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Details

Stereochemistry ACHIRAL
Molecular Formula C23H14F2NO2.Na
Molecular Weight 397.3493
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BREQUINAR SODIUM

SMILES

[Na+].CC1=C(N=C2C=CC(F)=CC2=C1C([O-])=O)C3=CC=C(C=C3)C4=CC=CC=C4F

InChI

InChIKey=PZOHOALJQOFNTB-UHFFFAOYSA-M
InChI=1S/C23H15F2NO2.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H14F2NO2
Molecular Weight 374.3596
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
30.6 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
54 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.1 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
BREQUINAR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
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:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
DLT: Thrombocytopenia, Thrombocytopenia...
Dose limiting toxicities:
Thrombocytopenia (grade 3, 40%)
Thrombocytopenia (grade 4, 20%)
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
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:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Thrombocytopenia, Leucopenia...
Other AEs:
Thrombocytopenia (grade 4, 50%)
Leucopenia (grade 2, 25%)
Anemia (grade 3, 25%)
Stomatitis (grade 3, 25%)
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Thrombocytopenia, Stomatitis...
Other AEs:
Thrombocytopenia (grade 3, 25%)
Stomatitis (grade 3, 25%)
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
AEs

AEs

AESignificanceDosePopulation
Anemia grade 1, 100%
Disc. AE
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Leucopenia grade 2, 100%
DLT, Disc. AE
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Stomatitis grade 3, 100%
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Thrombocytopenia grade 4, 100%
DLT, Disc. AE
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Thrombocytopenia grade 3, 40%
DLT
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Thrombocytopenia grade 4, 20%
DLT
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Maculopapular rash grade 3, 33.3%
DLT, Disc. AE
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Mucositis grade 3, 33.3%
DLT, Disc. AE
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Skin eruption grade 3, 33.3%
DLT, Disc. AE
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Thrombocytopenia grade 3, 66.7%
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Leucopenia grade 2, 25%
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Anemia grade 3, 25%
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Stomatitis grade 3, 25%
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Thrombocytopenia grade 4, 50%
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Stomatitis grade 3, 25%
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Thrombocytopenia grade 3, 25%
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

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

Patents

Sample Use Guides

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 Mon Mar 31 18:01:01 GMT 2025
Edited
by admin
on Mon Mar 31 18:01:01 GMT 2025
Record UNII
49EEF6HRUS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BREQUINAR SODIUM
MART.   USAN   WHO-DD  
USAN  
Official Name English
BREQUINAR SODIUM SALT
MI  
Preferred Name English
BREQUINAR SODIUM [USAN]
Common Name English
4-QUINOLINECARBOXYLIC ACID, 6-FLUORO-2-(2'-FLUORO(1,1'-BIPHENYL)-4-YL)-3-METHYL-, SODIUM SALT
Common Name English
NSC-368390
Code English
Brequinar sodium [WHO-DD]
Common Name English
BREQUINAR SODIUM [MART.]
Common Name English
BREQUINAR SODIUM SALT [MI]
Common Name English
DUP 785
Code English
6-FLUORO-2-(2'-FLUORO-1,1'-BIPHENYL-4-YL)-3-METHYL-4-QUINOLINECARBOXYLIC ACID SODIUM
Systematic Name English
DUP-785
Code English
Classification Tree Code System Code
NCI_THESAURUS C2169
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
NCI_THESAURUS C1557
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL38434
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
EPA CompTox
DTXSID30242173
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
MERCK INDEX
m2646
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY Merck Index
SMS_ID
300000055287
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
PUBCHEM
23663964
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
DRUG BANK
DBSALT002498
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
FDA UNII
49EEF6HRUS
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
USAN
Z-2
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
NCI_THESAURUS
C1078
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
CHEBI
177871
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
CAS
96201-88-6
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
NSC
368390
Created by admin on Mon Mar 31 18:01:01 GMT 2025 , Edited by admin on Mon Mar 31 18:01:01 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY