Benzthiazide

Names

[ CAS No. ]:
91-33-8

[ Name ]:
Benzthiazide

[Synonym ]:
Lemazide
benzotiazide
Exna
Benzothiazide
3-(benzylsulfanylmethyl)-6-chloro-1,1-dioxo-4H-1λ<sup>6</sup>,2,4-benzothiadiazine-7-sulfonamide
Benzthiazidum
EINECS 202-061-0
MFCD00078969
Freeuril
Aquatag
Dihydrex
Diucen
Benzotiazida

Biological Activity

[Description]:

Benzthiazide is a long-acting diuretic[1] and a hypertension agent. Benzthiazide is an inhibitor of carbonic anhydrase 9 (CA9), with Kis of 8.0, 8.8 and 10 nM for CA9, CA2 and CA1, respectively. Benzthiazide also suppresses proliferation of cancer cells[2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Carbonic Anhydrase

Research Areas >> Cardiovascular Disease

[Target]

Ki: 8.0 nM (CA9), 8.8 nM (CA2), 10 nM (CA1)[2]

[In Vitro]

Benzthiazide (0.4, 2, 10 μM) suppresses proliferation of cancer cell under hypoxic conditions in a dose-dependent manner . Benzthiazide is an inhibitor of carbonic anhydrase 9 (CA9), with Kis of 8.0, 8.8 and 10 nM for CA9, CA2 and CA1, respectively[2].

[In Vivo]

Benzthiazide (1, 1.5 mg/100 g BW) causes a marked decrease in urinary calcium excretion and the dissociation of calcium and sodium excretion in hyperprolactinemic rats[1].

[References]

[1]. Adler RA, et al. Hypercalciuria in hyperprolactinemic rats: effects of benzthiazide. Metabolism. 1986 Jul;35(7):668-72.

[2]. Lee HS, et al. Rational drug repositioning guided by an integrated pharmacological network of protein, disease and drug. BMC Syst Biol. 2012 Jul 2;6:80.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4176 (rough estimate)

[ Boiling Point ]:
680.6 °C at 760 mmHg

[ Melting Point ]:
231-232° (U.S. patent); mp 238-239° (P'an)

[ Molecular Formula ]:
C₁₅H₁₄ClN₃O₄S₃

[ Molecular Weight ]:
431.93700

[ Flash Point ]:
365.4 °C

[ Exact Mass ]:
430.98300

[ PSA ]:
160.75000

[ LogP ]:
4.86900

[ Index of Refraction ]:
1.6100 (estimate)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DK8400000

CHEMICAL NAME :: 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3-((benzylthio)menthyl)-6-chloro-, 1,1-dioxide

CAS REGISTRY NUMBER :: 91-33-8

LAST UPDATED :: 199610

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C15-H14-Cl-N3-O4-S3

MOLECULAR WEIGHT :: 431.95

WISWESSER LINE NOTATION :: T66 BSWM ENJ D1S1R& HG ISZW

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 :: >10 gm/kg

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

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 128,122,1960

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 422 mg/kg

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

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 128,122,1960

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,778,1982

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 410 mg/kg

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

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 128,122,1960

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 128,122,1960

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 200 mg/kg

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

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 128,122,1960 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84680 No. of Facilities: 68 (estimated) No. of Industries: 1 No. of Occupations: 6 No. of Employees: 2770 (estimated)

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H317-H334

[ Precautionary Statements ]:
P261-P280-P342 + P311

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
42/43

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DK8400000

[ HS Code ]:
2935009090

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

Interactions of diuretics with a neutral temperature-responsive polymer: study by capillary electroporesis and dynamic light scattering.

J. Capill. Electrophor. Microchip Technol. 6(5-6) , 163-8, (1999)

Interactions between diuretics and a recently synthesized temperature-responsive neutral copolymer, poly(N-isopropyl acrylamide) (PNIPA) grafted with poly(ethyleneoxide) (PEO) (PNIPA-g-PEO) were inves...

Rational drug repositioning guided by an integrated pharmacological network of protein, disease and drug.

BMC Syst. Biol. 6 , 80, (2012)

The process of drug discovery and development is time-consuming and costly, and the probability of success is low. Therefore, there is rising interest in repositioning existing drugs for new medical i...

Rapid screening for diuretic doping agents in urine by C60-assisted laser-desorption-ionization-time-of-flight mass spectrometry.

J. Anal. Toxicol. 23(5) , 337-42, (1999)

This study describes a matrix-assisted laser-desorption-ionization (MALDI) mass spectrometry for rapid screening of 12 diuretics in spiked urine. C60 is used as the matrix for MALDI. Diuretics are dir...