NAV

Brequinar

Identification

Generic Name
Brequinar
DrugBank Accession Number
DB03523
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 375.3675
Monoisotopic: 375.107085139
Chemical Formula
C23H15F2NO2
Synonyms
  • Brequinar
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDihydroorotate dehydrogenase (quinone), mitochondrialNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Brequinar.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Brequinar.
Adenovirus type 7 vaccine liveThe risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Brequinar.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Brequinar.
AlefaceptThe risk or severity of adverse effects can be increased when Alefacept is combined with Brequinar.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Brequinar sodium49EEF6HRUS96201-88-6PZOHOALJQOFNTB-UHFFFAOYSA-M

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Phenylquinolines
Direct Parent
Phenylquinolines
Alternative Parents
Quinoline carboxylic acids / Phenylpyridines / Biphenyls and derivatives / Haloquinolines / Pyridinecarboxylic acids / Fluorobenzenes / Methylpyridines / Aryl fluorides / Heteroaromatic compounds / Azacyclic compounds
show 8 more
Substituents
2-phenylpyridine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Biphenyl / Carboxylic acid / Carboxylic acid derivative / Fluorobenzene
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
5XL19F49H6
CAS number
96187-53-0
InChI Key
PHEZJEYUWHETKO-UHFFFAOYSA-N
InChI
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)
IUPAC Name
6-fluoro-2-{2'-fluoro-[1,1'-biphenyl]-4-yl}-3-methylquinoline-4-carboxylic acid
SMILES
CC1=C(N=C2C=CC(F)=CC2=C1C(O)=O)C1=CC=C(C=C1)C1=CC=CC=C1F

References

General References
Not Available
PubChem Compound
57030
PubChem Substance
46504783
ChemSpider
51422
BindingDB
15339
ChEMBL
CHEMBL38434
ZINC
ZINC000001587011
PDBe Ligand
BRF
Wikipedia
Brequinar
PDB Entries
1uuo

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCoronavirus Disease 2019 (COVID‑19) / Covid 19 Infection1
2TerminatedTreatmentCoronavirus Disease 2019 (COVID‑19)1
1, 2CompletedTreatmentCoronavirus Disease 2019 (COVID‑19)1
1, 2TerminatedTreatmentAcute Myeloid Leukemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000539 mg/mLALOGPS
logP5.05ALOGPS
logP6.27Chemaxon
logS-5.8ALOGPS
pKa (Strongest Acidic)3.38Chemaxon
pKa (Strongest Basic)0.75Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area50.19 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity102.61 m3·mol-1Chemaxon
Polarizability38.43 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9745
Caco-2 permeable+0.7523
P-glycoprotein substrateNon-substrate0.7193
P-glycoprotein inhibitor INon-inhibitor0.8927
P-glycoprotein inhibitor IINon-inhibitor0.9706
Renal organic cation transporterNon-inhibitor0.9035
CYP450 2C9 substrateNon-substrate0.7659
CYP450 2D6 substrateNon-substrate0.8467
CYP450 3A4 substrateNon-substrate0.6366
CYP450 1A2 substrateNon-inhibitor0.6456
CYP450 2C9 inhibitorInhibitor0.5743
CYP450 2D6 inhibitorNon-inhibitor0.9679
CYP450 2C19 inhibitorNon-inhibitor0.8437
CYP450 3A4 inhibitorNon-inhibitor0.9302
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9268
Ames testNon AMES toxic0.8381
CarcinogenicityNon-carcinogens0.8718
BiodegradationNot ready biodegradable0.9922
Rat acute toxicity2.6182 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9898
hERG inhibition (predictor II)Non-inhibitor0.8891
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-b4cf52e217fd4b6c4cc5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-78fe7f1b617ab6252ba4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-195a1cdd80435a799898
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-6c2855e4ef7864f4d580
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ff0-0089000000-9f6badc21349e134c03f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-0009000000-c87e3ad1e29546b123bb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.67552
predicted
DeepCCS 1.0 (2019)
[M+H]+186.03352
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.51091
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dihydroorotate dehydrogenase (quinone), mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquinone binding
Specific Function
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name
DHODH
Uniprot ID
Q02127
Uniprot Name
Dihydroorotate dehydrogenase (quinone), mitochondrial
Molecular Weight
42866.93 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51