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Substance Name: Fluorouracil [USAN:USP:INN:BAN:JAN]
RN: 51-21-8
UNII: U3P01618RT
InChIKey: GHASVSINZRGABV-UHFFFAOYSA-N

Note

  • 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 Formula

  • C4-H3-F-N2-O2

Molecular Weight

  • 130.078
 

Classification Codes

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Immunologic Factors
  • Immunosuppressive Agents
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 3
  • Threshold Planning Quantity (TPQ) = 500/10000 lb

Names and Synonyms

Name of Substance

  • Fluorouracil [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Fluorouracil

Synonyms

  • 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-
  • 2,4-Dioxo-5-fluoropyrimidine
  • 5-Faracil
  • 5-Fluor-2,4(1H,3H)-pyrimidindion
  • 5-Fluor-2,4(1H,3H)-pyrimidindion [Czech]
  • 5-Fluor-2,4-dihydroxypyrimidin
  • 5-Fluor-2,4-dihydroxypyrimidin [Czech]
  • 5-Fluor-2,4-pyrimidindiol
  • 5-Fluor-2,4-pyrimidindiol [Czech]
  • 5-Fluoracil
  • 5-Fluoracil [German]
  • 5-Fluoro-2,4(1H,3H)-pyrimidinedione
  • 5-Fluoropyrimidin-2,4-diol
  • 5-Fluoropyrimidine-2,4-dione
  • 5-Fluorouracil
  • 5-Fluoruracil
  • 5-Fluoruracil [German]
  • 5-FU
  • 5FU
  • Adrucil
  • AI3-25297
  • Arumel
  • Carac
  • Carzonal
  • CCRIS 2582
  • Cinco FU
  • EC 200-085-6
  • Effluderm (free base)
  • Efudex
  • EINECS 200-085-6
  • Fluoro-uracile
  • Fluoro-uracilo
  • Fluoroblastin
  • Fluoroplex
  • Fluorouracil
  • Fluorouracil Cream
  • Fluorouracile
  • Fluorouracile [DCIT]
  • Fluorouracilo
  • Fluorouracilo [INN-Spanish]
  • Fluorouracilum
  • Fluorouracilum [INN-Latin]
  • Fluracil
  • Fluracilum
  • Fluril
  • Fluro uracil
  • Fluroblastin
  • FU
  • HSDB 3228
  • Kecimeton
  • NSC 19893
  • NSC-19893
  • Phthoruracil
  • Queroplex
  • Ro 2-9757
  • Timazin
  • Tolak
  • U-8953
  • Ulup
  • UNII-U3P01618RT
  • Uracil, 5-fluoro-

Systematic Names

  • 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-
  • 5-Fluorouracil
  • Fluorouracil
  • Uracil, 5-fluoro-

Superlist Names

  • 5-Fluorouracil
  • Fluorouracil

Registry Numbers

CAS Registry Number

  • 51-21-8

FDA UNII

  • U3P01618RT

Other Registry Numbers

  • 1004-03-1
  • 4921-97-5
  • 79108-01-3

System Generated Number

  • 0000051218

Structure Descriptors

InChI

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

InChIKey

GHASVSINZRGABV-UHFFFAOYSA-N

Smiles

c1(c(c[nH]c([nH]1)=O)F)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 30mg/kg (30mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Oyo Yakuri. Pharmacometrics. Vol. 16, Pg. 303, 1978.
guinea pig LD50 intravenous 25mg/kg (25mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Japanese Journal of Pharmacology. Vol. 30, Pg. 871, 1980.
hamster LD10 parenteral 140mg/kg (140mg/kg)   Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
human TDLo intravenous 6mg/kg/3D (6mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
British Medical Journal. Vol. 1, Pg. 547, 1978.
human TDLo oral 450mg/kg/30D (450mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

GASTROINTESTINAL: OTHER CHANGES
Cancer Vol. 39, Pg. 1936, 1977.
man TDLo intravenous 39mg/kg/1D-I (39mg/kg) CARDIAC: CHANGES IN CORONARY ARTERIES American Heart Journal. Vol. 114, Pg. 433, 1987.
man TDLo intravenous 122mg/kg/9W-I (122mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Australian and New Zealand Journal of Medicine. Vol. 22, Pg. 385, 1992.
mouse LD50 intracrebral 41600ug/kg (41.6mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE
Chemotherapy Vol. 15, Pg. 519, 1967.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 7, Pg. 100, 1977.
mouse LD50 intravenous 81mg/kg (81mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
mouse LD50 oral 115mg/kg (115mg/kg)   Journal of Medicinal Chemistry. Vol. 21, Pg. 738, 1978.
mouse LD50 subcutaneous 169mg/kg (169mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
mouse LD50 unreported 171mg/kg (171mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
mouse LDLo intratracheal 200mg/kg (200mg/kg)   Toxicology Letters. Vol. 30, Pg. 63, 1986.
rabbit LD50 oral 18900ug/kg (18.9mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Kiso to Rinsho. Clinical Report. Vol. 8, Pg. 2603, 1974.
rabbit LDLo intravenous 15mg/kg (15mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Japanese Journal of Pharmacology. Vol. 30, Pg. 871, 1980.
rat LD50 intramuscular 240mg/kg (240mg/kg)   K'at'ollik Taehak Uihakpu Nonmunjip. Journal of Catholic Medical College. Vol. 38, Pg. 481, 1985.
rat LD50 intraperitoneal 70mg/kg (70mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 569, 1971.
rat LD50 intravenous 245mg/kg (245mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 569, 1971.
rat LD50 oral 230mg/kg (230mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
rat LD50 parenteral 500mg/kg (500mg/kg)   Recent Results in Cancer Research. Vol. 52, Pg. 76, 1975.
rat LD50 rectal 884mg/kg (884mg/kg) GASTROINTESTINAL: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Kiso to Rinsho. Clinical Report. Vol. 12, Pg. 1309, 1978.
rat LD50 subcutaneous 217mg/kg (217mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
women TDLo intravenous 27mg/kg/4D-C (27mg/kg) CARDIAC: OTHER CHANGES British Medical Journal. Vol. 294, Pg. 125, 1987.
women TDLo intravenous 150mg/kg/17W- (150mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA British Journal of Haematology. Vol. 65, Pg. 357, 1987.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 283 deg C   EXP
pKa Dissociation Constant 8.02 (none)   EXP
log P (octanol-water) -0.89 (none)   EXP
Water Solubility 1.11E+04 mg/L 22 EXP
Vapor Pressure 2.68E-06 mm Hg 25 EST
Henry's Law Constant 1.66E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.83E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.