BREQUINAR

Investigational

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 Search

SMILES

CC1=C(N=C2C=CC(F)=CC2=C1C(O)=O)C3=CC=C(C=C3)C4=CC=CC=C4F

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

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

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=40886 | http://en.pharmacodia.com/yaodu/html/v1/chemicals/27908be590d3ec381df976ecbf65df81.html | https://www.ncbi.nlm.nih.gov/pubmed/8623481

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 Target	Pharmacology	Condition	Potency
Dihydroorotate dehydrogenase 10 Target ID: CHEMBL1966 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9802339 \| https://www.ncbi.nlm.nih.gov/pubmed/26079043 \| https://www.ncbi.nlm.nih.gov/pubmed/8687451	Inhibitor 8504		10.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Advanced melanoma 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1450049	Primary	Phase II 1147	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2306795 https://www.ncbi.nlm.nih.gov/pubmed/9740540	Primary	Phase II 1147	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8256771	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
30.6 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8499153	170 mg/m² single, intravenous dose: 170 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BREQUINAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
54 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8499153	170 mg/m² single, intravenous dose: 170 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BREQUINAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8499153	170 mg/m² single, intravenous dose: 170 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BREQUINAR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7987984			BREQUINAR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2600 mg/m2 1 times / week multiple, intravenous Highest studied dose Dose: 2600 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2600 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/2591433	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2591433	DLT: Thrombocytopenia, Leucopenia... Disc. AE: Anemia... Other AEs: Stomatitis... Dose limiting toxicities: Thrombocytopenia (grade 4, 100%) Leucopenia (grade 2, 100%) AEs leading to discontinuation/dose reduction: Anemia (grade 1, 100%) Other AEs: Stomatitis (grade 3, 100%) Sources: https://pubmed.ncbi.nlm.nih.gov/2591433
210 mg/m2 1 times / day multiple, intravenous MTD Dose: 210 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 210 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8499153	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8499153	DLT: Thrombocytopenia, Thrombocytopenia... Dose limiting toxicities: Thrombocytopenia (grade 3, 40%) Thrombocytopenia (grade 4, 20%) Sources: https://pubmed.ncbi.nlm.nih.gov/8499153
2300 mg/m2 1 times / week multiple, intravenous MTD Dose: 2300 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2300 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/2591433	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2591433	DLT: Skin eruption, Maculopapular rash... Other AEs: Thrombocytopenia... Dose limiting toxicities: Skin eruption (grade 3, 33.3%) Maculopapular rash (grade 3, 33.3%) Mucositis (grade 3, 33.3%) Other AEs: Thrombocytopenia (grade 3, 66.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/2591433
600 mg/m2 2 times / week multiple, intravenous MTD Dose: 600 mg/m2, 2 times / week Route: intravenous Route: multiple Dose: 600 mg/m2, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/2591433	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2591433	Other AEs: Thrombocytopenia, Leucopenia... Other AEs: Thrombocytopenia (grade 4, 50%) Leucopenia (grade 2, 25%) Anemia (grade 3, 25%) Stomatitis (grade 3, 25%) Sources: https://pubmed.ncbi.nlm.nih.gov/2591433
850 mg/m2 2 times / week multiple, intravenous MTD Dose: 850 mg/m2, 2 times / week Route: intravenous Route: multiple Dose: 850 mg/m2, 2 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/2591433	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2591433	Other AEs: Thrombocytopenia, Stomatitis... Other AEs: Thrombocytopenia (grade 3, 25%) Stomatitis (grade 3, 25%) Sources: https://pubmed.ncbi.nlm.nih.gov/2591433
350 mg/m2 1 times / day multiple, intravenous Studied dose Dose: 350 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 350 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8499153	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8499153	Sources: https://pubmed.ncbi.nlm.nih.gov/8499153

AEs

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY113766	https://www.001chemical.com/chem/search?q=DY113766
1PlusChem LLC	1P006SVQ	https://www.1pchem.com/search?query=1P006SVQ
A2B Chem	AD16566	http://a2bchem.com/prod/AD16566
A2B Chem	AI68899	http://a2bchem.com/prod/AI68899
AA Blocks	AA006SCA	http://aablocks.com/goods/Goods/detail?id=AA006SCA
Achemo Scientific Limited	AC-89615	http://www.achemo.com/search/?Keyword=AC-89615
AK Scientific	X5917	https://aksci.com/item_detail.php?cat=X5917
Alfa Chemistry	278939	http://www.alfa-chemistry.com/search.aspx?q=278939
Alfa Chemistry	ACM96201886	http://www.alfa-chemistry.com/search.aspx?q=ACM96201886
Ambeed	A155500	http://www.ambeed.com/search/Search.html?keyword=A155500
Ambeed	A207630	http://www.ambeed.com/search/Search.html?keyword=A207630
AstaTech	F52273	http://astatechinc.com/CPSResult.php?CRNO=F52273
BLD Pharm	BD116738	http://www.bldpharm.com/search/Search.html?keyword=BD116738
BLD Pharm	BD118679	http://www.bldpharm.com/search/Search.html?keyword=BD118679
BOC Sciences	96187-53-0	http://www.bocsci.com/description.asp?cas=96187-53-0
BOC Sciences	96201-88-6	http://www.bocsci.com/description.asp?cas=96201-88-6
Chem Scene	CS-7842	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7842
ChemShuttle	101293	https://www.chemshuttle.com/catalogsearch/result/?q=101293
Combi-Blocks	QN-0134	http://www.combi-blocks.com/cgi-bin/find.cgi?QN-0134
Debye Scientific	DB-080409	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-080409
eMolecules	300620155	https://orderbb.emolecules.com/search/#?query=300620155
eMolecules	43451776	https://orderbb.emolecules.com/search/#?query=43451776
eMolecules	44786255	https://orderbb.emolecules.com/search/#?query=44786255
Enamine	EN300-263943	https://www.enaminestore.com/catalog/EN300-263943
eNovation Chemicals	D621765	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D621765&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals	D759561	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D759561&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A1515	http://www.excenen.com/searchresultlist.php?id=EX-A1515
Fluorochem	80292	http://www.fluorochem.co.uk/Products/Product?code=080292
Fluoropharm	YF10042	http://www.fluoropharm.com/product/YF10042.html
KeyOrganics	AS-74463	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-74463
KeyOrganics	DS-15411	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-15411
Lab Network	LN00191481	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00191481
Lab Network	LN03271013	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN03271013
Lab Seeker	SC-55381	http://www.labseeker.com/search.php?keywords=SC-55381&category=0
Matrix Scientific	93124	http://www.matrixscientific.com/093124.html
mcule	MCULE-7590091357	https://mcule.com/MCULE-7590091357/
mcule	MCULE-7868113779	https://mcule.com/MCULE-7868113779/
MedChem Express	HY-108325	https://www.medchemexpress.com/search.html?q=HY-108325&ft=&fa=&fp=
Molcore	MC113766	http://www.molcore.com/CatMC113766.html
MolPort	MolPort-006-169-119	https://www.molport.com/shop/molecule-link/MolPort-006-169-119
MolPort	MolPort-028-720-353	https://www.molport.com/shop/molecule-link/MolPort-028-720-353
MuseChem	M008880	https://www.musechem.com/product/M008880.html
ShangHai Biochempartner	BCP06006	http://www.biochempartner.com/search_BCP06006
TargetMol	T5013	https://www.targetmol.com/search?keyword=T5013

PubMed

Title	Date	PubMed
Immunosuppressive drugs: the first 50 years and a glance forward.	2000-05	10878284
Structural and functional comparison of agents interfering with dihydroorotate, succinate and NADH oxidation of rat liver mitochondria.	1998-10-15	9776318
Phase I clinical and pharmacokinetic trial of Brequinar sodium (DuP 785; NSC 368390).	1989-08-15	2743343

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 Created by `admin` on `Wed Apr 02 08:28:51 GMT 2025` Edited by `admin` on `Wed Apr 02 08:28:51 GMT 2025`
Record UNII	5XL19F49H6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BREQUINAR

Official Name

English

BREQUINAR [MI]

Preferred Name

English

4-QUINOLINECARBOXYLIC ACID, 6-FLUORO-2-(2'-FLUORO(1,1'-BIPHENYL)-4-YL)-3-METHYL-

Common Name

English

Brequinar [WHO-DD]

Common Name

English

brequinar [INN]

Common Name

English

6-FLUORO-2-(2'-FLUORO-4-BIPHENYLYL)-3-METHYL-4-QUINOLINECARBOXYLATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557