Basic information
- CAS
85650-56-2- Standard SMILES
CN1C[C@@H]2c3ccccc3Oc3ccc(Cl)cc3[C@H]2C1.O=C(O)/C=C\C(=O)O- InChIKey
GMDCDXMAFMEDAG-CHHFXETESA-N- Molecular formula
- C21H20ClNO5
- Average molar mass
- 401.8 g/mol
- Monoisotopic mass
- 401.10300042
Overview
(S,S)-asenapine maleate is a maleate salt obtained by combining equimolar amounts of (S,S)-asenapine and maleic acid. It contains a (S,S)-asenapine(1+). It is an enantiomer of a (R,R)-asenapine maleate.
Names & identifiers
- Preferred name
- Asenapine Maleate
- IUPAC
- (Z)-but-2-enedioic acid;(2S,6S)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene
- English name
- Asenapine Maleate
- Molecular formula
- C17H16ClNO.C4H4O4
- Molecular weight
- 401.84
Names & synonyms
Asenapine maleate85650-56-2SaphrisOrg-5222Org 5222Asenapine (as maleate)CU9463U2E2DTXSID301017360trans-5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole maleateRefChem:56546CHEBI:71245DTXCID401475569
Show more names
NSC62790NSC 62790NSC-62790Asenne maleateUnii-cu9463U2E2Org5222 MaleateSaphris MaleateOrg-5222 MaleateOrg 5222 Maleate
5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3-6,7)oxepino(4,5-c)pyrrole1H-Dibenz(2,3:6,7)oxepino(4,5-c)pyrrole, 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-,(3aR,12bR)-rel-, (2Z)-2-butenedioate (1:1)288-064-8Asenapine (maleate)(S,S)-Asenapine MaleateAsenapine maleate [USAN]MFCD00900588(Z)-but-2-enedioic acid;(2S,6S)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene
Database identifiers
- CAS
85650-56-2
Properties
Computed structural properties
- Topological polar surface area
- 87.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 482
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 141 · 141-145°
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: ≥10mg/mL
- pka
- 1 · pK1 <3, pK2 7.52, pK3 8.51(at 25℃)
- form
- powder
- color
- white to off-white
- Water Solubility
- 6.25 mg/mL · Water : 6.25 mg/mL (15.55 mM; Need ultrasonic and warming)
- InChIKey
- GMDCDXMAFMEDAG-CHHFXETESA-N
- SMILES
- C(/C(=O)O)=C/C(=O)O.CN1C[C@]2([H])C3C=CC=CC=3OC3C=CC(Cl)=CC=3[C@@]2([H])C1 |&1:11,27,r|
- FDA UNII
- 9463 U2E2 · CU9463U2E2
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (98.4%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 63 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (98.4%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29339900
- risk_code
- 22-36/37/38-50/53-39/23/24/25-23/24/25-11
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS09
- hazard_code
- Xn,N,T,F
- safety_code
- 26-60-61-45-36/37-16
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- target organs
- Respiratory system
- Hazard statements
- H301-H315-H319-H335-H400
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
ASENAPINE MALEATE
Atypical Antipsychotic [EPC]
MeSH Pharmacological Classification
Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.
Applications
DescriptionAsenapine, a dual antagonist of dopamine D2and serotonin 5-HT2receptors, was launched for the acute treatment of schizophreniaand manic or mixed episodes associated with bipolar I disorder in adults. Asenapine exhibits high affinity for serotonin 5-HT1A, 5-HT1B, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT5, 5-HT6, and 5-HT7 receptors (Ki = 2.5, 4.0, 0.06, 0.16, 0.03, 1.6, 0.25, and 0.13 nM, respectively); dopamine D1, D2, D3, and D4 receptors (Ki = 1.4, 0.42, 1.1, and 1.3 nM, respectively); a1- and a2-adrenergic receptors (Ki = 1.2 and 1.2 nM, respectively); and histamine H1 receptors (Ki = 1.0 nM), and moderate affinity for H2 receptors (Ki = 6.2 nM). In in vitro assays, asenapine acts as an antagonist at these receptors. Asenapine has no appreciable affinity for muscarinic cholinergic receptors (e.g., Ki = 8128 nM for M1). Despite its potent binding affinity for multiple receptors, the efficacy of asenapine in schizophrenia is thought to be primarily mediated through a combination of antagonist activity at D2 and 5-HT2A receptors.
UsesAsenapine maleate has been used as a stressor in studying the Fos expression in forebrain structures of rat models.
UsesAntipsychotic;serotonin 5-HT receptors
UsesAsenapine Maleate is a 5-HT receptor antagonist developed for the treatment of acute schizophrenia and bipolar mania.
Related reactions
2 records
Compound notes
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