QuickView for Diazepam (compound)

Summary
General Info

PubChem

PubChem Compound 11033472

Name:	Diazepam
PubChem Compound ID:	11033472
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.
Molecular formula:	C₁₆H₁₃ClN₂O
Molecular weight:	286.752 g/mol

DrugBank

Identification

Name:	Diazepam
Name (isomeric):	DB00829
Drug Type:	small molecule
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.
Synonyms:	DAP; Methyldiazepinone
Brand:	Condition, Serenamin, Valeo, Eridan, Levium, Cercine, Kiatrium, Sibazone, Dienpax, Q-Pam, Lamra, Mandrozep, Seduxen, Aliseum, Pms-Diazepam, Domalium, Diacepan, La-Iii, Bialzepam, Liberetas, Velium, Paceum, Eurosan, Alupram, Usempax Ap, Serenzin, Diastat, Pacitran, Seduksen, Dipezona, Pro-Pam, Vival, Evacalm, Gihitan, Dipam, Ansiolisina, Freudal, Ansiolin, Quiatril, Valaxona, Atensine, Bensedin, Kabivitrum, E-Pam, Alboral, Relanium, Ruhsitus, Paxate, Sibazon, Diazepan, Calmpose, Zetran, Dizac, Quievita, Gewacalm, Apaurin, Renborin, Valiquid, Duksen, Diazemulus, Diazetard, Duxen, Armonil, Diapam, Vivol, Apozepam, Tranimul, Valitran, Tranquo-Tablinen, Apo-Diazepam, Valium, Vatran, Tranquirit, Sedapam, Q-Pam Relanium, Unisedil, Umbrium, Assival, Tranquo-Puren, Novo-Dipam, Stesolid, Faustan,, Novazam, Tensopam, Dialar, Tranquase, Ceregulart, Frustan, Stesolin, Tranqdyn, Lembrol, Dialag, Quetinil, An-Ding, Paranten, Relaminal, Solis, Zipan, Neurolytril, Plidan, Faustan, Diazepam Intensol, Calmocitene, Sedipam, Serenack, Noan, Setonil, Valrelease, Atilen, Saromet, Amiprol, Servizepam, Sonacon, Diazemuls, LA III, Morosan, Paxel
Category:	Anesthetics, Intravenous, Adjuvants, Anesthesia, Anti-anxiety Agents, Muscle Relaxants, Central, GABA Modulators, Hypnotics and Sedatives, Antiemetics, Anticonvulsants
CAS number:	439-14-5

Pharmacology

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.
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 prod... show more » 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. show less «
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 (GABA_A) receptors, this enhances the effects of GABA by increasing GABA affinity for t... show more » 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 (GABA_A) 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. show less «
Absorption:	Essentially complete, with a bioavailability of 93%.
Protein binding:	98.5%
Biotransformation:	Hepatic via the Cytochrome P450 enzyme system. The main active metabolite is desmethyldiazepam, in addition to minor active metabolites including temazepam and oxazepam.
Route of elimination:	Diazepam and its metabolites are excreted mainly in the urine, predominantly as their glucuronide conjugates.
Half Life:	Biphasic 1-2 days and 2-5 days, active metabolites with long half lives.
Clearance:	20-30 mL/min
Toxicity:	Symptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

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.

Drug interaction:

Fosamprenavir	Fosamprenavir may increase the effect and toxicity of the benzodiazepine, diazepam.
Kava	Kava may increase the effect of the benzodiazepine, diazepam.
Tipranavir	Tipranavir may decrease the metabolism and clearance of Diazepam. Consider alternate therapy or monitor for Diazepam toxic effects if Tipranavir is initiated or dose increased.
Clarithromycin	The macrolide, clarithromycin, may increase the effect of the benzodiazepine, diazepam.
Indinavir	The protease inhibitor, indinavir, may increase the effect of the benzodiazepine, diazepam.

Fosamprenavir	Fosamprenavir may increase the effect and toxicity of the benzodiazepine, diazepam.
Kava	Kava may increase the effect of the benzodiazepine, diazepam.
Tipranavir	Tipranavir may decrease the metabolism and clearance of Diazepam. Consider alternate therapy or monitor for Diazepam toxic effects if Tipranavir is initiated or dose increased.
Clarithromycin	The macrolide, clarithromycin, may increase the effect of the benzodiazepine, diazepam.
Indinavir	The protease inhibitor, indinavir, may increase the effect of the benzodiazepine, diazepam.
Phenytoin	Phenytoin may increase the metabolism of diazepam via CYP3A4.
Rifampin	Rifampin may decrease the effect of the benzodiazepine, diazepam.
Fluconazole	Fluconazole may increase the effect of the benzodiazepine, diazepam.
Ketoconazole	Ketoconazole may increase the effect of the benzodiazepine, diazepam.
Josamycin	The macrolide, josamycin, may increase the effect of the benzodiazepine, diazepam.
St. John's Wort	St. John's Wort may decrease the effect of the benzodiazepine, diazepam.
Clozapine	Increased risk of toxicity
Ticlopidine	Ticlopidine may decrease the metabolism and clearance of Diazepam. Consider alternate therapy or monitor for adverse/toxic effects of Diazepam if Ticlopidine is initiated, discontinued or dose changed.
Fosphenytoin	Fosphenytoin may increase the metabolism of diazepam via CYP3A4.
Telithromycin	Telithromycin may reduce clearance of Diazepam. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Diazepam if Telithromycin is initiated, discontinued or dose changed.
Voriconazole	Voriconazole may increase the serum concentration of diazepam by decreasing its metabolism. Monitor for diazepam toxicity if voriconazole is initiated or dose increased.
Amprenavir	Amprenavir may increase the effect and toxicity of the benzodiazepine, diazepam.
Digoxin	The benzodiazepine, diazepam, may increase the effect of digoxin.
Nelfinavir	The protease inhibitor, nelfinavir, may increase the effect of the benzodiazepine, diazepam.
Erythromycin	The macrolide, erythromycin, may increase the effect of the benzodiazepine, diazepam.
Quinupristin	This combination presents an increased risk of toxicity
Mephenytoin	Mephenytoin may increase the metabolism of diazepam via CYP3A4.
Omeprazole	Omeprazole may increase the effect of the benzodiazepine, diazepam.
Triprolidine	The CNS depressants, Triprolidine and Diazepam, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Ethotoin	Ethotoin may increase the metabolism of diazepam via CYP3A4.
Ritonavir	The protease inhibitor, ritonavir, may increase the effect of the benzodiazepine, diazepam.
Saquinavir	The protease inhibitor, saquinavir, may increase the effect of the benzodiazepine, diazepam.
Cimetidine	Cimetidine may increase the effect of the benzodiazepine, diazepam.
Itraconazole	Itraconazole may increase the effect of the benzodiazepine, diazepam.