trans-5-Chlor-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol
5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate
Grundinformationen
- CAS
65576-45-6- Standard-SMILES
CN1CC2c3ccccc3Oc3ccc(Cl)cc3C2C1.O=C(O)/C=C\C(=O)O- InChIKey
GMDCDXMAFMEDAG-BTJKTKAUSA-N- Summenformel
- C21H20ClNO5
- Durchschnittliche Molmasse
- 401,8 g/mol
- Monoisotopische Masse
- 401,1030004
Überblick
Developed by Schering-Plough after its merger with Organon International, asenapine is a sublingually administered, atypical antipsychotic for treatment of schizophrenia and acute mania associated with bipolar disorder. Asenapine also belongs to the dibenzo-oxepino pyrrole class. It is also for severe post-traumatic stress disorder nightmares in soldiers as an off-label use. FDA approved on August 13, 2009.
Namen und Bezeichner
- Bevorzugter Name
- 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate
- IUPAC
- (Z)-but-2-enedioic acid;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
- Lokaler Name
- trans-5-Chlor-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol
- Englischer Name
- Asenapine
- Summenformel
- C17H16ClNO
- Molmasse
- 285.77
Namen und Synonyme
SCHEMBL6029138CHEMBL3544974SCHEMBL29374126GMDCDXMAFMEDAG-BTJKTKAUSA-NHMS5079P05EBC-26957DB06216EN300-16929915-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate(2Z)-but-2-enedioic acid; 9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),7(12),8,10,15,17-hexaeneSaphrisAsenapine Impurity 2
Weitere Namen anzeigen
HSDB8061AsenapineHSDB 8061HSDB-8061(±)-AsenapineUnii-jkz19V908oEinecs 265-829-4Asenapine [inn:ban]
Datenbank-Bezeichner
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 87,1 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 482
Physikochemische Eigenschaften
- Siedepunkt
- 357.9 · 357.9±42.0 °C(Predicted)
- Dichte
- 1.231 · 1.231
- storage temp.
- 4 °C · Store at +4°C
- Löslichkeit
- 50 · DMSO:50.0(Max Conc. mg/mL);174.97(Max Conc. mM)
- Aggregatzustand
- A solid
- pka
- 9.5 · 9.50±0.20(Predicted)
- Farbe
- White to off-white
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- Giftige Stoffe Daten
- 65576-45-6(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Protein Binding95% protein bound
Pharmacodynamics
Asenapine is a serotonin, dopamine, noradrenaline, and histamine antagonist in which asenapine possess more potent activity with serotonin receptors than dopamine. Sedation in patients is associated with asenapine's antagonist activity at histamine receptors. Its lower incidence of extrapyramidal effects are associated with the upregulation of D1 receptors. This upregulation occurs due to asenapine's dose-dependent effects on glutamate transmission in the brain. It does not have any significant activity with muscarinic, cholinergic receptors therefore symptoms associated with anticholinergic drug activity like dry mouth or constipation are not expected to be observed. Asenapine has a higher affinity for all aforementioned receptors compared to first-generation and second-generation antipsychotics except for 5-HT1A and 5-HT1B receptors.
Mechanism of Action
Asenapine is an atypical antipsychotic multireceptor neuroleptic drug which shows strong 5HT2A (serotonin) and D2 (dopamine) receptor antagonism, which has been shown to enhance dopamine (DA) and acetylcholine (Ach) efflux in rat brains. Asenapine may improve cognitive function and negative symptoms in patients with schizophrenia.
Biological Half-Life24 hours (range of 13.4 - 39.2 hours)
Metabolism/MetabolitesAsenapine is oxidized via CYP1A2 and undergoes direct glucuronidation via UGT1A4. Oxidation via CYP1A2 is asenapine's primary mode of metabolism.
Absorption, Distribution and Excretion
Cmax, single 5 mg dose = 4 ng/mL (within 1 hour); Bioavailability, sublingual administration = 35%; Bioavailability, oral administration (swallowed) = <2%; Time to steady state, 5 mg = 3 days; Peak plasma concentration occurs within 0.5 to 1.5 hours. Doubling dose of asenapine results in 1.7-fold increase in maximum concentration and exposure. Drinking water within 2-5 minutes post administration of asenapine results in a decrease in exposure.
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