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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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
InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)InChIKey
GHASVSINZRGABV-UHFFFAOYSA-NSmiles
FC1=CNC(=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.