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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL185
CHEMBL185
Compound Name FLUOROURACIL
ChEMBL Synonyms TOLAK | FLUORO-URACIL ROCHE | ACCUSITE | FLUOROPLEX | RO 2-9757 | FLURACIL | ACTIKERALL | 5-FU | 5-Fluorouracil | ADRUCIL | EFUDIX | CARAC | EFUDEX | FLUOROURACIL | 5.F.U.
Max Phase 4 (Approved)
Trade Names ACTIKERALL | TOLAK | CARAC | EFUDIX | 5.F.U. | FLUOROURACIL | ACCUSITE | FLUORO-URACIL ROCHE | FLUOROPLEX | ADRUCIL | EFUDEX
Molecular Formula C4H3FN2O2

Additional synonyms for CHEMBL185 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES FC1=CNC(=O)NC1=O
Standard InChI InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
Standard InChI Key GHASVSINZRGABV-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • HeCaToS Compounds
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL185

Molecule Features

CHEMBL185 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:Y Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA PubMed
RNA inhibitor RNA PubMed
Thymidylate synthase inhibitor Thymidylate synthase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Bile Duct NeoplasmsD001650EFO:0005540bile duct carcinoma2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma1ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma3ClinicalTrials
Biliary Tract NeoplasmsD001661EFO:0003891biliary tract neoplasm3ClinicalTrials
Carcinoma, Pancreatic DuctalD021441EFO:0002517pancreatic ductal adenocarcinoma2ClinicalTrials
Digestive System DiseasesD004066EFO:0000405digestive system disease2ClinicalTrials
EpendymomaD004806EFO:1000028ependymoma1ClinicalTrials
Esophageal NeoplasmsD004938EFO:0005922esophageal squamous cell carcinoma3ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma1ClinicalTrials
Colorectal NeoplasmsD015179EFO:0005842colorectal cancer3ClinicalTrials
Gallbladder NeoplasmsD005706EFO:0004606gallbladder neoplasm3ClinicalTrials
Laryngeal NeoplasmsD007822EFO:0003817laryngeal neoplasm2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia1ClinicalTrials
Urethral NeoplasmsD014523EFO:0003846urethral neoplasm2ClinicalTrials
AdenocarcinomaD000230EFO:0000228adenocarcinoma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma3ClinicalTrials
Colonic NeoplasmsD003110EFO:0004288colonic neoplasm3ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma3ClinicalTrials
Inflammatory Breast NeoplasmsD058922EFO:1000984inflammatory breast carcinoma3ClinicalTrials
Keratosis, ActinicD055623EFO:0002496actinic keratosis3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma1ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma3ClinicalTrials
CholangiocarcinomaD018281EFO:0005221cholangiocarcinoma2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0004284upper aerodigestive tract neoplasm3ClinicalTrials
MelanomaD008545EFO:0000756melanoma1ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ATC
ClinicalTrials
Skin NeoplasmsD012878EFO:0004198skin neoplasm2ClinicalTrials
Stomach NeoplasmsD013274EFO:0000503gastric adenocarcinoma3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
Carcinoma, Merkel CellD015266EFO:1001471Merkel cell skin cancer2ClinicalTrials
Colonic NeoplasmsD003110EFO:1001950colon carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma3ClinicalTrials
Lymphoma, AIDS-RelatedD016483EFO:1001365Lymphoma, AIDS-Related2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Peripheral Nervous System DiseasesD010523EFO:0003100peripheral neuropathy2ClinicalTrials
Stomach NeoplasmsD013274EFO:0003897stomach neoplasm3ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma3ClinicalTrials
Uterine Cervical DysplasiaD002578EFO:1000910dysplasia of cervix1ClinicalTrials
Anus NeoplasmsD001005EFO:0003835anal neoplasm3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma3ClinicalTrials
ChalazionD017043EFO:0007363meibomian cyst3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0000365colorectal adenocarcinoma3ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia3ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome1ClinicalTrials
Peritoneal NeoplasmsD010534EFO:1001100peritoneal neoplasm2ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer3ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma3ClinicalTrials
Vitreoretinopathy, ProliferativeD018630EFO:1001129proliferative vitreoretinopathy3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0004142colorectal neoplasm3ClinicalTrials
Gastrointestinal Stromal TumorsD046152Orphanet:44890Gastrointestinal stromal tumor1ClinicalTrials
GlaucomaD005901EFO:0000516glaucoma3ClinicalTrials
HepatoblastomaD018197EFO:1000292Hepatoblastoma3ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma3ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0003860pancreatic neoplasm3ClinicalTrials
Uterine NeoplasmsD014594EFO:0003859uterine neoplasm2ClinicalTrials

Clinical Data

ClinicalTrials.gov FLUOROURACIL
The Cochrane Collaboration FLUOROURACIL

Metabolites for CHEMBL185

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
130.1 130.0179 -0.8 0 65.72 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 2 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.73 - -.65 -1.64 1 9 0.48

Structural Alerts

There are 1 structural alerts for CHEMBL185. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BC - Pyrimidine analogues
L01BC02 - fluorouracil

L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BC - Pyrimidine analogues
L01BC52 - fluorouracil, combinations

ChemSpider ChemSpider:GHASVSINZRGABV-UHFFFAOYSA-N
DailyMed fluorouracil
PubChem SID: 104171158 SID: 11111190 SID: 124880118 SID: 124880121 SID: 144203701 SID: 144209533 SID: 144210432 SID: 170464762 SID: 17389875 SID: 174007005 SID: 26747342 SID: 26752979 SID: 50105574 SID: 8139872 SID: 82653 SID: 85231050 SID: 90341469
Wikipedia Fluorouracil

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL185



ACToR 1004-03-1
Atlas 5-fluorouracil 5-fluourouracil
BindingDB 50340677
Brenda 812 51649 155282
ChEBI 46345
ChemicalBook CB8162744
DrugBank DB00544
DrugCentral 26
eMolecules 512920 13386136
EPA CompTox Dashboard DTXSID2020634
FDA SRS U3P01618RT
Guide to Pharmacology 4789
Human Metabolome Database HMDB0014684
IBM Patent System 0C605755CCBA43F1F8AFB78DDB8C2CA6
KEGG Ligand C07649
LINCS LSM-4261
Mcule MCULE-6338086431
MolPort MolPort-003-990-447 MolPort-000-156-102
NIH Clinical Collection SAM002264615
Nikkaji J4.489J
NMRShiftDB 20027309
PDBe URF
PharmGKB PA128406956
PubChem 3385
PubChem: Thomson Pharma 15218968
Selleck Adrucil(Fluorouracil)
SureChEMBL SCHEMBL3646
ZINC ZINC000038212689

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/GHASVSINZRGABV-UHFFFAOYSA-N spacer
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