Carbutamide

Modify Date: 2024-01-04 21:00:01

Carbutamide Structure
Carbutamide structure
Common Name Carbutamide
CAS Number 339-43-5 Molecular Weight 271.33600
Density 1.266g/cm3 Boiling Point N/A
Molecular Formula C11H17N3O3S Melting Point 144-145ºC
MSDS N/A Flash Point N/A

 Use of Carbutamide


Carbutamide (BZ-55) is an orally active and first-generation sulfonylurea with hypoglycemic activity[1].

 Names

Name 1-(4-aminophenyl)sulfonyl-3-butylurea
Synonym More Synonyms

 Carbutamide Biological Activity

Description Carbutamide (BZ-55) is an orally active and first-generation sulfonylurea with hypoglycemic activity[1].
Related Catalog
In Vivo Carbutamide is a sulfonylurea derivative that will cause hypoglycemia when administered by mouth to normal animals[2].
References

[1]. Kleinsorge H, et al. Carbutamide--the first oral antidiabetic. A retrospect. Exp Clin Endocrinol Diabetes. 1998;106(2):149-51.

[2]. ROOT MA, et al. Pharmacology of carbutamide (p-aminophenylsulfonyl butylcarbamide). J Pharmacol Exp Ther. 1957 Apr;119(4):468-78.

 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

 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

~%

Carbutamide Structure

Carbutamide

CAS#:339-43-5

Literature: Dissertationes Pharmaceuticae, , vol. 9, p. 205,208 Chem.Abstr., , p. 6248

~%

Carbutamide Structure

Carbutamide

CAS#:339-43-5

Literature: Dissertationes Pharmaceuticae, , vol. 9, p. 205,208 Chem.Abstr., , p. 6248

~%

Carbutamide Structure

Carbutamide

CAS#:339-43-5

Literature: Journal of the Chemical Society [Section] C: Organic, , p. 701 - 702

~%

Carbutamide Structure

Carbutamide

CAS#:339-43-5

Literature: Journal of Medicinal and Pharmaceutical Chemistry, , vol. 5, p. 231 - 239

~%

Carbutamide Structure

Carbutamide

CAS#:339-43-5

Literature: Indian Journal of Applied Chemistry, , vol. 22, p. 38

 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%

 Synonyms

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