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Overview
| Generic Names: | DAP; Methyldiazepinone |
|---|---|
| IUPAC Name: | 7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one |
| Trade Names: | Alboral; Aliseum; Alupram; Amiprol; An-Ding; Ansiolin; Ansiolisina; Apaurin; Apo-Diazepam; Apozepam; Armonil; Assival; Atensine; Atilen; Bensedin; Bialzepam; Calmocitene; Calmpose; Cercine; Ceregulart; Diacepan; Dialag; Dialar; Diapam; Diastat; Diazemuls; Diazemulus; Diazepam Intensol; Diazepan; Diazetard; Dienpax; Dipam; Dipezona; Dizac; Domalium; Duksen; Duxen; E-Pam; Eridan; Eurosan; Evacalm; Faustan; Faustan,; Freudal; Frustan; Gewacalm; Gihitan; Kabivitrum; Kiatrium; LA III; La-Iii; Lamra; Lembrol; Levium; Liberetas; Mandrozep; Morosan; Neurolytril; Noan; Novazam; Novo-Dipam; Paceum; Pacitran; Paranten; Paxate; Paxel; Plidan; Pms-Diazepam; Pro-Pam; Q-Pam; Q-Pam Relanium; Quetinil; Quiatril; Quievita; Relaminal; Relanium; Renborin; Ruhsitus; Saromet; Sedapam; Sedipam; Seduksen; Seduxen; Serenack; Serenamin; Serenzin; Servizepam; Setonil; Sibazon; Sibazone; Solis; Sonacon; Stesolid; Stesolin; Tensopam; Tranimul; Tranqdyn; Tranquase; Tranquirit; Tranquo-Puren; Tranquo-Tablinen; Umbrium; Unisedil; Usempax Ap; Valaxona; Valeo; Valiquid; Valitran; Valium; Valrelease; Vatran; Velium; Vival; Vivol; Zetran; Zipan |
| PharmGKB Accession Id: | PA449283 |
Description
A 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)
Indication
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.
ATC Therapeutic Category
- N05BA:Benzodiazepine derivatives
Pharmacology and Interactions
Mechanism Of Action
Benzodiazepines bind nonspecifically to benzodiazepine receptors which mediate sleep, affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Pharmacology
Diazepam, a benzodiazepine, generates the same active metabolite as chlordiazepoxide and clorazepate. In animals, diazepam appears to act on parts of the limbic system, the thalamus and hypothalamus, and induces calming effects. Diazepam, unlike chlorpromazine and reserpine, has no demonstrable peripheral autonomic blocking action, nor does it produce extrapyramidal side effects; however, animals treated with diazepam do have a transient ataxia at higher doses. Diazepam was found to have transient cardiovascular depressor effects in dogs. Long-term experiments in rats revealed no disturbances of endocrine function. Injections into animals have produced localized irritation of tissue surrounding injection sites and some thickening of veins after intravenous use.
Food Interactions
Avoid alcohol. Avoid excessive quantities of coffee or tea (caffeine). Avoid taking with grapefruit or grapefruit juice as grapefruit can significantly increase serum levels of this product. Take with food.
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Hepatic via the Cytochrome P450 enzyme system. The main active metabolite is desmethyldiazepam, in addition to minor active metabolites including temazepam and oxazepam.
Protein Binding
98.5%
Absorption
Essentially complete, with a bioavailability of 93%.
Half Life
Biphasic 1-2 days and 2-5 days, active metabolites with long half lives.
Toxicity
Symptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.
Chemical Properties
Chemical Formula:
C16H13ClN2O
SMILES Code:
CN1c2ccc(cc2C(=NCC1=O)c3ccccc3)Cl
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
284.74 / 284.0716
Curated Information
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
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ACBD3 |
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Pathways |
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BZRAP1 |
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CYP2C19 |
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Publications |
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CYP2E1 |
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Publications |
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CYP3A |
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Publications |
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CYP3A4 |
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Publications |
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CYP3A5 |
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Publications |
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DBI |
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Publications, Pathways |
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GABRA1 |
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Publications, Pathways |
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GABRA6 |
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Publications |
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GABRB2 |
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Publications, Pathways |
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GABRG2 |
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Publications, Pathways |
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SLC25A4 |
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Pathways |
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SLC32A1 |
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Pathways |
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SLC6A1 |
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Pathways |
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SLC6A11 |
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Pathways |
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SLC6A12 |
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Pathways |
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SLC6A13 |
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Pathways |
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TSPO |
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Publications, Pathways |
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VDAC1 |
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Pathways |
Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
PharmGKB Curated Pathways
Curated Information
The following drugs are in curated knowledge about this drug.
| Drug | Relationship | Evidence | |
|---|---|---|---|
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fluoxetine |
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Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| amprenavir | Amprenavir increases the effect and toxicity of benzodiazepine |
| cimetidine | Cimetidine increases the effect of the benzodiazepine |
| clarithromycin | The macrolide increases the effect of the benzodiazepine |
| clozapine | Increased risk of toxicity |
| digoxin | The benzodiazepine increases the effect of digoxin |
| erythromycin | The macrolide increases the effect of the benzodiazepine |
| ethotoin | Possible increased levels of the hydantoin, decrease of benzodiazepine |
| fluconazole | Fluconazole increases the effect of the benzodiazepine |
| fosamprenavir | Amprenavir increases the effect and toxicity of benzodiazepine |
| fosphenytoin | Possible increased levels of the hydantoin, decrease of benzodiazepine |
| indinavir | The protease inhibitor increases the effect of the benzodiazepine |
| itraconazole | The imidazole increases the effect of the benzodiazepine |
| josamycin | The macrolide increases the effect of the benzodiazepine |
| kava | Kava increases the effect of the benzodiazepine |
| ketoconazole | The imidazole increases the effect of the benzodiazepine |
| mephenytoin | Possible increased levels of the hydantoin, decrease of benzodiazepine |
| nelfinavir | The protease inhibitor increases the effect of the benzodiazepine |
| omeprazole | Omeprazole increases the effect of benzodiazepine |
| phenytoin | Possible increased levels of the hydantoin, decrease of benzodiazepine |
| quinupristin | This combination presents an increased risk of toxicity |
| rifampin | Rifampin decreases the effect of benzodiazepine |
| ritonavir | The protease inhibitor increases the effect of the benzodiazepine |
| saquinavir | The protease inhibitor increases the effect of the benzodiazepine |
| st. john's wort | St. John's Wort could reduce the benzodiazepine effect |
| voriconazole | The imidazole increases the effect of the benzodiazepine |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
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Anxiety Disorders |
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Pathways |
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Epilepsy |
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Pathways |
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Panic Disorder |
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Pathways |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
Common Searches
Search PubMed
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.
