EFLUCIMIBE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H43NO2S
Molecular Weight	469.722
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCS[C@H](C(=O)NC1=CC(C)=C(O)C(C)=C1C)C2=CC=CC=C2

InChI

InChIKey=ZXEIEKDGPVTZLD-NDEPHWFRSA-N

InChI=1S/C29H43NO2S/c1-5-6-7-8-9-10-11-12-13-17-20-33-28(25-18-15-14-16-19-25)29(32)30-26-21-22(2)27(31)24(4)23(26)3/h14-16,18-19,21,28,31H,5-13,17,20H2,1-4H3,(H,30,32)/t28-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H43NO2S
Molecular Weight	469.722
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18466422
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/11137714 | https://www.ncbi.nlm.nih.gov/pubmed/12735237 | http://adisinsight.springer.com/drugs/800011031

Eflucimibe is a new and potent Acyl coenzyme A:cholesterol acyltransferases inhibitor. Eflucimibe effectively decreased plasma cholesterol in cholesterol-fed animals. In animal models, drug restores normolipodemia in endogenous hypercholesterolemic rabbits and prevents the progression of atherosclerosis by decreasing the number of macrophages in the foam cells. Eflucimibe has been in phase II clinical trials for the treatment of atherosclerosis and hyperlipidemia. However, this research has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acyl coenzyme A:cholesterol acyltransferase 1 15 Target ID: CHEMBL2782 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18466422	Inhibitor 8297		39.0 nM [IC50]
Acyl coenzyme A:cholesterol acyltransferase 2 4 Target ID: CHEMBL4465 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18466422	Inhibitor 8297		110.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18466422 https://www.ncbi.nlm.nih.gov/pubmed/11791003	Primary		Phase II 1132	Unknown Approved Use Unknown
Hyperlipidemia 80 Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/56ae29d4498e449970c307bd958b128b.html	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
MuseChem	I006627	https://www.musechem.com/product/I006627.html

PubMed

Title	Date	PubMed
Lack of toxic effects of F 12511, a novel potent inhibitor of acyl-coenzyme A: cholesterol O-acyltransferase, on human adrenocortical cells in culture.	2001 Feb 15	11226372

Patents

Sample Use Guides

In Vivo Use Guide

Rabbit: 8 mg/kg per day (during 24 weeks)

Route of Administration: Oral

In Vitro Use Guide

The addition of increasing concentrations of F12511 (10 to 10 mol/L) failed to modify the level of eNOS protein expressed in control bovine aortic endothelial cells (BAEC). F12511 (10 mol/L) failed to modify the expression of CD40L and PECAM in control and TNF-alpha-incubated BAEC.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:06:09 GMT 2023` Edited by `admin` on `Fri Dec 15 16:06:09 GMT 2023`
Record UNII	3DK1X2C37M
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EFLUCIMIBE

Official Name

English

F-12511

Code

English

(S)-2-(DODECYLTHIO)-4'-HYDROXY-2',3',5'-TRIMETHYL-2-PHENYLACETANILIDE

Systematic Name

English

eflucimibe [INN]

Common Name

English

(S)-2',3',5'-TRIMETHYL-4'-HYDROXY-.ALPHA.-DODECYLTHIOACETANILIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29703