61422-45-5

61422-45-5 structure

Name: Carmofur
Chemical Name: 5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
CAS Number: 61422-45-5
Molecular Formula: C₁₁H₁₆FN₃O₃
Molecular Weight: 257.261
Catalog: API Antineoplastic agents Antimetabolite antineoplastic
Create Date: 2018-03-16 08:00:00
Modify Date: 2026-07-11 17:49:28
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.

Name	5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-carboxamide
Synonyms	1-(N-HEXYLCBAMOYL)-5-FLUOROURACIL 5-FLUORO-1-HEXYLCBAMOYLURACIL 5-Fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide 5-fluoro-N-hexyl-2,4-dioxo-1,2,3,4-tetrahydropyriMidine-1-cboxaMide 5-Fluoro-1-(hexylcarbamoyl)uracil Cmofur //BP 5-Fluoro-N-hexyl-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinecboxamide 5-fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-cboxamide MFCD00866284 1-hexylcarbamoyl-5-fluorouracil 1(2H)-Pyrimidinecboxamide, 3,4-dihydro-2,4-dioxo-5-fluoro-N-hexyl Cmofur Cmofur Carmofurum [INN-Latin] 3,4-dihydro-2,4-dioxo-5-fluoro-n-hexyl-1(2h)-pyrimidinecboxamid Hexylcarbamoyl fluorouracil 2,4-dioxo-5-fluoro-n-hexyl-3,4-dihydro-1(2h)-pyrimidinecboxamidme 5-Fluoro-N-hexyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinecarboxamide Mifurol Cmofur - Bio-X Cmofur > CMOFUR HCFUTM, 3,4-Dihydro-2,4-dioxo-5-fluoro-N-hexylpyrimidine-1(2H)-cboxamide HCFU 1-hexylcbamoyl-5-fluorouracil 5-fluoro-N-hexyl-2,4-dioxopyrimidine-1-cboxamide HCFUTM Cmofur, Antimetabolite agent 1,2,3,4-tetrahydro-2,4-dioxo-5-fluoro-n-hexyl-1-pyrimidinecboxamid 5-fluoro-1-(n-hexylcarbamoyl)uracil 1(2H)-Pyrimidinecboxamide, 5-fluoro-N-hexyl-3,4-dihydro-2,4-dioxo 1-(Hexylcbamyl)-5-fluorouracil Cmofur, 10 mM in DMSO hcfu 5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-carboxylic acid hexylamide 1-(n-Hexylcarbamoyl)-5-fluorouracil 2,4-dioxo-5-fluoro-n-hexyl-1,2,3,4-tetrahydro-1-pyrimidinecboxamide Yamaful

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.

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

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

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 0
DownStream 1
51-21-8

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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