ICOFUNGIPEN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C7H11NO2
Molecular Weight	141.1677
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@H]1CC(=C)C[C@H]1C(O)=O

InChI

InChIKey=RKOUGZGFAYMUIO-RITPCOANSA-N

InChI=1S/C7H11NO2/c1-4-2-5(7(9)10)6(8)3-4/h5-6H,1-3,8H2,(H,9,10)/t5-,6+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C7H11NO2
Molecular Weight	141.1677
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/16940096 | https://www.ncbi.nlm.nih.gov/pubmed/16121691 | https://www.ncbi.nlm.nih.gov/pubmed/29562716

Icofungipen is a generic name of the compound, previously known as BAY 10-8888 or PLD-118. Icofungipen, a cyclic beta-amino acid was developed by PLIVA, under license from Bayer, for the potential oral treatment of fungal infection. The drug exerts its antifungal activity by inhibition of isoleucyl-tRNA synthetase activity and consequently disrupting protein biosynthesis. Phase II trials with an oral formulation of icofungipen were underway in Europe for Candida infection and for the treatment of vulvovaginal candidiasis in the USA, but these studies have been discontinued. In human toxicity studies, suppression of spermatogenesis in male volunteers was observed as a possible off-target adverse event.

Originator

Approval Year

PubMed

Title	Date	PubMed
Efficacy of PLD-118, a novel inhibitor of candida isoleucyl-tRNA synthetase, against experimental oropharyngeal and esophageal candidiasis caused by fluconazole-resistant C. albicans.	2004 Oct	15388459
Icofungipen (PLIVA).	2005 Aug	16121691
The novel antifungal agent PLD-118 is neither metabolized by liver microsomes nor inhibits cytochrome P450 in vitro.	2005 Jan	15593345
In vitro activity and in vivo efficacy of icofungipen (PLD-118), a novel oral antifungal agent, against the pathogenic yeast Candida albicans.	2006 Sep	16940096
LC-NMR and LC-MS identification of an impurity in a novel antifungal drug icofungipen.	2009 Aug 15	19410412

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:11 UTC 2023` Edited by `admin` on `Fri Dec 15 15:37:11 UTC 2023`
Record UNII	I20202Q8M8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ICOFUNGIPEN

Official Name

English

BAY-10-8888

Code

English

CYCLOPENTANECARBOXYLIC ACID, 2-AMINO-4-METHYLENE-, (1R-CIS)-

Systematic Name

English

icofungipen [INN]

Common Name

English

PLD-118

Code

English

(-)-BAY-10-8888

Code

English

(1R,2S)-2-AMINO-4-METHYLENECYCLOPENTANE-1-CARBOXYLIC ACID

Systematic Name

English

CYCLOPENTANECARBOXYLIC ACID, 2-AMINO-4-METHYLENE-, (1R,2S)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514