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Glicaramide

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Chemical compound

Pharmaceutical compound

Glicaramide
Clinical data

ATC code	None
Identifiers
IUPAC name N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-1-ethyl-3-methyl-4-(3-methylbutoxy)pyrazolo[3,4-b]pyridine-5-carboxamide
CAS Number	36980-34-4
PubChemCID	65799
ChemSpider	59215
UNII	UK5SR22C8Q
ChEMBL	ChEMBL2106430
CompTox Dashboard(EPA)	DTXSID60190471
Chemical and physical data
Formula	C₃₀H₄₂N₆O₅S
Molar mass	598.76 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C0CCCCC0NC(=O)NS(=O)(=O)c1ccc(cc1)CCNC(=O)c2cnc3n(CC)nc(C)c3c2OCCC(C)C

Glicaramide (SQ-65993) is an orally bioavailableanti-diabetic medication.^[1] It has a similar potency asglibenclamide (glyburide) in the class of medication known assulfonylureas. Its structure is similar since it has a cyclic acyl group which replaces the latter's 2-methoxy-5-chlorobenzyl.^[2] Same as glibenclamide, it is classified as a second-generation sulfonylurea. It may have more pronounced extra-pancreatic effects than glibenclamide ortolbutamide.^[2]

References

[edit]

^Höhn H, Polacek I, Schulze E (December 1973). "Potential antidiabetic agents. Pyrazolo(3,4-b)pyridines".Journal of Medicinal Chemistry.16 (12):1340–6.doi:10.1021/jm00270a006.PMID 4358224.
^^a ^bSarges R (1981)."Hypoglycemic Drugs". In Ellis GP, West GB (eds.).Progress in Medicinal Chemistry. Vol. 18. Elsevier Science. p. 202.ISBN 0-444-80345-9.Archived from the original on 2023-01-28. Retrieved2016-10-18.

Oraldiabetes medication,insulins andinsulin analogues, and other drugs used in diabetes (A10)

Insulins andinsulin analogues

Fast-acting	Insulin aspart Insulin glulisine Insulin lispro
Short-acting	Regular insulin^#
Long-acting	Insulin detemir^# Insulin glargine^# (+lixisenatide) NPH insulin Lente insulin^‡ Ultralente insulin^‡
Ultra-long-acting	Insulin degludec^# (+insulin aspart,+liraglutide) Insulin icodec^† (+semaglutide)
Inhalable	Exubera^‡ Afrezza
Oral	Insulin tregopil^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Non-insulins

Insulin sensitizers

Biguanides	Buformin^‡ Metformin^# Phenformin^‡
TZDs ("-glitazones") andPPAR agonists	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡
Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§
Amylin analogues andDACRAs	Cagrilintide^§ Pramlintide

Secretagogues

K⁺_ATP

Sulfonylureas	1st generation:Acetohexamide Carbutamide Chlorpropamide Glycyclamide Metahexamide Tolazamide Tolbutamide 2nd generation:Glibenclamide (glyburide) Glibornuride Glicaramide Gliclazide^# Glimepiride Glipizide Gliquidone Glisoxepide Glyclopyramide
Meglitinides ("-glinides")	Mitiglinide Nateglinide Repaglinide

GLP-1 receptor agonists

GLP1 poly-agonist peptides	Mazdutide (GLP-1/GCGR) Retatrutide^§ (GLP-1/GIP/GCGR) Tirzepatide (GLP-1/GIP)

DPP-4 inhibitors ("-gliptins")

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§
Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose
SGLT2 inhibitors ("-gliflozins")	Canagliflozin Dapagliflozin Empagliflozin^# Ertugliflozin Ipragliflozin Luseogliflozin Remogliflozin^§ Sergliflozin^§ Sotagliflozin Tofogliflozin^† Velagliflozin
Other	Benfluorex^‡ Bromocriptine Imeglimin

Combinations

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Ion channel modulators

Calcium

VDCCsTooltip Voltage-dependent calcium channels

Blockers

R-type-selective:SNX-482

Activators

L-type-selective:Bay K8644

Potassium

VGKCsTooltip Voltage-gated potassium channels

Blockers

Activators

KCNQ (K_v7)-specific:Flupirtine
Retigabine

IRKsTooltip Inwardly rectifying potassium channel

Blockers

K_ATPTooltip ATP-sensitive potassium channel-specific:Acetohexamide
Carbutamide
Chlorpropamide
Glibenclamide (glyburide)
Glibornuride
Glicaramide
Gliclazide
Glimepiride
Glipizide
Gliquidone
Glisoxepide
Glyclopyramide
Glycyclamide
Metahexamide
Mitiglinide
Nateglinide
Repaglinide
Tolazamide
Tolbutamide

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:Barium
Caramiphen
Cloperastine
Clozapine
Dextromethorphan
Ethosuximide
Ifenprodil
Tertiapin
Tipepidine

Activators

K_ATPTooltip ATP-sensitive potassium channel-specific:Aprikalim
Bimakalim
Cromakalim
Diazoxide
Emakalim
Levcromakalim
Mazokalim
Minoxidil
Minoxidil sulfate
Naminidil
Nicorandil
Pinacidil
Rilmakalim
Sarakalim

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:ML-297 (VU0456810)

K_CaTooltip Calcium-activated potassium channel

Blockers	BK_Ca-specific:Ethanol (alcohol) GAL-021
Activators	BK_Ca-specific:Flufenamic acid Meclofenamic acid Niflumic acid Nimesulide Rottlerin (mallotoxin) Tolfenamic acid

K2PsTooltip Tandem pore domain potassium channel

Blockers	12-O-Tetradecanoylphorbol-13-acetate Arachidonic acid Fluoxetine Norfluoxetine
Activators	Riluzole

Sodium

VGSCsTooltip Voltage-gated sodium channels

Blockers

Antianginals:Ranolazine

Activators

Aconitine
Atracotoxins (ω-Atracotoxin,Robustoxin,Versutoxin)
Batrachotoxin
Ciguatoxins
Grayanotoxins
Poneratoxin

ENaCTooltip Epithelial sodium channel

Blockers	Amiloride Benzamil Triamterene
Activators	Solnatide

ASICsTooltip Acid-sensing ion channel

Blockers	A-317567 Amiloride Aspirin Ibuprofen PcTX1

Chloride

CaCCsTooltip Calcium-activated chloride channel

Blockers	Crofelemer DIDS Ethacrynic acid Flufenamic acid Fluoxetine Furosemide Glibenclamide Mefloquine Mibefradil Niflumic acid
Activators	Carbachol

CFTRTooltip Cystic fibrosis transmembrane conductance regulator

Blockers	Glibenclamide Lonidamine Piretanide
Activators	1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Ivacaftor Phenanthridine

Unsorted

Blockers	Bumetanide Flufenamic acid Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Talniflumate Tolfenamic acid Trifluoperazine

Others

TRPsTooltip Transient receptor potential channels	Seehere instead.
LGICsTooltip Ligand gated ion channels	Seehere instead.

See also:Receptor/signaling modulators •Transient receptor potential channel modulators

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