Cariprazine

Cariprazine, sold under the brand names Vraylar, Reagila and Symvenu among others, is an atypical antipsychotic developed by Gedeon Richter, which is used in the treatment of schizophrenia, bipolar mania, bipolar depression, and major depressive disorder. It acts primarily as a D3 and D2 receptor partial agonist, with a preference for the D3 receptor. Cariprazine is also a partial agonist at the serotonin 5-HT1A receptor and acts as an antagonist at 5-HT2B and 5-HT2A receptors, with high selectivity for the D3 receptor. It is taken by mouth.

Cariprazine
Clinical data
Pronunciation/kəˈrɪprəˌzn/
Trade namesVraylar, Reagila, Symvenu
Other namesRGH-188
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: D
Routes of
administration
By mouth
Drug classAtypical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
BioavailabilityHigh
Protein binding91–97%
MetabolismLiver via CYP3A4 and to a lesser extent CYP2D6
Metabolitesdesmethylcariprazine, didesmethylcariprazine
Elimination half-life2–4 days for parent drug, and 1–3 weeks for active metabolites
ExcretionUrine (21%), bile
Identifiers
  • N'-[trans-4-[2-[4-(2,3-Dichlorophenyl)-1-piperazinyl]ethyl]cyclohexyl]-N,N-dimethylurea
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H32Cl2N4O
Molar mass427.41 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)C(=O)N[C@H]1CC[C@H](CCN2CCN(CC2)c2cccc(Cl)c2Cl)CC1
  • 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- Y
  • Key:KPWSJANDNDDRMB-QAQDUYKDSA-N Y

Cariprazine was approved for medical use in the United States in September 2015. It was approved as a generic medication in 2022, but is covered by patents until 2029.

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