145525-41-3 Usage
Description
Mitiglinide calcium is the calcium salt form of Mitiglinide, a drug used for the treatment of type II diabetes. It belongs to the meglitinide class of blood glucose-lowering drugs. Its mechanism of action involves stimulating insulin secretion by closing the ATP-sensitive potassium channels in pancreatic beta-cells, leading to depolarization and an influx of calcium through voltage-gated calcium channels. This results in the exocytosis of insulin granules, which helps alleviate the symptoms of type II diabetes.
Uses
Used in Pharmaceutical Industry:
Mitiglinide calcium is used as an antidiabetic drug for the treatment of type II diabetes. It is effective in lowering blood glucose levels by stimulating insulin secretion from pancreatic beta-cells. Its short duration of action and rapid onset of insulin release make it advantageous in preventing hypoglycemia, a common adverse effect associated with traditional sulfonylurea agents.
Used in Clinical Studies:
Mitiglinide calcium has been utilized in Phase III clinical trials, demonstrating significant improvement in blood glucose control indices, such as postprandial glucose and fasting plasma glucose levels. The incidence of hypoglycemia remained as low as placebo, and no episodes of hypoglycemia or abnormal clinical laboratory parameters were noted during the studies.
Brand Name:
Glufast
References
https://www.drugbank.ca/drugs/DB01252
https://en.wikipedia.org/wiki/Mitiglinide
Originator
Kissei (Japan)
Synthesis
A number of publications and
patents have disclosed the syntheses of mitiglinide.
One of the syntheses describing the preparation of
mitiglinide using bis-activated esters to obtain a selective
mono amide is described in Scheme 8. The synthesis starts
with racemic 2-benzylsuccinic acid (51) which was resolved into its enantiomer using chiral amine salt formation and
crystallization. Out of several amines used, (R)-1-
phenylethylamine gave the best results for the chiral
resolution (99.5% ee, 19.5%). Acid 52 was treated with
thionyl chloride and triethylamine followed by Nhydroxysuccinamide
to give doubly activated ester 53
(97%). Treatment of this double ester 53 with
tetrahydroisoindoline (54) gave selectively mono amide
to di-amide in 99:1 ratio. Hydrolysis of the activated ester in
55 with water gave desired product 56 in 99% yield.
Subsequent conversion in two steps to the half calcium salt
provided mitiglinide calcium hydrate (VIII) in 91% yield.
Check Digit Verification of cas no
The CAS Registry Mumber 145525-41-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,5,5,2 and 5 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 145525-41:
(8*1)+(7*4)+(6*5)+(5*5)+(4*2)+(3*5)+(2*4)+(1*1)=123
123 % 10 = 3
So 145525-41-3 is a valid CAS Registry Number.
InChI:InChI=1/C19H25NO3.Ca/c21-18(20-12-15-8-4-5-9-16(15)13-20)11-17(19(22)23)10-14-6-2-1-3-7-14;/h1-3,6-7,15-17H,4-5,8-13H2,(H,22,23);/q;+2/t15-,16+,17-;/m0./s1
