	-	0.7829	78.29%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7260	72.60%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.7908	79.08%
skin sensitisation	-	0.8505	85.05%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.5391	53.91%
Estrogen receptor binding	+	0.5366	53.66%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	-	0.8319	83.19%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	-	0.5860	58.60%
PPAR gamma	+	0.6154	61.54%
Honey bee toxicity	-	0.6834	68.34%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9829	98.29%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL229	P35348	Alpha-1a adrenergic receptor	0.05012 nM	Ki	via Super-PRED
CHEMBL232	P35368	Alpha-1b adrenergic receptor	0.631 nM	Ki	via Super-PRED
CHEMBL223	P25100	Alpha-1d adrenergic receptor	0.1 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL205	P00918	Carbonic anhydrase II	99.07%	98.44%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.39%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.97%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.49%	95.56%
CHEMBL3594	Q16790	Carbonic anhydrase IX	92.38%	99.23%
CHEMBL2535	P11166	Glucose transporter	92.19%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.06%	94.00%
CHEMBL1255126	O15151	Protein Mdm4	90.72%	90.20%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.46%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.55%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.15%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.25%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.10%	95.83%
CHEMBL3729	P22748	Carbonic anhydrase IV	83.52%	99.23%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.51%	90.24%
CHEMBL2321614	Q9NPC2	Potassium channel subfamily K member 9	81.49%	80.00%
CHEMBL261	P00915	Carbonic anhydrase I	81.28%	96.76%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.28%	97.21%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.23%	96.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.20%	86.33%

Plants that contains it

• Piper nigrum

Cross-Links

• PubChem: 60147
• NPASS: NPC68898