Cariprazine information

Cariprazine
Clinical data
Pronunciation	/kəˈrɪprəˌziːn/
Trade names	Vraylar, Reagila, Symvenu
Other names	RGH-188
AHFS/Drugs.com	Monograph
License data	US DailyMed: Cariprazine; US FDA: Cariprazine;
Pregnancy; category	AU: D; ;
Routes of; administration	By mouth
Drug class	Atypical antipsychotic
ATC code	N05AX15 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	High
Protein binding	91–97%
Metabolism	Liver via CYP3A4 and to a lesser extent CYP2D6
Metabolites	desmethylcariprazine, didesmethylcariprazine
Elimination half-life	2–4 days for parent drug, and 1–3 weeks for active metabolites
Excretion	Urine (21%), bile
Identifiers
	IUPAC name N'-[trans-4-[2-[4-(2,3-Dichlorophenyl)-1-piperazinyl]ethyl]cyclohexyl]-N,N-dimethylurea;
CAS Number	839712-12-8;
PubChem CID	11154555;
IUPHAR/BPS	7671;
DrugBank	DB06016;
ChemSpider	25999972;
UNII	F6RJL8B278;
KEGG	D09997; as HCl: D09876;
ChEBI	CHEBI:90933;
ChEMBL	ChEMBL2028019;
CompTox Dashboard (EPA)	DTXSID80232867 ;
Chemical and physical data
Formula	C21H32Cl2N4O
Molar mass	427.41 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)C(=O)N[C@H]1CC[C@H](CCN2CCN(CC2)c2cccc(Cl)c2Cl)CC1;
	InChI 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- ; Key:KPWSJANDNDDRMB-QAQDUYKDSA-N ;

Cariprazine, sold under the brand names Vraylar, Reagila and Symvenu among others, is an atypical antipsychotic developed by Gedeon Richter,^[8] which is used in the treatment of schizophrenia, bipolar mania,^[9] bipolar depression,^[10] and major depressive disorder.^[6] 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-HT_1A receptor and acts as an antagonist at 5-HT_2B and 5-HT_2A receptors, with high selectivity for the D₃ receptor.^[11] It is taken by mouth.^[6]

Cariprazine was approved for medical use in the United States in September 2015.^[12] It was approved as a generic medication in 2022,^[13] but is covered by patents until 2029.^[14]

^ ^a ^b "AusPAR: Cariprazine hydrochloride". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 18 April 2023.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Vraylar Product information". Health Canada. 25 April 2012. Archived from the original on 29 June 2022. Retrieved 29 June 2022.
^ "Summary Basis of Decision - Vraylar". Health Canada. 26 August 2022. Archived from the original on 29 September 2022. Retrieved 29 September 2022.
^ "Reagila 1.5 mg hard capsules - Summary of Product Characteristics (SmPC)". (emc). 9 August 2018. Archived from the original on 21 October 2020. Retrieved 20 October 2020.
^ ^a ^b ^c Cite error: The named reference Vraylar FDA label was invoked but never defined (see the help page).
^ "Reagila EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 24 October 2020. Retrieved 20 October 2020.
^ Laszlovszky I, Barabássy Á, Németh G (July 2021). "Cariprazine, A Broad-Spectrum Antipsychotic for the Treatment of Schizophrenia: Pharmacology, Efficacy, and Safety". Advances in Therapy. 38 (7): 3652–3673. doi:10.1007/s12325-021-01797-5. PMC 8279990. PMID 34091867.
^ Agai-Csongor E, Domány G, Nógrádi K, Galambos J, Vágó I, Keserű GM, et al. (May 2012). "Discovery of cariprazine (RGH-188): a novel antipsychotic acting on dopamine D3/D2 receptors". Bioorganic & Medicinal Chemistry Letters. 22 (10): 3437–3440. doi:10.1016/j.bmcl.2012.03.104. PMID 22537450.
^ Earley W, Burgess MV, Rekeda L, Dickinson R, Szatmári B, Németh G, et al. (June 2019). "Cariprazine Treatment of Bipolar Depression: A Randomized Double-Blind Placebo-Controlled Phase 3 Study". The American Journal of Psychiatry. 176 (6): 439–448. doi:10.1176/appi.ajp.2018.18070824. PMID 30845817.
^ Kiss B, Horváth A, Némethy Z, Schmidt E, Laszlovszky I, Bugovics G, et al. (April 2010). "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". The Journal of Pharmacology and Experimental Therapeutics. 333 (1): 328–340. doi:10.1124/jpet.109.160432. PMID 20093397. S2CID 42933132.
^ "FDA approves new drug to treat schizophrenia and bipolar disorder" (Press release). U.S. Food and Drug Administration. 17 September 2015. Archived from the original on 26 January 2018. Retrieved 16 December 2019.
^ "2022 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
^ "Generic Vraylar Availability". Drugs.com. 9 March 2023. Retrieved 26 March 2023.

[Reagila_AusPAR-1] "AusPAR: Cariprazine hydrochloride". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 18 April 2023.

[FDA-AllBoxedWarnings-2] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[3] "Vraylar Product information". Health Canada. 25 April 2012. Archived from the original on 29 June 2022. Retrieved 29 June 2022.

[4] "Summary Basis of Decision - Vraylar". Health Canada. 26 August 2022. Archived from the original on 29 September 2022. Retrieved 29 September 2022.

[Reagila_SmPC-5] "Reagila 1.5 mg hard capsules - Summary of Product Characteristics (SmPC)". (emc). 9 August 2018. Archived from the original on 21 October 2020. Retrieved 20 October 2020.

[Vraylar_FDA_label-6] Cite error: The named reference Vraylar FDA label was invoked but never defined (see the help page).

[Reagila_EPAR-7] "Reagila EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 24 October 2020. Retrieved 20 October 2020.

[:0-8] Laszlovszky I, Barabássy Á, Németh G (July 2021). "Cariprazine, A Broad-Spectrum Antipsychotic for the Treatment of Schizophrenia: Pharmacology, Efficacy, and Safety". Advances in Therapy. 38 (7): 3652–3673. doi:10.1007/s12325-021-01797-5. PMC 8279990. PMID 34091867.

[9] Agai-Csongor E, Domány G, Nógrádi K, Galambos J, Vágó I, Keserű GM, et al. (May 2012). "Discovery of cariprazine (RGH-188): a novel antipsychotic acting on dopamine D3/D2 receptors". Bioorganic & Medicinal Chemistry Letters. 22 (10): 3437–3440. doi:10.1016/j.bmcl.2012.03.104. PMID 22537450.

[10] Earley W, Burgess MV, Rekeda L, Dickinson R, Szatmári B, Németh G, et al. (June 2019). "Cariprazine Treatment of Bipolar Depression: A Randomized Double-Blind Placebo-Controlled Phase 3 Study". The American Journal of Psychiatry. 176 (6): 439–448. doi:10.1176/appi.ajp.2018.18070824. PMID 30845817.

[11] Kiss B, Horváth A, Némethy Z, Schmidt E, Laszlovszky I, Bugovics G, et al. (April 2010). "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". The Journal of Pharmacology and Experimental Therapeutics. 333 (1): 328–340. doi:10.1124/jpet.109.160432. PMID 20093397. S2CID 42933132.

[FDA_PR_20150917-12] "FDA approves new drug to treat schizophrenia and bipolar disorder" (Press release). U.S. Food and Drug Administration. 17 September 2015. Archived from the original on 26 January 2018. Retrieved 16 December 2019.

[13] "2022 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.

[14] "Generic Vraylar Availability". Drugs.com. 9 March 2023. Retrieved 26 March 2023.

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