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Sergliflozin etabonate

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Chemical compound

Pharmaceutical compound

Sergliflozin etabonate
Clinical data

Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name 2-(4-methoxybenzyl)phenyl 6-O-(ethoxycarbonyl)-β-D-glucopyranoside
CAS Number	408504-26-7^Y
PubChemCID	9824918
IUPHAR/BPS	4587
ChemSpider	21234810^N
UNII	4HY3523466
ChEMBL	ChEMBL450044^N
CompTox Dashboard(EPA)	DTXSID20961265
Chemical and physical data
Formula	C₂₃H₂₈O₉
Molar mass	448.468 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCOC(=O)OCC1C(C(C(C(O1)Oc2ccccc2Cc3ccc(cc3)OC)O)O)O
InChI InChI=1S/C23H28O9/c1-3-29-23(27)30-13-18-19(24)20(25)21(26)22(32-18)31-17-7-5-4-6-15(17)12-14-8-10-16(28-2)11-9-14/h4-11,18-22,24-26H,3,12-13H2,1-2H3^N Key:QLXKHBNJTPICNF-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

Sergliflozin etabonate (INN/USAN,^[1]^[2] codenamedGW869682X) is an investigationalanti-diabetic drug being developed byGlaxoSmithKline. It did not undergo further development after phase II.^{[citation needed]}

Method of action

[edit]

Sergliflozin inhibits subtype 2 of thesodium-glucose transport proteins (SGLT2), which is responsible for at least 90% of the glucosereabsorption in the kidney. Blocking this transporter causes blood glucose to be eliminated through the urine.^[3]^[4]

Chemistry

[edit]

Etabonate refers to the ethyl carbonate group. The remaining structure, which is the active substance, is calledsergliflozin.

References

[edit]

^World Health Organization (2008)."International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 59"(PDF).WHO Drug Information.22 (1): 66. Archived fromthe original(PDF) on February 19, 2009.
^"Statement on a nonproprietary name adopted by the USAN council: Sergliflozin etabonate"(PDF).American Medical Association. Retrieved2008-08-10.
^Katsuno K, Fujimori Y, Takemura Y, et al. (January 2007)."Sergliflozin, a novel selective inhibitor of low-affinity sodium glucose cotransporter (SGLT2), validates the critical role of SGLT2 in renal glucose reabsorption and modulates plasma glucose level".J Pharmacol Exp Ther.320 (1):323–30.doi:10.1124/jpet.106.110296.PMID 17050778.S2CID 8306408.
^"Prous Science: Molecule of the Month November 2007". Archived fromthe original on 2007-11-05. Retrieved2008-10-28.

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

Insulins /insulin 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" (PPAR)	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

v t e Sodium-glucose transporter modulators
SGLT1Tooltip Sodium-glucose transporter 1	Inhibitors:Phloretin Phlorizin T-1095 T-1095A
SGLT2Tooltip Sodium-glucose transporter 2	Inhibitors:Atigliflozin Bexagliflozin Canagliflozin Dapagliflozin Empagliflozin Enavogliflozin Ertugliflozin Henagliflozin Ipragliflozin Janagliflozin Licogliflozin Luseogliflozin Mizagliflozin Phloretin Phlorizin Remogliflozin Sergliflozin T-1095 T-1095A Tofogliflozin Velagliflozin Antisense oligonucleotides:ISIS-388626
SGLT1Tooltip Sodium-glucose transporter 1 &SGLT2Tooltip Sodium-glucose transporter 2	Inhibitors:Sotagliflozin
See also:Receptor/signaling modulators

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