CARIPRAZINE

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

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

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

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 311	Partial Agonist 297	0.49 nM [Ki]
Dopamine D3 receptor 97	Partial Agonist 297	0.085 nM [Ki]
Serotonin 1a (5-HT1a) receptor 177	Partial Agonist 297	2.6 nM [Ki]
Serotonin 2a (5-HT2a) receptor 237	Antagonist 2,849	18.8 nM [Ki]
Serotonin 2b (5-HT2b) receptor 60	Antagonist 2,849	0.58 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305	Primary		Approved 8,583	VRAYLAR
Bipolar I disorder 19	Primary		Approved 8,583	VRAYLAR

C_max

Value	Dose	Analyte	Population
10.2 ng/mL	3 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens
22.7 ng/mL	6 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens
28.8 ng/mL	9 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
156 ng × h/mL	3 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens
358 ng × h/mL	6 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens
466 ng × h/mL	9 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
68.4 h	3 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens
44.3 h	6 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens
31.6 h	9 mg 1 times / day multiple, oral	CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
9%	unknown, unknown		CARIPRAZINE HYDROCHLORIDE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
5.7 mg 1 times / day steady, oral Recommended	unhealthy, 39.1 years	Disc. AE: Schizophrenia aggravated, Psychotic disorder...
12 mg 1 times / day steady, oral Highest studied dose	unhealthy, 41,2 years (range: 18-65 years)	Disc. AE: Akathisia...
6 mg 1 times / day steady, oral Recommended	unhealthy, Elderly	Other AEs: Adverse event...
3 mg 1 times / day steady, oral Recommended	unhealthy	Disc. AE: Akathisia...

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AEs

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AE	Significance	Dose	Population
Dystonia	0.2% Disc. AE	5.7 mg 1 times / day steady, oral Recommended	unhealthy, 39.1 years
Musculoskeletal stiffness	0.2% Disc. AE	5.7 mg 1 times / day steady, oral Recommended	unhealthy, 39.1 years
Parkinsonism	0.2% Disc. AE	5.7 mg 1 times / day steady, oral Recommended	unhealthy, 39.1 years
Restlessness	0.2% Disc. AE	5.7 mg 1 times / day steady, oral Recommended	unhealthy, 39.1 years
Salivary hypersecretion	0.2% Disc. AE	5.7 mg 1 times / day steady, oral Recommended	unhealthy, 39.1 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 inducer 1,087	inhibitor 2,438	substrate 1,388 inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2C19 2,057 CYP3A5 136 P-gp 1,741 BCRP 910 OATP1B1 1,079 OATP1B3 961 OAT3 747 OCT2 779 CYP2A6 879 CYP2E1 1,060	CYP3A 220 P-gp 2,052 BCRP 697 OATP1B1 503 OATP1B3 435 OAT3 391 OCT2 434	CYP1A2 832

Drug as perpetrator

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Target	Modality	Activity	Metabolite
P-gp 1,932	inhibitor 4,027	inconclusive
BCRP 985	inhibitor 4,027	no
BCRP 985	inhibitor 4,027	no	DCAR 2
BCRP 985	inhibitor 4,027	no	DDCAR 2
CYP1A2 2,333	inducer 1,966	no

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Drug as victim

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Target	Modality	Activity	Metabolite
BCRP 697	substrate 4,014	no
BCRP 697	substrate 4,014	no	DCAR 2
BCRP 697	substrate 4,014	no	DDCAR 2
OAT3 391	substrate 4,014	no
OAT3 391	substrate 4,014	no	DCAR 2

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Tox targets

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Target	Modality	Metabolite
hERG 2,263	inhibitor 2,237
hERG 2,263	inhibitor 2,237	DCAR 2
hERG 2,263	inhibitor 2,237	DDCAR 2

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:90933	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:90933
ChemicalBook	CB22563442	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB22563442
MolPort	MolPort-039-139-594	https://www.molport.com/shop/molecule-link/MolPort-039-139-594
ZINC	ZINC000100907004	http://zinc15.docking.org/substances/ZINC000100907004

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PubMed

Title	Date	PubMed
No data available in table

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.

Show entries

Name

Type

Language

GED-129

Preferred Name

English

CARIPRAZINE

Official Name

English

CARIPRAZINE [USAN]

Common Name

English

FRI-7000188

Common Name

English

cariprazine [INN]

Common Name

English

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175430

Other antipsychotics

WHO-ATC

N05AX15

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Code System

Code

Type

Description

LACTMED

Cariprazine

PRIMARY

SMS_ID

100000128115

PRIMARY

MESH

C533287

PRIMARY

PUBCHEM

11154555

PRIMARY

EPA CompTox

DTXSID80232867

PRIMARY

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ACTIVE MOIETY


					F6RJL8B278

CARIPRAZINE

METABOLITE ACTIVE (PARENT)


					286RCD7025

DESMETHYL CARIPRAZINE

METABOLITE ACTIVE (PARENT)


					6AY300X9G3

DIDESMETHYL CARIPRAZINE

SALT/SOLVATE (PARENT)


					KQD7C255YG

CARIPRAZINE HYDROCHLORIDE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator