Chloroquinoxaline sulfonamide

Modify Date: 2024-01-18 16:18:52

Chloroquinoxaline sulfonamide Structure
Chloroquinoxaline sulfonamide structure
Common Name Chloroquinoxaline sulfonamide
CAS Number 97919-22-7 Molecular Weight 334.78100
Density 1.569g/cm3 Boiling Point 576.3ºC at 760mmHg
Molecular Formula C14H11ClN4O2S Melting Point N/A
MSDS N/A Flash Point 302.3ºC

 Use of Chloroquinoxaline sulfonamide


Chloroquinoxaline sulfonamide (Chloroquinoxaline), a structural analogue of sulfaquinoxaline, is a topoisomerase II alpha/beta poison. Chloroquinoxaline sulfonamide is used to control coccidiosis in poultry, rabbit, sheep, and cattle[1]. Antitumor activity[2].

 Names

Name 4-amino-N-(5-chloroquinoxalin-2-yl)benzenesulfonamide
Synonym More Synonyms

 Chloroquinoxaline sulfonamide Biological Activity

Description Chloroquinoxaline sulfonamide (Chloroquinoxaline), a structural analogue of sulfaquinoxaline, is a topoisomerase II alpha/beta poison. Chloroquinoxaline sulfonamide is used to control coccidiosis in poultry, rabbit, sheep, and cattle[1]. Antitumor activity[2].
Related Catalog
Target

topoisomerase II alpha

topoisomerase II beta

In Vitro The Chloroquinoxaline sulfonamide IC50 for CV-1cells, obtained using an MTT cytotoxicity assay, was 1.8 mM. Chloroquinoxaline sulfonamide causes dose-dependent protein-DNA cross-links to CV-1 monkey kidney cell chromosomal DNA when drug treatment was terminated by lysis with GuHCl. Chloroquinoxaline sulfonamide-induced protein-DNA cross-links in CV-1 cells. Chloroquinoxaline sulfonamide-induced topoisomerase II-DNA cross-links[1]. Chloroquinoxaline sulfonamide (Chloroquinoxaline), a chlorinated derivative of sulfaquinoxaline, inhibits proliferation of murine B16 melanoma cells, but only when relatively high drug concentrations (1 mM) are used[2]. Cell Proliferation Assay[2] Cell Line: B16 murine melanoma cells Concentration: 10 μM, 100 μM, 1 mM Incubation Time: 24, 48, 72 hours Result: Inhibited proliferation of murine B16 melanoma cells, but only when relatively high drug concentrations (1 mM) were used.
References

[1]. Gao H, et al. Chloroquinoxaline sulfonamide (NSC 339004) is a topoisomerase IIalpha/beta poison. Cancer Res. 2000 Nov 1;60(21):5937-40.

[2]. Branda RF, et al. Cellular pharmacology of chloroquinoxaline sulfonamide and a related compound in murine B16 melanoma cells. Biochem Pharmacol. 1988 Dec 1;37(23):4557-64.

 Chemical & Physical Properties

Density 1.569g/cm3
Boiling Point 576.3ºC at 760mmHg
Molecular Formula C14H11ClN4O2S
Molecular Weight 334.78100
Flash Point 302.3ºC
Exact Mass 334.02900
PSA 106.35000
LogP 4.40120
Index of Refraction 1.734

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DA9467000
CHEMICAL NAME :
Benzenesulfonamide, 4-amino-N-(5-chloro-2-quinoxalinyl)-
CAS REGISTRY NUMBER :
97919-22-7
BEILSTEIN REFERENCE NO. :
0312075
LAST UPDATED :
199612
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C14-H11-Cl-N4-O2-S
MOLECULAR WEIGHT :
334.80

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes Skin and Appendages - primary irritation (after topical exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB87-128658
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
607 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes Skin and Appendages - primary irritation (after topical exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB87-128658
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
12 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes Skin and Appendages - primary irritation (after topical exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB87-128658 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
600 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB87-128658

 Safety Information

HS Code 2935009090

 Synthetic Route

~%

Chloroquinoxaline sulfonamide Structure

Chloroquinoxali...

CAS#:97919-22-7

Literature: Wolf et al. Journal of the American Chemical Society, 1949 , vol. 71, p. 6,7

~%

Chloroquinoxaline sulfonamide Structure

Chloroquinoxali...

CAS#:97919-22-7

Literature: Wolf et al. Journal of the American Chemical Society, 1949 , vol. 71, p. 6,7

~%

Chloroquinoxaline sulfonamide Structure

Chloroquinoxali...

CAS#:97919-22-7

Literature: Wolf et al. Journal of the American Chemical Society, 1949 , vol. 71, p. 6,7

 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

Chlorsulfaquinoxaline
chloroquinoxaline sulfonamide
Sulfanilsaeure-(5-chlor-chinoxalin-2-ylamid)
4-Amino-N-(5-chloro-2-quinoxalinyl)benzenesulfonamide
5-Chloroquinoxaline-2-sulfanilamide
sulfanilic acid-(5-chloro-quinoxalin-2-ylamide)