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58-39-9 molecular structure
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2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol

ChemBase ID: 728
Molecular Formular: C21H26ClN3OS
Molecular Mass: 403.96864
Monoisotopic Mass: 403.14851115
SMILES and InChIs

SMILES:
Clc1cc2N(CCCN3CCN(CC3)CCO)c3c(Sc2cc1)cccc3
Canonical SMILES:
OCCN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(Cl)cc2
InChI:
InChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2
InChIKey:
RGCVKNLCSQQDEP-UHFFFAOYSA-N

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol
IUPAC Traditional name
perphenazine
Brand Name
Apo-Perphenazine
Decentan
Emesinal
Etrafon-A
Etrafon-Forte
F-Mon
Fentazin
Perphenan
Thilatazin
Trifaron
Trilafon
Trilifan
Triphenot
Synonyms
4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-(piperazine-d8)ethanol Dihydrochloride
1-(2-Hydroxyethyl)-4-[3-(2-chloro-10-phenothiazinyl)propyl]piperazine-d8-Dihydrochloride
Chloriprozine-d8
Chlorperphenazine-d8
Decentan-d8
Emesinal-d8
Etaperazin-d8
Perfenil-d8
Perphenan-d8
Perphenazin-d8
Sch 3940-d8
Thilatazin-d8
Perphenazine-d8 Dihydrochloride
2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol
PZC
Perphenazin
Perfenazine
Perfenazina
Chlorperphenazine
Etaperazin
Etaperazine
Ethaperazine
Perphenazine
Perphenazine
CAS Number
58-39-9
EC Number
200-381-5
MDL Number
MFCD00056798
PubChem SID
24278642
46507058
160964191
PubChem CID
4748
CHEBI ID
8028
ATC CODE
N05AB03
CHEMBL
567
Chemspider ID
4586
DrugBank ID
DB00850
IUPHAR ligand ID
209
KEGG ID
D00503
Unique Ingredient Identifier
FTA7XXY4EZ
Wikipedia Title
Perphenazine
Medline Plus
a682165

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 15.593098  H Acceptors
H Donor LogD (pH = 5.5) 1.0448196 
LogD (pH = 7.4) 2.8195775  Log P 3.6920178 
Molar Refractivity 116.0987 cm3 Polarizability 44.746113 Å3
Polar Surface Area 29.95 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.15  LOG S -4.23 
Solubility (Water) 2.37e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
28.3 mg/L expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
190-193°C expand Show data source
Hydrophobicity(logP)
3.807 expand Show data source
3.9 expand Show data source
Storage Condition
-20°C Freezer, Under Inert Atmosphere expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-43 expand Show data source
Safety Statements
28-36/37/39-45 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H317 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
oral and i.m. expand Show data source
Bioavailability
40% expand Show data source
Half Life
8-12 (up to 20) hours expand Show data source
Metabolism
hepatic expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
C (Australia) expand Show data source
C (US) expand Show data source
Gene Information
human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), ADRA2A(150), ADRA2B(151), ADRA2C(152), DRD2(1813), OPRS1(10280) expand Show data source
Purity
95% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00850 external link
Item Information
Drug Groups approved
Description An antipsychotic phenothiazine derivative with actions and uses similar to those of chlorpromazine. [PubChem]
Indication For use in the management of the manifestations of psychotic disorders and for the control of severe nausea and vomiting in adults.
Pharmacology Perphenazine is a piperazinyl phenothiazine, acts on the central nervous system, and has a greater behavioral potency than other phenothiazine derivatives whose side chains do not contain a piperazine moiety. It is a member of a class of drugs called phenothiazines, which are dopamine D1/D2 receptor antagonists. Perphenazine is 10 to 15 times as potent as chlorpromazine; that means perphenazine is a highly potent antipsychotic. In equivalent doses it has approximately the same frequency and severity of early and late extrapypramidal side-effects compared to Haloperidol.
Toxicity Symptoms of overdose include stupor or coma, and children may have convulsive seizures. Signs of arousal may not occur for 48 hours. Oral LD50=318 mg/kg (rat); IPR LD50=64 mg/kg (mouse)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption Absolute bioavailability is 40% following oral administration.
Half Life 8-12 hours, but ranges up to 20 hours.
Elimination Perphenazine is extensively metabolized in the liver to a number of metabolites by sulfoxidation, hydroxylation, dealkylation, and glucuronidation.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - P6402 external link
Biochem/physiol Actions
D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P6402.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - P291102 external link
Labelled Perphenazine. D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro. Antipsychotic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Gaertner, H.J., et al.: Drug Metab. Dispos., 3, 437 (1975)
  • • O Brien, S., et al.: J. Med. Chem., 48, 1287 (1975)
  • • Briggs, K., et al.: Toxicology, 231, 113 (1975)
  • • Toga, T., et al.: J. Pharmacol. Sci., 105, 207 (1975)
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PATENTS

PATENTS

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