2-[(1S)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol

• ChemBase ID: 908
• Molecular Formular: C22H31NO
• Molecular Mass: 325.48764
• Monoisotopic Mass: 325.24056462
• SMILES: Oc1c([C@@H](CCN(C(C)C)C(C)C)c2ccccc2)cc(cc1)C
• Canonical SMILES: Cc1ccc(c(c1)[C@H](c1ccccc1)CCN(C(C)C)C(C)C)O
• InChI: InChI=1S/C22H31NO/c1-16(2)23(17(3)4)14-13-20(19-9-7-6-8-10-19)21-15-18(5)11-12-22(21)24/h6-12,15-17,20,24H,13-14H2,1-5H3/t20-/m0/s1
• InChIKey: OOGJQPCLVADCPB-FQEVSTJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
• IUPAC Traditional name: detrol
• Brand Name: Detrol; Detrol LA
• Synonyms: 2-[(1S)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methyl-phenol; (S)-Tolterodine; S-(-)-Tolterodine; Tolterodina [INN-Spanish]; Tolterodine L-Tartrate; Tolterodine Tartrate; Tolterodine [INN]; Tolterodinum [INN-Latin]; Tolterondine Tartrate; tolterodine extended release capsules; Tolterodine; TOLTERODINE TARTRATE; 2-[(1S)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol

Database IDs

• CAS Number: 124937-51-5; 124937-53-7
• MDL Number: MFCD15147030
• PubChem SID: 160964371
• PubChem CID: 60774

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.279249
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.3333476
• LogD (pH = 7.4): 2.7616951
• Log P: 5.116409
• Molar Refractivity: 103.9572 cm^3
• Polarizability: 40.39475 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.39
• LOG S: -4.78
• Solubility (Water): 5.34e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 5.24; 5.6

Product Information

• Purity: 95%; 98%

DETAILS

DrugBank - DB01036

• Drug Groups: approved; investigational
• Description: Tolterodine is an antimuscarinic drug that is used to treat urinary incontinence. Tolterodine acts on M2 and M3 subtypes of muscarinic receptors.
• Indication: For the treatment of overactive bladder (with symptoms of urinary frequency, urgency, or urge incontinence).
• Pharmacology: Tolterodine is a competitive muscarinic receptor antagonist. Both urinary bladder contraction and salivation are mediated via cholinergic muscarinic receptors. After oral administration, tolterodine is metabolized in the liver, resulting in the formation of the 5-hydroxymethyl derivative, a major pharmacologically active metabolite. The 5-hydroxymethyl metabolite, which exhibits an antimuscarinic activity similar to that of tolterodine, contributes significantly to the therapeutic effect. Both tolterodine and the 5-hydroxymethyl metabolite exhibit a high specificity for muscarinic receptors, since both show negligible activity or affinity for other neurotransmitter receptors and other potential cellular targets, such as calcium channels. Tolterodine has a pronounced effect on bladder function. The main effects of tolterodine are an increase in residual urine, reflecting an incomplete emptying of the bladder, and a decrease in detrusor pressure, consistent with an antimuscarinic action on the lower urinary tract.
• Affected Organisms: Humans and other mammals
• Half Life: 1.9-3.7 hours
• Protein Binding: Approximately 96.3%.
• Elimination: Following administration of a 5-mg oral dose of 14C-tolterodine solution to healthy volunteers, 77% of radioactivity was recovered in urine and 17% was recovered in feces in 7 days.
• Distribution: * 113 ± 26.7 L
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - T535796

A muscarinic receptor antagonist. Used in the treatment of urinary incontinence.

REFERENCES

• Nilvebrant, L., et al.: Life Sci., 60, 1129 (1997)
• Nilvebrant, L., et al.: Eur. J. Pharmacol., 327, 195 (1997)
• Brynne, N., et al.: Int. J. Clin. Pharmacol. Ther., 35, 287 (1997)