Grundinformationen
- Standard-SMILES
Clc1ccc2c(c1)N=C(N1CCNCC1)c1ccccc1N2- InChIKey
JNNOSTQEZICQQP-UHFFFAOYSA-N- Summenformel
- C17H17ClN4
- Durchschnittliche Molmasse
- 312,8 g/mol
- Monoisotopische Masse
- 312,11417422
Überblick
N-desmethylclozapine is a dibenzodoazepine substituted with chloro and piperazino groups which is a major metabolite of clozapine; a potent and selective 5-HT2C serotonin receptor antagonist. It has a role as a metabolite, a serotonergic antagonist and a delta-opioid receptor agonist. It is a member of piperazines, an organochlorine compound and a dibenzodiazepine.
Namen und Bezeichner
- Bevorzugter Name
- N-Desmethylclozapine
- IUPAC
- 3-chloro-6-piperazin-1-yl-11H-benzo[b][1,4]benzodiazepine
- Englischer Name
- N-Desmethylclozapine
- Summenformel
- C17H17ClN4
- Molmasse
- 312.8
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
6104-71-8- PubChem CID
- 135409468
- DTXSID
DTXSID0042616- ChEMBL
CHEMBL845- ChEBI
CHEBI:64050- UNII
- 1I9001LWY8
- EC Number
- 636-421-7
- Nikkaji
- J3.754.591K、J446.142H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,6
- Polarare Oberfläche (TPSA)
- 39,7 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 421
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Antipsychotics
Pharmaceuticals -> Metabolite of Clozapine
Physikochemische Eigenschaften
- Schmelzpunkt
- 120 · 120-125°C
- Siedepunkt
- 502.6 · 502.6±60.0 °C(Predicted)
- Dichte
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- Flammpunkt
- 9 ℃ · 9℃
- storage temp.
- Store at RT
- Löslichkeit
- Chloroform (Slightly), DMSO, Methanol (Slightly)
- Aggregatzustand
- Yellow solid.
- pka
- 8.49 · 8.49±0.10(Predicted)
- Farbe
- Light Yellow to Yellow
- InChI
- 1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19-20H,7-10H2
- InChIKey
- JNNOSTQEZICQQP-UHFFFAOYSA-N
- SMILES
- Clc1ccc2Nc3ccccc3C(=Nc2c1)N4CCNCC4
- CAS Datenbank
- 6104 · 6104-71-8(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (95.1%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Sicherheitsdaten
- wgk
- 3
- ridadr
- 3249
- risk_code
- 20/22-36/37/38-39/23/24/25-23/24/25-11
- hazard_code
- Xn,T,F
- safety_code
- 22-36-45-36/37-16-7
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
ACP-104 is a small molecule drug candidate we are developing as a novel therapy for schizophrenia. It is known that large amounts of ACP-104, or N-desmethylclozapine, are formed in the body after administration of clozapine. That is, clozapine is metabolized to ACP-104. We discovered that ACP-104 has a unique ability to stimulate m1 muscarinic receptors, a key muscarinic receptor. The m1 muscarinic receptors are widely known to play an important role in cognition. Since clozapine itself blocks the m1 muscarinic receptor, patients need to extensively metabolize clozapine into ACP-104 to stimulate this receptor and thereby overcome the blocking action of clozapine. Administration of ACP-104 will avoid the variability of this metabolic process and the competing action of clozapine. Like clozapine, ACP-104 is a dopamine antagonist and a 5-HT2A inverse agonist. We believe that ACP-104 represents a new approach to schizophrenia therapy that combines an atypical antipsychotic efficacy profile with the added advantage of beneficial cognitive effects.
Mechanism of Action
ACP-104 combines M1 muscarinic agonism, 5-HT2A inverse agonism, and D2 and D3 dopamine partial agonism in a single compound. ACP-104 uniquely stimulates brain cells known as M1 muscarinic receptors that play an important role in cognition. ACP-104 is a partial-agonist that causes weak activation of dopamine D2 and D3 receptors. These partial agonist properties of ACP-104 may lead to less motoric side effects than seen with most other antipsychotic drugs.
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.
Verwendung und Herstellung
Anwendungen
VerwendenN-Desmethylclozapine has been used as standard to quantify the clozapine plasma levels in treatment-refractory Chinese schizophrenic patients.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A dibenzodoazepine substituted with chloro and piperazino groups which is a major metabolite of clozapine; a potent and selective 5-HT2C serotonin receptor antagonist.
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