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Identification
NameAcetophenazine
Accession NumberDB01063  (APRD00462)
TypeSmall Molecule
GroupsApproved
DescriptionAcetophenazine is an antipsychotic drug of moderate-potency. It is used in the treatment of disorganized and psychotic thinking. It is also used to help treat false perceptions (e.g. hallucinations or delusions). It primarily targets the dopamine D2 receptor.
Structure
Thumb
Synonyms
Acetophenazine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
TindalSchering
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Acetophenazine maleate
ThumbNot applicableDBSALT001415
Categories
UNII8620H6K4QH
CAS number2751-68-0
WeightAverage: 411.56
Monoisotopic: 411.198047877
Chemical FormulaC23H29N3O2S
InChI KeyWNTYBHLDCKXEOT-UHFFFAOYSA-N
InChI
InChI=1S/C23H29N3O2S/c1-18(28)19-7-8-23-21(17-19)26(20-5-2-3-6-22(20)29-23)10-4-9-24-11-13-25(14-12-24)15-16-27/h2-3,5-8,17,27H,4,9-16H2,1H3
IUPAC Name
1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)ethan-1-one
SMILES
CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1
Pharmacology
IndicationFor the treatment of disorganized and psychotic thinking. Also used to help treat false perceptions (e.g. hallucinations or delusions.)
Structured Indications Not Available
PharmacodynamicsAcetophenzine is a phenothiazine antipsychotic intended for the management of schizophrenia and other psychotic disorders.
Mechanism of actionAcetophenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
TargetKindPharmacological actionActionsOrganismUniProt ID
D(2) dopamine receptorProteinyes
antagonist
HumanP14416 details
D(1A) dopamine receptorProteinyes
antagonist
HumanP21728 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamineAcetophenazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.Experimental, Illicit
3,4-MethylenedioxyamphetamineAcetophenazine may decrease the stimulatory activities of 3,4-Methylenedioxyamphetamine.Experimental, Illicit
3,4-MethylenedioxymethamphetamineAcetophenazine may decrease the stimulatory activities of 3,4-Methylenedioxymethamphetamine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamineAcetophenazine may decrease the stimulatory activities of 4-Bromo-2,5-dimethoxyamphetamine.Experimental, Illicit
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Acetophenazine.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Acetophenazine.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Acetophenazine.Approved
AmphetamineAcetophenazine may decrease the stimulatory activities of Amphetamine.Approved, Illicit
BenzphetamineAcetophenazine may decrease the stimulatory activities of Benzphetamine.Approved, Illicit
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Acetophenazine.Approved, Investigational
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Acetophenazine.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Acetophenazine.Approved
ChlorphentermineAcetophenazine may decrease the stimulatory activities of Chlorphentermine.Illicit, Withdrawn
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Acetophenazine.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Acetophenazine.Approved, Vet Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Acetophenazine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Acetophenazine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Acetophenazine.Approved
DextroamphetamineAcetophenazine may decrease the stimulatory activities of Dextroamphetamine.Approved, Illicit
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Acetophenazine.Approved
DiethylpropionAcetophenazine may decrease the stimulatory activities of Diethylpropion.Approved, Illicit
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Acetophenazine.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Acetophenazine.Approved
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Acetophenazine.Approved
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Acetophenazine.Approved, Investigational
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Acetophenazine.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Acetophenazine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Acetophenazine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Acetophenazine.Approved, Investigational
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Acetophenazine.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Acetophenazine.Approved, Vet Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Acetophenazine.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Acetophenazine.Approved, Investigational
Hydroxyamphetamine hydrobromideAcetophenazine may decrease the stimulatory activities of Hydroxyamphetamine hydrobromide.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Acetophenazine.Approved
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Acetophenazine.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Acetophenazine.Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Acetophenazine.Approved, Investigational
LisdexamfetamineAcetophenazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
LithiumLithium may increase the neurotoxic activities of Acetophenazine.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Acetophenazine.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Acetophenazine.Approved
MephedroneAcetophenazine may decrease the stimulatory activities of Mephedrone.Investigational
MephentermineAcetophenazine may decrease the stimulatory activities of Mephentermine.Approved
MequitazineAcetophenazine may increase the arrhythmogenic activities of Mequitazine.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Acetophenazine.Approved
MethamphetamineAcetophenazine may decrease the stimulatory activities of Methamphetamine.Approved, Illicit
MethylphenidateThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Methylphenidate.Approved, Investigational
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Acetophenazine.Approved, Investigational
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Acetophenazine.Approved
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Acetophenazine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Acetophenazine.Approved
MMDAAcetophenazine may decrease the stimulatory activities of MMDA.Experimental, Illicit
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Acetophenazine.Approved
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Acetophenazine.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Acetophenazine.Approved, Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Acetophenazine.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Acetophenazine.Approved, Investigational
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Acetophenazine.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Acetophenazine.Approved
PhentermineAcetophenazine may decrease the stimulatory activities of Phentermine.Approved, Illicit
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Acetophenazine.Approved
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Acetophenazine.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Acetophenazine.Approved
PseudoephedrineAcetophenazine may decrease the stimulatory activities of Pseudoephedrine.Approved
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Acetophenazine.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Acetophenazine.Approved
RitobegronAcetophenazine may decrease the stimulatory activities of Ritobegron.Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Acetophenazine.Approved
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Acetophenazine.Approved, Investigational, Vet Approved
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Acetophenazine.Approved
SulpirideThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Sulpiride.Approved
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Acetophenazine.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Acetophenazine.Approved
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Acetophenazine.Approved
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Acetophenazine.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Acetophenazine.Approved, Investigational
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Acetophenazine.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Acetophenazine.Approved, Investigational
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Acetophenazine.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Acetophenazine.Approved
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Acetophenazine.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Acetophenazine.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Acetophenazine.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceUS2985654
General References
  1. Jones GL, Woodbury DM: Spin-label study of phenothiazine interactions with erythrocyte ghost membranes: a possible membrane-mediated antisickling action. J Pharmacol Exp Ther. 1978 Oct;207(1):203-11. [PubMed:702341 ]
  2. Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851 ]
External Links
ATC CodesN05AB07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9893
Blood Brain Barrier+0.9469
Caco-2 permeable-0.5303
P-glycoprotein substrateSubstrate0.846
P-glycoprotein inhibitor IInhibitor0.8809
P-glycoprotein inhibitor IIInhibitor0.6834
Renal organic cation transporterInhibitor0.5248
CYP450 2C9 substrateNon-substrate0.6788
CYP450 2D6 substrateSubstrate0.7697
CYP450 3A4 substrateNon-substrate0.644
CYP450 1A2 substrateInhibitor0.8354
CYP450 2C9 inhibitorNon-inhibitor0.9186
CYP450 2D6 inhibitorInhibitor0.8979
CYP450 2C19 inhibitorNon-inhibitor0.8746
CYP450 3A4 inhibitorNon-inhibitor0.7426
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.817
CarcinogenicityNon-carcinogens0.891
BiodegradationNot ready biodegradable0.9893
Rat acute toxicity2.7720 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8509
hERG inhibition (predictor II)Inhibitor0.7117
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point167-168.5Sherlock, M.H. and Sperber, N.;U .S. Patent 2,985,654; May 23,1961; assigned to Schering Corporation
logP2.62SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0601 mg/mLALOGPS
logP3.48ALOGPS
logP2.65ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.46ChemAxon
pKa (Strongest Basic)8.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.02 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity121.7 m3·mol-1ChemAxon
Polarizability46.68 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • N-alkylpiperazine
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • 1,2-aminoalcohol
  • Azacycle
  • Thioether
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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:17016423 ]
  3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
  4. Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular Weight:
49292.765 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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:17016423 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23