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Details

Stereochemistry RACEMIC
Molecular Formula C20H23Cl2N3O2
Molecular Weight 408.322
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PERACLOPONE

SMILES

OC(CO\N=C\C1=CC=C(Cl)C=C1)CN2CCN(CC2)C3=CC=CC=C3Cl

InChI

InChIKey=IAKCDZCRAWGHFD-YDZHTSKRSA-N
InChI=1S/C20H23Cl2N3O2/c21-17-7-5-16(6-8-17)13-23-27-15-18(26)14-24-9-11-25(12-10-24)20-4-2-1-3-19(20)22/h1-8,13,18,26H,9-12,14-15H2/b23-13+

HIDE SMILES / InChI

Molecular Formula C20H23Cl2N3O2
Molecular Weight 408.322
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Peraclopone is a hypolidemic drug. It is an inhibitor of 7-Dehydrocholesterol reductase. Peraclopone potently inhibits the final step in cholesterol biosynthesis. Feeding this agent to rats leads to a rapid replacement of membrane cholesterol with its immediate precursor 7-dehydrocholesterol, and a dramatic reduction in plasma sterol concentration. Peraclopone caused a dose-dependent decrease in cholesterol and a concomitant accumulation of provitamin D3 (7-dehydrocholesterol) in the skin, which is accompanied by an increase in the plasma level of 25-hydroxyvitamin D3. Treatment with peraclopone dramatically alters membrane sterol content in many membranes including the microvillus membrane of both the jejunum and ileum. In the jejunal microvillus membrane a major change in chemical composition occurred, presumably in response to the alteration in membrane sterol. The net result was a significant decline in both the static and dynamic component of membrane fluidity.

Approval Year

PubMed

PubMed

TitleDatePubMed
Lipid permeability of the intestinal microvillus membrane may be modulated by membrane fluidity in the rat.
1989-09-04
The increase in skin 7-dehydrocholesterol induced by an hypocholesterolemic agent is associated with elevated 25-hydroxyvitamin D3 plasma level.
1987-09

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Rats data
0.3 mg/kg or 5.0 mg/kg for 13 days
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:57:31 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:31 GMT 2025
Record UNII
231HZQ66PD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PERACLOPONE
INN  
INN  
Official Name English
BENZALDEHYDE, 4-CHLORO-, O-(3-(4-(2-CHLOROPHENYL)-1-PIPERAZINYL)-2-HYDROXYPROPYL)OXIME, (C(E))-
Preferred Name English
BENZALDEHYDE, 4-CHLORO-, O-(3-(4-(2-CHLOROPHENYL)-1-PIPERAZINYL)-2-HYDROXYPROPYL)OXIME, (E)-
Common Name English
peraclopone [INN]
Common Name English
BENZALDEHYDE, 4-CHLORO-, O-(3-(4-(2-CHLOROPHENYL)-1-PIPERAZINYL)-2-HYDROXYPROPYL)OXIME, (E)-(±)-
Common Name English
P-CHLOROBENZALDEHYDE (±)-(E)-O-(3-(4-(O-CHLOROPHENYL)-1-PIPERAZINYL)-2-HYDROXYPROPYL)OXIME
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29703
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL2107502
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
PRIMARY
SMS_ID
100000082540
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
PRIMARY
NCI_THESAURUS
C66348
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
PRIMARY
FDA UNII
231HZQ66PD
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
PRIMARY
EVMPD
SUB09710MIG
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
PRIMARY
PUBCHEM
9576876
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
PRIMARY
CAS
96164-19-1
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
PRIMARY
INN
5736
Created by admin on Mon Mar 31 17:57:31 GMT 2025 , Edited by admin on Mon Mar 31 17:57:31 GMT 2025
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY