LAFLUNIMUS

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H13F3N2O2
Molecular Weight	310.2711
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(NC(=O)C(\C#N)=C(/O)C2CC2)=CC=C1C(F)(F)F

InChI

InChIKey=GDHFOVCRYCPOTK-QBFSEMIESA-N

InChI=1S/C15H13F3N2O2/c1-8-6-10(4-5-12(8)15(16,17)18)20-14(22)11(7-19)13(21)9-2-3-9/h4-6,9,21H,2-3H2,1H3,(H,20,22)/b13-11-

HIDE SMILES / InChI

Molecular Formula	C15H13F3N2O2
Molecular Weight	310.2711
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9223572 | https://www.ncbi.nlm.nih.gov/pubmed/12100469 | https://www.ncbi.nlm.nih.gov/pubmed/9802339

LAFLUNIMUS is an immunomodulator with anti-inflammatory activities. It inhibits prostaglandin endoperoxide H synthases 1 and 2 in vitro and in vivo. It also acts as an immunosuppressive agent being an inhibitor of mitochondrial dihydroorotate dehydrogenase and concomitant reducing agent of pyrimidine nucleotide pools.

Approval Year

PubMed

Title	Date	PubMed
In vitro and in Vivo inhibition of immunoglobulin secretion by the immunosuppressive compound HR325 is reversed by exogenous uridine.	2002-07	12100469
Species-related inhibition of human and rat dihydroorotate dehydrogenase by immunosuppressive isoxazol and cinchoninic acid derivatives.	1998-11-01	9802339
Structural and functional comparison of agents interfering with dihydroorotate, succinate and NADH oxidation of rat liver mitochondria.	1998-10-15	9776318
Immunosuppressant HR-325 attenuates progression of malignant arteritis in the kidney of Dahl salt-sensitive rats.	1997-06	9220272

Sample Use Guides

In Vitro Use Guide

LAFLUNIMUS (HR325) was a potent inhibitor of PGHS in guinea pig polymorphonuclear leukocytes (IC50 = 415 nM) and isolated ovine PGHS-1 (IC50 = 64 microM) and PGHS-2 (IC50 = 100 microM). In vivo, in rat carrageenan air pouch inflammation, HR325 at 25 mg/kg inhibited accumulation of leukocytes (48%) and prostaglandin E2 (PGE2) (61%). HR325 was also active against human peripheral blood mononuclear cell PGHS-1 [IC50 = 1.6 microM (thromboxane B2 production) or 1.1 microM (PGE2 production)] and lipopolysaccharide-induced PGHS-2 in human adherent peripheral blood mononuclear cells (IC50 = 435 nM) and peripheral blood polymorphonuclear leukocytes (IC50 = 91 nM microM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:04 GMT 2025`
Record UNII	44EH625IUS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAFLUNIMUS

Official Name

English

(Z).ALPHA.-CYANO-.ALPHA.(SUP 4'),.ALPHA.(SUP 4'),.ALPHA.(SUP 4')-TRIFLUORO-.BETA.-HYDROXYCYCLOPROPANEACRYLO-3',4'-XYLIDE

Preferred Name

English

laflunimus [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C574