Glipizide

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| _has_physiological_data= | _has_gene_therapy=

| vaccine_type= | mab_type= | _number_of_combo_chemicals=Script error: No such module "ParameterCount". | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=212754O=C(c1ncc(nc1)C)NCCc2ccc(cc2)S(=O)(=O)NC(=O)NC3CCCCC31S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)ZJJXGWJIGJFDTL-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite208209 | _combo_data= | _physiological_data= | _clinical_data=Template:Drugs.coma684060Glipizide CBy mouthGlucotrol, Glucotrol XL, othersSulfonylureaA10 | _legal_data=POMRx only

| _other_data=N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-5-methylpyrazine-2-carboxamide

| _image_0_or_2 = Glipizide.svgGlipizide ball-and-stick.png | _image_LR =

| _datapage = Glipizide (data page) | _vaccine_target=_type_not_vaccine | _legal_all=POMRx only | _ATC_prefix_supplemental=A10 | _has_EMA_link = | CAS_number=29094-61-9 | PubChem=3478 | ChemSpiderID=3359 | ChEBI=5384 | ChEMBL=1073 | DrugBank=DB01067 | KEGG=D00335 | _hasInChI_or_Key=yes | UNII=X7WDT95N5C | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs=Script error: No such module "ParameterCount". | _countIndexlabels=Script error: No such module "ParameterCount". | _trackListSortletter= |QID = |QID2 = |Verifiedfields=changed |Watchedfields=changed |verifiedrevid=444731264}} Glipizide, sold under the brand name Glucotrol among others, is an anti-diabetic medication of the sulfonylurea class used to treat type 2 diabetes.[1][2] It is used together with a diabetic diet and exercise.[1][2] It is not indicated for use by itself in type 1 diabetes.[1][2] It is taken by mouth.[1][2] Effects generally begin within half an hour and can last for up to a day.[1]

Common side effects include nausea, diarrhea, low blood sugar, and headache.[1] Other side effects include sleepiness, skin rash, and shakiness.[3] The dose may need to be adjusted in those with liver or kidney disease.[1] Use during pregnancy or breastfeeding is not recommended.[3] It works by stimulating the pancreas to release insulin and increases tissue sensitivity to insulin.[1]

Glipizide was approved for medical use in the United States in 1984.[1] It is available as a generic medication.[1] In 2023, it was the 42nd most commonly prescribed medication in the United States, with more than 15Script error: No such module "String".million prescriptions.[4][5]

Mechanism of action

Glipizide sensitizes the beta cells of pancreatic islets of Langerhans insulin response, meaning that more insulin is released in response to glucose than would be without glipizide ingestion.[2] Glipizide acts by partially blocking potassium channels among beta cells of pancreatic islets of Langerhans. By blocking potassium channels, the cell depolarizes, which results in the opening of voltage-gated calcium channels. The resulting calcium influx encourages insulin release from beta cells.[6]

History

It was patented in 1969, and approved for medical use in 1971.[7] Glipizide was approved for medical use in the United States in 1984.[1]

Synthesis

Synthesis of glipizide:[8][9] Alternative:[10] Cmp#3:[11] Related article:[12]

File:Glipizide synthesis.svg

5-Methylpyrazine-2-carboxylic acid [5521-55-1] (1) is converted to its acid chloride. A Schotten-Baumann reaction is then performed with 4-(2-aminoethyl)benzene sulfonamide [35303-76-5] (2) to give the corresponding amide PC9883549 [33288-71-0] (3). This forms glipizide on reaction with cyclohexylisocyanide and base in acetone.

References

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  1. ↑ a b c d e f g h i j k Script error: No such module "citation/CS1".
  2. ↑ a b c d e Script error: No such module "citation/CS1".
  3. ↑ a b Script error: No such module "citation/CS1".
  4. ↑ Script error: No such module "citation/CS1".
  5. ↑ Script error: No such module "citation/CS1".
  6. ↑ Script error: No such module "Citation/CS1".
  7. ↑ Script error: No such module "citation/CS1".
  8. ↑ Ambrogi et al., Arzneim.-Forsch. 21, 200 (1971).
  9. ↑ DE2012138 idem Vittorio Bresso Mailand Ambrogi, Willy Mailand Logemann, US3669966 (1978 to Carlo Erba S.P.A., Mailand (Italien)).
  10. ↑ Mikael Dahlström & Yngve Malmen, EP0149592 (1985 to LAKEMEDELSFABRIKEN-MEDICA AB).
  11. ↑ R. K. Sarma & P. L. Kamat, US5516906 (1995 to USV Pvt Ltd).
  12. ↑ Ambrogi, V.; Bloch, K.; Daturi, S.; Logemann, W.; Parenti, M.A. (1972). "Synthesis of Pyrazine Derivatives as Potential Hypoglycemic Agents". Journal of Pharmaceutical Sciences. 61 (9): 1483–1486. doi:10.1002/jps.2600610933.

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