LUFIRONIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H19N3O4
Molecular Weight	281.3077
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COCCNC(=O)C1=CC(=NC=C1)C(=O)NCCOC

InChI

InChIKey=JUCNGMPTCXPMNB-UHFFFAOYSA-N

InChI=1S/C13H19N3O4/c1-19-7-5-15-12(17)10-3-4-14-11(9-10)13(18)16-6-8-20-2/h3-4,9H,5-8H2,1-2H3,(H,15,17)(H,16,18)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8589346 | https://www.ncbi.nlm.nih.gov/pubmed/1667666 | https://www.ncbi.nlm.nih.gov/pubmed/8666329 | https://adisinsight.springer.com/drugs/800003265

Lufironil (HOE 077) is an inhibitor of prolyl 4-hydroxylase. In preclinical studies, it prevented liver fibrosis by inhibiting not only the hydroxylation of proline but also the activation of Ito cells, which are considered the main collagen-producing cells, resulting in reduced expression of procollagen mRNA. Lufironil was being developed for the treatment of chronic liver diseases including alcoholic hepatitis and liver cirrhosis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prolyl 4-hydroxylase alpha-1 subunit 1 Target ID: CHEMBL3301 Sources: https://adisinsight.springer.com/drugs/800003265 \| DOI: 10.1016/S1357-2725(96)00121-5 \| https://www.researchgate.net/profile/Mahmoud_El-Ashmawy/publication/51200068_Current_progress_in_antifibrotics/links/544f358c0cf2bca5ce90cacb/Current-progress-in-antifibrotics.pdf	Inhibitor 8504

PubMed

Title	Date	PubMed
The prolyl 4-hydroxylase inhibitor HOE 077 prevents activation of Ito cells, reducing procollagen gene expression in rat liver fibrosis induced by choline-deficient L-amino acid-defined diet.	1996-04	8666329
New prolyl 4-hydroxylase inhibitor reduces procollagen gene expression and enzyme-altered lesions in rat liver cirrhosis.	1995	8589346
Beneficial effects of inhibitors of prolyl 4-hydroxylase in CCl4-induced fibrosis of the liver in rats.	1991	1667666

Patents

Name

Type

Language

HOE 077

Preferred Name

English

LUFIRONIL

Official Name

English

lufironil [INN]

Common Name

English

HOE-077

Code

English

2,4-PYRIDINEDICARBOXAMIDE,N,N'-BIS(2-METHOXYETHYL)-

Common Name

English

LUFIRONIL [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471