Carmofur

Names

[ Name ]:
Carmofur

[Synonym ]:
Hexylcarbamoyl fluorouracil
1(2H)-Pyrimidinecarboxamide, 5-fluoro-N-hexyl-3,4-dihydro-2,4-dioxo-
5-Fluoro-N-hexyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinecarboxamide
Mifurol
Uracil, 5-fluoro-1-hexylcarbamoyl-
5-Fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
Carmofur
HCFU
5-Fluoro-1-(hexylcarbamoyl)uracil
5-fluoro-1-(n-hexylcarbamoyl)uracil
MFCD00866284
1-hexylcarbamoyl-5-fluorouracil
Carmofurum [INN-Latin]
5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-carboxylic acid hexylamide
1-(n-Hexylcarbamoyl)-5-fluorouracil
Yamaful

Biological Activity

[Description]:

Carmofur is a derivative of fluorouracil, an antimetabolite used as an antineoplastic agent. Target: Nucleoside antimetabolite/analogCarmofur, which is used in the clinic to treat colorectal cancers, is a potent AC inhibitor and that this property is essential to its anti-proliferative effects. Carmofur inhibited AC activity with a median effective concentration (IC50) of 29 ± 5 nM (mean ± standard error of the mean, s.e.m.; n = 4), whereas 5-FU had no such effect (IC50>1 mM). systemic administration of carmofur (10 or 30 mg-kg-1, intraperitoneal, i.p.) to mice produced a dose-dependent inhibition of AC activity in various tissues, including lungs and brain cortex.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Research Areas >> Cancer

[References]

[1]. Realini, N., et al., Discovery of highly potent acid ceramidase inhibitors with in vitro tumor chemosensitizing activity. Sci Rep, 2013. 3: p. 1035.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Melting Point ]:
110-111

[ Molecular Formula ]:
C₁₁H₁₆FN₃O₃

[ Molecular Weight ]:
257.261

[ Exact Mass ]:
257.117584

[ PSA ]:
83.96000

[ LogP ]:
2.58

[ Index of Refraction ]:
1.525

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UV7714000

CHEMICAL NAME :: 1(2H)-Pyrimidinecarboxamide, 3,4-dihydro-2,4-dioxo-5-fluoro-N-hexyl-

CAS REGISTRY NUMBER :: 61422-45-5

BEILSTEIN REFERENCE NO. :: 0888898

LAST UPDATED :: 199612

DATA ITEMS CITED :: 21

MOLECULAR FORMULA :: C11-H16-F-N3-O3

MOLECULAR WEIGHT :: 257.30

WISWESSER LINE NOTATION :: T6NVMVJ AVM6 EF

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 1152 mg/kg/14W-I

TOXIC EFFECTS :: Brain and Coverings - encephalitis Behavioral - hallucinations, distorted perceptions Behavioral - ataxia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1749 mg/kg/29W-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - toxic psychosis Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 268 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 93 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 260 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1129 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - excitement

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 96 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 532 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 65 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 55 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6 gm/kg/30D-C

TOXIC EFFECTS :: Blood - changes in erythrocyte (RBC) count Related to Chronic Data - death Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 182 gm/kg/26W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - interstitial nephritis Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1365 mg/kg/13W-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1820 mg/kg/26W-I

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 275 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 110 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 550 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3 gm/kg

SEX/DURATION :: male 4 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 19,363,1980

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H361

[ Precautionary Statements ]:
P281-P301 + P310

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
60-61-25

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 2811 6.1 / PGII

[ HS Code ]:
2933599090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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