N-Desmethylclozapine

HCID 135409468CAS 6104-71-8

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

N-DesmethylclozapineNorclozapine6104-71-8DesmethylclozapineNDMC8-chloro-11-(piperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine8-Chloro-11-(1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine1I9001LWY88-Chloro-11-(1-piperazinyl)-5H-dibenzo[b,E][1,4]diazepineDTXSID0042616CHEBI:640508-chloro-11-piperazin-1-yl-5H-dibenzo(B,E)(1,4)diazepine
Weitere Namen anzeigen
Norclozapine (ACP-104)NormethylclozapineClozapine EP IMpurity CClozapine Impurity C(EP)Norclozapine in methanolD8-N-Desmethyl Clozapine HCL
8-Chloro-11-piperazin-1-yl-5H-dibenzo[b,e][1,4]diazepine3-chloro-6-piperazin-1-yl-5H-benzo(c)(1,5)benzodiazepine3-chloro-6-piperazin-1-yl-5H-benzo[c][1,5]benzodiazepine8-chloro-11-(piperazin-1-yl)-5H-dibenzo(b,e)(1,4)diazepineRefChem:829786DTXCID8022616N-desmethyl clozapineDemethylclozapine

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

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Antipsychotics

Pharmaceuticals -> Metabolite of Clozapine

Dissociation Constants8.9
Collision Cross Section173.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

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)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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

Hazard Classes and CategoriesAcute Tox. 4 (95.1%)

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)

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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.

Metabolism/MetabolitesN-Desmethylclozapine has known human metabolites that include Desmethylclozapine N-glucuronide.
MeSH Pharmacological Classification · 1 Eintrag

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.

Tissue LocationsKidney
Cellular LocationsCytoplasm

Verwendung und Herstellung

Use ClassificationPharmaceuticals -> Transformation products

Anwendungen

VerwendenN-Desmethylclozapine has been used as standard to quantify the clozapine plasma levels in treatment-refractory Chinese schizophrenic patients.

Anbieter50 Anbieter

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

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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