Details of the Drug

General Information of Drug (ID: DMHTB31)

Drug Name

Carphenazine

Synonyms

Carfenazine; Carphenazin; Procethazine; Proketazin; Carfenazina [INN-Spanish]; Carfenazine [INN:BAN]; Carfenazinum [INN-Latin]; 1-(10-(3-(4-(2-Hydroxyethyl)-1-piperazinyl)propyl)phenothiazin-2-yl)-1-propanone; 1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one; 1-[10-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]phenothiazin-2-yl]propan-1-one

Indication

Disease Entry	ICD 11	Status	REF
Insomnia	7A00-7A0Z	Approved	[1]
Schizophrenia	6A20	Withdrawn from market	[2], [3]

Therapeutic Class

Antipsychotic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

425.6

Topological Polar Surface Area (xlogp)

3.1

Rotatable Bond Count (rotbonds)

8

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

6

Chemical Identifiers

Formula: C24H31N3O2S
IUPAC Name: 1-[10-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]phenothiazin-2-yl]propan-1-one
Canonical SMILES: CCC(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN4CCN(CC4)CCO
InChI: InChI=1S/C24H31N3O2S/c1-2-22(29)19-8-9-24-21(18-19)27(20-6-3-4-7-23(20)30-24)11-5-10-25-12-14-26(15-13-25)16-17-28/h3-4,6-9,18,28H,2,5,10-17H2,1H3
InChIKey: XZSMZRXAEFNJCU-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 18104
CAS Number: 2622-30-2
DrugBank ID: DB01038
TTD ID: D01QML

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	[4], [5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Insomnia

ICD Disease Classification

7A00-7A0Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine D2 receptor (D2R)	DTT	DRD2	2.20E-03	-0.51	-1.35

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	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: 7140).
3	Drug information of Carphenazine, 2008. eduDrugs.
4	Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38.
5	Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7.
6	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.
7	Dopaminergic synapses in the matrix of the ventrolateral striatum after chronic haloperidol treatment. Synapse. 2002 Aug;45(2):78-85.
8	CYP2D6 and DRD2 genes differentially impact pharmacodynamic sensitivity and time course of prolactin response to perphenazine. Pharmacogenet Genomics. 2007 Nov;17(11):989-93.
9	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.
10	Screening of domperidone in wastewater by high performance liquid chromatography and solid phase extraction methods. Talanta. 2006 Jan 15;68(3):928-31.
11	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).
12	Receptor reserve-dependent properties of antipsychotics at human dopamine D2 receptors. Eur J Pharmacol. 2009 Apr 1;607(1-3):35-40.
13	[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome]. Nervenarzt. 2007 Mar;78(3):264, 266-8, 270-1.
14	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.
15	Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.