Zicronapine

Zicronapine
Identifiers
	IUPAC name 4-[(1R,3S)-6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-yl]-1,2,2-trimethylpiperazine;
CAS Number	170381-16-5;
PubChem CID	11465618;
DrugBank	DB05828;
ChemSpider	9640456;
UNII	QZV11V7G6A;
KEGG	D10329 ;
CompTox Dashboard (EPA)	DTXSID30168849 ;
Chemical and physical data
Formula	C22H27ClN2
Molar mass	354.9 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc4c(c1)[C@H](N2CC(N(C)CC2)(C)C)C[C@H]4c3ccccc3;
	InChI InChI=1S/C22H27ClN2/c1-22(2)15-25(12-11-24(22)3)21-14-19(16-7-5-4-6-8-16)18-10-9-17(23)13-20(18)21/h4-10,13,19,21H,11-12,14-15H2,1-3H3/t19-,21+/m0/s1; Key:BYPMJBXPNZMNQD-PZJWPPBQSA-N;

Zicronapine (/zaɪˈkrɒnəpiːn/ zye-KRON-ə-peen, previously known as Lu 31-130) is an atypical antipsychotic medication formerly under development by H. Lundbeck A/S. In phase II studies zicronapine showed statistically significant separation from placebo and convincing efficacy and safety data when compared to olanzapine.^[1]

Zicronapine exhibits monoaminergic activity and has a multi-receptorial profile. In vitro and in vivo it has shown potent antagonistic effects at dopamine D₁, D₂ and serotonin 5HT_2A receptors.^[2]

In 2014 Lundbeck removed zicronapine from its development portfolio in favor of pursuing the more promising antipsychotic Lu AF35700 (a prodrug of Lu AF356152).^[3]

References

^ "The clinical phase III programme commenced on zicronapine". January 20, 2011. Retrieved 6 February 2014.
^ "Zicronapine shows significant positive data in clinical phase II in the treatment of patients with schizophrenia - planning for continued clinical work". December 18, 2009. Retrieved 6 February 2014.
^ "Performance in 2014 positions Lundbeck well for 2015 and beyond" (PDF). February 5, 2015. Retrieved 18 June 2015.

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[1] "The clinical phase III programme commenced on zicronapine". January 20, 2011. Retrieved 6 February 2014.

[2] "Zicronapine shows significant positive data in clinical phase II in the treatment of patients with schizophrenia - planning for continued clinical work". December 18, 2009. Retrieved 6 February 2014.

[3] "Performance in 2014 positions Lundbeck well for 2015 and beyond" (PDF). February 5, 2015. Retrieved 18 June 2015.

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v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Others/unknown: Azacyclonol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III