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

• ChemBase ID: 130892
• Molecular Formular: C22H32ClNO3
• Molecular Mass: 393.94738
• Monoisotopic Mass: 393.20707157
• SMILES: CCN(CC)CC#CCOC(=O)C(c1ccccc1)(C1CCCCC1)O.Cl
• Canonical SMILES: CCN(CC#CCOC(=O)C(c1ccccc1)(C1CCCCC1)O)CC.Cl
• InChI: InChI=1S/C22H31NO3.ClH/c1-3-23(4-2)17-11-12-18-26-21(24)22(25,19-13-7-5-8-14-19)20-15-9-6-10-16-20;/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3;1H
• InChIKey: SWIJYDAEGSIQPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(diethylamino)but-2-yn-1-yl (2S)-2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride; 4-(diethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride; 4-(diethylamino)but-2-yn-1-yl (2R)-2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride
• IUPAC Traditional name: esoxybutynin hydrochloride; oxybutynin hydrochloride; transdermal patch hydrochloride
• Synonyms: α-Phenylcyclohexaneglycolic Acid 4-(Diethylamino)-2-butynyl Ester, Hydrochloride; Oxybutynin Chloride; (S)-α-Phenylcyclohexaneglycolic Acid 4-(Diethylamino)-2-butynyl Ester, Hydrochloride; (S)-Oxybutynin Chloride; α-Phenylcyclohexaneglycolic acid 4-(diethylamino)-2-butynyl ester hydrochloride; Oxybutynin chloride; (R)-α-Phenylcyclohexaneglycolic Acid 4-(Diethylamino)-2-butynyl Ester, Hydrochloride; (R)-Oxybutynin Chloride; α-苯基环己烷乙醇酸 4-(二乙基氨基)-2-丁炔酯 盐酸盐; 盐酸奥昔布宁

Database IDs

• CAS Number: 230949-16-3; 1508-65-2; 1207344-05-5
• EC Number: 216-139-7
• MDL Number: MFCD00072150
• PubChem SID: 24278608; 24898008; 162225170
• PubChem CID: 91505

CALCULATED PROPERTIES

• Acid pKa: 11.532723
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3698729
• LogD (pH = 7.4): 3.0553124
• Log P: 4.4380755
• Molar Refractivity: 105.2623 cm^3
• Polarizability: 40.873947 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; H2O: soluble50 mg/mL; Methanol
• Apperance: Off-White Solid; white powder; White Solid; White to Off-White Solid
• Melting Point: 107-109°C; 122-124°C; 52-54°C

Safety Information

• Storage Condition: -20°C Freezer; Hygroscopic, Refrigerator, Under Inert Atmosphere; Refrigerator, Under Inert Atmosphere
• RTECS: GV2800000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Target: AChR
• Gene Information: human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)

Product Information

• Purity: ≥98% (TLC)
• Salt Data: Chloride
• Suitability: meets EP, USP testing specifications
• Empirical Formula (Hill Notation): C22H31NO3 · HCl

DETAILS

Sigma Aldrich - O2881

Biochem/physiol Actions
Muscarinic acetylcholine receptor antagonist; inhibits proliferation of bladder smooth muscle cells, perhaps by downregulation of growth promoting genes.

Sigma Aldrich - O5015

Biochem/physiol Actions
毒蕈碱型乙酰胆碱受体拮抗剂；可能通过下调生长促进基因，抑制膀胱平滑肌细胞的增殖。

Toronto Research Chemicals - O868525

An inhibitor of proliferation and supresses gene expression in bladder smooth muscle cells.

Toronto Research Chemicals - O868510

The optically avtice inhibitor of proliferation and supresses gene expression in bladder smooth muscle cells.

Toronto Research Chemicals - O868515

The optically avtice inhibitor of proliferation and supresses gene expression in bladder smooth muscle cells.

REFERENCES

• Park, J.M., et al.: J. Urol., 162, 1110 (1999)
• Watson, M., et al.: Brit. J. Pharmacol., 127, 590 (1999)
• Park, J.M., et al.: J. Urol., 162, 1110 (1999)
• Watson, M., et al.: Brit. J. Pharmacol., 127, 590 (1999)
• Park, J.M., et al.: J. Urol., 162, 1110 (1999)
• Watson, M., et al.: Brit. J. Pharmacol., 127, 590 (1999)