Chemistry:Nateglinide

Short description: Chemical compound

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 Y
PubChem CID	60026
IUPHAR/BPS	6833
DrugBank	DB00731 Y
ChemSpider	10482084 Y
UNII	41X3PWK4O2
KEGG	D01111 N
ChEBI	CHEBI:31897 N
ChEMBL	ChEMBL286559 N
Chemical and physical data
Formula	C19H27NO3
Molar mass	317.429 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 Y Key:OELFLUMRDSZNSF-BRWVUGGUSA-N Y
NY (what is this?)  (verify)

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". 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.

See also

• Repaglinide

External links

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