Fesoterodine

Base Information

• Chemical Name: Fesoterodine
• CAS No.: 286930-03-8
• Molecular Formula: (x)C₄H₄O₄*C₂₆H₃₇NO₃
• Molecular Weight: 527.65
• European Community (EC) Number: 658-058-3
• UNII: 621G617227
• DSSTox Substance ID: DTXSID80182853
• Nikkaji Number: J2.587.519B
• Wikipedia: Fesoterodine
• Wikidata: Q4482372
• NCI Thesaurus Code: C74138
• RXCUI: 797195
• Pharos Ligand ID: XU7ZMW28734Z
• Metabolomics Workbench ID: 43683
• ChEMBL ID: CHEMBL1201764
• Mol file: 286930-03-8.mol

Synonyms:fesoterodine;fesoterodine fumarate;toviaz

Chemical Property of Fesoterodine

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 72-78 °C
• Boiling Point: 518.9 °C at 760 mmHg
• Flash Point: 267.6 °C
• PSA: 124.37000
• LogP: 5.09290
• Storage Temp.: Hygroscopic, Store under Inert atmosphere -20°C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 411.27734404
• Heavy Atom Count: 30
• Complexity: 491

Purity/Quality:

99.5% ^*data from raw suppliers

(R)-FesoterodineFumarate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticholinergic Agents
• Canonical SMILES: CC(C)C(=O)OC1=C(C=C(C=C1)CO)C(CCN(C(C)C)C(C)C)C2=CC=CC=C2
• Isomeric SMILES: CC(C)C(=O)OC1=C(C=C(C=C1)CO)[C@H](CCN(C(C)C)C(C)C)C2=CC=CC=C2
• Recent ClinicalTrials: Fall Prevention in Older Adults With OAB
• Recent EU Clinical Trials: A 24-WEEK RANDOMIZED, OPEN-LABEL, STUDY TO EVALUATE THE SAFETY AND EFFICACY OF FESOTERODINE IN SUBJECTS AGED 6 TO 17 YEARS WITH SYMPTOMS OF DETRUSOR OVERACTIVITY ASSOCIATED WITH A NEUROLOGICAL CONDITION (NEUROGENIC DETRUSOR OVERACTIVITY)
• Recent NIPH Clinical Trials: The efficacy of Fesoterodine for the treatment of neurogenic detrusor overactivity and/or low-compliance bladder
• Description: Fesoterodine fumarate is a new drug for the treatment of overactive bladder syndrome developed by Pfizer, which was approved by the US FDA in October 2008. Fesoterodine fumarate is a prodrug, which is rapidly hydrolyzed in blood after oral administration to 5-hydroxymethyl tolterodine (5-HMT), which is also the active metabolite of tolterodine.
• Uses: Fesoterodine fumarate (Toviaz) is an antimuscarinic agent and is rapidly de-esterified to its active metabolite 5-hydroxymethyl tolterodine that is a muscarinic receptor antagonist. Fesoterodine fumarate (Toviaz) is used to treat the symptoms of overactiv (R)-Fesoterodine Fumarate is a muscarinic receptor antagonist for the treatment of Lower Urininary Tract Symptoms (LUTS). It is very similar to Tolterodine (T535800).
• Clinical Use: Antimuscarinic:Symptomatic treatment of urinary incontinence, frequency or urgency
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: increased risk of antimuscarinic side effects with disopyramide. Antifungals: dose reduction advised with itraconazole and ketoconazole. Antivirals: dose reduction advised with atazanavir, indinavir, ritonavir and saquinavir. Induction of CYP3A4 may lead to subtherapeutic plasma levels. Concomitant use with CYP3A4 inducers (e.g. carbamazepine, rifampicin, phenobarbital, phenytoin, St John's Wort) is not recommended. Co-administration of a potent CYP2D6 inhibitor may result in increased exposure and adverse events. A dose reduction to 4 mg may be needed' See 'Other information'

Technology Process of Fesoterodine

There total 114 articles about Fesoterodine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.7%

isobutyryl chloride (79-30-1) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) + (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol (207679-81-0) → fesoterodine fumarate (286930-03-8,1333234-73-3)

Guidance literature:

isobutyryl chloride; (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol; With sodium hydrogencarbonate; In dichloromethane; water; at 5 - 20 ℃;

(2E)-but-2-enedioic acid; In butanone; at 0 - 35 ℃; for 3h; Product distribution / selectivity;

Reference yield: 85.7%

(2E)-but-2-enedioic acid (110-17-8,26099-09-2) + (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol (207679-81-0) → fesoterodine fumarate (286930-03-8,1333234-73-3)

Guidance literature:

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)-phenol; With sodium hydrogencarbonate; isobutyryl chloride; In dichloromethane; water; at 5 ℃;

(2E)-but-2-enedioic acid; In butanone; at 35 ℃; Product distribution / selectivity;

Reference yield: 83.1%

fesoterodine (286930-02-7,250214-44-9) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → fesoterodine fumarate (286930-03-8,1333234-73-3)

Guidance literature:

In cyclohexane; butanone; at 20 ℃; for 18h; Heating;

upstream raw materials:

fesoterodine

(2E)-but-2-enedioic acid

isobutyryl chloride

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

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF OPTICALLY PURE FESOTERODINE DERIVATIVES". Paragraph 0249; 0250. . Retrieved 2015/04/15.
• 2、 -. "PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 3,3-DIPHENYLPROPYLAMINES". . . Retrieved 2013/08/15.