Carbutamide

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Names

[ CAS No. ]:
339-43-5

[ Name ]:
Carbutamide

[Synonym ]:
Glybutamide
1-butyl-3-sulfanilylurea
Bukarban
N-Butyl-N'-sulfanilyl-harnstoff
Glucidoral
Bucarban
Carbutamid
Butisulfina
tolbutamide
N-butyl-N'-sulfanilyl-urea
Diaboral
Glucofren
4-amino-N-butylcarbamoyl-benzenesulfonamide
Orasulin
Carbutamide

Chemical & Physical Properties

[ Density]:
1.266g/cm3

[ Melting Point ]:
144-145ºC

[ Molecular Formula ]:
C₁₁H₁₇N₃O₃S

[ Molecular Weight ]:
271.33600

[ Exact Mass ]:
271.09900

[ PSA ]:
109.67000

[ LogP ]:
3.50060

[ Index of Refraction ]:
1.564

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YS4200000

CHEMICAL NAME :: Urea, 1-butyl-3-sulfanilyl-

CAS REGISTRY NUMBER :: 339-43-5

BEILSTEIN REFERENCE NO. :: 2218915

LAST UPDATED :: 199707

DATA ITEMS CITED :: 26

MOLECULAR FORMULA :: C11-H17-N3-O3-S

MOLECULAR WEIGHT :: 271.37

WISWESSER LINE NOTATION :: ZR DSWMVM4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7800 mg/kg

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

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 25,93,1962

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 980 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold

REFERENCE :: DIAEAZ Diabetes. (American Diabetes Assoc., 2 Park Ave., New York, NY 10016) V.1- 1952- Volume(issue)/page/year: 6,2,1957

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2800 mg/kg

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

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 25,93,1962

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

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

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD691-490

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2640 mg/kg

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

REFERENCE :: DIAEAZ Diabetes. (American Diabetes Assoc., 2 Park Ave., New York, NY 10016) V.1- 1952- Volume(issue)/page/year: 6,2,1957

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1920 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold

REFERENCE :: DIAEAZ Diabetes. (American Diabetes Assoc., 2 Park Ave., New York, NY 10016) V.1- 1952- Volume(issue)/page/year: 6,2,1957 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 307 gm/kg/29W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - other changes Related to Chronic Data - death

REFERENCE :: DIAEAZ Diabetes. (American Diabetes Assoc., 2 Park Ave., New York, NY 10016) V.1- 1952- Volume(issue)/page/year: 6,2,1957

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 6 gm/kg/24D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from stomach Endocrine - other changes Related to Chronic Data - death

REFERENCE :: DIAEAZ Diabetes. (American Diabetes Assoc., 2 Park Ave., New York, NY 10016) V.1- 1952- Volume(issue)/page/year: 6,2,1957

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 40950 mg/kg/78W-I

TOXIC EFFECTS :: Blood - hemorrhage Nutritional and Gross Metabolic - dehydration Related to Chronic Data - death

REFERENCE :: HEPHD2 Handbook of Experimental Pharmacology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.50- 1978- Volume(issue)/page/year: 119,185,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 36500 mg/kg/10W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - chronic pulmonary edema Lungs, Thorax, or Respiration - other changes Related to Chronic Data - death

REFERENCE :: DIAEAZ Diabetes. (American Diabetes Assoc., 2 Park Ave., New York, NY 10016) V.1- 1952- Volume(issue)/page/year: 6,2,1957 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1056 mg/kg

SEX/DURATION :: female 7-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: PSDTAP Proceedings of the European Society for the Study of Drug Toxicity. (Princeton, NJ 08540) V.1-15, 1963-74. For publisher information, see PESTD5. Volume(issue)/page/year: 11,151,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 28,616,1965

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5 gm/kg

SEX/DURATION :: female 9-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - homeostasis

REFERENCE :: ANENAG Annales d'Endocrinologie. (Masson Editeur, 120 Blvd. Saint-Germain, F-25280 Paris Cedex 06, France) V.1- 1939- Volume(issue)/page/year: 19,167,1958

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3200 mg/kg

SEX/DURATION :: female 7-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: PSDTAP Proceedings of the European Society for the Study of Drug Toxicity. (Princeton, NJ 08540) V.1-15, 1963-74. For publisher information, see PESTD5. Volume(issue)/page/year: 11,151,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 gm/kg

SEX/DURATION :: female 1-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear

REFERENCE :: BANMAC Bulletin de l'Academie Nationale de Medicine (Paris). (Imprimeries Reunies de Chambray, 226, route d'Apremont, F-73490 La Ravoire, France) V.1- 1836- Volume(issue)/page/year: 143,238,1959

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 3 gm/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear

REFERENCE :: AKGIAO Akushcherstvo i Ginekologiya (Moscow). (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) No.1- 1936- Volume(issue)/page/year: 42(12),35,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 3 gm/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: AKGIAO Akushcherstvo i Ginekologiya (Moscow). (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) No.1- 1936- Volume(issue)/page/year: 42(12),35,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 1 gm/kg

SEX/DURATION :: female 1 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: AKGIAO Akushcherstvo i Ginekologiya (Moscow). (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) No.1- 1936- Volume(issue)/page/year: 42(12),35,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 4400 mg/kg

SEX/DURATION :: female 5-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: BSVMA8 Bulletin de la Societe des Sciences Veterinaires et de Medecine Comparee de Lyon. (Lyons, France) V.1-83, 1898-1981. Volume(issue)/page/year: 71,289,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 4400 mg/kg

SEX/DURATION :: female 5-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: BSVMA8 Bulletin de la Societe des Sciences Veterinaires et de Medecine Comparee de Lyon. (Lyons, France) V.1-83, 1898-1981. Volume(issue)/page/year: 71,289,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 8800 mg/kg

SEX/DURATION :: female 5-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: BSVMA8 Bulletin de la Societe des Sciences Veterinaires et de Medecine Comparee de Lyon. (Lyons, France) V.1-83, 1898-1981. Volume(issue)/page/year: 71,289,1969 *** REVIEWS *** TOXICOLOGY REVIEW CLPTAT Clinical Pharmacology and Therapeutics (St. Louis). (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1960- Volume(issue)/page/year: 5,480,1964 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966 TOXICOLOGY REVIEW LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 2,408,1963

Safety Information

[ Hazard Codes ]:
Xn

[ HS Code ]:
2935009090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

1-butyl-3-(4-nitrophenyl)sulfonylurea
N-butylcarbamoyl chloride
1,3-Dibutylurea
sodium,(4-aminophenyl)sulfonylazanide
Sulfanilamide
1-Isocyanatobutane
N-butyl-N'-nitrourea

DownStream

N-Butylurea
4-isocyanato-N-(oxomethylidene)benzenesulfonamide

Customs

[ HS Code ]: 2935009090

[ Summary ]:
2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Related Compounds

Carbutamide-d9
N-(4-Methyl-3-nitro-2-pyridinyl)-2-quinoxalinamine
1-(2-(4-Fluorophenyl)-2-morpholinoethyl)-3-(thiophen-2-yl)urea
N-(2-chlorobenzyl)-2-(5-methoxy-2-(((4-methylpyrimidin-2-yl)thio)methyl)-4-oxopyridin-1(4H)-yl)acetamide
(4Z)-4-[(4-carbamoylphenyl)imino]-N-(4-methylphenyl)-3-oxa-13-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1,5,7,9(17)-tetraene-5-carboxamide
4-Nitro-N-pentyl-5-benzothiazolamine
3-Piperidin-1-yl-1-[4-[4-(3-piperidin-1-ylpropanoyl)phenyl]phenyl]propan-1-one
1-(4-(2-(1H-pyrazol-1-yl)ethyl)piperazin-1-yl)-2-(1H-indol-3-yl)ethanone
1-(4-(2-(1H-pyrazol-1-yl)ethyl)piperazin-1-yl)-2-(4-chlorophenoxy)ethanone
2-{[1-(4-chlorophenyl)ethyl](cyclopropyl)amino}-N-(1-cyano-1-cyclopropylethyl)acetamide
2-[4-(4-Methoxypyrimidin-2-yl)piperazin-1-yl]-1-(4-phenylpiperazin-1-yl)ethan-1-one

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