QuickView for Nefazodone (compound)

Summary
General Info

PubChem

PubChem Compound 4449

Name:	nefazodone
PubChem Compound ID:	4449
Molecular formula:	C₂₅H₃₂ClN₅O₂
Molecular weight:	470.007 g/mol
Synonyms:	1-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-3-ethyl-4-(2-phenoxyethyl)-delta2-1,2,4-triazolin-5-one; Nefazodona [Spanish]; 2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one; Nefazodone; Nefazodonum [Latin]; 3H-1,2,4-Triazol-3-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-; 83366-66-9; 3H-1,2,4-Triazol-3-one, 2,4-dihydro-2-3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-5-ethyl-4-(2-phenoxyethyl)-; 1-(3-(4-(3-Chlorpheyl-1-piperazinylpropyl)-3-ethyl-4,5-dihydro-4-(2-phenoxyethyl)-1,2,4-triazol-5-on; C07256. show more » 1-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-3-ethyl-4-(2-phenoxyethyl)-delta2-1,2,4-triazolin-5-one; Nefazodona [Spanish]; 2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one; Nefazodone; Nefazodonum [Latin]; 3H-1,2,4-Triazol-3-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-; 83366-66-9; 3H-1,2,4-Triazol-3-one, 2,4-dihydro-2-3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-5-ethyl-4-(2-phenoxyethyl)-; 1-(3-(4-(3-Chlorpheyl-1-piperazinylpropyl)-3-ethyl-4,5-dihydro-4-(2-phenoxyethyl)-1,2,4-triazol-5-on; C07256; 82752-99-6 show less «

DrugBank

Identification

Name:	nefazodone
Name (isomeric):	DB01149
Drug Type:	small molecule
Synonyms:	Nefazodona [Spanish]; Nefazodonum [Latin]; Nefazodone Hcl; Nefazodone Hydrochloride
Brand:	Serzone, Dutonin
Category:	Antidepressants, Serotonin Agents, Analgesics, Antidepressive Agents, Second-Generation
CAS number:	83366-66-9

Pharmacology

Indication:	For the treatment of depression.
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 slee... show more » 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. show less «
Mechanism of Action:	Within the serotonergic system, nefazodone acts as an antagonist at type 2 serotonin (5-HT₂) 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, nefa... show more » Within the serotonergic system, nefazodone acts as an antagonist at type 2 serotonin (5-HT₂) 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. show less «
Absorption:	Nefazodone is rapidly and completely absorbed. Its absolute bioavailability is low (about 20%).
Protein binding:	Greater than 99% (in vitro, human plasma proteins).
Biotransformation:	Hepatic.
Route of elimination:	Nefazodone is extensively metabolized after oral administration by n-dealkylation and aliphatic and aromatic hydroxylation, and less than 1% of administered nefazodone is excreted unchanged in urine.
Half Life:	2-4 hours
Toxicity:	Cases of life-threatening hepatic failure have been reported in patients treated with nefazodone.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid avocado.

Avoid alcohol.

Limit garlic, ginger, gingko, and horse chestnut.

Take this medication either consistently with or without food as instructed by your doctor.

Drug interaction:

Erlotinib	This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Phenelzine	Possible severe adverse reaction with this combination
Terbinafine	Terbinafine may reduce the metabolism and clearance of Nefazodone. Consider alternate therapy or monitor for therapeutic/adverse effects of Nefazodone if Terbinafine is initiated, discontinued or dose changed.
Almotriptan	Increased risk of CNS adverse effects
Cerivastatin	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of cerivastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cerivastatin if nefazodone is initiated, discontinued or dose changed.

Erlotinib	This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Phenelzine	Possible severe adverse reaction with this combination
Terbinafine	Terbinafine may reduce the metabolism and clearance of Nefazodone. Consider alternate therapy or monitor for therapeutic/adverse effects of Nefazodone if Terbinafine is initiated, discontinued or dose changed.
Almotriptan	Increased risk of CNS adverse effects
Cerivastatin	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of cerivastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cerivastatin if nefazodone is initiated, discontinued or dose changed.
Zolpidem	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if nefazodone is initiated, discontinued or dose changed.
Tranylcypromine	Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Zopiclone	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of zopiclone by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if nefazodone is initiated, discontinued or dose changed.
Trazodone	Increased risk of serotonin syndrome. The CYP3A4 inhibitor, Nefazodone, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Consider alternate therapy or monitor for symtpoms of sertonin syndrome and changes in Trazodone efficacy/toxicity if Nefazodone is initiated, discontinued or dose changed.
Isocarboxazid	Possible severe adverse reaction with this combination
Simvastatin	Nefazodone may increase the effect and toxicity of simvastatin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of simvastatin if nefazodone is initiated, discontinued or dose changed.
Lovastatin	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of lovastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of lovastatin if nefazodone is initiated, discontinued or dose changed.
Dihydroergotamine	Possible ergotism and severe ischemia with this combination
Dabigatran etexilate	P-Glycoprotein inducers such as nefazodone may decrease the serum concentration of dabigatran etexilate. This combination should be avoided.
Triprolidine	The CNS depressants, Triprolidine and Nefazodone, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Solifenacin	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Carbamazepine	Nefazodone increases the effect of carbamazepine
Rasagiline	Possible severe adverse reaction with this combination
Naratriptan	Increased risk of CNS adverse effects
Tramadol	Nefazodone may increase tramadol toxicity by decreasing tramadol metabolism and clearance. Increased risk of serotonin syndrome. Monitor for tramadol toxicity and symptoms of serotonin syndrome.
Aprepitant	This CYP3A4 inhibitor increases the effect and toxicity of aprepitant
Vinblastine	Nefazodone, a strong CYP3A4 inhibitor, may decrease the metabolism of Vinblastine. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Nefazodone is initiated, discontinued or dose changed.
Pimozide	Nefazodone may increase the effect and toxicity of pimozide.
Tamoxifen	Nefazodone may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
Astemizole	Increased risk of cardiotoxicity and arrhythmias
Buspirone	Nefazodone increases the effect of buspirone
Eletriptan	Increased risk of CNS adverse effects
Dantrolene	Nefazodone may increase the serum concentration of dantrolene by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of dantrolene if nefazodone is initiated, discontinued or dose changed.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of nefazodone by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nefazodone if voriconazole is initiated, discontinued or dose changed.
Cilostazol	Nefazodone increases the effect of cilostazol
Atorvastatin	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of atorvastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of atorvastatin if nefazodone is initiated, discontinued or dose changed.
St. John's Wort	St. John's Wort increases the effect and toxicity of the SSRI, nefazodone.
Rizatriptan	Increased risk of CNS adverse effects
Sunitinib	Possible increase in sunitinib levels
Tadalafil	Nefazodone may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
Cyclosporine	The antidepressant increases the effect and toxicity of cyclosporine
Tiagabine	The strong CYP3A4 inhibitor, Nefazodone, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Nefazodone is initiated, discontinued or dose changed.
Triazolam	Nefazodone increases the effect of triazolam
Verapamil	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Nefazodone is initiated, discontinued or dose changed.
Linezolid	Combination associated with possible serotoninergic syndrome
Cisapride	Nefazodone increases serum levels of cisapride
Venlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tolterodine	Nefazodone may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Tamsulosin	Nefazodone, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Nefazodone is initiated, discontinued, or dose changed.
Vardenafil	Nefazodone, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
Darifenacin	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Vincristine	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of Vincristine by decreasing its metabolism. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Nefazodone is initiated, discontinued or dose changed.
Bromazepam	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if nefazodone is initiated, discontinued or dose changed. Dosage adjustments may be required.
Eplerenone	Nefazodone increases the effect and toxicity of eplerenone
Desvenlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Frovatriptan	Increased risk of CNS adverse effects
Temsirolimus	Nefazodone may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome. Nefazodone, a strong CYP3A4 inhibitor, may also decrease the metabolism and clearance of Trimipramine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Nefazodone is initiated, discontinued or dose changed.
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
Zolmitriptan	Use of two serotonin modulators, such as zolmitriptan and nafazodone, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Vinorelbine	Nafazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of Vinorelbine by decreasing its metabolism. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Nefazodone is initiated, discontinued or dose changed.
Sibutramine	Risk of serotoninergic syndrome
Sumatriptan	Increased risk of CNS adverse effects
Telithromycin	Co-administration may result in altered plasma concentrations of Nefazodone and/or Telithromycin. Consider alternate therapy or monitor the therapeutic/adverse effects of both agents.
Loratadine	Increased risk of cardiotoxicity
Ergotamine	Possible ergotism and severe ischemia with this combination
Zonisamide	Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of zonisamide by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zonisamide if nefazodone is initiated, discontinued or dose changed.
Tacrolimus	Nefazodone may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Nefazodone therapy is initiated, discontinued or altered.
Teniposide	The strong CYP3A4 inhibitor, Nefazodone, may decrease the metabolism and clearance of Teniposide, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Teniposide if Nefazodone is initiated, discontinued or dose changed.