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	354.92 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^[1] 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.^[2]

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.^[3]

In 2014 Lundbeck removed zicronapine from its development portfolio in favor of pursuing the more promising antipsychotic Lu AF35700 (a prodrug of Lu AF356152).^[4]

References

^ Citrome L (November 2013). "A review of the pharmacology, efficacy and tolerability of recently approved and upcoming oral antipsychotics: an evidence-based medicine approach". CNS Drugs. 27 (11): 879–911. doi: 10.1007/s40263-013-0105-7. PMID 24062193. S2CID 23867019.
^ "The clinical phase III programme commenced on zicronapine". January 20, 2011. Archived from the original on 2 February 2017. 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. Archived from the original on 8 October 2016. Retrieved 6 February 2014.
^ "Performance in 2014 positions Lundbeck well for 2015 and beyond" (PDF). February 5, 2015. Archived from the original (PDF) on 18 June 2015. Retrieved 18 June 2015.

External links

Media related to Zicronapine at Wikimedia Commons

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[pmid24062193-1] Citrome L (November 2013). "A review of the pharmacology, efficacy and tolerability of recently approved and upcoming oral antipsychotics: an evidence-based medicine approach". CNS Drugs. 27 (11): 879–911. doi: 10.1007/s40263-013-0105-7. PMID 24062193. S2CID 23867019.

[2] "The clinical phase III programme commenced on zicronapine". January 20, 2011. Archived from the original on 2 February 2017. Retrieved 6 February 2014.

[3] "Zicronapine shows significant positive data in clinical phase II in the treatment of patients with schizophrenia - planning for continued clinical work". December 18, 2009. Archived from the original on 8 October 2016. Retrieved 6 February 2014.

[4] "Performance in 2014 positions Lundbeck well for 2015 and beyond" (PDF). February 5, 2015. Archived from the original (PDF) on 18 June 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

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

References

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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^Y
CompTox Dashboard ( EPA)	DTXSID30168849
Chemical and physical data
Formula	C₂₂H₂₇ClN₂
Molar mass	354.92 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