Drug

D0001 | Fluorouracil

Molecular Formula C4H3FN2O2
Molecular Weight 130.08
Structure
State solid
Route of elimination Seven percent to 20% of the parent drug is excreted unchanged in the urine in 6 hours; of this over 90% is excreted in the first hour. The remaining percentage of the administered dose is metabolized, primarily in the liver.
Protein binding 8-12%
Half life 10-20 minutes
Absorption 28-100%
Trade names Adrucil, Carac, Efudex, Efudix
Description Anti-cancer; an antineoplastic antimetabolite; a pyrimidine analog; blocking the thymidylate synthetase

L

L01BC52 Fluorouracil, combinations


[L01BC] Pyrimidine analogues


[L01B] ANTIMETABOLITES


[L01] ANTINEOPLASTIC AGENTS


[L] Antineoplastic and immunomodulating agents


L01BC02 Fluorouracil


[L01BC] Pyrimidine analogues


[L01B] ANTIMETABOLITES


[L01] ANTINEOPLASTIC AGENTS


[L] Antineoplastic and immunomodulating agents


Toxicity Dose Time Species Model Method Action Positive criterion Reference
APOPTOSIS 0.5 - 800 μM Colo320; DLD1; HT29; LoVo; SW480 increase 164

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 166 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 55 of 166 companies. For more detailed information, please visit ECHA C&L website


Of the 14 notification(s) provided by 111 of 166 companies with hazard statement code(s):


H301 (98.2%): Toxic if swallowed [Danger Acute toxicity, oral]


H312 (53.15%): Harmful in contact with skin [Warning Acute toxicity, dermal]


H315 (55.86%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (55.86%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (54.05%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H340 (54.95%): May cause genetic defects [Danger Germ cell mutagenicity]


H360 (58.56%): May damage fertility or the unborn child [Danger Reproductive toxicity]


H412 (36.04%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]


H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]


H360: May damage fertility or the unborn child [Danger Reproductive toxicity]


H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


P201, P202, P260, P264, P270, P281, P301+P310, P308+P313, P314, P321, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 oral 115mg/kg (115mg/kg) Journal of Medicinal Chemistry. Vol. 21, Pg. 738, 1978.
dog LD50 oral 30mg/kg (30mg/kg) gastrointestinal: nausea or vomiting Oyo Yakuri. Pharmacometrics. Vol. 16, Pg. 303, 1978.
mouse LD50 subcutaneous 169mg/kg (169mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
hamster LD10 parenteral 140mg/kg (140mg/kg) Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
rat LD50 subcutaneous 217mg/kg (217mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
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.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg) Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 7, Pg. 100, 1977.
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 intravenous 245mg/kg (245mg/kg) Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 569, 1971.
mouse LD50 intravenous 81mg/kg (81mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
rabbit LD50 oral 18900ug/kg (18.9mg/kg) Kiso to Rinsho. Clinical Report. Vol. 8, Pg. 2603, 1974.
rat LD50 oral 230mg/kg (230mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
women TDLo intravenous 150mg/kg/17W- (150mg/kg) blood: other hemolysis with or without anemia British Journal of Haematology. Vol. 65, Pg. 357, 1987.
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 parenteral 500mg/kg (500mg/kg) Recent Results in Cancer Research. Vol. 52, Pg. 76, 1975.
rat LD50 rectal 884mg/kg (884mg/kg) Kiso to Rinsho. Clinical Report. Vol. 12, Pg. 1309, 1978.
mouse LD50 unreported 171mg/kg (171mg/kg) Cancer Research. Vol. 46, Pg. 2703, 1986.
women TDLo intravenous 27mg/kg/4D-C (27mg/kg) cardiac: other changes British Medical Journal. Vol. 294, Pg. 125, 1987.
mouse LD50 intracrebral 41600ug/kg (41.6mg/kg) Chemotherapy Vol. 15, Pg. 519, 1967.
human TDLo intravenous 6mg/kg/3D (6mg/kg) British Medical Journal. Vol. 1, Pg. 547, 1978.
human TDLo oral 450mg/kg/30D (450mg/kg) 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 LDLo intratracheal 200mg/kg (200mg/kg) Toxicology Letters. Vol. 30, Pg. 63, 1986.
rat LD50 intraperitoneal 70mg/kg (70mg/kg) Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 569, 1971.

  • Actinic keratosis

  • Bowen's disease

  • Cervix carcinoma

  • Colon cancer

  • Dihydropyrimidine dehydrogenase deficiency

  • Hyperkeratosis

  • Oesophageal carcinoma

  • Renal cell carcinoma

  • Seborrhoeic keratosis

  • Skin cancer

  • Application site reaction (0.946)

  • Eye irritation

  • Musculoskeletal discomfort

  • Myalgia

  • Sinusitis

  • (5-fluorouracil)5-Fluoro-1H-pyrimidine-2,4-dione 1-fluoro-1h-pyrimidine-2,4-dione 191047-65-1
    1upf 2,3H)-Pyrimidinedione, 5-fluoro- 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-
    2,4-Dihydroxy-5-fluoropyrimidine 2,4-Dihydroxy-5-fluoropyrimidine 2,4-Dioxo-5-fluoropryimidine
    2,4-Dioxo-5-fluoropyrimidine 2,4-Pyrimidinedione, 5-fluoro- 2794-13-0
    29507-EP2270008A1 29507-EP2270505A1 29507-EP2272827A1
    29507-EP2289892A1 29507-EP2292234A1 29507-EP2292617A1
    29507-EP2295426A1 29507-EP2295427A1 29507-EP2298305A1
    29507-EP2308861A1 29507-EP2311842A2 42164-EP2272827A1
    42164-EP2275420A1 42164-EP2277565A2 42164-EP2277566A2
    42164-EP2277567A1 42164-EP2277568A2 42164-EP2277569A2
    42164-EP2277570A2 42164-EP2277876A1 42164-EP2292280A1
    42164-EP2292614A1 42164-EP2295412A1 42164-EP2295413A1
    42164-EP2295416A2 42164-EP2298748A2 42164-EP2298764A1
    42164-EP2298765A1 42164-EP2298778A1 42164-EP2305642A2
    42164-EP2308833A2 42164-EP2311808A1 42164-EP2311829A1
    42164-EP2311840A1 4CA-0544 5 Fluorouracil
    5-FU 5-FU 5-FU (TN)
    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-Fluoracyl 5-Fluoro-1H-pyrimidine-2,4-dione (5-FU) 5-Fluoro-1H-pyrimidine-2,4-dione (5-Fluorouracil)
    5-Fluoro-1H-pyrimidine-2,4-dione(5-FU) 5-Fluoro-1H-pyrimidine-2,4-dione(5-FUra) 5-Fluoro-1H-pyrimidine-2,4-dione(5-fluoro uracil)
    5-Fluoro-1H-pyrimidine-2,4-dione(5-fluorouracil)(5-FU) 5-Fluoro-1H-pyrimidine-2,4-dione(5FU) 5-Fluoro-2,3H)-pyrimidinedione
    5-Fluoro-2,4(1H,3H)-pyrimidinedione 5-Fluoro-2,4(1H,3H)-pyrimidinedione 5-Fluoro-2,4-(1H,3H)-pyrimidinedione
    5-Fluoro-2,4-pyrimidinedione 5-Fluoropyrimidin-2,4-diol 5-Fluoropyrimidine-2,4-dione
    5-Fluorouracil 5-Fluorouracil, 99% 5-Fluorouracil, >=99% (HPLC), powder
    5-Fluorouracil, Vetec(TM) reagent grade, >=99% 5-Fluorouracil, analytical standard 5-Fluorouracil, certified reference material, TraceCERT(R)
    5-Fluoruracil 5-Fluoruracil [German] 5-Fluracil
    5-Ftouracyl 5-florouracil 5-fluoro uracil
    5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione 5-fluoro-1,3-dihydropyrimidine-2,4-dione 5-fluoro-1H-pyrimidine-2,4-dione
    5-fluoro-2,4-Pyrimidinediol 5-fluoro-2,4-dioxo-pyrimidin 5-fluoro-pyrimidine-2,4-diol
    5-fluoro-uracil 5-fluoropyrimidine-2,4(1H,3H)-dione 5-fluoropyrimidine-2,4-diol
    5-fluorouacil 5-fluorourasil 5-fluorpyrimidin-2,4-diol
    51-21-8 51F218 5F-uracil
    5FU 7375-EP2269989A1 7375-EP2269994A1
    7375-EP2270008A1 7375-EP2270018A1 7375-EP2272827A1
    7375-EP2272832A1 7375-EP2275102A1 7375-EP2275412A1
    7375-EP2275413A1 7375-EP2277876A1 7375-EP2280012A2
    7375-EP2281563A1 7375-EP2281815A1 7375-EP2287156A1
    7375-EP2289892A1 7375-EP2292233A2 7375-EP2292614A1
    7375-EP2292615A1 7375-EP2292617A1 7375-EP2295416A2
    7375-EP2295426A1 7375-EP2295427A1 7375-EP2298748A2
    7375-EP2298768A1 7375-EP2298772A1 7375-EP2298780A1
    7375-EP2301928A1 7375-EP2301933A1 7375-EP2305219A1
    7375-EP2305243A1 7375-EP2305640A2 7375-EP2305642A2
    7375-EP2305671A1 7375-EP2305689A1 7375-EP2308833A2
    7375-EP2308839A1 7375-EP2308855A1 7375-EP2308861A1
    7375-EP2311807A1 7375-EP2311808A1 7375-EP2311825A1
    7375-EP2311827A1 7375-EP2311829A1 7375-EP2311840A1
    7375-EP2314590A1 7375-EP2316459A1 7375-EP2316831A1
    7375-EP2316834A1 7375-EP2316974A1 7375-EP2374454A1
    766-63-2 AB1000177 AC-11201
    ACMC-1ATRK AI3-25297 AK-46307
    AKOS000119162 AKOS003237897 AKOS008044307
    AM20100252 ANW-31214 Adrucil
    Adrucil (Fluorouracil) Adrucil (ICN) Adrucil (TN)
    Adrucil(Fluorouracil) Arumel BBL009635
    BCP02083 BCP9000239 BCPP000428
    BDBM50340677 BRD-K24844714-001-02-1 BSPBio_002048
    C07649 C4H3FN2O2 CAS-51-21-8
    CCG-39879 CCRIS 2582 CF0033
    CHEBI:46345 CHEMBL185 CPD000038082
    CS-0993 CTK1H0569 CTK8H4220
    Carac Carac (TN) Carzonal
    Certified Reference Material Cinco FU D00584
    DB-051923 DB-065735 DB00544
    DL-399 DSSTox_CID_634 DSSTox_GSID_20634
    DSSTox_RID_75705 DTXSID2020634 DivK1c_000054
    EC 200-085-6 EINECS 200-085-6 EU-0100536
    Effluderm Effluderm (free base) Efudex
    Efudix Efurix F 6627
    F0151 FT-0082524 FT-0601511
    FT-0707652 FU Fluoro Uracil
    Fluoro-uracile Fluoro-uracilo Fluoroblastin
    Fluoroplex Fluoroplex (TN) Fluorouracil (5-Fluoracil, 5-FU)
    Fluorouracil (Adrucil) Fluorouracil (JP17/USP/INN) Fluorouracil - Adrucil
    Fluorouracil Cream Fluorouracil [USAN:INN:BAN:JAN] Fluorouracil [USAN:USP:INN:BAN:JAN]
    Fluorouracil, 5- Fluorouracil, British Pharmacopoeia (BP) Reference Standard Fluorouracil, European Pharmacopoeia (EP) Reference Standard
    Fluorouracil, Pharmaceutical Secondary Standard Fluorouracil, United States Pharmacopeia (USP) Reference Standard Fluorouracil, meets USP testing specifications
    Fluorouracile Fluorouracile [DCIT] Fluorouracilo
    Fluorouracilo [INN-Spanish] Fluorouracilum Fluorouracilum [INN-Latin]
    Fluouracil Fluracil Fluracilum
    Fluri Fluril Fluro Uracil
    Fluroblastin Ftoruracil GHASVSINZRGABV-UHFFFAOYSA-N
    GTPL4789 HMS1920O18 HMS2090I04
    HMS2091F19 HMS3259O03 HMS3261L13
    HMS3654K22 HMS3715H03 HMS500C16
    HSDB 3228 HY-90006 IDI1_000054
    InChI=1/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9 KBio1_000054 KBio2_001321
    KBio2_003889 KBio2_006457 KBio3_001268
    KBioGR_001253 KBioSS_001321 KS-00000DY3
    KS-5129 KSC270K6T Kecimeton
    LP00536 LS-153 LS40596
    Lopac-F-6627 Lopac0_000536 MCULE-6338086431
    MFCD00006018 MLS000069498 MLS002415705
    NC00454 NCGC00015442-01 NCGC00015442-02
    NCGC00015442-03 NCGC00015442-04 NCGC00015442-05
    NCGC00015442-06 NCGC00015442-07 NCGC00015442-08
    NCGC00015442-09 NCGC00015442-10 NCGC00015442-11
    NCGC00015442-12 NCGC00015442-15 NCGC00015442-16
    NCGC00091349-01 NCGC00091349-02 NCGC00091349-03
    NCGC00091349-04 NCGC00091349-05 NCGC00091349-07
    NCGC00091349-08 NCGC00254023-01 NCGC00259884-01
    NCGC00261221-01 NCI60_001652 NINDS_000054
    NSC 19893 NSC-19893 NSC-757036
    NSC19893 NSC757036 Opera_ID_134
    Pharmakon1600-01500305 Phthoruracil Phtoruracil
    Q238512 Queroplex RW2456
    Ro 2-9757 Ro-2-9757 Ro-29757
    SAM002264615 SBB085751 SBI-0050519.P004
    SC-09038 SCHEMBL3646 SMR000038082
    SPBio_000291 SPECTRUM1500305 SR-01000075881
    SR-01000075881-1 SR-01000075881-3 SR-01000075881-5
    SRI-10792-04 SRI-10792-05 SRI-10792-06
    SRI-10792_07 SRI-10792_08 ST45025877
    STK297802 STL367375 SW199617-3
    Spectrum2_000076 Spectrum3_000434 Spectrum4_000557
    Spectrum5_000718 Spectrum_000841 Timazin
    Tolak Tox21_110150 Tox21_110150_1
    Tox21_202335 Tox21_300112 Tox21_500536
    U 8953 U-8953 U3P01618RT
    UNII-U3P01618RT UPCMLD-DP130 UPCMLD-DP130:001
    URF Ulup Uracil, 5-fluoro-
    W-202929 W-5036 W-60379
    WLN: T6MVMVJ EF Z275128052 ZINC38212689
    fluorouracil inhibits thymilidate synthetase pyrimidine antimetabolite: inhibits nucleic acid replication
    s1209 tetratogen

    DrugBank Name Fluorouracil
    DrugBank DB00544
    CAS Number 1004-03-1, 191047-64-0, 191047-65-1, 191115-88-5, 51-21-8, 68941-95-7, 790299-79-5, 90344-84-6
    PubChem Compound 3385
    KEGG Compound ID C07649
    KEGG Drug D00584
    PubChem.Substance 46508557
    ChEBI 46345
    PharmGKB PA128406956
    ChemSpider 3268
    BindingDB 50340677.0
    TTD DAP000829
    Wikipedia Fluorouracil
    HET URF
    DPD 6311

    1. Ya?ez et al., 2003