(2R,3R)-2,3-dihydroxybutanedioic acid; 2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol

• ChemBase ID: 73101
• Molecular Formular: C26H37NO7
• Molecular Mass: 475.57448
• Monoisotopic Mass: 475.25700253
• SMILES: c1c(cc(c(c1)O)[C@@H](c1ccccc1)CCN(C(C)C)C(C)C)C.O=C(O)[C@@H]([C@H](C(=O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.Cc1ccc(c(c1)[C@@H](c1ccccc1)CCN(C(C)C)C(C)C)O
• InChI: InChI=1S/C22H31NO.C4H6O6/c1-16(2)23(17(3)4)14-13-20(19-9-7-6-8-10-19)21-15-18(5)11-12-22(21)24;5-1(3(7)8)2(6)4(9)10/h6-12,15-17,20,24H,13-14H2,1-5H3;1-2,5-6H,(H,7,8)(H,9,10)/t20-;1-,2-/m11/s1
• InChIKey: TWHNMSJGYKMTRB-KXYUELECSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid; 2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
• IUPAC Traditional name: L-tartaric acid; tolterodine; (+)-tolterodine; L(+)-tartaric acid
• Synonyms: Detrol LA; Kabi-2234; PNU-200583E; Tolterodine tartrate; Tolterodine tartrate; 2-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methyl phenol (2R,3R)-2,3-Dihydroxybutanedioate; R-(+)-N,N-Diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine L-Tartarte; PNU-20058E; Detrol; R-(+)-Toltaridine L-Tartrate; Tolterodine Tartaric Acid; Tolterodine L-Tartrate; 2-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methyl-phenol tartrate; Detrusitol; Tolterodine L-tartrate

Database IDs

• CAS Number: 124937-51-5(freebase); 124937-52-6
• MDL Number: MFCD07771985
• PubChem SID: 162038021
• PubChem CID: 443878

CALCULATED PROPERTIES

• Acid pKa: 10.279249
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.3333476
• LogD (pH = 7.4): 2.7616951
• Log P: 5.116409
• Molar Refractivity: 103.9572 cm^3
• Polarizability: 40.39475 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL; Methanol; Water
• Apperance: white to off-white powder; White-to-Off-White Solid
• Melting Point: 205-207°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-51/53
• Safety Statements: 22-36/37-57
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H361
• GHS Precautionary statements: P281-P301 + P310
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: tartrate
• Empirical Formula (Hill Notation): C22H31NO·C4H6O6

DETAILS

Selleck Chemicals - S2550

Biological Activity:
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, urgency and frequency. Both urinary bladder contraction and salivation are mediated via cholinergic muscarinic receptors. In the anesthetized cat, tolterodine tartrate (Detrol LA) shows a selectivity for the urinary bladder over salivary glands. [1][2]References on Tolterodine tartrate (Detrol LA)[] European Journal of Pharmacology , 1997 , 327 :195–207

Sigma Aldrich - PZ0009

Biochem/physiol Actions
Tolterodine L-tartrate is a bladder-specific muscarinic antagonist.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - T535800

A muscarinic receptor antagonist. Used in the treatment of urinary incontinence.

REFERENCES

• Rahimy M et al. Arzneimittelforschung. 2002; 52(12):890-5.
• Nilvebrant, L., et al.: Life Sci., 60, 1129 (1997)
• Nilvebrant, L., et al.: Eur. J. Pharmacol., 327, 195 (1997)
• Brynne, N., et al.: Int. J. Clin. Pharmacol. Ther., 35, 287 (1997)