Details of the Drug

General Information of Drug (ID: DMZV2PJ)

• Drug Name: Acetophenazine
• Synonyms: Acephenazinum; Acetophenazina; Acetophenazinum; Tindal; Acetophenazine [INN]; Acetophenazina [INN-Spanish]; Acetophenazinum [INN-Latin]; Ketone, 10-(3-(4-(2-hydroxyethyl-1-piperazinyl)propyl)phenothiazin-2-yl methyl; 1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)ethanone; 1-[10-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]phenothiazin-2-yl]ethanone; 10-(3-(4-(2-Hydroxyethyl)-1-piperazinyl)propyl)phenothiazin-2-yl methyl ketone; 2-acetyl-10-[3-[4-(b-hydroxyethyl)piperazinyl]propyl]phenothiazine

Indication

Disease Entry	ICD 11	Status	REF
Bipolar disorder	6A60	Approved	[1], [2]

• Therapeutic Class: Antipsychotic Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 411.6
  Topological Polar Surface Area (xlogp); 2.6
  Rotatable Bond Count (rotbonds); 7
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 6
• Chemical Identifiers:
  Formula: C23H29N3O2S
  IUPAC Name: 1-[10-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]phenothiazin-2-yl]ethanone
  Canonical SMILES: CC(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN4CCN(CC4)CCO
  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
  InChIKey: WNTYBHLDCKXEOT-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 17676
  ChEBI ID: CHEBI:2401
  CAS Number: 2751-68-0
  DrugBank ID: DB01063
  TTD ID: D0L0MB

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dopamine D2 receptor (D2R)	TTEX248	DRD2_HUMAN	Antagonist	[3], [4]

Molecular Expression Atlas of This Drug

• The Studied Disease: Bipolar disorder
• ICD Disease Classification: 6A60

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine D2 receptor (D2R)	DTT	DRD2	2.50E-02	-0.08	-0.49

References

• [1] FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 012254.
• [2] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
• [3] Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38.
• [4] Specific therapeutic actions of acetophenazine, perphenazine, and benzquinamide in newly admitted schizophrenic patients. Clin Pharmacol Ther. 1967 Mar-Apr;8(2):249-55.
• [5] The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74.
• [6] Dopaminergic synapses in the matrix of the ventrolateral striatum after chronic haloperidol treatment. Synapse. 2002 Aug;45(2):78-85.
• [7] CYP2D6 and DRD2 genes differentially impact pharmacodynamic sensitivity and time course of prolactin response to perphenazine. Pharmacogenet Genomics. 2007 Nov;17(11):989-93.
• [8] Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. Bioorg Med Chem. 2005 Jan 3;13(1):77-87.
• [9] Screening of domperidone in wastewater by high performance liquid chromatography and solid phase extraction methods. Talanta. 2006 Jan 15;68(3):928-31.
• [10] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3639).
• [11] Receptor reserve-dependent properties of antipsychotics at human dopamine D2 receptors. Eur J Pharmacol. 2009 Apr 1;607(1-3):35-40.
• [12] [The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome]. Nervenarzt. 2007 Mar;78(3):264, 266-8, 270-1.
• [13] Modulatory role of dopamine D2 receptors and fundamental role of L-type Ca2+ channels in the induction of long-term potentiation in the basolateral... Eur J Pharmacol. 2009 Mar 15;606(1-3):90-3.
• [14] Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.