Telenzepine

Telenzepine is a thienobenzodiazepine acting as selective M1 antimuscarinic. It is used in the treatment of peptic ulcers.[1] Telenzepine is atropisomeric, in other words the molecule has a stereogenic C–N-axis. In neutral aqueous solution it displays a half-life for racemization of the order of 1000 years. The enantiomers have been resolved. The activity is related to the (+)-isomer which is about 500-fold more active than the (–)-isomer at muscarinic receptors in the rat cerebral cortex.[2]

Telenzepine
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 1-methyl-10-[2-(4-methylpiperazin-1-yl)acetyl]-5H-thieno[3,4-b][1,5]benzodiazepin-4-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H22N4O2S
Molar mass370.47 g·mol−1
3D model (JSmol)
SMILES
  • C1CN(C)CCN1CC(=O)N2c3ccccc3NC(=O)c4csc(C)c42
InChI
  • InChI=1S/C19H22N4O2S/c1-13-18-14(12-26-13)19(25)20-15-5-3-4-6-16(15)23(18)17(24)11-22-9-7-21(2)8-10-22/h3-6,12H,7-11H2,1-2H3,(H,20,25)
  • Key:VSWPGAIWKHPTKX-UHFFFAOYSA-N

See also

References
  1. Eveleigh P, Hulme EC, Schudt C, Birdsall NJ (April 1989). "The existence of stable enantiomers of telenzepine and their stereoselective interaction with muscarinic receptor subtypes". Molecular Pharmacology. 35 (4): 477–83. PMID 2704371.
  2. Clayden J, Moran WJ, Edwards PJ, LaPlante SR (2009). "The challenge of atropisomerism in drug discovery". Angewandte Chemie. 48 (35): 6398–401. doi:10.1002/anie.200901719. PMID 19637174.
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