Bumetanide

Names

[ Name ]:
Bumetanide

[Synonym ]:
3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid
Segurex
Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-
EINECS 249-004-6
MFCD00078949
3-(aminosulfonyl)-5-(butylamino)-4-(phenyloxy)benzoic acid
Burinex
Lunetoron
Butinat
Bumetanidum
2-phenoxy-3-butylamino-5-carboxybenzenesulfonamide
Bumex
3-(butylamino-)-4-phenoxy-5-sulfamoylbenzoic acid
Bumetanida
[3H]-Bumetanide
Fordiuran
Bumetanide
Fontego
Lixil
3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acid

Biological Activity

[Description]:

Bumetanide(Ro 10-6338; PF 1593) is an inhibitor of Na(+)-K(+)-2Cl(-) co-transporter (NKCC) with an IC50 of 0.6 uM.IC50 Value: 0.6 uM [1]Target: NKCC (Na-K-Cl cotransporter)in vitro: Cultured chick cardiac cells possess a Na+K+Cl-co-transport system that is inhibited by the "loop diuretics" bumetanide (IC50 = 0.6 microM). The K0.5 values for Cl- and Na+ activation of thebumetanide-sensitive 86Rb+ uptake are 59 mM and 40mM respectively. Bumetanide also inhibits a 22Na+ uptake component that is suppressed when external Cl- or K+ are substituted by impermeant ions. The ratio of bumetanide-sensitive 86Rb+ to 22Na+ uptake is close to 1. The cardiac Na+/K+/Cl- cotransport is a major uptake pathway for Na+ and K+ [1]. Bumetanide inhibits ouabain-resistant 86Rb(K+) influx with IC50of 0.1, 5.0, and 0.05 microM for J774.2, CT2 and J7H1 macrophages, respectively [2]. in vivo:Intraperitoneal injection of 50 or 100 mg bumetanide/kg body weight resulted in an acute and transient hyperglycaemia. Pretreatment with 240 mg probenecid/kg body weight reduced the diuretic effect but potentiated the hyperglycaemic effect of bumetanide (50 mg/kg body weight). The glucose tolerance was impaired, and there was an elevated serum glucose and glucose/insulin ratio 2 h after a single injection of bumetanide (100 mg/kg body weight) [3].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> NKCC

Research Areas >> Cardiovascular Disease

[References]

[1]. Frelin C, et al. Biochemical characterization of the Na+/K+/Cl- co-transport in chick cardiac cells. Biochem Biophys Res Commun. 1986 Jan 14;134(1):326-31.

[2]. Bourrit A, et al. Basic characterization of an ouabain-resistant, bumetanide-sensitive K+ carrier-mediated transport system in J774.2 mouse macrophage-like cell line and in variants deficient in adenylate cyclase and cAMP-dependent protein kinase activiti

[3]. Sandstr?m PE. Evidence for diabetogenic action of bumetanide in mice. Eur J Pharmacol. 1988 May 20;150(1-2):35-41.

[Related Small Molecules]

Furosemide

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
571.2±60.0 °C at 760 mmHg

[ Melting Point ]:
230-2310C

[ Molecular Formula ]:
C₁₇H₂₀N₂O₅S

[ Molecular Weight ]:
364.416

[ Flash Point ]:
299.3±32.9 °C

[ Exact Mass ]:
364.109283

[ PSA ]:
127.10000

[ LogP ]:
2.78

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.612

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DG4910000

CHEMICAL NAME :: Benzoic acid, 3-(butylamino)-4-phenoxy-5-sulfamoyl-

CAS REGISTRY NUMBER :: 28395-03-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C17-H20-N2-O5-S

MOLECULAR WEIGHT :: 364.45

WISWESSER LINE NOTATION :: ZSWR CVQ FOR& EM4

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 :: >6 gm/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 7,614,1976

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 891 mg/kg

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

REFERENCE :: YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 21,775,1979

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 7,614,1976

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >200 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 7,614,1976

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 mg/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 27,1057,1976

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4624 mg/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: 6,683,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 519 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 7,614,1976

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1660 mg/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: 6,683,1982

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >200 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 7,614,1976

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >25 mg/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 27,1057,1976

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >500 ug/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,66,1972

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >500 ug/kg

TOXIC EFFECTS :: Behavioral - tetany Behavioral - muscle contraction or spasticity Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,66,1972

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 350 mg/kg

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

REFERENCE :: PMESAJ Postgraduate Medical Journal, Supplement. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1949- Volume(issue)/page/year: 51(Suppl 6),14,1975

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 70 mg/kg

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

REFERENCE :: PMESAJ Postgraduate Medical Journal, Supplement. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1949- Volume(issue)/page/year: 51(Suppl 6),14,1975

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 6200 ug/kg

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

REFERENCE :: JCPCBR Journal of Clinical Pharmacology. (Hall Assoc., PO Box 482, Stamford, CT 06904) V.13- 1973- Volume(issue)/page/year: 21,543,1981

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DG4910000

[ HS Code ]:
2935009090

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%

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