Asenapine

Asenapine
Clinical data
Trade names	Saphris, Sycrest, Secuado
Other names	ORG-5222
AHFS/Drugs.com	Monograph
MedlinePlus	a610015
License data	EU EMA: by INN; US DailyMed: Asenapine; US FDA: Asenapine;
Pregnancy; category	AU: C;
Routes of; administration	Sublingual, transdermal
Drug class	Atypical antipsychotic
ATC code	N05AH05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	35% (sublingual), <2% (oral), transdermal bioavailability is significantly higher than sublingual
Protein binding	95%
Metabolism	hepatic (glucurinodation by UGT1A4 and oxidative metabolism by CYP1A2)
Elimination half-life	24 hours (sublingual), 30 hours (transdermal), 33.9 hours (transdermal)
Excretion	Kidney (50%), Faecal (40%; ~5–16% as unchanged drug in faeces)
Identifiers
	IUPAC name (3aRS,12bRS)-rel-5-Chloro-2,3,3a,12b-tetrahydro-; 2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole;
CAS Number	65576-45-6 ; as salt: 85650-56-2;
PubChem CID	163091; as salt: 6917875;
IUPHAR/BPS	22;
DrugBank	DB06216; as salt: DBSALT000010;
ChemSpider	2300725 ; as salt: 5293095;
UNII	JKZ19V908O; as salt: CU9463U2E2;
KEGG	D11769; as salt: D02995;
ChEBI	CHEBI:71253 ; as salt: CHEBI:71245;
ChEMBL	ChEMBL1201756 ; as salt: ChEMBL2040684;
ECHA InfoCard	100.059.828
Chemical and physical data
Formula	C17H16ClNO
Molar mass	285.77 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc4cc2c(Oc1c(cccc1)[C@@H]3CN(C[C@@H]23)C)cc4;
	InChI InChI=1S/C17H16ClNO/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19/h2-8,14-15H,9-10H2,1H3/t14-,15-/m0/s1 ; Key:VSWBSWWIRNCQIJ-GJZGRUSLSA-N ; ; as salt: InChI=1S/C17H16ClNO.C4H4O4/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19;5-3(6)1-2-4(7)8/h2-8,14-15H,9-10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15-;/m1./s1; Key:GMDCDXMAFMEDAG-CHHFXETESA-N;
	(what is this?) (verify)

Asenapine, sold under the brand name Saphris among others, is an atypical antipsychotic medication used to treat schizophrenia and acute mania associated with bipolar disorder as well as the medium to long-term management of bipolar disorder.^[3]^[9]

It was chemically derived via altering the chemical structure of the tetracyclic (atypical) antidepressant, mianserin.^[10]

It was initially approved in the United States in 2009^[11] and approved as a generic medication in 2020.^[12]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c ^d ^e ^f "Sycrest 5mg sublingual tablets - Summary of Product Characteristics (SmPC)". (emc). Retrieved 9 September 2020.
^ ^a ^b "Sycrest EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 9 September 2020.
^ ^a ^b ^c ^d ^e "Product Information Saphris (asenapine maleate)" (PDF). TGA eBusiness Services. Merck Sharp & Dohme (Australia) Pty Limited. 14 January 2013. Retrieved 23 October 2013.
^ ^a ^b ^c ^d ^e "Saphris (asenapine maleate) tablet". DailyMed. Organon Pharmaceuticals. March 2013. Retrieved 23 October 2013.
^ ^a ^b ^c ^d ^e "Product information Sycrest – EMEA/H/C/001177 –II/0012" (PDF). European Medicines Agency. N.V. Organon. 21 February 2013. Archived from the original (PDF) on 28 July 2017. Retrieved 23 October 2013.
^ ^a ^b Cite error: The named reference Carrithers 2020 was invoked but never defined (see the help page).
^ ^a ^b Suzuki K, Castelli M, Komaroff M, Starling B, Terahara T, Citrome L (2021-03-16). "Pharmacokinetic Profile of the Asenapine Transdermal System (HP-3070)". Journal of Clinical Psychopharmacology. 41 (3): 286–294. doi:10.1097/JCP.0000000000001383. PMC 8083160. PMID 33734167.
^ Cite error: The named reference pmid23719049 was invoked but never defined (see the help page).
^ Minassian A, Young JW (August 2010). "Evaluation of the clinical efficacy of asenapine in schizophrenia". Expert Opinion on Pharmacotherapy. 11 (12): 2107–2115. doi:10.1517/14656566.2010.506188. PMC 2924192. PMID 20642375.
^ "Saphris (asenapine) prescribing information" (PDF). Schering Corporation. 2009-08-01. Archived from the original (PDF) on 2009-11-22. Retrieved 2009-09-05.
^ "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). Retrieved 13 February 2021.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[EMC-2] ^ ^a ^b ^c ^d ^e ^f "Sycrest 5mg sublingual tablets - Summary of Product Characteristics (SmPC)". (emc). Retrieved 9 September 2020.

[Sycrest_EPAR-3] "Sycrest EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 9 September 2020.

[TGA-4] "Product Information Saphris (asenapine maleate)" (PDF). TGA eBusiness Services. Merck Sharp & Dohme (Australia) Pty Limited. 14 January 2013. Retrieved 23 October 2013.

[DM-5] "Saphris (asenapine maleate) tablet". DailyMed. Organon Pharmaceuticals. March 2013. Retrieved 23 October 2013.

[EMA-6] "Product information Sycrest – EMEA/H/C/001177 –II/0012" (PDF). European Medicines Agency. N.V. Organon. 21 February 2013. Archived from the original (PDF) on 28 July 2017. Retrieved 23 October 2013.

[Carrithers_2020-7] Cite error: The named reference Carrithers 2020 was invoked but never defined (see the help page).

[suzuki-pk-2021-8] Suzuki K, Castelli M, Komaroff M, Starling B, Terahara T, Citrome L (2021-03-16). "Pharmacokinetic Profile of the Asenapine Transdermal System (HP-3070)". Journal of Clinical Psychopharmacology. 41 (3): 286–294. doi:10.1097/JCP.0000000000001383. PMC 8083160. PMID 33734167.

[pmid23719049-9] Cite error: The named reference pmid23719049 was invoked but never defined (see the help page).

[10] Minassian A, Young JW (August 2010). "Evaluation of the clinical efficacy of asenapine in schizophrenia". Expert Opinion on Pharmacotherapy. 11 (12): 2107–2115. doi:10.1517/14656566.2010.506188. PMC 2924192. PMID 20642375.

[asenapinepi-11] "Saphris (asenapine) prescribing information" (PDF). Schering Corporation. 2009-08-01. Archived from the original (PDF) on 2009-11-22. Retrieved 2009-09-05.

[12] "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). Retrieved 13 February 2021.

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