EXPERIMENT – 2

DATE:26/10/09

AIM: To study and draw the structure of Antidiabetic agents or antiglycemic drugs.

PRINCIPLE:

  • ACD/ChemSketch is the powerful all-purpose chemical drawing and graphics package from ACD/Labs developed to help chemists quickly and easily draw molecules, reactions, and schematic diagrams, calculate chemical properties, and design professional reports and presentations.
  • Anti-diabetic drugs :

Anti-diabetic drugs treat diabetes mellitus by lowering glucose levels in the blood. With the exceptions of insulin, exenatide, and pramlintide, all are administered orally and are thus also called oral hypoglycemic agents or oral antihyperglycemic agents.

There are different classes of anti-diabetic drugs, and their selection depends on the nature of the diabetes, age and situation of the person, as well as other factors

METHOD AND SPECIFICATIONS:

1.PROGRAMME: ACD/ChemSketch

2.SPECIFICATION: ACD/ChemSketch includes:

  1. Structure mode for drawing chemical structures and calculating their properties.
  2. Draw mode or text and graphics processing.
  3. Additional modules that extend the ChemSketch possibilities (most of them should be purchased separately).

PRINCIPLE OUTCOME:

List of Antidiabetic drugs and their structures drawn in chemsketch.

1. Rosiglitazone

  • Is an anti-diabetic drug in the thiazolidinedione class of drugs. It is marketed by the pharmaceutical company GlaxoSmithKline as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl)
  • I.U.P.A.C name: (RS)-5-[4-(2-[methyl(pyridin-2-yl)amino]ethoxy)benzyl]thiazolidine-2,4-dione
  • Structure:

2. Acetohexamide (Dymelor)

  • Is a first-generation sulfonylureamedication used to treat diabetes mellitus type 2, particularly in people whose diabetes cannot be controlled by diet alone.
  • I.U.P.A.C name: 4-acetyl-N-(cyclohexylcarbamoyl)benzenesulfonamide
  • Structure:

3.Glipizide

  • Is an oral medium-to-long acting anti-diabetic drug from the sulfonylurea class.
  • It is classified as a second generation sulfonylurea, which means that it undergoes enterohepatic circulation.
  • The structure on the R2 group is a much larger cyclo or aromatic group compared to the 1st generation sulfonylureas.
  • I.U.P.A.C name: N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-5-methylpyrazine-2-carboxamide
  • Structure:

4.Glimepiride

  • Is a medium-to-long acting sulfonylureaanti-diabetic drug. It is marketed as Amaryl by Sanofi-Aventis. Glimepiride is the first third-generation sulfonylurea, and is very potent.
  • I.U.P.A.C name: 3-ethyl-4-methyl-N-(4-[N-((1r,4r)-4- methylcyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
  • Structure:

5.Repaglinide(Prandin in the U.S., GlucoNorm in Canada, NovoNormelsewhere)

  • Is for the treatment of type II diabetes. It is supplied by Novo Nordisk.
  • Repaglinide belongs to the meglitinide class of blood glucose-lowering drugS
  • I.U.P.A.C name: S(+)-2-ethoxy-4-[2-(3-methyl-1-[2-(piperidin-1-yl)phenyl]butylamino)-2-oxoethyl]benzoic acid
  • Structure:

6.Vildagliptin(previously identified as LAF237, trade name Galvus)

  • Is a new oral anti-hyperglycemic agent (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs.
  • I.U.P.A.C name: (2S)-1-[N-(3-hydroxy-1-adamantyl)glycyl]pyrrolidine-2-carbonitrile
  • Structure:

7. Mitiglinide:

  • Mitiglinide is a drug for the treatment of type 2 diabetes .Mitiglinide is thought to stimulate insulin secretion by closing the ATP-sensitive K(+) (K(ATP)) channels in pancreatic beta-cells.
  • I.U.P.A.C name: (2S)-2-benzyl-4-[(3aR,7aS)-octahydro-2H-isoindol- 2-yl]-4-oxobutanoic acid
  • Structure:

8.Troglitazone(Rezulin, Resulin or Romozin)

  • Is an anti-diabetic and antiinflammatory drug, and a member of the drug class of the thiazolidinediones. It was developed by Daiichi Sankyo Co.(Japan).
  • I.U.P.A.C name: 5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione
  • Structure:

9. Pioglitazone

  • Is a prescription drug of the class thiazolidinedione (TZD) with hypoglycemic (antihyperglycemic, antidiabetic) action.
  • I.U.P.A.C name: 5-(4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl)thiazolidine-2,4-dione
  • Structure:

10. Nateglinide (INN, trade name Starlix)

  • Is a drug for the treatment of type 2 diabetes. Nateglinide was developed by the Swiss pharmaceutical company Novartis
  • I.U.P.A.C name: (R)-2-(4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic acid
  • Structure:

11.Gliquidone (INN, sold under the trade name Glurenorm)

  • Is an anti-diabetic drug in the sulfonylurea class. It is used in the treatment of diabetes mellitus type 2. It is marketed by the pharmaceutical company Boehriger Ingelheim, Germany.
  • I.U.P.A.C name: N-(cyclohexylcarbamoyl)-4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]benzenesulfonamide
  • Structure:

12 Sitagliptin (INN; previously identified as MK-0431, trade name Januvia)

  • Is an oral antihyperglycemic (anti-diabetic drug) of the dipeptidyl peptidase-4 (DPP-4) inhibitor class, Sitagliptin being the only 2nd Generation DPP4 inhibitor currently available in the USA.
  • This enzyme-inhibiting drug is used either alone or in combination with other oral antihyperglycemic agents (such as metformin or a thiazolidinedione) for treatment of diabetes mellitus type 2.
  • I.U.P.A.C. NAME:

(R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5- trifluorophenyl)butan-2-amine.

  • STRUCTURE:

13.Miglitol

  • Is an oral anti-diabetic drug that acts by inhibiting the ability of the patient to breakdown complex carbohydrates into glucose. It is primarily used in diabetes mellitus type 2.
  • I.U.P.A.C. NAME: (2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)
    piperidine-3,4,5-triol
  • STRUCTURE:

14.Troglitazone (Rezulin, Resulin or Romozin)

  • Is an anti-diabetic and antiinflammatory drug, and a member of the drug class of the thiazolidinediones. It was developed by Daiichi Sankyo Co.(Japan).
  • I.U.P.A.C. NAME:

5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione

  • STRUCTURE:

15. Rosiglitazone

Is an anti-diabetic drug in the thiazolidinedione class of drugs. It is marketed by the pharmaceutical company GlaxoSmithKline as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl

  • I.U.P.A.C. NAME:

(RS)-5-[4-(2-[methyl(pyridin-2-yl)amino]ethoxy)benzyl]thiazolidine-2,4-dione

  • STRUCTURE:

16. Phenformin

  • Is an anti-diabetic drug from the biguanide class. Marked under the brand name Debeone, it is no longer widely available because it is known to induce lactic acidosis
  • I.U.P.A.C. NAME:

2-(N-phenethylcarbamimidoyl)guanidine

  • STRUCTURE:

CONCLUSION:

The sructure of ANTIDIABETIC drugs are drawn Successfully using CHEMSKETCH.

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