Telenzepine

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

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]

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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