CAS 207679-81-0|5-hydroxymethyl Tolterodine (PNU 200577, 5-HMT, 5-HM)

Introduction：Basic information about CAS 207679-81-0|5-hydroxymethyl Tolterodine (PNU 200577, 5-HMT, 5-HM), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Customs
6. Synonyms

Common Name	5-hydroxymethyl Tolterodine (PNU 200577, 5-HMT, 5-HM)
CAS Number	207679-81-0	Molecular Weight	341.487
Density	1.1±0.1 g/cm3	Boiling Point	490.7±45.0 °C at 760 mmHg
Molecular Formula	C₂₂H₃₁NO₂	Melting Point	68-72°C
MSDS	/	Flash Point	233.2±27.4 °C

Names

Name	5-hydroxymethyl Tolterodine
Synonym	More Synonyms

BiologicalActivity

Description	(R)-5-Hydroxymethyl Tolterodine(PNU-200577; Desfesoterodine) is a potent and selective muscarinic receptor antagonist with a Kb and a pA2 of 0.84 nM and 9.14, respectively. IC50 value: 0.84 nM (Kb)Target: mAChR(R)-5-Hydroxymethyl Tolterodine is a major pharmacologically active metabolite of tolterodine. In vitro, (R)-5-Hydroxymethyl Tolterodine prevented carbachol-induced contraction of guinea-pig isolated urinary bladder strips in a competitive and concentration-dependent manner. In vivo, (R)-5-Hydroxymethyl Tolterodine 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, (R)-5-Hydroxymethyl Tolterodine was not selective for any muscarinic receptor subtype. Thus, (R)-5-Hydroxymethyl Tolterodine 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 (R)-5-Hydroxymethyl Tolterodine contributes to the therapeutic action of tolterodine, in view of its high antimuscarinic potency, similar serum concentration and lower degree of protein binding.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>mAChRSignaling Pathways >>Neuronal Signaling >>mAChRResearch Areas >>Neurological Disease
References	[1]. Nilvebrant L, Gillberg PG, Sparf B. Antimuscarinic potency and bladder selectivity of PNU-200577, a major metabolite of tolterodine. Pharmacol Toxicol. 1997 Oct;81(4):169-72. [2]. Fullhase, Claudius; Soler, Roberto; Gratzke, Christian et al. Spinal effects of the fesoterodine metabolite 5-hydroxymethyl tolterodine and/or doxazosin in rats with or without partial urethral obstruction. Journal of Urology (New York, NY, United States) (2010), 184(2), 783-789. [3]. Nilvebrant, Lisbeth Tolterodine and its active 5-hydroxymethyl metabolite: pure muscarinic receptor antagonists. Pharmacology & Toxicology (Oxford, United Kingdom) (2002), 90(5), 260-267. [4]. Yono, Makoto; Yoshida, Masaki; Wada, Yoshihiro et al. Pharmacological effects of tolterodine on human isolated urinary bladder. European Journal of Pharmacology (1999), 368(2/3), 223-230.

Description

(R)-5-Hydroxymethyl Tolterodine(PNU-200577; Desfesoterodine) is a potent and selective muscarinic receptor antagonist with a Kb and a pA2 of 0.84 nM and 9.14, respectively. IC50 value: 0.84 nM (Kb)Target: mAChR(R)-5-Hydroxymethyl Tolterodine is a major pharmacologically active metabolite of tolterodine. In vitro, (R)-5-Hydroxymethyl Tolterodine prevented carbachol-induced contraction of guinea-pig isolated urinary bladder strips in a competitive and concentration-dependent manner. In vivo, (R)-5-Hydroxymethyl Tolterodine 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, (R)-5-Hydroxymethyl Tolterodine was not selective for any muscarinic receptor subtype. Thus, (R)-5-Hydroxymethyl Tolterodine 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 (R)-5-Hydroxymethyl Tolterodine contributes to the therapeutic action of tolterodine, in view of its high antimuscarinic potency, similar serum concentration and lower degree of protein binding.

Related Catalog

Signaling Pathways >>GPCR/G Protein >>mAChRSignaling Pathways >>Neuronal Signaling >>mAChRResearch Areas >>Neurological Disease

References

[1]. Nilvebrant L, Gillberg PG, Sparf B. Antimuscarinic potency and bladder selectivity of PNU-200577, a major metabolite of tolterodine. Pharmacol Toxicol. 1997 Oct;81(4):169-72.

[2]. Fullhase, Claudius; Soler, Roberto; Gratzke, Christian et al. Spinal effects of the fesoterodine metabolite 5-hydroxymethyl tolterodine and/or doxazosin in rats with or without partial urethral obstruction. Journal of Urology (New York, NY, United States) (2010), 184(2), 783-789.

[3]. Nilvebrant, Lisbeth Tolterodine and its active 5-hydroxymethyl metabolite: pure muscarinic receptor antagonists. Pharmacology & Toxicology (Oxford, United Kingdom) (2002), 90(5), 260-267.

[4]. Yono, Makoto; Yoshida, Masaki; Wada, Yoshihiro et al. Pharmacological effects of tolterodine on human isolated urinary bladder. European Journal of Pharmacology (1999), 368(2/3), 223-230.

Chemical & Physical Properties

Density	1.1±0.1 g/cm3
Boiling Point	490.7±45.0 °C at 760 mmHg
Melting Point	68-72°C
Molecular Formula	C₂₂H₃₁NO₂
Molecular Weight	341.487
Flash Point	233.2±27.4 °C
Exact Mass	341.235474
PSA	43.70000
LogP	4.12
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.563
InChIKey	DUXZAXCGJSBGDW-HXUWFJFHSA-N
SMILES	CC(C)N(CCC(c1ccccc1)c1cc(CO)ccc1O)C(C)C
Storage condition	-20?C Freezer

Safety Information

HS Code	2922509090

Customs

HS Code	2922509090
Summary	2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Synonyms

(R)-2-(3-(Diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol

2-[(1R)-3-(Diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol

(R)-5-Hydroxymethyl tolterodine

5-hydroxymethyl tolterodine (PNU 200577)

(R)-HYDROXYTOLTERODINE-D14

(R)-5-HYDROXYTOLTERODINE

R-(+)-2(3-DIISOPROPYLAMINO-1-PHENYLPROPYL)-4-HYDROXYMETHYLPHENOL

R-(+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethylphenol

R-5-Hydroxymethyl Tolterodine

3-[(1R)-3-[Bis(1-Methylethyl)Amino]-1-Phenylpropyl]-4-Hydroxy-Benzenemethanol

Desfesoterodine

3-[(1R)-3-[BIS(1-METHYLETHYL)AMINO]-1-PHENYLPROPYL]-4-HYDROXYBENZENEMETHANOL

Benzenemethanol, 3-[(1R)-3-[bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxy-

Fesoterodine fumarate Intermediate 2

Fesoterodine Impurity 1

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