General
Preferred name
CHLORPROTHIXENE
Synonyms
Taractan ()
Truxal ()
Clorprotixeno ()
Minithixen hydrochloride ()
Truxal hydrochloride ()
NSC 169899 ()
NSC 56379 ()
NSC 78193 ()
Minithixen ()
Chlorprothixene (hydrochloride) ()
CHLORPROTHIXENE HYDROCHLORIDE ()
Minithixen,Truxal ()
Minithixen hydrochloride, Truxal hydrochloride, NSC 169899, NSC 56379, NSC 78193 ()
RO-4-0403 ()
N-714 ()
NSC-18720 ()
RO 4-0403 ()
N-714RO 4-0403 ()
Ro-40403 ()
Chlorprothixene HCl ()
P&D ID
PD012153
CAS
113-59-7
6469-93-8
Tags
available
drug
Approved by
FDA
First approval
1967
Drug indication
Psychotic disorder
Antipsychotic
Drug Status
experimental
approved
withdrawn
investigational
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
INDICATION For treatment of psychotic disorders (e.g. schizophrenia) and of acute mania occuring as part of bipolar disorders.
PHARMACODYNAMICS Chlorprothixene is a typical antipsychotic drug of the thioxanthine class. It has a low antipsychotic potency (half to 2/3 of chlorpromazine). Chlorprothixene has not thoroughly demonstrated an antidepressant or analgesic effect but it has demonstrated antiemetic effects. It is used in the treatment of nervous, mental, and emotional conditions. Improvement in such conditions is thought to result from the effect of the medicine on nerve pathways in specific areas of the brain. Chlorprothixene has a similar side effect profile to chlorpromazine, though allergic side effects and liver damage are less frequent.
MOA Chlorprothixene 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.
TOXICITY Symptoms of overdose include difficulty in breathing (severe), dizziness (severe), drowsiness (severe), muscle trembling, jerking, stiffness, or uncontrolled movements (severe), small pupils, unusual excitement, and unusual tiredness or weakness (severe).
METABOLISM Hepatic
HALF-LIFE 8 to 12 hours
ABSORPTION Incomplete bioavailability.
DESCRIPTION Chlorprothixene can be classified as a (tricyclic) typical antipsychotic drug. The INN record stipulates the (Z) conformer. Mechanistically it acts at multiple GPCRs to mediate its neurological effects. Direct interactions with 5-HT2, dopamine D1, D2, D3, histamine H1, muscarinic and α1 adrenergic receptors have been demonstrated. (GtoPdb)
DESCRIPTION Chlorprothixene has strong binding affinities to dopamine and histamine receptors, such as D1, D2, D3, D5, H1, 5-HT2, 5-HT6 and 5-HT7, with Ki of 18 nM, 2.96 nM, 4.56 nM, 9 nM, 3.75 nM, 9.4 nM, 3 nM and 5.6 nM, respectively. (BOC Sciences Bioactive Compounds)
DESCRIPTION Chlorprothixene hydrochloride is the hydrochloride salt form of chlorprothixene, a typical thioxanthine antipsychotic that functions by antagonizing dopamine D2 receptors. It can block a subset of GABAA receptors in rat cortex that is also blocked by clozapine. It exerts strong blocking effects by blocking the 5-HT2 D1, D2, D3, histamine H1, muscarinic and alpha1 adrenergic receptors. It has also been shown to be effective against P. falciparum growth with an EC50 value of 1.7 µM. (BOC Sciences Bioactive Compounds)
Cell lines
0
Organisms
1
Compound Sets
19
AdooQ Bioactive Compound Library
A10207
BOC Sciences Bioactive Compounds
chlorprothixene-cas-113-59-7-item-84-54903
chlorprothixene-hydrochloride-cas-6469-93-8-item-74392
Cayman Chemical Bioactives
20772
ChEMBL Approved Drugs
CHEMBL908
ChEMBL Drugs
CHEMBL908
Drug Repurposing Hub
DrugBank
DB01239
DrugBank Approved Drugs
DB01239
DrugCentral
623
DrugCentral Approved Drugs
623
DrugMAP
DMY0KGJ
DrugMAP Approved Drugs
DMY0KGJ
Enamine BioReference Compounds
Guide to Pharmacology
11976
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL908
MedChem Express Bioactive Compound Library
HY-B0274
HY-B0274A
ReFrame library
Selleckchem Bioactive Compound Library
Chlorprothixene
chlorprothixene-hydrochloride
TargetMol Bioactive Compound Library
T0074
External IDs
39
Properties
(calculated by RDKit )
Molecular Weight
315.08
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
0
Rotatable Bonds
3
Ring Count
3
Aromatic Ring Count
2
cLogP
5.19
TPSA
3.24
Fraction CSP3
0.22
Chiral centers
0.0
Largest ring
6.0
QED
0.65
Structural alerts
1
styrene_B(8)
c:1:c:c-2:c(:c:c:1)-[#6](-c:3:c(-[$([#16;X2]),$([#6;X4])]-2):c:c:[c;!H0,$(c-[#17]),$(c-[#6;X4])](:c:3))=[#6]-[#6]
PAINS Family C
Related compounds
Custom attributes
(extracted from source data)
Pathway
GPCR/G protein
Immunology/Inflammation
Neuroscience
Anti-infection
Neuronal Signaling
Target
5-HT6
5-HT7
D2
D3
H1 receptor
CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, DRD1, DRD2, DRD3, HRH1, HTR2A, HTR2B, HTR2C
Bacterial
Dopamine Receptor
Histamine Receptor
Indication
schizophrenia, bipolar disorder
MOA
Dopamine Receptor antagonist
Therapeutic Class
Antipsychotic Agents
Solubility
~10 mg/ml in PBS (pH 7.2)
~30 mg/ml in EtOH, DMSO, & DMF.
Source data