Title: Tolterodine
CAS Registry Number: 124937-51-5
CAS Name: 2-[(1
R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol
Synonyms: (+)-(
R)-2-[a-[2-(diisopropylamino)ethyl]benzyl]-
p-cresol; (+)-
N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine
Manufacturers' Codes: Kabi 2234
Molecular Formula: C22H31NO
Molecular Weight: 325.49
Percent Composition: C 81.18%, H 9.60%, N 4.30%, O 4.92%
Literature References: Muscarinic receptor antagonist. Prepn: N. A. J?nsson
et al., EP 325571 (1989 to KabiVitrum);
eidem, US 5382600 (1995 to Pharmacia). Asymmetric total synthesis: C. Hedberg, P. G. Andersson,
Adv. Synth. Catal. 347, 662 (2005). Pharmacology: L. Nilvebrant
et al., Life Sci. 60, 1129 (1997). Receptor binding study:
idem et al., Eur. J. Pharmacol. 327, 195 (1997). GC-MS determn in biological fluids: L. Palmér
et al., J. Pharm. Biomed. Anal. 16, 155 (1997). Clinical pharmacokinetics: N. Brynne
et al., Int. J. Clin. Pharmacol. Ther. 35, 287 (1997). Review of clinical trials: R. A. Appell,
Urology 50, Suppl. 6A, 90-96 (1997); of use in overactive bladder: E. S. Rovner,
Expert Opin. Pharmacother. 6, 653-666 (2005).
Properties: [a]D25 +72° (c = 1.0 in CH2Cl2).
Optical Rotation: [a]D25 +72° (c = 1.0 in CH2Cl2)
Derivative Type: Tartrate
CAS Registry Number: 124937-52-6
Manufacturers' Codes: PNU-200583E
Trademarks: Detrol (Pharmacia & Upjohn); Detrusitol (Pharmacia & Upjohn)
Molecular Formula: C22H31NO.C4H6O6
Molecular Weight: 475.57
Percent Composition: C 65.66%, H 7.84%, N 2.95%, O 23.55%
Properties: Crystals from ethanol. [a]54625 +36.0°. pKa 9.87. Soly in water: 12 mg/ml. Sol in methanol; slightly sol in ethanol. Practically insol in toluene. Partition coefficient (
n-octanol/water): 1.83 (pH 7.3). LD50 i.v. in male mice: 10-20 mg/kg (J?nsson).
pKa: pKa 9.87
Optical Rotation: [a]54625 +36.0°
Log P: Partition coefficient (
n-octanol/water): 1.83 (pH 7.3)
Toxicity data: LD50 i.v. in male mice: 10-20 mg/kg (J?nsson)
Therap-Cat: In treatment of urinary incontinence.
Keywords: Antimuscarinic.
