chlorprothixene 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
623 113-59-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • chlorprothixene
  • chlorprothixen
  • chlorprotixen
  • chlorprotixene
  • chlothixen
  • chorprothixene
  • chlorprothixene hydrochloride
  • chlorprothixene HCl
  • taractan
A thioxanthine with effects similar to the phenothiazine antipsychotics.
  • Molecular weight: 315.86
  • Formula: C18H18ClNS
  • CLOGP: 5.48
  • LIPINSKI: 1
  • HAC: 1
  • HDO: 0
  • TPSA: 3.24
  • ALOGS: -5.94
  • ROTB: 3
  • Status: OFM
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 g O
50 mg P

ADMET properties:

PropertyValueReference
BA (Bioavailability) 41 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 13.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 11.50 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 25.80 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 3.870 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.832 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 10.889 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 180.302 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 1.060 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 2.350 % High 1
herg hERG pIC50 5.862 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 17.022 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 19.953 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.980 % High 1
kinase-safety-class ACVR2B,AKT1,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,CHEK1,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,JAK3,MAP3K21,MAP3K7,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MET,MTOR,NTRK2,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,TTK 46
kinase-selectivity-class AXL,EIF2AK3,PDK4,STK33,TTK 5
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.501 High 1
mh-clint Mouse hepatocyte intrinsic clearance 209.411 High 1
mppb Mouse plasma protein binding (% unbound) 1.320 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.750 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 3.270 % High 1
rh-clint Rat hepatocyte intrinsic clearance 292.415 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 6.650 % High 1
rppb Rat plasma protein binding (% unbound) 1.420 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 68.865 uM High 1

Approvals:

DateAgencyCompanyOrphan
June 19, 1967 FDA ROCHE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Intentional self-injury 122.66 46.22 40 2135 29294 90596978
Intentional overdose 114.08 46.22 52 2123 93782 90532490
Serotonin syndrome 105.07 46.22 38 2137 37849 90588423
Toxicity to various agents 95.28 46.22 68 2107 287778 90338494
Drug interaction 93.08 46.22 66 2109 276387 90349885
Extrapyramidal disorder 79.46 46.22 25 2150 16278 90609994
Neuroleptic malignant syndrome 77.13 46.22 24 2151 15072 90611200
Suicide attempt 73.74 46.22 36 2139 75363 90550909
Rhabdomyolysis 57.78 46.22 27 2148 51229 90575043
Myoglobin blood increased 57.37 46.22 12 2163 1540 90624732
Suicidal ideation 56.82 46.22 30 2145 73825 90552447
Depressed level of consciousness 54.40 46.22 29 2146 72755 90553517
Apallic syndrome 52.65 46.22 10 2165 786 90625486
Tremor 47.78 46.22 35 2140 153138 90473134

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Neuroleptic malignant syndrome 103.11 36.98 35 1352 21437 42598511
Toxicity to various agents 77.87 36.98 62 1325 229074 42390874
Ileus paralytic 68.14 36.98 20 1367 7621 42612327
Suicidal ideation 57.46 36.98 29 1358 48132 42571816
Akathisia 53.89 36.98 18 1369 10433 42609515
Suicide attempt 47.03 36.98 25 1362 46075 42573873
Gastrointestinal necrosis 42.09 36.98 12 1375 4116 42615832
Tardive dyskinesia 40.00 36.98 13 1374 6911 42613037

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Neuroleptic malignant syndrome 180.20 35.05 59 3353 34000 110551887
Toxicity to various agents 145.28 35.05 119 3293 480436 110105451
Suicidal ideation 110.18 35.05 55 3357 93882 110492005
Suicide attempt 108.06 35.05 56 3356 103338 110482549
Drug interaction 107.17 35.05 102 3310 500081 110085806
Serotonin syndrome 94.94 35.05 43 3369 59110 110526777
Intentional overdose 92.43 35.05 55 3357 132446 110453441
Extrapyramidal disorder 76.53 35.05 30 3382 28837 110557050
Intentional self-injury 75.59 35.05 32 3380 37397 110548490
Akathisia 72.06 35.05 25 3387 17088 110568799
Restlessness 69.04 35.05 34 3378 56225 110529662
Ileus paralytic 60.65 35.05 20 3392 11717 110574170
Muscle rigidity 56.81 35.05 23 3389 24008 110561879
Somnolence 52.97 35.05 55 3357 297394 110288493
Rhabdomyolysis 49.63 35.05 36 3376 120365 110465522
Myoglobin blood increased 46.97 35.05 13 3399 4219 110581668
Apallic syndrome 46.85 35.05 10 3402 1096 110584791
Tremor 44.51 35.05 42 3370 202190 110383697
Gastrointestinal necrosis 37.07 35.05 12 3400 6628 110579259
Psychomotor retardation 35.19 35.05 12 3400 7780 110578107

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AF03 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Thioxanthene derivatives
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:35717 sedative
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:48873 cholinergic antagonist
CHEBI has role CHEBI:50919 antiemetic
CHEBI has role CHEBI:65190 first generation antipsychotic
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014150 Antipsychotic Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018492 Dopamine Antagonists
CHEBI has role CHEBI:176497 geroprotector

Related Drugs by ATC class:

N05AF Thioxanthene derivatives 4 drugs
clopenthixolflupentixolthiothixenezuclopenthixol

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Schizophrenia indication 58214004 DOID:5419
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Senile dementia contraindication 15662003
Agranulocytosis contraindication 17182001 DOID:12987
Shock contraindication 27942005
Parkinsonism contraindication 32798002
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Stupor contraindication 89458003
Tardive dyskinesia contraindication 102449007
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Alcohol withdrawal syndrome contraindication 191480000
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Neutropenic disorder contraindication 303011007 DOID:1227
Coma contraindication 371632003
Angle-closure glaucoma contraindication 392291006 DOID:13550
Breastfeeding (mother) contraindication 413712001
Carcinoma of female breast contraindication 447782002
Drug Induced CNS Depression contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.66 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.53 CHEMBL CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 9.37 PDSP
5-hydroxytryptamine receptor 6 GPCR Ki 8.52 CHEMBL
D(3) dopamine receptor GPCR ANTAGONIST Ki 8.34 CHEMBL
D(1B) dopamine receptor GPCR Ki 8.05 CHEMBL
Histamine H1 receptor GPCR Ki 8.43 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 7.96 PDSP
Muscarinic acetylcholine receptor M2 GPCR Ki 7.55 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 7.66 PDSP
Muscarinic acetylcholine receptor M4 GPCR Ki 7.75 PDSP
Muscarinic acetylcholine receptor M5 GPCR Ki 7.60 PDSP
D(4) dopamine receptor GPCR Ki 9.19 PDSP
ATP-binding cassette sub-family G member 2 Transporter IC50 4.38 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.11 CHEMBL
D(1A) dopamine receptor GPCR Ki 7.74 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 8.25 CHEMBL
Histamine H1 receptor GPCR IC50 8.97 CHEMBL
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.29 CHEMBL

External reference:

IDSource
4017788 VUID
N0000146149 NUI
D00790 KEGG_DRUG
2406 RXNORM
C0008290 UMLSCUI
CHEBI:3651 CHEBI
CHEMBL908 ChEMBL_ID
DB01239 DRUGBANK_ID
D002749 MESH_DESCRIPTOR_UI
667467 PUBCHEM_CID
11976 IUPHAR_LIGAND_ID
886 INN_ID
6469-93-8 SECONDARY_CAS_RN
9S7OD60EWP UNII
001516 NDDF
005139 NDDF
387317000 SNOMEDCT_US
57002000 SNOMEDCT_US
88585004 SNOMEDCT_US
CHEMBL1256658 ChEMBL_ID
4017788 VANDF
9S7OD60EWP INXIGHT DRUGS

Pharmaceutical products:

None