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A7861

Sigma-Aldrich

Asenapine maleate

≥98% (HPLC)

Synonym(s):

(3aRS,12bRS)-5-Chloro-2-methyl-2,3,3a,12btetrahydro-1Hdibenzo[2,3:6,7]oxepino[4,5-c]pyrrole (2Z)-2-butenedioate, Org 5222, trans-5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole maleate

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About This Item

Empirical Formula (Hill Notation):
C17H16ClNO ·C4H4O4
CAS Number:
Molecular Weight:
401.84
EC Number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

H2O: ≥10 mg/mL

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

storage temp.

2-8°C

SMILES string

OC(=O)\C=C/C(O)=O.CN1C[C@H]2[C@H](C1)c3cc(Cl)ccc3Oc4ccccc24

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

InChI key

GMDCDXMAFMEDAG-CHHFXETESA-N

General description

Asenapine maleate acts as an antimanic. It belongs to the family of dibenzoxepinopyrrolidines. Asenapine is considered to be a weak inhibitor of cytochrome P450 2D6 (CYP2D6). It increases the level of dopamine, norepinephrine and acetylcholine in brain.

Application

Asenapine maleate has been used as a stressor in studying the Fos expression in forebrain structures of rat models.
Asenapine maleate is a serotonin 5-HT and dopamine D2 receptor antagonist. Asenapine maleate can be used to treat schizophrenia and bipolar mania.

Biochem/physiol Actions

Asenapine maleate is a 5-HT receptor antagonist (5-HT1A,1B, 5-HT2A, 2B, 2C, 5-HT5A, 5-HT6 and 5-HT7), a D2 antagonist, and an antipsychotic.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Masayo Ohyama et al.
Acta neuropsychiatrica, 28(6), 327-336 (2016-11-03)
Asenapine is an atypical antipsychotic that is currently available for the treatment of schizophrenia and bipolar I disorder. Although the atypical antipsychotics clozapine and olanzapine are effective for depression and anxiety in schizophrenia, as demonstrated by animal model studies, this
Asenapine: a clinical review of a second-generation antipsychotic
Stoner SC and Pace HA
Clinical Therapeutics, 34(5), 1023-1040 (2012)
Ahmed A Abu-Hassan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 239, 118474-118474 (2020-05-26)
Asenapine maleate was approved by the FDA for the treatment of schizophrenia and mania or mixed episodes with bipolar I disorder. In the present article, two spectroscopic methods were developed and validated for the determination of asenapine. Both methods depend
Maddalena D Caiati et al.
Frontiers in cellular neuroscience, 7, 63-63 (2013-05-04)
Fluoxetine (Prozac), an antidepressant known to selectively inhibit serotonin reuptake, is widely used to treat mood disorders in women suffering from depression during pregnancy and postpartum period. Several lines of evidence suggest that this drug, which crosses the human placenta
Asenapine maleate: a new drug for the treatment of schizophrenia and bipolar mania.
Tarazi FI and Shahid M
Drugs Today (Barc), 45(12), 865-876 (2009)

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