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Identification
NameNefazodone
Accession NumberDB01149  (APRD00402)
Typesmall molecule
Groupsapproved, withdrawn
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, which could lead to the need for a liver transplant, or even death. The incidence of severe liver damage is 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. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-3-ethyl-4-(2-phenoxyethyl)-delta2-1,2,4-triazolin-5-oneNot AvailableNot Available
NefazodonaSpanishINN
NefazodoneNot AvailableNot Available
NefazodonumLatinINN
Salts
Name/CAS Structure Properties
Nefazodone Hydrochloride
82752-99-6
Thumb
  • InChI Key: DYCKFEBIOUQECE-UHFFFAOYSA-N
  • Monoisotopic Mass: 505.201130739
  • Average Mass: 506.468
DBSALT000406
Brand names
NameCompany
DutoninNot Available
SerzoneNot Available
Brand mixturesNot Available
Categories
CAS number83366-66-9
WeightAverage: 470.007
Monoisotopic: 469.224453
Chemical FormulaC25H32ClN5O2
InChI KeyVRBKIVRKKCLPHA-UHFFFAOYSA-N
InChI
InChI=1S/C25H32ClN5O2/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22/h3-6,8-11,20H,2,7,12-19H2,1H3
IUPAC Name
1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-ethyl-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one
SMILES
CCC1=NN(CCCN2CCN(CC2)C2=CC(Cl)=CC=C2)C(=O)N1CCOC1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPiperazines
SubclassPhenylpiperazines
Direct parentPhenylpiperazines
Alternative parentsPhenol Ethers; Alkyl Aryl Ethers; Chlorobenzenes; Aryl Chlorides; Diazinanes; Triazoles; Tertiary Amines; Polyamines; Organochlorides
Substituentsphenol ether; alkyl aryl ether; chlorobenzene; aryl halide; 1,4-diazinane; benzene; aryl chloride; azole; 1,2,4-triazole; tertiary amine; ether; polyamine; amine; organochloride; organonitrogen compound; organohalogen
Classification descriptionThis compound belongs to the phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
Pharmacology
IndicationFor the treatment of depression.
PharmacodynamicsNefazodone, 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.
Mechanism of actionWithin 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.
AbsorptionNefazodone is rapidly and completely absorbed. Its absolute bioavailability is low (about 20%).
Volume of distribution
  • 0.22 to 0.87 L/kg
Protein bindingGreater than 99% (in vitro, human plasma proteins).
Metabolism

Hepatic.

SubstrateEnzymesProduct
Nefazodone
hydroxynefazodoneDetails
Route of eliminationNefazodone 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 life2-4 hours
ClearanceNot Available
ToxicityCases of life-threatening hepatic failure have been reported in patients treated with nefazodone.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9744
Caco-2 permeable + 0.5296
P-glycoprotein substrate Substrate 0.5809
P-glycoprotein inhibitor I Inhibitor 0.8564
P-glycoprotein inhibitor II Inhibitor 0.8373
Renal organic cation transporter Inhibitor 0.5685
CYP450 2C9 substrate Non-substrate 0.7898
CYP450 2D6 substrate Non-substrate 0.9115
CYP450 3A4 substrate Substrate 0.7506
CYP450 1A2 substrate Non-inhibitor 0.7931
CYP450 2C9 substrate Inhibitor 0.5999
CYP450 2D6 substrate Non-inhibitor 0.8799
CYP450 2C19 substrate Non-inhibitor 0.5434
CYP450 3A4 substrate Non-inhibitor 0.8711
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8028
Ames test Non AMES toxic 0.5208
Carcinogenicity Non-carcinogens 0.7388
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.9067 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.8749
hERG inhibition (predictor II) Inhibitor 0.7288
Pharmacoeconomics
Manufacturers
  • Dr reddys laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Bristol myers squibb co pharmaceutical research institute
Packagers
Dosage forms
FormRouteStrength
TabletOral100 mg
TabletOral150 mg
TabletOral200 mg
TabletOral250 mg
TabletOral50 mg
Prices
Unit descriptionCostUnit
Nefazodone hcl 250 mg tablet1.82USDtablet
Nefazodone hcl 200 mg tablet1.78USDtablet
Nefazodone hcl 150 mg tablet1.75USDtablet
Nefazodone hcl 100 mg tablet1.72USDtablet
Nefazodone hcl 50 mg tablet1.68USDtablet
Serzone 100 mg tablet1.53USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point83.5 °CPhysProp
logP4.7Not Available
Predicted Properties
PropertyValueSource
water solubility6.98e-02 g/lALOGPS
logP3.71ALOGPS
logP4.65ChemAxon
logS-3.8ALOGPS
pKa (strongest basic)7.09ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count0ChemAxon
polar surface area51.62ChemAxon
rotatable bond count10ChemAxon
refractivity132.38ChemAxon
polarizability51.85ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US4338317
General Reference
  1. Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. Pubmed
External Links
ResourceLink
KEGG CompoundC07256
PubChem Compound4449
PubChem Substance46508323
ChemSpider4294
ChEBI7494
ChEMBLCHEMBL623
Therapeutic Targets DatabaseDAP000042
PharmGKBPA450603
Drug Product Database2242822
RxListhttp://www.rxlist.com/cgi/generic/nefaz.htm
Drugs.comhttp://www.drugs.com/cdi/nefazodone.html
WikipediaNefazodone
ATC CodesN06AX06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(152 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbirateroneStrong CYP3A4 inhibitors may increase levels of abiraterone. Monitor concomitant therapy closely.
AlmotriptanIncreased risk of CNS adverse effects
AprepitantThis CYP3A4 inhibitor increases the effect and toxicity of aprepitant
AstemizoleIncreased risk of cardiotoxicity and arrhythmias
AtorvastatinNefazodone, 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.
BromazepamNefazodone, 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.
BuspironeNefazodone increases the effect of buspirone
CabazitaxelConcomitant therapy with a strong CYP3A4 inhibitor may increase concentrations of cabazitaxel. Avoid concomitant therapy.
CarbamazepineNefazodone increases the effect of carbamazepine
CerivastatinNefazodone, 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.
CilostazolNefazodone increases the effect of cilostazol
CisaprideNefazodone increases serum levels of cisapride
CyclosporineThe antidepressant increases the effect and toxicity of cyclosporine
Dabigatran etexilateP-Glycoprotein inducers such as nefazodone may decrease the serum concentration of dabigatran etexilate. This combination should be avoided.
DabrafenibStrong CYP3A4 inhibitors may increase levels of dabrafenib. Consider alternate therapy.
DantroleneNefazodone 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.
DarifenacinThis potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
DesvenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
DihydroergotaminePossible ergotism and severe ischemia with this combination
DronedaroneNefazodone is a strong CYP3A4 inhibitor in which concomitant use with dronedarone will significantly increase its exposure. Avoid concomitant use.
EletriptanIncreased risk of CNS adverse effects
EplerenoneNefazodone increases the effect and toxicity of eplerenone
ErgotaminePossible ergotism and severe ischemia with this combination
ErlotinibThis CYP3A4 inhibitor increases levels/toxicity of erlotinib
FrovatriptanIncreased risk of CNS adverse effects
IsocarboxazidPossible severe adverse reaction with this combination
LinezolidCombination associated with possible serotoninergic syndrome
LoratadineIncreased risk of cardiotoxicity
LovastatinNefazodone, 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.
NaratriptanIncreased risk of CNS adverse effects
PazopanibAffects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib. Consider alternate therapy.
PhenelzinePossible severe adverse reaction with this combination
PimozideNefazodone may increase the effect and toxicity of pimozide.
PonatinibStrong CYP3A4 inhibitors may increase levels of ponatinib. Monitor concomitant therapy closely.
RasagilinePossible severe adverse reaction with this combination
RizatriptanIncreased risk of CNS adverse effects
SaxagliptinNefazodone is an inhibitor of CYP3A4 which increases exposure of saxagliptin. Decrease dose of saxagliptin to 2.5 mg per day.
SibutramineRisk of serotoninergic syndrome
SimvastatinNefazodone 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.
SolifenacinThis potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
St. John's WortSt. John's Wort increases the effect and toxicity of the SSRI, nefazodone.
SumatriptanIncreased risk of CNS adverse effects
SunitinibPossible increase in sunitinib levels
TacrolimusNefazodone 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.
TadalafilNefazodone may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
TamoxifenNefazodone may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
TamsulosinNefazodone, 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.
TelithromycinCo-administration may result in altered plasma concentrations of Nefazodone and/or Telithromycin. Consider alternate therapy or monitor the therapeutic/adverse effects of both agents.
TemsirolimusNefazodone may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
TeniposideThe 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.
TerbinafineTerbinafine 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.
TerfenadineIncreased risk of cardiotoxicity and arrhythmias
TiagabineThe 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.
TolterodineNefazodone may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
TolvaptanNefazodone is a strong inhibitor of CYP3A4 and will increase serum concentrations of tolvaptan.
TramadolNefazodone may increase tramadol toxicity by decreasing tramadol metabolism and clearance. Increased risk of serotonin syndrome. Monitor for tramadol toxicity and symptoms of serotonin syndrome.
TranylcypromineIncreased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
TrazodoneIncreased 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.
TriazolamNefazodone increases the effect of triazolam
TrimipramineIncreased 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.
TriprolidineThe CNS depressants, Triprolidine and Nefazodone, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
VardenafilNefazodone, 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.
VemurafenibStrong CYP3A4 inhibitors may increase levels of vemurafenib. Monitor concomitant therapy closely.
VenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
VerapamilNefazodone, 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.
VinblastineNefazodone, 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.
VincristineNefazodone, 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.
VinorelbineNafazodone, 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.
VoriconazoleVoriconazole, 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.
ZolmitriptanUse 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.
ZolpidemNefazodone, 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.
ZonisamideNefazodone, 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.
ZopicloneNefazodone, 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.
Food Interactions
  • Avoid alcohol.
  • Avoid avocado.
  • Limit garlic, ginger, gingko, and horse chestnut.
  • Take this medication either consistently with or without food as instructed by your doctor.

Targets

1. 5-hydroxytryptamine receptor 2A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details

References:

  1. Hidalgo R, Hertzberg MA, Mellman T, Petty F, Tucker P, Weisler R, Zisook S, Chen S, Churchill E, Davidson J: Nefazodone in post-traumatic stress disorder: results from six open-label trials. Int Clin Psychopharmacol. 1999 Mar;14(2):61-8. Pubmed
  2. Meyer JH, Cho R, Kennedy S, Kapur S: The effects of single dose nefazodone and paroxetine upon 5-HT2A binding potential in humans using [18F]-setoperone PET. Psychopharmacology (Berl). 1999 Jun;144(3):279-81. Pubmed
  3. Horton JC, Trobe JD: Akinetopsia from nefazodone toxicity. Am J Ophthalmol. 1999 Oct;128(4):530-1. Pubmed
  4. Eckler JR, Rabin RA, Winter JC: Nefazodone in the rat: mimicry and antagonism of [-]-DOM-induced stimulus control. Pharmacol Biochem Behav. 2003 May;75(2):405-10. Pubmed
  5. Avila A, Cardona X, Martin-Baranera M, Maho P, Sastre F, Bello J: Does nefazodone improve both depression and Parkinson disease? A pilot randomized trial. J Clin Psychopharmacol. 2003 Oct;23(5):509-13. Pubmed
  6. Taylor DP, Carter RB, Eison AS, Mullins UL, Smith HL, Torrente JR, Wright RN, Yocca FD: Pharmacology and neurochemistry of nefazodone, a novel antidepressant drug. J Clin Psychiatry. 1995;56 Suppl 6:3-11. Pubmed
  7. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed
  8. Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. Pubmed

2. 5-hydroxytryptamine receptor 2C

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2C P28335 Details

References:

  1. Millan MJ: Serotonin 5-HT2C receptors as a target for the treatment of depressive and anxious states: focus on novel therapeutic strategies. Therapie. 2005 Sep-Oct;60(5):441-60. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

References:

  1. Owens MJ, Ieni JR, Knight DL, Winders K, Nemeroff CB: The serotonergic antidepressant nefazodone inhibits the serotonin transporter: in vivo and ex vivo studies. Life Sci. 1995;57(24):PL373-80. Pubmed
  2. Narayan M, Anderson G, Cellar J, Mallison RT, Price LH, Nelson JC: Serotonin transporter-blocking properties of nefazodone assessed by measurement of platelet serotonin. J Clin Psychopharmacol. 1998 Feb;18(1):67-71. Pubmed
  3. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed
  4. Taylor DP, Carter RB, Eison AS, Mullins UL, Smith HL, Torrente JR, Wright RN, Yocca FD: Pharmacology and neurochemistry of nefazodone, a novel antidepressant drug. J Clin Psychiatry. 1995;56 Suppl 6:3-11. Pubmed
  5. Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. Pubmed

4. 5-hydroxytryptamine receptor 1A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 1A P08908 Details

References:

  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed

5. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Owens MJ, Ieni JR, Knight DL, Winders K, Nemeroff CB: The serotonergic antidepressant nefazodone inhibits the serotonin transporter: in vivo and ex vivo studies. Life Sci. 1995;57(24):PL373-80. Pubmed
  2. Owen D, Du L, Bakish D, Lapierre YD, Hrdina PD: Norepinephrine transporter gene polymorphism is not associated with susceptibility to major depression. Psychiatry Res. 1999 Jul 30;87(1):1-5. Pubmed
  3. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed
  4. Taylor DP, Carter RB, Eison AS, Mullins UL, Smith HL, Torrente JR, Wright RN, Yocca FD: Pharmacology and neurochemistry of nefazodone, a novel antidepressant drug. J Clin Psychiatry. 1995;56 Suppl 6:3-11. Pubmed
  5. Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. Pubmed

6. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed

7. Alpha-1B adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: other/unknown

Components

Name UniProt ID Details
Alpha-1B adrenergic receptor P35368 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

8. Alpha-2A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

References:

  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed

9. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: no

Actions: antagonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

References:

  1. Taylor DP, Carter RB, Eison AS, Mullins UL, Smith HL, Torrente JR, Wright RN, Yocca FD: Pharmacology and neurochemistry of nefazodone, a novel antidepressant drug. J Clin Psychiatry. 1995;56 Suppl 6:3-11. Pubmed
  2. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed

Enzymes

1. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Davis R, Whittington R, Bryson HM: Nefazodone. A review of its pharmacology and clinical efficacy in the management of major depression. Drugs. 1997 Apr;53(4):608-36. Pubmed
  2. DeVane CL, Donovan JL, Liston HL, Markowitz JS, Cheng KT, Risch SC, Willard L: Comparative CYP3A4 inhibitory effects of venlafaxine, fluoxetine, sertraline, and nefazodone in healthy volunteers. J Clin Psychopharmacol. 2004 Feb;24(1):4-10. Pubmed
  3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  5. von Moltke LL, Greenblatt DJ, Granda BW, Grassi JM, Schmider J, Harmatz JS, Shader RI: Nefazodone, meta-chlorophenylpiperazine, and their metabolites in vitro: cytochromes mediating transformation, and P450-3A4 inhibitory actions. Psychopharmacology (Berl). 1999 Jul;145(1):113-22. Pubmed

4. CYP2B protein

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
CYP2B protein Q14097 Details

References:

  1. Haduch A, Wojcikowski J, Daniel WA: Effect of selected antidepressant drugs on cytochrome P450 2B (CYP2B) in rat liver. An in vitro and in vivo study. Pharmacol Rep. 2008 Nov-Dec;60(6):957-65. Pubmed

5. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. von Moltke LL, Greenblatt DJ, Granda BW, Grassi JM, Schmider J, Harmatz JS, Shader RI: Nefazodone, meta-chlorophenylpiperazine, and their metabolites in vitro: cytochromes mediating transformation, and P450-3A4 inhibitory actions. Psychopharmacology (Berl). 1999 Jul;145(1):113-22. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Stormer E, von Moltke LL, Perloff MD, Greenblatt DJ: P-glycoprotein interactions of nefazodone and trazodone in cell culture. J Clin Pharmacol. 2001 Jul;41(7):708-14. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:24