FLUOROURACIL

First approved in 1962

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H3FN2O2
Molecular Weight	130.0774
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1c(c(nc(n1)O)O)F

InChI

InChIKey=GHASVSINZRGABV-UHFFFAOYSA-N

InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

HIDE SMILES / InChI

Molecular Formula	C4H3FN2O2
Molecular Weight	130.0774
Charge	0
Count

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

Description
Sources: http://www.drugbank.ca/drugs/DB00544
Curator's Comment:: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/012209s040lbl.pdf

Fluorouracil is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances from becoming incorporated into DNA during the "S" phase (of the cell cycle), stopping normal development and division. Fluorouracil blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Fluorouracil blocks the incorporation of the thymidine nucleotide into the DNA strand. Fluorouracil is used for the topical treatment of multiple actinic or solar keratoses. In the 5% strength it is also useful in the treatment of superficial basal cell carcinomas when conventional methods are impractical, such as with multiple lesions or difficult treatment sites. Fluorouracil injection is indicated in the palliative management of some types of cancer, including colon, esophageal, gastric, rectum, breast, biliary tract, stomach, head and neck, cervical, pancreas, renal cell, and carcinoid.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thymidylate synthase 31 Target ID: CHEMBL1952 Sources: http://www.drugbank.ca/drugs/DB00544	Inhibitor 7701	Adenocarcinoma of the colon Gastric adenocarcinoma Breast adenocarcinoma
Colon carcinoma cells 2 Target ID: CHEMBL614464 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27503679	Inhibitor 7701	Adenocarcinoma of the colon	29.5 µM [IC50]
PC-3 13 Target ID: CHEMBL390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19423198	Inhibitor 7701		16 nM [IC50]
AGS 2 Target ID: CHEMBL613860 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26821004	Inhibitor 7701	Gastric adenocarcinoma	43.7999999999999972 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Adenocarcinoma of the colon 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/012209s040lbl.pdf	Primary	Thymidylate synthase Colon carcinoma cells	Approved 7997	FLUOROURACIL Approved Use Fluorouracil is indicated for the treatment of patients with: Adenocarcinoma of the Colon and Rectum Adenocarcinoma of the Breast Gastric Adenocarcinoma Pancreatic Adenocarcinoma Launch Date -242697600000
Gastric adenocarcinoma 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/012209s040lbl.pdf	Primary	Thymidylate synthase AGS	Approved 7997	FLUOROURACIL Approved Use Fluorouracil is indicated for the treatment of patients with: Adenocarcinoma of the Colon and Rectum Adenocarcinoma of the Breast Gastric Adenocarcinoma Pancreatic Adenocarcinoma Launch Date -242697600000
Breast adenocarcinoma 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/012209s040lbl.pdf	Primary	Thymidylate synthase	Approved 7997	FLUOROURACIL Approved Use Fluorouracil is indicated for the treatment of patients with: Adenocarcinoma of the Colon and Rectum Adenocarcinoma of the Breast Gastric Adenocarcinoma Pancreatic Adenocarcinoma Launch Date -242697600000

C_max

Value	Dose	Co-administered	Analyte	Population
11.49 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20985lbl.pdf	1 g 2 times / day steady-state, topical dose: 1 g route of administration: Topical experiment type: STEADY-STATE co-administered:		FLUOROURACIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
278 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12907286	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUOROURACIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
22.39 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20985lbl.pdf	1 g 2 times / day steady-state, topical dose: 1 g route of administration: Topical experiment type: STEADY-STATE co-administered:		FLUOROURACIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
205 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12907286	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUOROURACIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.24 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12907286	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUOROURACIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
90% EXPERIMENT http://www.acutetox.eu/pdf_human_short/17-5-fluorouracil%20revised.pdf			FLUOROURACIL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
3400 mg/m2 1 times / week multiple, intravenous Highest studied dose Dose: 3400 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 3400 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/3373260	unhealthy, 54 years (range: 24-78 years) Health Status: unhealthy Age Group: 54 years (range: 24-78 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3373260	DLT: Ataxia... Other AEs: Anorexia, Nausea... Dose limiting toxicities: Ataxia (grade 3, 4 patients) Other AEs: Anorexia (3 patients) Nausea (severe, 2 patients) Vomiting (2 patients) Stomatitis (severe, 1 patient) Diarrhea (3 patients) Weakness (1 patient) Hair loss (1 patient) Peeling (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3373260
2600 mg/m2 1 times / week multiple, intravenous MTD 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/3373260	unhealthy, 54 years (range: 24-78 years) Health Status: unhealthy Age Group: 54 years (range: 24-78 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3373260	Other AEs: Ataxia, Anorexia... Other AEs: Ataxia (3 patients) Anorexia (4 patients) Nausea (severe, 2 patients) Vomiting (3 patients) Stomatitis (mild, 3 patients) Diarrhea (2 patients) Weakness (2 patients) Hair loss (2 patients) Loss of eyelashes (1 patient) Peeling (2 patients) Peeling (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/3373260
2800 mg/m2 1 times / week multiple, intravenous Dose: 2800 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2800 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8262730	unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8262730	DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8262730
3000 mg/m2 1 times / week multiple, intravenous Dose: 3000 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 3000 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8262730	unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8262730	DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3-4, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/8262730
3250 mg/m2 1 times / week multiple, intravenous Dose: 3250 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 3250 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/8262730	unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8262730	DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3-4, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/8262730
0.5 % 1 times / day multiple, topical Recommended Dose: 0.5 %, 1 times / day Route: topical Route: multiple Dose: 0.5 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20985lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20985lbl.pdf	Disc. AE: Irritation skin... AEs leading to discontinuation/dose reduction: Irritation skin (12%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20985lbl.pdf
1250 mg 1 times / 2 days multiple, oral Dose: 1250 mg, 1 times / 2 days Route: oral Route: multiple Dose: 1250 mg, 1 times / 2 days Sources: https://pubmed.ncbi.nlm.nih.gov/7302355	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/7302355	Sources: https://pubmed.ncbi.nlm.nih.gov/7302355
500 mg single, oral Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7463330	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7463330	Sources: https://pubmed.ncbi.nlm.nih.gov/7463330
5 % 2 times / day steady, topical Dose: 5 %, 2 times / day Route: topical Route: steady Dose: 5 %, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00847912	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00847912	Other AEs: Anaemia, Angina unstable... Other AEs: Anaemia (serious, 2 patients) Angina unstable (serious, 5 patients) Arrhythmia (serious, 2 patients) Arteriosclerosis coronary artery (serious, 1 patient) Atrial flutter (serious, 3 patients) Atrial tachycardia (serious, 1 patient) Atrial thrombosis (serious, 1 patient) Cardiac disorder (serious, 1 patient) Cardiac failure congestive (serious, 7 patients) Cardio-respiratory arrest (serious, 2 patients) Coronary artery stenosis (serious, 1 patient) Myocardial ischaemia (serious, 1 patient) Palpitations (serious, 1 patient) Pericarditis (serious, 1 patient) Ventricular tachycardia (serious, 2 patients) Vertigo (serious, 1 patient) Vertigo positional (serious, 1 patient) Disorder vestibular (serious, 1 patient) Goitre (serious, 1 patient) Inappropriate antidiuretic hormone secretion (serious, 1 patient) Abdominal hernia (serious, 1 patient) Colitis ischaemic (serious, 1 patient) Gastritis (serious, 2 patients) Haemorrhoids (serious, 1 patient) Impaired gastric emptying (serious, 1 patient) Hernia inguinal (serious, 1 patient) Intestinal obstruction (serious, 2 patients) Obstruction gastric (serious, 1 patient) Oesophageal obstruction (serious, 1 patient) Pancreatitis (serious, 1 patient) Vomiting (serious, 1 patient) Adhesion (serious, 1 patient) Chest discomfort (serious, 1 patient) Generalised oedema (serious, 1 patient) Non-cardiac chest pain (serious, 3 patients) Cholelithiasis (serious, 2 patients) Hepatitis alcoholic (serious, 1 patient) Arthritis infective (serious, 1 patient) Bacteraemia (serious, 1 patient) Bronchopneumonia (serious, 1 patient) Cholecystitis infective (serious, 1 patient) Clostridium difficile infection (serious, 3 patients) Cystitis (serious, 1 patient) Endocarditis (serious, 1 patient) Incision site cellulitis (serious, 1 patient) Infection (serious, 2 patients) Septic shock (serious, 1 patient) Upper respiratory tract infection (serious, 1 patient) Urinary tract infection (serious, 6 patients) Viral infection (serious, 1 patient) Device toxicity (serious, 1 patient) Fall (serious, 11 patient) Hip fracture (serious, 2 patients) Intentional overdose (serious, 1 patient) Limb injury (serious, 1 patient) Lower limb fracture (serious, 1 patient) Meniscus injury (serious, 2 patients) Periprosthetic fracture (serious, 1 patient) Postoperative fever (serious, 1 patient) Procedural nausea (serious, 1 patient) Procedural pain (serious, 1 patient) Radiation oesophagitis (serious, 1 patient) Road traffic accident (serious, 2 patients) Traumatic haematoma (serious, 1 patient) Vascular bypass dysfunction (serious, 1 patient) Blood glucose increased (serious, 1 patient) Electrocardiogram abnormal (serious, 1 patient) Haemoglobin decreased (serious, 1 patient) International normalised ratio increased (serious, 2 patients) White blood cell count increased (serious, 1 patient) Dehydration (serious, 5 patients) Diabetes mellitus inadequate control (serious, 2 patients) Failure to thrive (serious, 3 patients) Hyperglycaemia (serious, 2 patients) Hyponatraemia (serious, 3 patients) Iron deficiency (serious, 1 patient) Arthralgia (serious, 3 patients) Bursa disorder (serious, 1 patient) Exostosis (serious, 1 patient) Muscular weakness (serious, 1 patient) Osteoarthritis (serious, 10 patients) Tendonitis (serious, 1 patient) Basal cell carcinoma (serious, 1 patient) Benign salivary gland neoplasm (serious, 1 patient) Brain neoplasm (serious, 2 patients) Colorectal cancer (serious, 1 patient) Diffuse large B-cell lymphoma stage IV (serious, 1 patient) Haemangioma (serious, 1 patient) Lung neoplasm malignant (serious, 4 patients) Malignant melanoma (serious, 3 patients) Metastases to central nervous system (serious, 1 patient) Metastatic squamous cell carcinoma (serious, 1 patient) Neuroendocrine carcinoma (serious, 1 patient) Prostate cancer (serious, 5 patients) Prostate cancer recurrent (serious, 1 patient) Renal cancer (serious, 2 patients) Renal cancer metastatic (serious, 1 patient) Renal cell carcinoma (serious, 1 patient) Salivary gland cancer (serious, 1 patient) Squamous cell carcinoma (serious, 2 patients) Basilar artery stenosis (serious, 1 patient) Cognitive disorder (serious, 1 patient) Dementia (serious, 4 patients) Epilepsy (serious, 1 patient) Headache (serious, 1 patient) Hypoaesthesia (serious, 1 patient) Parkinson's disease (serious, 2 patients) Haemorrhage subarachnoid (serious, 1 patient) Transient ischaemic attack (serious, 4 patients) Transient ischaemic attack (serious, 4 patients) Dementia vascular (serious, 1 patient) Alcohol abuse (serious, 2 patients) Binge drinking (serious, 1 patient) Completed suicide (serious, 1 patient) Confusional state (serious, 1 patient) Delirium tremens (serious, 1 patient) Depression (serious, 3 patients) Mental disorder (serious, 1 patient) Mental status changes (serious, 2 patients) Post-traumatic stress disorder (serious, 1 patient) Suicidal behaviour (serious, 1 patient) Suicidal ideation (serious, 3 patients) Hydronephrosis (serious, 2 patients) Nephropathy (serious, 1 patient) Renal failure chronic (serious, 1 patient) Erectile dysfunction (serious, 1 patient) Prostatic haemorrhage (serious, 1 patient) Prostatitis (serious, 1 patient) Chronic obstructive pulmonary disease (serious, 9 patients) Dyspnoea (serious, 2 patients) Dyspnoea exertional (serious, 1 patient) Haemoptysis (serious, 1 patient) Pleural effusion (serious, 1 patient) Pulmonary embolism (serious, 3 patients) Respiratory failure (serious, 1 patient) Rash (serious, 1 patient) Angioplasty (serious, 1 patient) Cholecystectomy (serious, 1 patient) Coronary angioplasty (serious, 1 patient) Elective procedure (serious, 1 patient) Hip arthroplasty (serious, 1 patient) Knee arthroplasty (serious, 1 patient) Medical device removal (serious, 1 patient) Oesophagogastric fundoplasty (serious, 1 patient) Parotidectomy (serious, 1 patient) Wound treatment (serious, 1 patient) Aortic aneurysm (serious, 2 patients) Aortic occlusion (serious, 1 patient) Arterial occlusive disease (serious, 1 patient) Femoral artery occlusion (serious, 1 patient) Labile hypertension (serious, 1 patient) Orthostatic hypotension (serious, 2 patients) Disorder peripheral vascular (serious, 1 patient) Lymphadenopathy (below serious, 1 patient) Vertigo (below serious, 1 patient) Adrenal mass (below serious, 1 patient) Eye haemorrhage (below serious, 1 patient) Eye irritation (below serious, 3 patients) Eye pain (below serious, 2 patients) Eye pruritus (below serious, 1 patient) Eye swelling (below serious, 4 patients) Photophobia (below serious, 1 patient) Visual acuity reduced (below serious, 1 patient) Abdominal pain upper (below serious, 2 patients) Cheilitis (below serious, 1 patient) Diarrhoea (below serious, 3 patients) Diverticulum (below serious, 1 patient) Dyspepsia (below serious, 1 patient) Gastrooesophageal reflux disease (below serious, 1 patient) Gingival pain (below serious, 1 patient) Nausea (below serious, 5 patients) Fatigue (below serious, 3 patients) Feeling of body temperature change (below serious, 1 patient) Hernia (below serious, 1 patient) Local swelling (below serious, 1 patient) Malaise (below serious, 1 patient) Pain (below serious, 11 patient) Syringe issue (below serious, 1 patient) Temperature intolerance (below serious, 1 patient) Tenderness (below serious, 2 patients) Vessel puncture site haematoma (below serious, 1 patient) Hypersensitivity (below serious, 1 patient) Seasonal allergy (below serious, 1 patient) Bronchitis (below serious, 4 patients) Cellulitis (below serious, 1 patient) Folliculitis (below serious, 1 patient) Fungal infection (below serious, 1 patient) Herpes zoster (below serious, 2 patients) Infection (below serious, 2 patients) Influenza (below serious, 1 patient) Nasopharyngitis (below serious, 5 patients) Oral herpes (below serious, 1 patient) Pneumonia (below serious, 2 patients) Accidental exposure to product (below serious, 1 patient) Arthropod sting (below serious, 1 patient) Fall (below serious, 5 patients) Laceration (below serious, 1 patient) Muscle rupture (below serious, 1 patient) Body temperature increased (below serious, 1 patient) Emergency care examination (below serious, 1 patient) Gout (below serious, 1 patient) Arthralgia (below serious, 1 patient) Back pain (below serious, 3 patients) Foot deformity (below serious, 1 patient) Musculoskeletal pain (below serious, 1 patient) Neck pain (below serious, 1 patient) Pain in extremity (below serious, 1 patient) Polymyalgia rheumatica (below serious, 1 patient) Basal cell carcinoma (below serious, 1 patient) Haemangioma (below serious, 1 patient) Transitional cell carcinoma (below serious, 1 patient) Burning sensation (below serious, 1 patient) Dizziness (below serious, 4 patients) Headache (below serious, 5 patients) Hypoaesthesia (below serious, 2 patients) Syncope (below serious, 1 patient) Tunnel vision (below serious, 1 patient) Abnormal dreams (below serious, 1 patient) Anxiety (below serious, 1 patient) Psychotic disorder (below serious, 1 patient) Sleep disorder (below serious, 22 patients) Dysuria (below serious, 1 patient) Haemorrhage urinary tract (below serious, 1 patient) Pollakiuria (below serious, 1 patient) Chronic obstructive pulmonary disease (below serious, 1 patient) Nasal congestion (below serious, 1 patient) Productive cough (below serious, 1 patient) Pulmonary mass (below serious, 1 patient) Rhinorrhoea (below serious, 1 patient) Sinus disorder (below serious, 1 patient) Acne (below serious, 5 patients) Blister (below serious, 2 patients) Blood blister (below serious, 1 patient) Decubitus ulcer (below serious, 1 patient) Dermatitis (below serious, 447 patients) Dermatitis allergic (below serious, 1 patient) Hyperhidrosis (below serious, 2 patients) Photosensitivity reaction (below serious, 5 patients) Post inflammatory pigmentation change (below serious, 1 patient) Scab (below serious, 1 patient) Seborrhoea (below serious, 1 patient) Dermatitis seborrhoeic (below serious, 2 patients) Skin discomfort (below serious, 1 patient) Skin haemorrhage (below serious, 3 patients) Skin tightness (below serious, 1 patient) Skin ulcer (below serious, 1 patient) Urticaria (below serious, 1 patient) Oral surgery (below serious, 1 patient) Wound drainage (below serious, 1 patient) Haemorrhage (below serious, 7 patients) Temporal arteritis (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT00847912

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1172	inhibitor 1318 supressor 13	inhibitor 1421

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1268 CYP2C19 1215 CYP2C8 761 CYP2E1 761

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1406	inhibitor 2614 Sources: https://jpet.aspetjournals.org/content/297/3/1166 Page: -	no
CYP2C19 1277	inhibitor 2614 Sources: https://jpet.aspetjournals.org/content/297/3/1166 Page: -	no
CYP2C8 810	inhibitor 2614 Sources: https://jpet.aspetjournals.org/content/297/3/1166 Page: -	no
CYP2C9 1362	inhibitor 2614 Sources: https://jpet.aspetjournals.org/content/297/3/1166 Page: -	no
CYP2D6 1455	inhibitor 2614 Sources: https://jpet.aspetjournals.org/content/297/3/1166 Page: -	no
CYP2E1 841	inhibitor 2614 Sources: https://jpet.aspetjournals.org/content/297/3/1166 Page: -	no
CYP3A4 1462	inhibitor 2614 Sources: https://jpet.aspetjournals.org/content/297/3/1166 Page: -	no
CYP2C9 1362	supressor 128 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/j.1742-7843.2006.pto_304.x Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY41650
1PlusChem LLC	1P003N8I
A2B Chem	AB69282
A2Z Synthesis	A2Z00084917
A2Z Synthesis	A2Z00085314
AA Blocks	AA003MP2
ACT Chemical	ACT11737
AChemBlock	K12016
AK Scientific	C526
AK Scientific	J10960
AK Scientific	J92559
APExBIO	A4071
AbovChem LLC	HY-90006
Aceschem	ACF015286
Acros Organics	22844
Alfa Chemistry	A13456
Alinda	IBS-E0752211
Alinda	IBS-L0127067
Ambeed	A370752
Angene	AGN-PC-0JE2HI
Apollo Scientific	BIF0123
Apollo Scientific	PC4380
Aromalake	LS40596
AsisChem	ACLSC-017330
AsisChem	D51260
AstaTech	28568
BOC Sciences	51-21-8
Bide Pharmatech	BD9397
BioSynth	W-202929
BlocksMatrix Scientific	5763
Bosche Scientific	F0040
Cayman Chemical	14416
Chem Scene	CS-0993
Chem-Impex International	1786
ChemDiv	R052-0877
ChemShuttle	109766
Chemik	CHH06500
Chemspace	CSC016300286
Chemspace	CSC021367054
Chemspace	CSC021379420
Chemspace	CSC054607912
Chemspace	CSC055360488
Combi-Blocks	ST-0302
Compound Cloud	3385
Compound Cloud	46174081
Debye Scientific	DB-051923
Debye Scientific	DB-065735
EDASA Scientific	BB0267836
Enamine	BBV-50166820
Enamine	BBV-92912598
Enamine	BBV-92912819
Enamine	BBV-92912820
Enamine	BBV-92959345
Enamine	BBV-93184155
Enamine	EN300-33909
Fluorochem	3241
Fluoropharm	OF17144
Frontier Scientific Services	500042977
Hairui	HR126763
Hangzhou APIChem Technology	AC-11201
Hangzhou Yuhao Chemical Technology	RT16644
IBScreen	BB_NC-00576
IBScreen	STOCK1S-13695
Innovapharm	BBS-00024224
Innovapharm	BBV-00039847
Innovapharm	STT-00358722
KeyOrganics	KS-5129
Lab Network	LN00115439
Lab Seeker	SC-09038
MedChem Express	HY-90006
MolPort	MolPort-000-156-102
MolPort	MolPort-003-990-447
Molcore	MC41650
Molnova	M14770
MuseChem	R005685
NCI Plated 2007	168664
NCI Plated 2007	19893
Nanjing Pope Bio-tech	NSTH-D02980
Norris Pharm	NSTH-D02980
Oakwood	3241
Otava	2826654
Otava	3665872
PI Chemicals	PI-16620
Pharmeks	PHBB_NC-00691
Princeton BioMolecular Research	OSSL_012481
Scientific Exchange	POD_09/0733
Scientific Exchange	Z-001862
ShangHai Biochempartner	BCP02083
Sigma Aldrich	03738\|SIAL
Sigma Aldrich	04541\|SIAL
Sigma Aldrich	1279000
Sigma Aldrich	1279000\|USP
Sigma Aldrich	3738
Sigma Aldrich	4541
Sigma Aldrich	858471
Sigma Aldrich	858471\|ALDRICH
Sigma Aldrich	BP995
Sigma Aldrich	F0250000
Sigma Aldrich	F0250000\|SIAL
Sigma Aldrich	F6627
Sigma Aldrich	F6627\|SIGMA
Sigma Aldrich	F8423
Sigma Aldrich	F8423\|SIGMA
Sigma Aldrich	PHR1227
Sigma Aldrich	PHR1227\|SIAL
Sigma Aldrich	V900394
Sigma Aldrich	V900394\|VETEC
StruChem	SC-09038
SynQuest	18934
SynQuest	4H53-3-01
Tetrahedron	TS05693
Tetrahedron	TS71555
TimTec	SBB085751
TimTec	ST45025877
Tocris	3257
Toronto Research Chemicals	F596000
UORSY	PB275205520
Vitas-M Laboratory	STK297802
Vitas-M Laboratory	STL367375
W&J PharmaChem	50A180939
W&J PharmaChem	RT-
Wonderchem	WD06951
ZINC	ZINC000038212689	http://zinc15.docking.org/substances/ZINC000038212689
eMolecules	37162817
eMolecules	512920
mcule	MCULE-6338086431

PubMed

Title	Date	PubMed
PEG-rHuMGDF promotes multilineage hematopoietic recovery in myelosuppressed mice.	1999 Dec	10641595
Multifocal demyelinative leukoencephalopathy associated with 5-fluorouracil and levamisole.	2000	10752665
Combined chemotherapy of murine mammary tumors by local activation of the prodrugs ifosfamide and 5-fluorocytosine.	2000 Apr	10811482
Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma.	2000 Dec 15	11135211
Fluorouracil-induced neurotoxicity.	2000 Jan	10669184
5-Fluorouracil induces apoptosis through the suppression of NF-kappaB activity in human salivary gland cancer cells.	2000 Jul 14	10891390
Continuous intra-arterial 5-FU chemotherapy in a patient with a repeated recurrence of rectal cancer: report of a case.	2000 Jun	10859091
[Emergency coronary angioplasty following treatment with 5-fluorouracil].	2000 May	10874764
Morphological change, loss of deltapsi(m) and activation of caspases upon apoptosis of colorectal adenocarcinoma induced by 5-FU.	2000 May 29	10779637
Role of BAX in the apoptotic response to anticancer agents.	2000 Nov 3	11062132
Acute reversible cardiomyopathy and thromboembolism after cisplatin and 5-fluorouracil chemotherapy--a case report.	2000 Oct	11108333
Severe heart failure secondary to 5-fluorouracil and low-doses of folinic acid: usefulness of an intra-aortic balloon pump.	2000 Oct	11057817
Irinotecan plus fluorouracil/leucovorin for metastatic colorectal cancer: a new survival standard.	2001	11161231
The role of capecitabine, an oral, enzymatically activated fluoropyrimidine, in the treatment of metastatic breast cancer.	2001	11161228
Activity of gemcitabine and continuous infusion fluorouracil in advanced pancreatic cancer.	2001	11150907
Early postoperative intraperitoneal chemotherapy with mitomycin C, 5-fluorouracil and cisplatin for advanced gastric cancer.	2001	11150904
Phase II study of combined 5-fluorouracil/ Ginkgo biloba extract (GBE 761 ONC) therapy in 5-fluorouracil pretreated patients with advanced colorectal cancer.	2001 Feb	11180520
Quantitative short-term study of anal sphincter function after chemoradiation for rectal cancer.	2001 Feb	11177140
Immunomodulation by anticancer chemotherapy: more is not always better (review).	2001 Feb	11172612
Analysis of uracil DNA glycosylase in human colorectal cancer.	2001 Feb	11172609
Enhancement of antitumor effect by intratumoral administration of bax gene in combination with anticancer drugs in gastric cancer.	2001 Feb	11172605
Reconstitution of liver mass via cellular hypertrophy in the rat.	2001 Feb	11172335
Thrombopoietin signaling is required for in vivo expansion of IL-11--responsive hematopoietic progenitor cells in the steady state.	2001 Feb	11166452
Phase Ib trial of intravenous recombinant humanized monoclonal antibody to vascular endothelial growth factor in combination with chemotherapy in patients with advanced cancer: pharmacologic and long-term safety data.	2001 Feb 1	11157039
Long-term results of combined-modality therapy for locally advanced breast cancer with ipsilateral supraclavicular metastases: The University of Texas M.D. Anderson Cancer Center experience.	2001 Feb 1	11157012
Benefit of a high-dose epirubicin regimen in adjuvant chemotherapy for node-positive breast cancer patients with poor prognostic factors: 5-year follow-up results of French Adjuvant Study Group 05 randomized trial.	2001 Feb 1	11157009
Multicenter phase I-II trial of docetaxel, cisplatin, and fluorouracil induction chemotherapy for patients with locally advanced squamous cell cancer of the head and neck.	2001 Feb 15	11181674
Dose-intensive epirubicin-based chemotherapy is superior to an intensive intravenous cyclophosphamide, methotrexate, and fluorouracil regimen in metastatic breast cancer: a randomized multinational study.	2001 Feb 15	11181656
Tamoxifen and chemotherapy for axillary node-negative, estrogen receptor-negative breast cancer: findings from National Surgical Adjuvant Breast and Bowel Project B-23.	2001 Feb 15	11181655
Crystal structure of dihydropyrimidine dehydrogenase, a major determinant of the pharmacokinetics of the anti-cancer drug 5-fluorouracil.	2001 Feb 15	11179210
Survival in patients with intermediate or high grade non-Hodgkin's lymphoma: meta-analysis of randomized studies comparing third generation regimens with CHOP.	2001 Feb 2	11161392
Interleukin-6 serum level correlates with survival in advanced gastrointestinal cancer patients but is not an independent prognostic indicator.	2001 Jan	11177580
Intraoperative radiation therapy for locally advanced recurrent rectal or rectosigmoid cancer.	2001 Jan	11165686
Expression of thymidylate synthase in gastric cancer patients treated with 5-fluorouracil and doxorubicin-based adjuvant chemotherapy after curative resection.	2001 Jan	11161374
Mobilization of hematopoietic progenitor cells with a combination of docetaxel, adriamycin, 5-fluorouracil and filgrastim in breast cancer patients.	2001 Jan	11146579
Value and cost of follow-up after adjuvant treatment of patients with Dukes' C colonic cancer.	2001 Jan	11136320
Rapidly progressive glomerulonephritis and carcinoma of the hypopharynx.	2001 Jan	11136192
Crystallization and preliminary X-ray study of pig liver dihydropyrimidine dehydrogenase.	2001 Jan	11134942
Toward a biologically based dose-response model for developmental toxicity of 5-fluorouracil in the rat: a mathematical construct.	2001 Jan	11134543
Toward a biologically based dose-response model for developmental toxicity of 5-fluorouracil in the rat: acquisition of experimental data.	2001 Jan	11134542
Combination cisplatin, 5-fluorouracil and radiation therapy for locally advanced unresectable or medically unfit bladder cancer cases: a Southwest Oncology Group Study.	2001 Jan	11125363
Bystander effect in uracil phosphoribosyltransferase/5-fluorouracil-mediated suicide gene therapy is correlated with the level of intercellular communication.	2001 Jan	11115547
Retroviral expression of Escherichia coli thymidylate synthase cDNA confers high-level antifolate resistance to hematopoietic cells.	2001 Jan 1	11177542
Effective pelvic symptom control using initial chemoradiation without colostomy in metastatic rectal cancer.	2001 Jan 1	11163503
Cyclophosphamide and 5-fluorouracil act synergistically in ovarian clear cell adenocarcinoma cells.	2001 Jan 10	11121861
Enzyme-catalyzed therapeutic agent (ECTA) design: activation of the antitumor ECTA compound NB1011 by thymidylate synthase.	2001 Jan 15	11163332
Monohydroxylation and esterification as determinants of the effects of cis- and trans-9-octadecenoic acids on the permeation of hydrocortisone and 5-fluorouracil across hairless mouse skin in vitro.	2001 Jan 16	11165072
Adjuvant chemotherapy for colon cancer.	2001 Mar	11177740
Antioxidants enhance the susceptibility of colon carcinoma cells to 5-fluorouracil by augmenting the induction of the bax protein.	2001 Mar 10	11166918
Uracil salvage pathway in PC12 cells.	2001 Nov 15	11078957

Patents

Sample Use Guides

In Vivo Use Guide

Recommended Dosage for Adenocarcinoma of the Colon and Rectum:

Route of Administration: Intravenous

In Vitro Use Guide

Fluorouracil treatment (0.4uM) inhibited LXA4 secretion in colorectal cancer RKO cells

Substance Class	Chemical Created by `admin` on `Fri Jun 25 20:53:58 UTC 2021` Edited by `admin` on `Fri Jun 25 20:53:58 UTC 2021`
Record UNII	U3P01618RT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUOROURACIL

Official Name

English

2,4(1H,3H)-PYRIMIDINEDIONE, 5-FLUORO-

Systematic Name

English

ADRUCIL

Brand Name

English

FLUOROURACILUM [WHO-IP LATIN]

Common Name

English

5-FU

Code

English

PHTHORURACIL

Common Name

English

5-FLUOROURACIL [IARC]

Common Name

English

EMTRICITABINE IMPURITY F [WHO-IP]

Common Name

English

QUEROPLEX

Common Name

English

EFUDEX

Brand Name

English

5-FLUOROPYRIMIDIN-2,4(1H,3H)-DIONE [WHO-IP]

Systematic Name

English

5-FLUORURACIL

Common Name

English

FLUOROURACIL [ORANGE BOOK]

Common Name

English

FLUOROURACIL [EP MONOGRAPH]

Common Name

English

5 FU

Code

English

CARAC

Brand Name

English

TOLAK

Systematic Name

English

RO-29757

Code

English

FLUOROURICIL

Common Name

English

FLUOROURACIL [MI]

Common Name

English

RO-2-9757

Code

English

FLUOROURACIL [USP-RS]

Common Name

English

5-FLUOROURACIL

Systematic Name

English

FLUOROURACIL [VANDF]

Common Name

English

5 FLUOROURACIL

Systematic Name

English

FLUOROURACIL [WHO-DD]

Common Name

English

FLUOROURACIL [USAN]

Common Name

English

FLUCYTOSINE IMPURITY A [EP]

Common Name

English

FLUCYTOSINE IMPURITY A [WHO-IP]

Common Name

English

FLUOROURACIL [WHO-IP]

Common Name

English

FLUOROURACIL [JAN]

Common Name

English

NSC-19893

Code

English

RO 2-9757

Code

English

FLUOROURACIL [HSDB]

Common Name

English

5-FLUOROURACIL [WHO-IP]

Common Name

English

FLUOROURACIL [MART.]

Common Name

English

5-FLUORO-URACIL

Systematic Name

English

FLUOROURACIL [USP MONOGRAPH]

Common Name

English

FLUOROURACIL [INN]

Common Name

English

FLUOROPLEX

Brand Name

English

Classification Tree Code System Code

LIVERTOX

423