Nateglinide

Nateglinide
Clinical data
Trade names	Starlix
AHFS/Drugs.com	Monograph
MedlinePlus	a699057
License data	EU EMA: by INN; US FDA: Nateglinide;
Routes of; administration	Oral
ATC code	A10BX03 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only) ; US: ℞-only ;
Pharmacokinetic data
Protein binding	98%
Elimination half-life	1.5 hours
Identifiers
	IUPAC name (2R)-2-({[trans-4-(1-methylethyl)cyclohexyl]carbonyl}amino)-3-phenylpropanoic acid;
CAS Number	105816-04-4 ;
PubChem CID	60026;
IUPHAR/BPS	6833;
DrugBank	DB00731 ;
ChemSpider	10482084 ;
UNII	41X3PWK4O2;
KEGG	D01111 ;
ChEBI	CHEBI:31897 ;
ChEMBL	ChEMBL286559 ;
CompTox Dashboard (EPA)	DTXSID9040687 ;
ECHA InfoCard	100.170.086
Chemical and physical data
Formula	C19H27NO3
Molar mass	317.423 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N[C@H](Cc1ccccc1)C(O)=O)[C@H]2CC[C@@H](CC2)C(C)C;
	InChI InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1 ; Key:OELFLUMRDSZNSF-BRWVUGGUSA-N ;
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Nateglinide (INN, trade name Starlix) is a drug for the treatment of type 2 diabetes. Nateglinide was developed by Ajinomoto, a Japanese company and sold by the Swiss pharmaceutical company Novartis.

Nateglinide belongs to the meglitinide class of blood glucose-lowering drugs.

Pharmacology

Nateglinide lowers blood glucose by stimulating the release of insulin from the pancreas. It achieves this by closing ATP-dependent potassium channels in the membrane of the β cells. This depolarizes the β cells and causes voltage-gated calcium channels to open. The resulting calcium influx induces fusion of insulin-containing vesicles with the cell membrane, and insulin secretion occurs.

Contraindications

Nateglinide is contraindicated in patients who:

have known hypersensitivity to the compound or any ingredient in the formulation.
are affected with type 1 (namely insulin-dependent) diabetes mellitus.
are in diabetic ketoacidosis.

Comparisons with other drugs for type 2 diabetes

A study funded by Novo Nordisk, the U.S. distributor for Repaglinide, compared their product with Nateglinide in "A randomized, parallel-group, open-label, multicenter 16-week clinical trial".[1] They concluded that the two were similar, but "repaglinide monotherapy was significantly more effective than nateglinide monotherapy in reducing HbA1c and FPG values after 16 weeks of therapy."

Dosage

Nateglinide is delivered in 60 mg & 120 mg tablet form.

References

Rosenstock, Julio Rosenstock; Hassman, David R.; Madder, Robert D.; Brazinsky, Shari A.; Farrell, James; Khutoryansky, Naum; Hale, Paula M. (June 2004), "Repaglinide Versus Nateglinide Monotherapy: A randomized, multicenter study", Diabetes Care, American Diabetes Association, 27 (6): 1265–1270, doi:10.2337/diacare.27.6.1265, retrieved 2014-11-20

External links

Starlix - website of the manufacturer.
How Nateglinide Works - website of the manufacturer.

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[1] Rosenstock, Julio Rosenstock; Hassman, David R.; Madder, Robert D.; Brazinsky, Shari A.; Farrell, James; Khutoryansky, Naum; Hale, Paula M. (June 2004), "Repaglinide Versus Nateglinide Monotherapy: A randomized, multicenter study", Diabetes Care, American Diabetes Association, 27 (6): 1265–1270, doi:10.2337/diacare.27.6.1265, retrieved 2014-11-20