ENPIROLINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H18F6N2O
Molecular Weight	404.3494
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H]([C@H]1CCCCN1)C2=CC(=NC(=C2)C3=CC=C(C=C3)C(F)(F)F)C(F)(F)F

InChI

InChIKey=OCVRKDMRZFCUEE-RHSMWYFYSA-N

InChI=1S/C19H18F6N2O/c20-18(21,22)13-6-4-11(5-7-13)15-9-12(10-16(27-15)19(23,24)25)17(28)14-3-1-2-8-26-14/h4-7,9-10,14,17,26,28H,1-3,8H2/t14-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H18F6N2O
Molecular Weight	404.3494
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22470113 | https://www.ncbi.nlm.nih.gov/pubmed/3277459 | https://www.ncbi.nlm.nih.gov/pubmed/6385737

Enpiroline (WR 180,409) is an antimalarial compound. It demonstrates activity against Plasmodium falciparum both in vitro and in non-immune infected subjects. Additionally, it exerts antischistosomal activity.

Approval Year

PubMed

Title	Date	PubMed
Antischistosomal activities of mefloquine-related arylmethanols.	2012-06	22470113
Evaluation of an in vitro assay system for drug susceptibility of field isolates of Plasmodium falciparum from southern Thailand.	1988-01	3277459
Evaluation of the 4-pyridinemethanol WR 180,409 (enpiroline) in the treatment of induced Plasmodium falciparum infections in healthy, non-immune subjects.	1984-09	6385737

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:42:24 GMT 2025` Edited by `admin` on `Wed Apr 02 09:42:24 GMT 2025`
Record UNII	8M7Y72EP9K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-(R*,R*)-.ALPHA.-((2-(TRIFLUOROMETHYL)-6-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-P-TOLYL)-4-PYRIDYL)-2-PIPERIDINEMETHANOL

Preferred Name

English

ENPIROLINE

Official Name

English

4-PYRIDINEMETHANOL, .ALPHA.-(2-PIPERIDINYL)-2-(TRIFLUOROMETHYL)-6-(4-(TRIFLUOROMETHYL)PHENYL)-, (R*,R*)-(±)-

Common Name

English

enpiroline [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C271