Kenazepine

Kenazepine

Clinical data
Trade names	Kenazepine
Other names	Acetamide
Identifiers
IUPAC name 2-bromo-N-[2-[7-chloro-5-(2-fluorophenyl)-2-oxo-3H-1,4-benzodiazepin-1-yl]ethyl]acetamide
CAS Number	75887-99-9  Y
PubChem CID	173485
ChemSpider	151427  Y
CompTox Dashboard (EPA)	DTXSID00226809
Chemical and physical data
Formula	C19H16BrClFN3O2
Molar mass	452.71 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1C(=O)N(C2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3F)CCNC(=O)CBr
InChI InChI=InChI=1S/C19H16BrClFN3O2/c20-10-17(26)23-7-8-25-16-6-5-12(21)9-14(16)19(24-11-18(25)27)13-3-1-2-4-15(13)22/h1-6,9H,7-8,10-11H2,(H,23,26) Key:RUMBKDGXDMTRBI-UHFFFAOYSA-N
NY  (what is this?)

Kenazepine is a benzodiazepine containing a functional alkylating moiety. ^[1] The chemical formula is C₁₉H₁₆BrClFN₃O₂. ^[2]

Uses

The compound functions as a research tool in pharmacology. It binds irreversibly and non-competitively to some brain benzodiazepine receptors and competitively to others, providing evidence for the existence of different receptor populations within the central nervous system. Kenazepine exhibits long-lasting anticonvulsant effects, likely due to its irreversible binding mechanism, and is used to study the heterogeneity and function of benzodiazepine receptors. ^[3]

Studies show that kenazepine provides a long-lasting protection against convulsions caused by pentylenetetrazole in vivo, suggesting a similar irreversible binding mechanism in the body. ^[2]

References

1. Skolnick P, Paul SM (1982). "Benzodiazepine receptors in the central nervous system". International Review of Neurobiology. 23: 103–140 (115). doi:10.1016/S0074-7742(08)60623-6. ISBN   978-0-12-366823-3. PMID   6288605. Kenazepine , a derivative of the benzodiazepine Ro 7/1986 has a bromoacetyl moiety that can react with binucleophiles such as SH and - NH2.
2. Williams EF, Rice KC, Mattson M, Paul SM, Skolnick P (April 1981). "In vivo effects of two novel alkylating benzodiazepines, irazepine and kenazepine". Pharmacology, Biochemistry, and Behavior . 14 (4): 487–91. doi:10.1016/0091-3057(81)90307-5. PMID   7232472.
3. Williams EF, Rice KC, Paul SM, Skolnick P (1980). "Heterogeneity of Benzodiazepine Receptors in the Central Nervous System Demonstrated with Kenazepine, an Alkylating Benzodiazepine" . Journal of Neurochemistry . 35 (3): 591–597. doi:10.1111/j.1471-4159.1980.tb03695.x. ISSN   1471-4159. PMID   6256492 . Retrieved 14 September 2025.