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Identification
Name Acetophenazine
Accession Number DB01063 (APRD00462)
Type small molecule
Groups approved
Description

Acetophenazine 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Tindal
Brand mixtures Not Available
Categories
  • Antipsychotics
CAS number 2751-68-0
Weight Average: 411.56
Monoisotopic: 411.198047877
Chemical Formula C23H29N3O2S
InChI Key InChIKey=WNTYBHLDCKXEOT-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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of disorganized and psychotic thinking. Also used to help treat false perceptions (e.g. hallucinations or delusions.)
Pharmacodynamics Acetophenzine is a phenothiazine antipsychotic intended for the management of schizophrenia and other psychotic disorders.
Mechanism of action Acetophenazine 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 2.62 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 6.01e-02 g/l ALOGPS
logP 3.48 ALOGPS
logP 2.65 ChemAxon
logS -3.8 ALOGPS
pKa (strongest acidic) 15.46 ChemAxon
pKa (strongest basic) 8.07 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 47.02 ChemAxon
rotatable bond count 7 ChemAxon
refractivity 121.7 ChemAxon
polarizability 46.68 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
  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
External Links
Resource Link
KEGG Compound C06807 Link_out
ChEBI 2401 Link_out
ChEMBL 2401 Link_out
Therapeutic Targets Database DAP000844 Link_out
PharmGKB PA164781360 Link_out
Wikipedia http://en.wikipedia.org/wiki/Acetophenazine Link_out
ATC Codes
  • N05AB07
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Bromocriptine The phenothiazine decreases the effect of bromocriptine
Cisapride Increased risk of cardiotoxicity and arrhythmias
Dexfenfluramine Decreased anorexic effect, may increase psychotic symptoms
Diethylpropion Decreased anorexic effect, may increase psychotic symptoms
Fenfluramine Decreased anorexic effect, may increase psychotic symptoms
Guanethidine Acetophenazine may decrease the effect of guanethidine.
Mazindol Decreased anorexic effect, may increase psychotic symptoms
Phentermine Decreased anorexic effect, may increase psychotic symptoms
Phenylpropanolamine Decreased anorexic effect, may increase psychotic symptoms
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor (AChEI), Tacrine, and/or the anticholinergic/antipsychotic, Acetophenazine, may be reduced due to antagonism. This interaction may be beneficial when the anticholinergic action is a side effect. AChEIs may also augment the central neurotoxic effect of antipsychotics. Monitor for extrapyramidal symptoms and decreased efficacy of both agents.
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Tetrabenazine May cause dopamine deficiency. Monitor for Tetrabenazine adverse effects. Similar pharmacologic properties thus combination therapy will worsen the severity of sedative, parkinsonian, and extrapyramidal adverse effects.
Trimethobenzamide Trimethobenzamide and Acetophenazine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine The antihistamine, Triprolidine, may increase the arrhythmogenic effect of the phenothiazine, Acetophenazine. Monitor for symptoms of ventricular arrhythmias. Additive anticholinergic and CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Trospium Trospium and Acetophenazine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions Not Available
Targets

1. D(2) dopamine receptor

Pharmacological action: yes
Actions: antagonist

This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase

Organism class: human
UniProt ID: P14416 Link_out
Gene: DRD2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. Pubmed
  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
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. D(1A) dopamine receptor

Pharmacological action: yes
Actions: antagonist

This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase

Organism class: human
UniProt ID: P21728 Link_out
Gene: DRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19