Repositioning Candidate Details
| Candidate ID: | R0425 |
| Source ID: | DB01149 |
| Source Type: | approved; withdrawn |
| Compound Type: | small molecule |
| Compound Name: | Nefazodone |
| Synonyms: | 1-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-3-ethyl-4-(2-phenoxyethyl)-delta2-1,2,4-triazolin-5-one; Nefazodone |
| Molecular Formula: | C25H32ClN5O2 |
| SMILES: | CCC1=NN(CCCN2CCN(CC2)C2=CC(Cl)=CC=C2)C(=O)N1CCOC1=CC=CC=C1 |
| Structure: |
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| DrugBank Description: | Nefazodone hydrochloride (trade name Serzone) is an antidepressant drug marketed by Bristol-Myers Squibb. Its sale was discontinued in 2003 in some countries, due to the small possibility of hepatic (liver) injury. Drug-induced hepatic injuries were associated with an risk of elevated need for a liver transplant, or even death, with the incidence of severe liver damage was shown to be approximately 1 in 250,000 to 300,000 patient-years. On May 20, 2004, Bristol-Myers Squibb discontinued the sale of Serzone in the United States. |
| CAS Number: | 83366-66-9 |
| Molecular Weight: | 470.007 |
| DrugBank Indication: | For the treatment of depression. |
| DrugBank Pharmacology: | Nefazodone, an antidepressant synthetically derived phenylpiperazine, is used to treat major depression. Although it is structurally similar to trazodone, nefazodone has a mechanism of action different from other antidepressants and, hence, lacks the risk for major cardiovascular toxicity seen with tricyclics and insomnia and inhibition of REM sleep seen with the selective serotonin reuptake inhibitors. |
| DrugBank MoA: | Within the serotonergic system, nefazodone acts as an antagonist at type 2 serotonin (5-HT<sub>2</sub>) post-synaptic receptors and, like fluoxetine-type antidepressants, inhibits pre-synaptic serotonin (5-HT) reuptake. These mechanisms increase the amount of serotonin available to interact with 5-HT receptors. Within the noradrenergic system, nefazodone inhibits norepinephrine uptake minimally. Nefazodone also antagonizes alpha(1)-adrenergic receptors, producing sedation, muscle relaxation, and a variety of cardiovascular effects. Nefazodone's affinity for benzodiazepine, cholinergic, dopaminergic, histaminic, and beta or alpha(2)-adrenergic receptors is not significant. |
| Targets: | 5-hydroxytryptamine receptor 2A antagonist; 5-hydroxytryptamine receptor 2C antagonist; Sodium-dependent serotonin transporter inhibitor; 5-hydroxytryptamine receptor 1A antagonist; Sodium-dependent noradrenaline transporter inhibitor; Sodium-dependent dopamine transporter inhibitor; Alpha-1B adrenergic receptor other/unknown; Alpha-2A adrenergic receptor antagonist; Alpha-1A adrenergic receptor antagonist; Potassium voltage-gated channel subfamily H member 2 antagonist |
| Inclusion Criteria: | Indication associated |
