Basic information
- CAS
26615-21-4- Standard SMILES
CN(C)CCOC1=Cc2ccccc2Sc2ccc(Cl)cc21- InChIKey
HDOZVRUNCMBHFH-UHFFFAOYSA-N- Molecular formula
- C18H18ClNOS
- Average molar mass
- 331.9 g/mol
- Monoisotopic mass
- 331.0797631
Overview
Zotepine is a dibenzothiepine and a tertiary amino compound. It has a role as a serotonergic drug, an alpha-adrenergic drug and a second generation antipsychotic.
Names & identifiers
- Preferred name
- Zotepine
- IUPAC
- 2-(3-chlorobenzo[b][1]benzothiepin-5-yl)oxy-N,N-dimethylethanamine
- English name
- ZOTEPINE
- Molecular formula
- C18H18ClNOS
- Molecular weight
- 331.86
Names & synonyms
zotepine26615-21-4NipoleptLodopinZotepinaSetousZotepinumZotepinDTXSID90237562-[(8-chlorodibenzo[b,f]thiepin-10-yl)oxy]-N,N-dimethylethanamine2-Chloro-11-(2-(dimethylamino)ethoxy)dibenzo(b,f)thiepinU29O83JAZW
Show more names
(ring-dMajorpinEtoxazole Impurity 9Zotepine, 10 mM in DMSO8-Chloro-10-[2-(dimethylamino)ethoxy]dibenzo[b,f]thiepinf)thiepin,2-chloro-11-(2-(dimethylamino)ethoxy)-dibenzo(
DTXCID603756CHEBI:323162-((8-Chlorodibenzo(b,f)thiepin-10-yl)oxy)-N,N-dimethylethanamine2-(8-chlorobenzo(b)(1)benzothiepin-6-yl)oxy-N,N-dimethylethanamine2-(8-chlorobenzo[b][1]benzothiepin-6-yl)oxy-N,N-dimethylethanamineZoleptil 25Zoleptil 50Zoleptil 100
Database identifiers
- CAS
26615-21-4- PubChem CID
- 5736
- DTXSID
DTXSID9023756- ChEMBL
CHEMBL285802
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 37.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 401
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
SolubilityPoorly soluble
Boiling Point478.4ºC
Melting Point90ºC
Physicochemical properties
- Melting point
- 90 · 90-91°
- Boiling point
- 478.4 · 478.4±45.0 °C(Predicted)
- Density
- 1.0675 · 1.0675 (rough estimate)
- refractive index
- 1.61 · 1.6100 (estimate)
- storage temp.
- Store at RT
- solubility
- 20 mg/mL · DMSO: ≥20mg/mL
- form
- powder
- pka
- 8.72 · 8.72±0.28(Predicted)
- color
- white to off-white
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
Hazard information
Hazard Classes and Categories
Acute Tox. 4 (100%)
Reproductive toxicity - Category 2, Additional category: Effects on or via lactation
Safety data
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- Toxicity
- LD50 in male mice, rats (mg/kg): 108, 458 orally; 43.3, 39.7 i.v.; 40.0, 97.0 i.p.; 84.9, 2080 s.c. (Fukuhara)
- risk_code
- 25-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS09
- hazard_code
- T
- safety_code
- 45-60-61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H301-H410
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
- Precautionary statements
- P264-P270-P273-P301+P310-P391-P405
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Protein BindingPlasma protein binding of zotepine and its major active metabolite norzotepine account for 97% of the administered dose.
Pharmacodynamics
In preclinical studies, zotepine is characterized by the presence of a strong antiserotonergic activity when compared with other neuroleptic drugs. It has also been reported to present elevations in the seizure threshold in the amygdaloid nucleus. When zotepine's effects were analyzed by electroencephalography, it was noted a typical response of a low-potency neuroleptics of the sedative type. Administration of zotepine has shown improvements in numerical movements and complex reaction. These effects tend to be accompanied by increases in pulse rate, increase in prolactin levels and some typical neuroleptic side effects.
Mechanism of Action
Zotepine is a dopamine antagonist that has a high affinity for D1- and D2-like receptors. It presents a strong antagonism for several serotonin receptors, such as 5-HT2a, 5-HT2c, 5-HT6 and 5-HT7. Zotepine activities are also related to the inhibition of noradrenaline reuptake and serotonergic activity. All these effects allow zotepine to improve the negative and cognitive symptoms of schizophrenia.
Biological Half-LifeThe half-life of zotepine is reported to be of 21 hours.
Metabolism/Metabolites
Zotepine is well metabolized in the body, it actually undergoes extensive first-pass metabolism to the metabolite norzotepine and several inactive metabolites. The main enzymes involved in zotepine metabolism are CYP1A2 and CYP3A4. Some of the main metabolic pathways include N-demethylation and oxygenation of N or S atoms, hydroxylation of the aromatic ring and consecutive conjugation.
Zotepine has known human metabolites that include 2-hydroxy-zotepine, Norzotepine, Zotepine -oxide, 3-hydroxy-zotepine, and Zotepine N-oxide.
MeSH Pharmacological Classification
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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