Tolterodine tartrate

Base Information

• Chemical Name: Tolterodine tartrate
• CAS No.: 124937-52-6
• Molecular Formula: C22H31NO^.C4H6O6
• Molecular Weight: 475.582
• Hs Code.: 29222990
• European Community (EC) Number: 620-503-4
• UNII: 5T619TQR3R
• DSSTox Substance ID: DTXSID80924972
• Wikidata: Q27114836
• NCI Thesaurus Code: C29504
• RXCUI: 221174
• ChEMBL ID: CHEMBL1200871
• Mol file: 124937-52-6.mol

Synonyms:Detrol;Detrol LA;Detrusitol;PHA 686464B;PHA-686464B;PHA686464B;Tartrate, Tolterodine;tolterodine;tolterodine tartrate;Unidet;Urotrol

Chemical Property of Tolterodine tartrate

Chemical Property:

• Appearance/Colour: white-to-off-white crystalline powder
• Vapor Pressure: 1.97E-08mmHg at 25°C
• Melting Point: 205-210 °C
• Boiling Point: 442.2 °C at 760 mmHg
• PKA: 9.87(at 25℃)
• Flash Point: 192.1 °C
• PSA: 138.53000
• Density: 1.003 g/cm³
• LogP: 3.21880
• Storage Temp.: Store at +4°C
• Solubility.: Methanol (Sparingly), Water (Slightly)
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 475.25700252
• Heavy Atom Count: 34
• Complexity: 474

Purity/Quality:

98%min ^*data from raw suppliers

Tolterodine, Tartrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)O)C(CCN(C(C)C)C(C)C)C2=CC=CC=C2.C(C(C(=O)O)O)(C(=O)O)O
• Isomeric SMILES: CC1=CC(=C(C=C1)O)[C@H](CCN(C(C)C)C(C)C)C2=CC=CC=C2.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
• Recent ClinicalTrials: Tolterodine Relieves Overactive Bladder Symptoms in Women With Moderate-to-severe Obstructive Sleep Apnea Syndrome
• Recent EU Clinical Trials: An International Phase 3, Randomized, Double-Blind, Active (Tolterodine)-Controlled Multicenter Extension Study to Evaluate the Long-Term Safety and Efficacy of Vibegron in Patients with Symptoms of Overactive Bladder
• Recent NIPH Clinical Trials: A randomized controlled trial for beta agonist on ulolithiasis patients associated with overactive bladder.
• Uses: Tolterodine tartrate (Detrol LA) is a tartrate salt of tolterodine that is a competitive muscarinic receptor antagonist. Tolterodine tartrate (Detrol LA) is indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urge Tolterodine (tartrate) is a competitive antagonist of muscarinic (M) receptors (Ki = 1.4, 2.7, 3.6, 3.1, and 2.2 nM for M1 through M5, respectively). Antagonists of muscarinic receptors, including tolterodine, are effective in treating overactive bladder symptoms.[Cayman Chemical]
• Therapeutic Function: Anticholinergic
• Clinical Use: Selective vasopressin V2 -receptor antagonist: Treatment of hyponatraemia secondary to SIADH To slow the progression of autosomal dominant polycystic kidney disease (ADPKD)
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone, disopyramide and flecainide; increased risk of antimuscarinic side effects with disopyramide. Antifungals: avoid concomitant use with itraconazole and ketoconazole. Antivirals: avoid concomitant use with fosamprenavir, indinavir, lopinavir, ritonavir and saquinavir. Beta-blockers: increased risk of ventricular arrhythmias with sotalol.

Technology Process of Tolterodine tartrate

There total 27 articles about Tolterodine tartrate 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: 88.0%

N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride + L-Tartaric acid (87-69-4,138508-61-9) → tolterodine tartrate (124937-52-6,209747-05-7)

Guidance literature:

N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride; With sodium carbonate; sodium hydroxide; In dichloromethane; water; at 20 ℃; for 1h;

L-Tartaric acid; In methanol; acetone; for 1h; Reflux;

DOI:10.1021/op7001134

Reference yield: 39.0%

3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide (837376-36-0) + L-Tartaric acid (87-69-4,138508-61-9) → tolterodine tartrate (124937-52-6,209747-05-7)

Guidance literature:

3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide; With sodium hydroxide; In dichloromethane; water;

L-Tartaric acid; In ethanol; at 60 - 85 ℃;

Reference yield: 37.0%

(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide (897314-72-6) + L-Tartaric acid (87-69-4,138508-61-9) → tolterodine tartrate (124937-52-6,209747-05-7)

Guidance literature:

(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide; With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 5 - 40 ℃; for 6h; Cooling with ice;

L-Tartaric acid; In ethanol; at 0 - 70 ℃; Reflux;

upstream raw materials:

L-Tartaric acid

N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine

3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide

N,N-Diisopropyl-3-(2-hydroxyphenyl)-3-phenylpropylamine

Downstream raw materials:

(R)-3-[2-(benzyloxy)-5-methylphenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

propane

(R)-5-hydroxymethyl tolterodine fumarate salt

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

Refernces

• 1、 Korenaga, Toshinobu,Sasaki, Ryo,Takemoto, Toshihide,Yasuda, Toshihisa,Watanabe, Masahito. "Computationally-Led Ligand Modification using Interplay between Theory and Experiments: Highly Active Chiral Rhodium Catalyst Controlled by Electronic Effects and CH–π Interactions". . p. 322 - 333. Retrieved 2018/01/22.
• 2、 -. "Process for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)- 3-phenyl propylamine and its salts starting from a novel intermediate". Page/Page column 11. . Retrieved 2012/07/28.