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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32Cl2N4O
Molecular Weight 427.411
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARIPRAZINE

SMILES

CN(C)C(=O)N[C@H]1CC[C@H](CCN2CCN(CC2)C3=CC=CC(Cl)=C3Cl)CC1

InChI

InChIKey=KPWSJANDNDDRMB-QAQDUYKDSA-N
InChI=1S/C21H32Cl2N4O/c1-25(2)21(28)24-17-8-6-16(7-9-17)10-11-26-12-14-27(15-13-26)19-5-3-4-18(22)20(19)23/h3-5,16-17H,6-15H2,1-2H3,(H,24,28)/t16-,17-

HIDE SMILES / InChI

Molecular Formula C21H32Cl2N4O
Molecular Weight 427.411
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cariprazine is an antipsychotic approved by FDA for the treatment of schizophrenia and bipolar I disorder. The drug has a unique clinical action which is explained by its ability to act on dopamine D3 receptors. Pharmacology studies revealed that cariprazine is a dual partial agonist of dopamine D2 and D3 receptors as well as serotonin 5HT1a, 2a and 2b receptors.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Cariprazine (RGH-188), a dopamine D(3) receptor-preferring, D(3)/D(2) dopamine receptor antagonist-partial agonist antipsychotic candidate: in vitro and neurochemical profile.
2010 Apr
Discovery of cariprazine (RGH-188): a novel antipsychotic acting on dopamine D3/D2 receptors.
2012 May 15
Cariprazine: First Global Approval.
2015 Nov
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose is from 1.5 mg to 6 mg/day (schizophrenia) and 3 mg to 6 mg/day (bipolar mania).
Route of Administration: Oral
In Vitro Use Guide
Rat striatal and hippocampal membrane preparation were treated with a range of cariprazine concentrations from 0.1 nM to 0.1 mM to study [35S]GTPgammaS binding.
Substance Class Chemical
Created
by admin
on Tue Oct 22 01:45:04 UTC 2019
Edited
by admin
on Tue Oct 22 01:45:04 UTC 2019
Record UNII
F6RJL8B278
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARIPRAZINE
DASH   INN   USAN   WHO-DD  
USAN   INN  
Official Name English
CARIPRAZINE [USAN]
Common Name English
FRI-7000188
Common Name English
CARIPRAZINE [WHO-DD]
Common Name English
CARIPRAZINE [INN]
Common Name English
GED-129
Code English
3-(TRANS-4-(2-(4-(2,3-DICHLOROPHENYL)PIPERAZIN-1-YL)ETHYL)CYCLOHEXYL)-1,1-DIMETHYLUREA
Systematic Name English
MP-214
Code English
RGH-188
Code English
Classification Tree Code System Code
NDF-RT N0000175430
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
WHO-ATC N05AX15
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
Code System Code Type Description
MESH
C533287
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
PUBCHEM
11154555
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
EPA CompTox
839712-12-8
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
LactMed
839712-12-8
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
CAS
839712-12-8
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
EVMPD
SUB34830
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
WIKIPEDIA
Cariprazine
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
IUPHAR
7671
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
INN
8920
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
RXCUI
1667655
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY RxNorm
HSDB
839712-12-8
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
ChEMBL
CHEMBL2028019
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
DRUG BANK
DB06016
Created by admin on Tue Oct 22 01:45:04 UTC 2019 , Edited by admin on Tue Oct 22 01:45:04 UTC 2019
PRIMARY
Related Record Type Details
TARGET->WEAK INHIBITOR
Ki
TARGET->PARTIAL AGONIST
Ki
TARGET->PARTIAL AGONIST
Most of the clinically used antipsychotics display fairly high affinity for D3 receptors in vitro, they lack significant D3 receptor binding in vivo. They also do not occupy D3 receptors in schizophrenic patients at clinically-relevant doses, despite having significant and expected D2 receptor occupancy. The lack of in vivo D3 receptor occupancy of currently used antipsychotics may be due to their inability to displace endogenous DA from these sites; especially since DA has approximately 20- fold higher affinity for D3 vs D2 receptors and D3 (but not D2) receptors exist predominantly in a high affinity state for DA€?
Ki
TARGET->WEAK INHIBITOR
Ki
SALT/SOLVATE -> PARENT
TARGET->PARTIAL AGONIST
Ki
TARGET -> INHIBITOR
Ki
TRANSPORTER -> NON-INHIBITOR
Ki
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PARENT
minor enzyme involved in metabolism
MINOR
PLASMA
METABOLITE ACTIVE -> PARENT
activity same as CARIPRAZINE; steady state plasma level 400% of CARIPRAZINE
MAJOR
PLASMA
METABOLITE ACTIVE -> PARENT
MINOR
PLASMA
METABOLITE ACTIVE -> PARENT
activity same as CARIPRAZINE, steady state level 30% of CARIPRAZINE
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC