2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenol

• ChemBase ID: 73214
• Molecular Formular: C22H31NO2
• Molecular Mass: 341.48704
• Monoisotopic Mass: 341.23547924
• SMILES: c1ccccc1[C@H](c1c(ccc(c1)CO)O)CCN(C(C)C)C(C)C
• Canonical SMILES: OCc1ccc(c(c1)[C@@H](c1ccccc1)CCN(C(C)C)C(C)C)O
• InChI: InChI=1S/C22H31NO2/c1-16(2)23(17(3)4)13-12-20(19-8-6-5-7-9-19)21-14-18(15-24)10-11-22(21)25/h5-11,14,16-17,20,24-25H,12-13,15H2,1-4H3/t20-/m1/s1
• InChIKey: DUXZAXCGJSBGDW-HXUWFJFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenol
• IUPAC Traditional name: 2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol
• Synonyms: PNU 200577; 5-hydroxymethyl tolterodine; 3-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol; (+)-N,N-Diisopropyl-3-(2-hydroxy-5-hydroxymethylphenyl)-3-phenylpropylamine; (R)-5-Hydroxymethyl Tolterodine

Database IDs

• CAS Number: 207679-81-0
• PubChem SID: 162038134
• PubChem CID: 9819382

CALCULATED PROPERTIES

• Acid pKa: 9.5834055
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.0560644
• LogD (pH = 7.4): 1.572271
• Log P: 3.42528
• Molar Refractivity: 105.7319 cm^3
• Polarizability: 41.04398 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 68-72°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Pharmacology Properties

• Target: mAChRs

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2659

Biological Activity:
5-hydroxymethyl tolterodine (PNU 200577) is a potent and selective muscarinic receptor antagonist with a Kb and a pA2 of 0.84 nM and 9.14, respectively. 5-hydroxymethyl tolterodine (PNU 200577) is a major pharmacologically active metabolite of tolterodine. In vitro, PNU-200577 prevented carbachol-induced contraction of guinea-pig isolated urinary bladder strips in a competitive and concentration-dependent manner. In vivo, PNU-200577 was significantly more potent at suppressing acetylcholine-induced urinary bladder contraction than electrically induced salivation in the anaesthetised cat (ID50=15 and 40 nmol/kg, respectively). In radioligand binding studies carried out in homogenates of guinea-pig tissues and Chinese hamster ovary cell lines expressing human muscarinic m1-m5 receptors, 5-hydroxymethyl tolterodine (PNU 200577) was not selective for any muscarinic receptor subtype. Thus, 5-hydroxymethyl tolterodine (PNU 200577) is similar to tolterodine in terms of antimuscarinic potency, functional selectivity for the urinary bladder in vivo and absence of selectivity for muscarinic receptor subtypes in vitro. The results of this study clearly indicate that 5-hydroxymethyl tolterodine (PNU 200577) contributes to the therapeutic action of tolterodine, in view of its high antimuscarinic potency, similar serum concentration and lower degree of protein binding. [1] References on 5-hydroxymethyl tolterodine (PNU 200577)[1] Pharmacol Toxicol, 1997 Oct, 81(4):169-72

Toronto Research Chemicals - H948363

A metabolite of Tolterodine (T535800), a muscarinic receptor antagonist used in the treatment of urinary incontinence.

REFERENCES

• Nilvebrant L et al. Pharmacol Toxicol. 1997 Oct;81(4):169-72.
• Palmer, L., et al.: J. Pharm. Biomed. Anal., 16, 155 (1997)
• Hills, C., et al.: Drugs, 55, 813 (1997)
• Wefer, J., et al.: World J. Urol., 19, 312 (1997)