Glibornuride

Names

[ Name ]:
Glibornuride

[Synonym ]:
Ro 6-4563
endo,endo-1-((1R)-(2-Hydroxy-3-bornyl))-3-(p-tolylsulfonyl)urea
1-((1R)-2endo-hydroxy-bornan-3endo-yl)-3-(toluene-4-sulfonyl)-urea
Glibornurida [INN-Spanish]
1-(p-Tolylsulfonyl)-3-(2-endo-hydroxy-3-endo-L-bornyl)harnstoff
Glibornuridum [INN-Latin]
EINECS 248-124-6
Glibornuride
Glutril
1-((1R)-2-endo-Hydroxy-3-endo-bornyl)-3-(p-tolylsulfonyl)urea
1-(p-Tolylsulfonyl)-3-(2-endo-hydroxy-3-endo-D-bornyl)harnstoff
Ro 6-4563/8

Biological Activity

[Description]:

Glibornuride is a blocker of ATP-sensitive K+ channels (KATP channel) with a pKi of 5.75[1]. Antidiabetic agent[2].

[Related Catalog]:

Research Areas >> Metabolic Disease

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

[Target]

pKi: 5.75 (KATP channel)[1]

[In Vivo]

Administration of Glibornuride (5 mg/kg; gavage, daily for 28 days) for 28 days causes an increase in body weights in the diabetic groups in Swiss albino rats[2]. Treatment with Glibornuride for 28 days decreases the serum uric acid levels in diabetic rats[2]. Administration of Glibornuride for 28 days, insignificantly increases the liver lipid peroxidation levels in diabetic rats[2]. Animal Model: 6-6.5-month-old male Swiss Albino rats, weighing 150-200 g[2] Dosage: 5 mg/kg Administration: Given by gavage, daily for 28 days Result: Administration for 28 days caused an increase in body weights in the diabetic groups. Treatment for 28 days decreased the serum uric acid levels in diabetic rats.

[References]

[1]. Löffler C, et al. Pharmacological characterization of the sulphonylurea receptor in rat isolated aorta. Br J Pharmacol. 1997 Feb;120(3):476-80.

[2]. Ozsoy-Sacan O, et al. Effects of parsley (Petroselinum crispum) extract versus Glibornuride on the liver of streptozotocin-induced diabetic rats. J Ethnopharmacol. 2006 Mar 8;104(1-2):175-81.

Chemical & Physical Properties

[ Density]:
1.3g/cm3

[ Melting Point ]:
192-195° (ethanol-water); also reported as 195-198°

[ Molecular Formula ]:
C₁₈H₂₆N₂O₄S

[ Molecular Weight ]:
366.47500

[ Exact Mass ]:
366.16100

[ PSA ]:
107.37000

[ LogP ]:
3.84460

[ Index of Refraction ]:
1.6

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YT4902000

CHEMICAL NAME :: Urea, 1-(2-hydroxy-3-bornyl)-3-(p-tolylsulfonyl)-, (1R,2R,3S,4S)-

CAS REGISTRY NUMBER :: 26944-48-9

LAST UPDATED :: 199612

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C18-H26-N2-O4-S

MOLECULAR WEIGHT :: 366.52

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 :: 18 gm/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1925,1972

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1360 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1925,1972

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10800 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1925,1972

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >20 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - antipsychotic

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1925,1972

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1530 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - cyanosis Kidney, Ureter, Bladder - urine volume increased

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1925,1972

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20 gm/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1925,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 109 gm/kg/78W-C

TOXIC EFFECTS :: Brain and Coverings - changes in brain weight

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,2188,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 67 gm/kg/30D-I

TOXIC EFFECTS :: Behavioral - muscle weakness Kidney, Ureter, Bladder - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1930,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 390 gm/kg/26W-I

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1943,1972 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 70 mg/kg

SEX/DURATION :: female 7-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1969,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 90 mg/kg

SEX/DURATION :: female 8-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1983,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2250 mg/kg

SEX/DURATION :: female 8-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,1983,1972

Related Compounds

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