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Details

Stereochemistry ACHIRAL
Molecular Formula C23H15F2NO2
Molecular Weight 375.3675
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BREQUINAR

SMILES

CC1=C(N=C2C=CC(F)=CC2=C1C(O)=O)C3=CC=C(C=C3)C4=C(F)C=CC=C4

InChI

InChIKey=PHEZJEYUWHETKO-UHFFFAOYSA-N
InChI=1S/C23H15F2NO2/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12H,1H3,(H,27,28)

HIDE SMILES / InChI

Molecular Formula C23H15F2NO2
Molecular Weight 375.3675
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Brequinar is a synthetic quinolinecarboxylic acid analogue with antineoplastic properties. Brequinar inhibits the enzyme dihydroorotate dehydrogenase, thereby blocking de novo pyrimidine biosynthesis. This agent may also enhance the in vivo antitumor effect of antineoplastic agents such as 5-FU. Brequinar had been in phase II clinical trials by Bristol-Myers Squibb for the treatment of cancer and transplant rejection. However, this research has been discontinued. Brequinar had been also in preclinical studys for the treatment of cytomegalovirus infections. However, this research has been discontinued.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
10.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Advanced melanoma: Brequinar was given at a median weekly dose of 1200 mg/m2 intravenously.
Route of Administration: Intravenous
In Vitro Use Guide
10 uM of brequinar sodium completely inhibited the dihydroorotate-induced oxygen consumption of rat liver mitochondria.
Substance Class Chemical
Record UNII
5XL19F49H6
Record Status Validated (UNII)
Record Version