fluorouracil indications/contra

Stem definitionDrug idCAS RN
uracil type antineoplastics 26 51-21-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • 5-fluorouracil
  • adrucil
  • fluoroblastin
  • fluorouracil
  • 5-FU
A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.
  • Molecular weight: 130.08
  • Formula: C4H3FN2O2
  • CLOGP: -0.58
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 58.20
  • ALOGS: -1.35
  • ROTB: 0

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
April 25, 1962 FDA SPECTRUM PHARMS

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Neutropenia 4617.94 49.41 1532 18403 31854 3334070
Diarrhoea 4402.62 49.41 2015 17920 102333 3263591
Febrile neutropenia 3442.40 49.41 1073 18862 17902 3348022
Disease progression 2628.24 49.41 1003 18932 31256 3334668
Mucosal inflammation 2445.43 49.41 679 19256 7304 3358620
Vomiting 2244.11 49.41 1222 18713 88309 3277615
Nausea 2242.71 49.41 1389 18546 128256 3237668
Thrombocytopenia 2058.04 49.41 863 19072 34405 3331519
Stomatitis 1783.28 49.41 583 19352 11269 3354655
Dehydration 1686.40 49.41 740 19195 32909 3333015
Leukopenia 1576.87 49.41 572 19363 15251 3350673
Neuropathy peripheral 1469.82 49.41 552 19383 16255 3349669
Pyrexia 1314.80 49.41 838 19097 80277 3285647
Decreased appetite 1180.05 49.41 619 19316 40871 3325053
Interstitial lung disease 1122.34 49.41 432 19503 13584 3352340
Anaemia 1018.88 49.41 617 19318 53716 3312208
Palmar-plantar erythrodysaesthesia syndrome 943.26 49.41 312 19623 6220 3359704
Abdominal pain 907.58 49.41 541 19394 45684 3320240
Sepsis 859.79 49.41 462 19473 31911 3334013
Pulmonary embolism 791.08 49.41 416 19519 27472 3338452
Fatigue 769.89 49.41 681 19254 106559 3259365
Asthenia 743.37 49.41 545 19390 65120 3300804
Death 688.88 49.41 751 19184 151573 3214351
Bone marrow failure 665.75 49.41 258 19677 8229 3357695
Neurotoxicity 660.74 49.41 204 19731 3217 3362707
Malignant neoplasm progression 619.34 49.41 305 19630 17488 3348436
Hypokalaemia 616.49 49.41 281 19654 13524 3352400
Neutropenic sepsis 606.64 49.41 181 19754 2525 3363399
Neutrophil count decreased 601.24 49.41 253 19682 10020 3355904
White blood cell count decreased 600.63 49.41 334 19601 24613 3341311

Pharmacologic Action:

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SourceCodeDescription
ATC L01BC02 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
ATC L01BC52 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
CHEBI has role CHEBI:132992 radiosensitizing agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35705 immunosuppressive agent
FDA MoA N0000000233 Nucleic Acid Synthesis Inhibitors
FDA EPC N0000175595 Nucleoside Metabolic Inhibitor
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D007155 Immunologic Factors
MeSH PA D007166 Immunosuppressive Agents
MeSH PA D009676 Noxae

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Actinic keratosis indication 201101007 DOID:8866
Metastasis from malignant tumor of colon indication 314998002
Malignant tumor of stomach indication 363349007 DOID:10534
Malignant tumor of colon indication 363406005 DOID:219
Superficial basal cell carcinoma indication 403914000
Adenocarcinoma of pancreas indication 700423003 DOID:4074
Metastatic Breast Carcinoma indication
Nutritional disorder contraindication 2492009 DOID:374
Acute vomiting contraindication 23971007
Stomatitis contraindication 61170000 DOID:9637
Diarrhea contraindication 62315008
Acute infectious disease contraindication 63171007
Gastrointestinal hemorrhage contraindication 74474003
Dihydrouracil dehydrogenase (NADP^+^) deficiency contraindication 77365006 DOID:14218
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:2527
Superficial ulcer of skin contraindication 93448009
Secondary malignant neoplasm of bone marrow contraindication 94217008
Bleeding contraindication 131148009
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Pharyngitis contraindication 405737000 DOID:2275
Breastfeeding (mother) contraindication 413712001
Palmar-Plantar Erythrodysesthesia contraindication
Carcinoid syndrome off-label use 35868009
Actinic cheilitis off-label use 46795000 DOID:8866
Radiation dermatitis off-label use 49084001
Neoplasm of glans penis off-label use 126898002
Carcinoma of breast off-label use 254838004 DOID:3459
Malignant tumor of head and/or neck off-label use 255056009
Malignant tumor of cervix off-label use 363354003 DOID:4362
Malignant tumor of esophagus off-label use 363402007
Malignant tumor of anus off-label use 363490009 DOID:14110
Malignant tumor of urinary bladder off-label use 399326009 DOID:11054
Leukoplakia of oral mucosa off-label use 414603003
Metastatic Malignant Tumor of Anus off-label use
Pancreatic Neuroendocrine Tumor off-label use
Biliary Tract Malignancy off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.02 acidic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.5% CARAC VALEANT PHARMS NORTH N020985 Oct. 27, 2000 RX CREAM TOPICAL 6670335 June 2, 2021 TREATMENT OF ACTINIC KERATOSIS

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
4% TOLAK HILL DERMACEUTICALS N022259 Sept. 18, 2015 RX CREAM TOPICAL Sept. 18, 2018 NEW PRODUCT

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thymidylate synthase Enzyme INHIBITOR WOMBAT-PK CHEMBL
ATP-binding cassette sub-family C member 11 Transporter WOMBAT-PK
Multidrug resistance-associated protein 5 Transporter WOMBAT-PK
Thymidylate synthase Enzyme IC50 7.70 CHEMBL
Uracil phosphoribosyltransferase Unclassified Ki 4.89 CHEMBL

External reference:

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IDSource
CHEBI:46345 CHEBI
DB00544 DRUGBANK_ID
4017806 VUID
N0000146166 NUI
C0016360 UMLSCUI
4789 IUPHAR_LIGAND_ID
D00584 KEGG_DRUG
6969 MMSL
4492 RXNORM
3127006 SNOMEDCT_US
387172005 SNOMEDCT_US
4745 MMSL
d00235 MMSL
4017806 VANDF
N0000007099 NDFRT
N0000146166 NDFRT
002646 NDDF
CHEMBL185 ChEMBL_ID
D005472 MESH_DESCRIPTOR_UI
U3P01618RT UNII
1421 INN_ID
3385 PUBCHEM_CID
URF PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Efudex HUMAN PRESCRIPTION DRUG LABEL 1 0187-3202 SOLUTION 0.50 g TOPICAL NDA 12 sections
Efudex HUMAN PRESCRIPTION DRUG LABEL 1 0187-3203 SOLUTION 1.25 g TOPICAL NDA 12 sections
Efudex HUMAN PRESCRIPTION DRUG LABEL 1 0187-3204 CREAM 2 g TOPICAL NDA 12 sections
Carac HUMAN PRESCRIPTION DRUG LABEL 1 0187-5200 CREAM 5 mg TOPICAL NDA 13 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 0378-4791 CREAM 5 mg TOPICAL NDA 12 sections
Adrucil HUMAN PRESCRIPTION DRUG LABEL 1 0703-3015 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Adrucil HUMAN PRESCRIPTION DRUG LABEL 1 0703-3018 INJECTION, SOLUTION 2.50 g INTRAVENOUS ANDA 17 sections
Adrucil HUMAN PRESCRIPTION DRUG LABEL 1 0703-3019 INJECTION, SOLUTION 5 g INTRAVENOUS ANDA 17 sections
Fluoroplex HUMAN PRESCRIPTION DRUG LABEL 1 16110-812 CREAM 10 mg TOPICAL NDA 14 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 16729-276 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 21695-829 CREAM 50 mg TOPICAL ANDA 11 sections
fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 25021-215 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
TOLAK HUMAN PRESCRIPTION DRUG LABEL 1 28105-421 CREAM 0.04 g TOPICAL NDA 17 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 43547-258 SOLUTION 50 mg TOPICAL NDA 12 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 43547-259 SOLUTION 20 mg TOPICAL NDA 12 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 51672-4062 SOLUTION 20 mg TOPICAL ANDA 12 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 51672-4063 SOLUTION 50 mg TOPICAL ANDA 12 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 51672-4118 CREAM 50 mg TOPICAL ANDA 12 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 52549-4118 CREAM 50 mg TOPICAL ANDA 12 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 54868-6293 CREAM 50 mg TOPICAL ANDA 11 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 63323-117 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
TOLAK HUMAN PRESCRIPTION DRUG LABEL 1 64370-421 CREAM 40 mg TOPICAL NDA 17 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 66530-249 CREAM 50 mg TOPICAL ANDA 11 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 66530-252 CREAM 5 mg TOPICAL ANDA 15 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 66530-258 CREAM 5 mg TOPICAL NDA authorized generic 13 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 66758-044 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 14 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 66758-054 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 13 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 68001-266 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 68083-269 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 68083-270 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections