기본 정보
- CAS
158018-50-9- 표준 SMILES
CN1CC2c3ccccc3Oc3ccc(Cl)cc3C2C1- InChIKey
VSWBSWWIRNCQIJ-UHFFFAOYSA-N- 분자식
- C17H16ClNO
- 평균 분자량
- 285.8 g/mol
- 단동위원소 질량
- 285.0920418
개요
5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole is an organic heterotetracyclic compound that is 2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole bearing methyl and chloro substituents at positions 2 and 5 respectively. It is an organochlorine compound, a cyclic ether, an organic heterotetracyclic compound and a tertiary amino compound.
이름 및 식별자
- 우선 이름
- 5-Chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo(2,3:6,7)oxepino(4,5-c)pyrrole
- IUPAC
- 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
이름 및 동의어
5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrroleCHEBI:712555-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo(2,3:6,7)oxepino(4,5-c)pyrrole5-Chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo(2,3:6,7)oxepino(4,5-c)pyrroleRefChem:302428cis-AsenapineAsenapine-d3158018-50-9SCHEMBL2221502CHEMBL3187365SCHEMBL29365680
이름 더 보기
SCHEMBL30413463SCHEMBL30544842BDBM84994DTXSID50860813VSWBSWWIRNCQIJ-UHFFFAOYSA-NFXB84372QCA62178CAS_163091
데이터베이스 식별자
- CAS
158018-50-9、65576-45-6- PubChem CID
- 9903970
- DTXSID
DTXSID50860813- ChEMBL
CHEMBL3187365- ChEBI
CHEBI:71255- Nikkaji
- J608.443E
물성
구조 계산 물성
- XLogP
- 3.8
- 극성 표면적
- 12.5 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 20
- 형식 전하
- 0
- 복잡도
- 363
화학 및 산업
약리 정보
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.
Urine (50%) and feces (50%)
20-25 L/kg
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