CARIPRAZINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H32Cl2N4O.ClH
Molecular Weight	463.872
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=GPPJWWMREQHLQT-BHQIMSFRSA-N

InChI=1S/C21H32Cl2N4O.ClH/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);1H/t16-,17-;

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H32Cl2N4O
Molecular Weight	427.411
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
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

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 297	Partial Agonist 290	0.49 nM [Ki]
Dopamine D3 receptor 91	Partial Agonist 290	0.085 nM [Ki]
Serotonin 1a (5-HT1a) receptor 172	Partial Agonist 290	2.6 nM [Ki]
Serotonin 2a (5-HT2a) receptor 231	Antagonist 2,778	18.8 nM [Ki]
Serotonin 2b (5-HT2b) receptor 60	Antagonist 2,778	0.58 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298	Primary		Approved 8,429	VRAYLAR
Bipolar I disorder 17	Primary		Approved 8,429	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

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Dose	Population	Adverse events
5.7 mg 1 times / day steady, oral (mean) Recommended	unhealthy, 39.1 years n = 586	Disc. AE: Schizophrenia aggravated, Psychotic disorder...
12 mg 1 times / day steady, oral (mean) Highest studied dose	unhealthy, 41,2 years (range: 18-65 years) n = 169	Disc. AE: Akathisia...
6 mg 1 times / day steady, oral Recommended	unhealthy, Elderly n = 17	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 (mean) Recommended	unhealthy, 39.1 years n = 586
Musculoskeletal stiffness	0.2% Disc. AE	5.7 mg 1 times / day steady, oral (mean) Recommended	unhealthy, 39.1 years n = 586
Parkinsonism	0.2% Disc. AE	5.7 mg 1 times / day steady, oral (mean) Recommended	unhealthy, 39.1 years n = 586
Restlessness	0.2% Disc. AE	5.7 mg 1 times / day steady, oral (mean) Recommended	unhealthy, 39.1 years n = 586
Salivary hypersecretion	0.2% Disc. AE	5.7 mg 1 times / day steady, oral (mean) Recommended	unhealthy, 39.1 years n = 586

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 inducer 781	inhibitor 1,767	substrate 1,217 inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C19 1,478 CYP3A5 73 P-gp 1,461 BCRP 699 OATP1B1 788 OATP1B3 706 OAT3 642 OCT2 647 CYP2A6 707 CYP2E1 882	CYP3A 191 P-gp 1,537 BCRP 561 OATP1B1 406 OATP1B3 350 OAT3 339 OCT2 355	CYP1A2 701

Drug as perpetrator

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Target	Modality	Activity	Metabolite
P-gp 1,650	inhibitor 3,277	inconclusive
BCRP 773	inhibitor 3,277	no
BCRP 773	inhibitor 3,277	no	DCAR 2
BCRP 773	inhibitor 3,277	no	DDCAR 2
CYP1A2 1,692	inducer 1,573	no

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Drug as victim

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Target	Modality	Activity	Metabolite
BCRP 561	substrate 3,367	no
BCRP 561	substrate 3,367	no	DCAR 2
BCRP 561	substrate 3,367	no	DDCAR 2
OAT3 339	substrate 3,367	no
OAT3 339	substrate 3,367	no	DCAR 2

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Tox targets

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Target	Modality	Metabolite
hERG 1,647	inhibitor 1,626
hERG 1,647	inhibitor 1,626	DCAR 2
hERG 1,647	inhibitor 1,626	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

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Title	Date	PubMed
Cariprazine: chemistry, pharmacodynamics, pharmacokinetics, and metabolism, clinical efficacy, safety, and tolerability.	2013 Feb	23320989

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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
Record UNII	KQD7C255YG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARIPRAZINE HYDROCHLORIDE

Official Name

English

VRAYLAR

Brand Name

English

CARIPRAZINE HYDROCHLORIDE [MI]

Common Name

English

CARIPRAZINE HYDROCHLORIDE [JAN]

Common Name

English

CARIPRAZINE HYDROCHLORIDE [USAN]

Common Name

English

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Code System

Code

Type

Description

CHEBI

90932

PRIMARY

DRUG BANK

DBSALT001260

PRIMARY

RXCUI

1721073

PRIMARY

RxNorm

NCI_THESAURUS

C169827

PRIMARY

ChEMBL

CHEMBL2028019

PRIMARY

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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