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	80880-90-6
PubChem CID	5387
ChemSpider	5194
UNII	0990EG3K10
ChEMBL	ChEMBL253978
CompTox Dashboard (EPA)	DTXSID5045209
Chemical and physical data
Formula	C19H22N4O2S
Molar mass	370.47 g·mol−1
3D model (JSmol)	Interactive image
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

• Pirenzepine

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.

External links

• Londong W, Londong V, Meierl A, Voderholzer U (July 1987). "Telenzepine is at least 25 times more potent than pirenzepine--a dose response and comparative secretory study in man". Gut. 28 (7): 888–95. doi:10.1136/gut.28.7.888. PMC 1433086. PMID 3653758.