LONAPALENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H15ClO6
Molecular Weight	338.74
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C(OC(C)=O)=C2C=C(Cl)C=CC2=C1OC(C)=O

InChI

InChIKey=IFWMVQUGSGWCRP-UHFFFAOYSA-N

InChI=1S/C16H15ClO6/c1-8(18)22-13-11-6-5-10(17)7-12(11)14(23-9(2)19)16(21-4)15(13)20-3/h5-7H,1-4H3

HIDE SMILES / InChI

Molecular Formula	C16H15ClO6
Molecular Weight	338.74
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800003802 | https://www.ncbi.nlm.nih.gov/pubmed/2164070 | https://www.ncbi.nlm.nih.gov/pubmed/1409395 | https://www.ncbi.nlm.nih.gov/pubmed/2516737

Lonapalene (6-chloro-2,3-dimethoxynaphthalene-1,4-diol-diacetate; RS-43179) is a topically effective 5-lipoxygenase inhibitor. Lonapalene was shown to inhibit platelet cyclooxygenase. Lonapalene has been studied in the treatment of psoriasis. Development of lonapalene has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
In vitro inhibition of leukotriene B4 formation by exogeneous 5-lipoxygenase inhibitors is associated with enhanced generation of 15-hydroxy-eicosatetraenoic acid (15-HETE) by human neutrophils.	1988	2849922

Sample Use Guides

In Vivo Use Guide

The pharmacologic and clinical effects of the 5-lipoxygenase inhibitor, lonapalene, have been determined in a double-blind, placebo-controlled, topical study in ten volunteers with psoriasis. A statistically significant clinical improvement was seen in lesions treated with 2% lonapalene ointment as compared with vehicle-treated sites.

Route of Administration: Transdermal

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:33:08 UTC 2023` Edited by `admin` on `Fri Dec 15 15:33:08 UTC 2023`
Record UNII	WIF31Q54NJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LONAPALENE

Official Name

English

LONAPALENE [MART.]

Common Name

English

lonapalene [INN]

Common Name

English

RS-43179

Code

English

6-Chloro-2,3-dimethoxy-1,4-naphthalenediol diacetate

Systematic Name

English

LONAPALENE [MI]

Common Name

English

LONAPALENE [USAN]

Common Name

English

1,4-NAPHTHALENEDIOL, 6-CHLORO-2,3-DIMETHOXY-, DIACETATE

Systematic Name

English

Code System Code Type Description

PUBCHEM

56237