Chemical Component Summary

Name7-CHLORO-1-METHYL-5-PHENYL-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONE
Identifiers7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
FormulaC16 H13 Cl N2 O
Molecular Weight284.74
TypeNON-POLYMER
Isomeric SMILESCN1c2ccc(cc2C(=NCC1=O)c3ccccc3)Cl
InChIInChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
InChIKeyAAOVKJBEBIDNHE-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count33
Chiral Atom Count0
Bond Count35
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB00829?
NameDiazepam
Groups
  • approved
  • illicit
  • investigational
  • vet_approved
DescriptionA benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of gamma-aminobutyric acid activity. It is used in the treatment of severe anxiety disorders, as a hypnotic in the short-term management of insomnia, as a sedative and premedicant, as an anticonvulsant, and in the management of alcohol withdrawal syndrome. (From Martindale, The Extra Pharmacopoeia, 30th ed, p589) Given diazepam's storied history as a commonly used and effective medication for a variety of indications, contemporary advancements in the formulation and administration of the agent include the development and US FDA approval of an auto-injectable formulation for the rapid treatment of uncontrolled seizures in 2015-2016 [L5200]. Combining diazepam, a proven effective therapy for acute repetitive seizures, with an auto-injector designed for subcutaneous administration that is quickly and easily administered offers the potential for complete, consistent drug absorption and rapid onset of effect [L5200]. This current development is subsequently an important addition to the rescue therapy tool chest for patients with epilepsy [L5200].
Synonyms
  • 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one
  • Methyl diazepinone
  • Diazepam hydrochloride
  • Diazepam
  • NRL-1
Brand Names
  • Valium Inj Roche 5mg/ml
  • PMS-diazepam
  • Diazemuls
  • Diazepam Injection USP
  • Meval 5
IndicationIn general, diazepam is useful in the symptomatic management of mild to moderate degrees of anxiety in conditions dominated by tension, excitation, agitation, fear, or aggressiveness such as may occur in psychoneurosis, anxiety reactions due to stress conditions, and anxiety states with somatic expression.[F3160] Moreover, in acute alcoholic withdrawal, diazepam may be useful in the symptomatic relief of acute agitation, tremor, and impending acute delirium tremens.[F3160] Furthermore, diazepam is a useful adjunct for the relief of skeletal muscle spasm due to reflex spasm to local pathologies, such as inflammation of the muscle and joints or secondary to trauma; spasticity caused by upper motor neuron disorders, such as cerebral palsy and paraplegia; athetosis and the rare "stiff man syndrome".[F3160] Particular label information from the United Kingdom also lists particular age-specific indications, including for adults: (1) The short-term relief (2-4 weeks) only, of anxiety which is severe, disabling, or subjecting the individual to unacceptable distress, occurring alone or in association with insomnia or short-term psychosomatic, organic or psychotic illness, (2) cerebral palsy, (3) muscle spasm, (4) as an adjunct to certain types of epilepsy (eg. myoclonus), (5) symptomatic treatment of acute alcohol withdrawal, (6) as oral premedication for the nervous dental patient, and (7) for premedication before surgery.[L5188] In the same UK label information, diazepam is indicated in children for: (1) control of tension and irritability in cerebral spasticity in selected cases, (2) as an adjunct to the control of muscle spasm in tetanus, and for (3) oral premedication.[L5188] A diazepam nasal spray is indicated in patients 6 years and older to treat intermittent, stereotypic episodes of frequent seizure activity that are different than the patient's usual seizure pattern.[L11247]
Categories
  • Adjuvants, Anesthesia
  • Anesthetics
  • Anesthetics, General
  • Anesthetics, Intravenous
  • Anti-Anxiety Agents
ATC-CodeN05BA01
CAS number439-14-5

Drug Targets

NameTarget SequencePharmacological ActionActions
GABA(A) ReceptorMRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLL...unknownpositive allosteric modulator
GABA(A) Receptor Benzodiazepine Binding SiteMRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLL...unknownligand
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
Cytochrome P450 3A7MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

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