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Pinazepam
Clinical data
Other names9-chloro-6-phenyl-2-prop-2-ynyl-2,5-diazabicyclo[5.4.0]undeca-5,8,10,12-tetraen-3-one
AHFS/ Drugs.com International Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal
Identifiers
  • 7-chloro-5-phenyl-1-prop-2-yn-1-yl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
DrugBank
  • ? ☒N
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard ( EPA)
ECHA InfoCard 100.052.650 Edit this at Wikidata
Chemical and physical data
FormulaC18H13ClN2O
Molar mass308.77 g·mol−1
3D model ( JSmol)
  • Clc3cc\1c(N(C(=O)C/N=C/1c2ccccc2)CC#C)cc3
  • InChI=1S/C18H13ClN2O/c1-2-10-21-16-9-8-14(19)11-15(16)18(20-12-17(21)22)13-6-4-3-5-7-13/h1,3-9,11H,10,12H2 checkY
  • Key:MFZOSKPPVCIFMT-UHFFFAOYSA-N checkY
 ☒NcheckY  (what is this?)   (verify)

Pinazepam (marketed under the brand name Domar and Duna) is a benzodiazepine drug. [2] It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. [3]

Pinazepam and its metabolite N-desmethyldiazepam are transferred to the developing fetus in utero, but the plasma drug level in the mother is usually significantly higher than in the fetus. [4]

Pinazepam differs from other benzodiazepines in that it has a propargyl group at the N-1 position of the benzodiazepine structure. It is less toxic than diazepam and in animal studies it appears to produce anxiolytic and anti-agitation properties with limited hypnotic and motor coordination impairing properties. [5] Pinazepam is rapidly absorbed after oral administration. The main active metabolites of pinazepam are depropargylpinazepam (N-desmethyldiazepam, nordazepam) and oxazepam. [6] In humans pinazepam acts as a pure anxiolytic agent in that it does not possess to any significant degree the other pharmacological characteristics of benzodiazepines. Its lack of intellectual, motor and hypnotic impairing effects makes it more appropriate than other benzodiazepines for day time use. [7] [8] [9] The elimination half-life is longer in the elderly. [10]

See also

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Schütz H, Holland EM, Kazemian-Erdmann F, Schölermann K (September 1988). "[Screening of the new benzodiazepine derivative, pinazepan, and its major metabolites]". Arzneimittel-Forschung. 38 (9): 1372–5. PMID  3146986.
  3. ^ Janbroers, J. M. (1984). "Pinazepam: review of pharmacological properties and therapeutic efficacy". Clinical Therapeutics. 6 (4): 434–450. ISSN  0149-2918. PMID  6147192.
  4. ^ Pacifici GM, Cuoci L, Guarneri M, Fornaro P, Arcidiacono G, Cappelli N, et al. (1984). "Placental transfer of pinazepam and its metabolite N-desmethyldiazepam in women at term". European Journal of Clinical Pharmacology. 27 (3): 307–10. doi: 10.1007/BF00542165. PMID  6150857. S2CID  1389302.
  5. ^ "Diazepam Injection BP - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 2021-08-23.
  6. ^ Dinis-Oliveira, Ricardo Jorge (Sep 14, 2017). "Metabolic profile of oxazepam and related benzodiazepines: clinical and forensic aspects". Drug Metabolism Reviews. 49 (4): 451–463. doi: 10.1080/03602532.2017.1377223. ISSN  1097-9883. PMID  28903606. S2CID  4528255.
  7. ^ Janbroers JM (1984). "Pinazepam: review of pharmacological properties and therapeutic efficacy". Clinical Therapeutics. 6 (4): 434–50. PMID  6147192.
  8. ^ Pacifici GM, Placidi GF, Fornaro P, Gomeni R (1983). "Pharmacokinetics of pinazepam in healthy volunteers". International Journal of Clinical Pharmacology Research. 3 (5): 331–7. PMID  6147314.
  9. ^ Pacifici GM, Placidi GF, Fornaro P, Gomeni R (1982). "Pinazepam: a precursor of N-desmethyldiazepam". European Journal of Clinical Pharmacology. 22 (3): 225–8. doi: 10.1007/BF00545219. PMID  6809477. S2CID  1977572.
  10. ^ Pacifici GM, Cuoci L, Placidi GF, Fornaro P, Gomeni R (Jan 1982). "Elimination kinetics of desmethyldiazepam in two young and two elderly subjects". European Journal of Drug Metabolism and Pharmacokinetics. 7 (1): 69–72. doi: 10.1007/bf03189546. PMID  6802645. S2CID  21836038.

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