chlorpropamide

Names

[ CAS No. ]:
94-20-2

[ Name ]:
chlorpropamide

[Synonym ]:
Chloropropamide
Benzenesulfonamide, 4-chloro-N-((propylamino)carbonyl)-
chlorpropamide
Benzenesulfonamide, 4-chloro-N-[(Z)-hydroxy(propylimino)methyl]-
EINECS 202-314-5
4-chloro-N-(propylaminocarbonyl)benzenesulfonamide
N-[(4-Chlorophenyl)sulfonyl]-N'-propylcarbamimidic acid
MFCD00079004
Benzenesulfonamide, 4-chloro-N-[(propylamino)carbonyl]-
clorpropamida [INN_es]
1-(4-chlorophenyl)sulfonyl-3-propylurea
4-Chloro-N-(propylcarbamoyl)benzenesulfonamide

Biological Activity

[Description]:

Chlorpropamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM).Target:Chlorpropamide belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin.Chlorpropamide is not recommended for the treatment of NIDDM as it increases blood pressure and the risk of retinopathy. Up to 80% of the single oral dose of chlorpropramide is metabolized, likely in the liver; 80-90% of the dose is excreted in urine as unchanged drug and metabolites.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Na+/K+ ATPase

Research Areas >> Endocrinology

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
433.5±47.0 °C at 760 mmHg

[ Melting Point ]:
128 °C

[ Molecular Formula ]:
C₁₀H₁₃ClN₂O₃S

[ Molecular Weight ]:
276.740

[ Flash Point ]:
216.0±29.3 °C

[ Exact Mass ]:
276.033539

[ PSA ]:
83.65000

[ LogP ]:
2.80

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.585

[ Stability ]:
Stable. Combustible.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YS6650000

CHEMICAL NAME :: Urea, 1-((p-chlorophenyl)sulfonyl)-3-propyl-

CAS REGISTRY NUMBER :: 94-20-2

BEILSTEIN REFERENCE NO. :: 2218363

LAST UPDATED :: 199706

DATA ITEMS CITED :: 40

MOLECULAR FORMULA :: C10-H13-Cl-N2-O3-S

MOLECULAR WEIGHT :: 276.76

WISWESSER LINE NOTATION :: GR DSWMVM3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 14 mg/kg

TOXIC EFFECTS :: Cardiac - pulse rate increase, without fall in BP Nutritional and Gross Metabolic - changes in potassium Nutritional and Gross Metabolic - metabolic acidosis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Behavioral - coma Endocrine - hypoglycemia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 25 mg/kg/5D-I

TOXIC EFFECTS :: Blood - other hemolysis with or without anemia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 300 mg/kg/4W

TOXIC EFFECTS :: Blood - granulocytopenia Blood - leukopenia Nutritional and Gross Metabolic - body temperature increase

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 83 mg/kg/25D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from large intestine Liver - jaundice, cholestatic

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2150 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 :: 580 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 :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 590 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 :: 1100 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 - mouse

DOSE/DURATION :: 409 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 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 - species unspecified

DOSE/DURATION :: 1039 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

DOSE :: 884 mg/kg

SEX/DURATION :: female 1-35 week(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 840 mg/kg

SEX/DURATION :: female 9-39 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - Apgar score (human only)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 240 mg/kg

SEX/DURATION :: female 32-38 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - biochemical and metabolic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 1358 mg/kg

SEX/DURATION :: female 1-26 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 180 mg/kg

SEX/DURATION :: female 26-39 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 450 mg/kg

SEX/DURATION :: female 26-39 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

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

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

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 - Fertility - abortion Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1800 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 45 mg/kg

SEX/DURATION :: female 1-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :: Rodent - hamster

DOSE/DURATION :: 7100 ug/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 77,349,1980 *** REVIEWS *** TOXICOLOGY REVIEW KDYIA5 Kidney International. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus Secaucus, NJ 07094) V.1- 1972- Volume(issue)/page/year: 10,82,1976 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 BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 1,59,1963 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3997 No. of Facilities: 35 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 311 (estimated) No. of Female Employees: 198 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H312-H332-H351

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YS6650000

[ HS Code ]:
2935009090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

Articles

Sulfa drugs inhibit sepiapterin reduction and chemical redox cycling by sepiapterin reductase.

J. Pharmacol. Exp. Ther. 352(3) , 529-40, (2015)

Sepiapterin reductase (SPR) catalyzes the reduction of sepiapterin to dihydrobiopterin (BH2), the precursor for tetrahydrobiopterin (BH4), a cofactor critical for nitric oxide biosynthesis and alkylgl...

Evaluation of the in vitro/in vivo potential of five berries (bilberry, blueberry, cranberry, elderberry, and raspberry ketones) commonly used as herbal supplements to inhibit uridine diphospho-glucuronosyltransferase.

Food Chem. Toxicol. 72 , 13-9, (2014)

In this study, we evaluated inhibitory potentials of popularly-consumed berries (bilberry, blueberry, cranberry, elderberry, and raspberry ketones) as herbal supplements on UGT1A1, UGT1A4, UGT1A6, UGT...

Evaluation of thein vitro/in vivodrug interaction potential of BST204, a purified dry extract of ginseng, and its four bioactive ginsenosides through cytochrome P450 inhibition/induction and UDP-glucuronosyltransferase inhibition

Food Chem. Toxicol. 68 , 117-27, (2014)

• BST204 is a purified dry extract of ginseng containing high amounts of Rh2 and Rg3. • BST204 had only weak inhibitory effects on nine CYPs and five UGTs. • It is unlikely that BST204 alter pharmacok...