4-(ethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride

• ChemBase ID: 166233
• Molecular Formular: C20H28ClNO3
• Molecular Mass: 365.89422
• Monoisotopic Mass: 365.17577144
• SMILES: C1CCCC(C1)C(C(=O)OCC#CCNCC)(O)c1ccccc1.Cl
• Canonical SMILES: CCNCC#CCOC(=O)C(c1ccccc1)(C1CCCCC1)O.Cl
• InChI: InChI=1S/C20H27NO3.ClH/c1-2-21-15-9-10-16-24-19(22)20(23,17-11-5-3-6-12-17)18-13-7-4-8-14-18;/h3,5-6,11-12,18,21,23H,2,4,7-8,13-16H2,1H3;1H
• InChIKey: DSWCYTSHCYXHGW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(ethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride
• IUPAC Traditional name: 4-(ethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride
• Synonyms: α-Cyclohexyl-α-hydroxybenzeneacetic Acid 4-(Ethylamino)-2-butynyl Ester Hydrochloride Salt; rac Desethyl Oxybutynin Hydrochloride; (αR)-α-Cyclohexyl-α-hydroxybenzeneacetic Acid 4-(Ethylamino)-2-butyn-1-yl Ester Hydrochloride; (R)-N-Desethyl Oxybutynin Hydrochloride; (αS)-α-Cyclohexyl-α-hydroxybenzeneacetic Acid 4-(Ethylamino)-2-butyn-1-yl Ester Hydrochloride; (S)-N-Desethyl Oxybutynin Hydrochloride

Database IDs

• CAS Number: 81039-77-2; 181647-14-3; 181647-12-1
• PubChem SID: 162260366
• PubChem CID: 9842085

CALCULATED PROPERTIES

• Acid pKa: 11.533728
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.60267043
• LogD (pH = 7.4): 1.9653311
• Log P: 3.6982195
• Molar Refractivity: 95.219 cm^3
• Polarizability: 37.187916 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dimethyl Sulfoxide; DMSO; Methanol; Water
• Apperance: White to Off-White; White to Off-White Solid
• Melting Point: 136-138°C; 155-157°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D289465

(R)-Metabolite of the drug Oxybutynin. Used in the treatmentment of incontinence.

Toronto Research Chemicals - D289475

A metabolite of the drug Oxybutynin. Used in the treatmentment of incontinence.

Toronto Research Chemicals - D289470

(S)-Metabolite of the drug Oxybutynin. Used in the treatmentment of incontinence.

REFERENCES

• Ehlert, F., et al.: Life Sci., 74, 355 (2003)
• Matsui-Sakata, A., et al.: Drug Metab. Pharmacokinet., 20, 187 (2003)
• Hegde, S., et al.: Br. J. Pharmacol., 147, S80 (2003)
• Tashiro, M., et al.: Br. J. Clin. Pharmacol., 61, 16 (2003)
• Hughes, K., et al.: Xenobiotica, 22, 859 (1992)
• Oki, T., et al.: Biol. Pharm. Bull., 24, 491 (1992)
• Fetscher, C., et al.: Br. J. Pharmacol., 136, 64 (1992)
• Zobrist, R., et al.: Pharm. Res., 20, 103 (2003)
• Ehlert, F., et al.: Life Sci., 74, 355 (2003)
• Matsui-Sakata, A., et al.: Drug Metab. Pharmacokinet., 20, 187 (2003)
• Hegde, S., et al.: Br. J. Pharmacol., 147, S80 (2003)
• Tashiro, M., et al.: Br. J. Clin. Pharmacol., 61, 16 (2003)