nateglinide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antihyperglycaemics 1886 105816-04-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nateglinide
  • D-Nateglinide
  • glinate
  • glunate
  • natelide
  • senaglinide
A phenylalanine and cyclohexane derivative that acts as a hypoglycemic agent by stimulating the release of insulin from the pancreas. It is used in the treatment of TYPE 2 DIABETES.
  • Molecular weight: 317.43
  • Formula: C19H27NO3
  • CLOGP: 4.30
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 66.40
  • ALOGS: -4.57
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.36 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.32 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 13 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 16.20 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 73 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.15 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.80 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.03 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 22, 2000 FDA NOVARTIS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Blood glucose increased 86.33 19.56 51 2380 71962 46611669
Glycosylated haemoglobin increased 41.45 19.56 17 2414 10859 46672772
Lactic acidosis 37.90 19.56 23 2408 33886 46649745
Hypoglycaemia 32.40 19.56 25 2406 54324 46629307
Pancreatitis 21.58 19.56 18 2413 43609 46640022
Decreased appetite 21.31 19.56 37 2394 193799 46489832
Cardiac failure congestive 21.24 19.56 25 2406 91725 46591906
Blood potassium increased 20.21 19.56 12 2419 16955 46666676

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Myocardial infarction 35.46 20.60 46 2275 125579 29824578
Cardiac failure congestive 33.86 20.60 37 2284 84370 29865787
Coronary artery disease 27.60 20.60 26 2295 49686 29900471
Hypoglycaemia 21.55 20.60 23 2298 50958 29899199

Pharmacologic Action:

SourceCodeDescription
ATC A10BX03 ALIMENTARY TRACT AND METABOLISM
DRUGS USED IN DIABETES
BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
Other blood glucose lowering drugs, excl. insulins
FDA EPC N0000175428 Glinide
FDA MoA N0000175448 Potassium Channel Antagonists
MeSH PA D007004 Hypoglycemic Agents
CHEBI has role CHEBI:35526 hypoglycemic drug
CHEBI has role CHEBI:68612 dpp-4 inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Diabetes mellitus type 2 indication 44054006 DOID:9352
Infectious disease contraindication 40733004
Hypopituitarism contraindication 74728003 DOID:9406
Disease of liver contraindication 235856003 DOID:409
Hypoglycemic disorder contraindication 237630007
Primary adrenocortical insufficiency contraindication 373662000
Fever contraindication 386661006
Surgical procedure contraindication 387713003
Traumatic injury contraindication 417746004

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.79 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sulfonylurea receptor 1, Kir6.2 Ion channel BLOCKER Ki 6.46 WOMBAT-PK CHEMBL
Sulfonylurea receptor 2, Kir6.2 Ion channel BLOCKER Ki 4.99 WOMBAT-PK
Solute carrier family 22 member 6 Transporter Ki 5.04 CHEMBL

External reference:

IDSource
4021252 VUID
N0000148693 NUI
D01111 KEGG_DRUG
4021252 VANDF
C0903898 UMLSCUI
CHEBI:31897 CHEBI
CHEMBL783 ChEMBL_ID
CHEMBL249263 ChEMBL_ID
D000077715 MESH_DESCRIPTOR_UI
DB00731 DRUGBANK_ID
6833 IUPHAR_LIGAND_ID
7594 INN_ID
41X3PWK4O2 UNII
5311309 PUBCHEM_CID
274332 RXNORM
15875 MMSL
167424 MMSL
d04743 MMSL
009028 NDDF
134604002 SNOMEDCT_US
387070004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Starlix HUMAN PRESCRIPTION DRUG LABEL 1 0078-0351 TABLET 60 mg ORAL NDA 25 sections
Starlix HUMAN PRESCRIPTION DRUG LABEL 1 0078-0352 TABLET 120 mg ORAL NDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 0591-3354 TABLET 60 mg ORAL ANDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 0591-3355 TABLET 120 mg ORAL ANDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 0615-7585 TABLET, COATED 60 mg ORAL ANDA 24 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 0615-7586 TABLET, COATED 120 mg ORAL ANDA 24 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 42291-636 TABLET, COATED 60 mg ORAL ANDA 24 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 42291-637 TABLET, COATED 120 mg ORAL ANDA 24 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 49884-984 TABLET, COATED 60 mg ORAL ANDA 24 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 49884-985 TABLET, COATED 120 mg ORAL ANDA 24 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 54868-6255 TABLET, COATED 120 mg ORAL ANDA 24 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 55111-328 TABLET 60 mg ORAL ANDA 19 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 55111-329 TABLET 120 mg ORAL ANDA 19 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 60429-434 TABLET, COATED 60 mg ORAL ANDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 60429-435 TABLET, COATED 120 mg ORAL ANDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 68084-458 TABLET, COATED 60 mg ORAL ANDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 68084-459 TABLET, COATED 120 mg ORAL ANDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 68382-721 TABLET, FILM COATED 60 mg ORAL ANDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 68382-722 TABLET, FILM COATED 120 mg ORAL ANDA 25 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 70771-1015 TABLET, FILM COATED 60 mg ORAL ANDA 1 sections
Nateglinide HUMAN PRESCRIPTION DRUG LABEL 1 70771-1016 TABLET, FILM COATED 120 mg ORAL ANDA 1 sections
Nateglinide Human Prescription Drug Label 1 71209-030 TABLET, COATED 60 mg ORAL ANDA 26 sections
Nateglinide Human Prescription Drug Label 1 71209-031 TABLET, COATED 120 mg ORAL ANDA 26 sections
NULLTEGLINIDE HUMAN PRESCRIPTION DRUG LABEL 1 75834-205 TABLET, COATED 60 mg ORAL ANDA 28 sections
NULLTEGLINIDE HUMAN PRESCRIPTION DRUG LABEL 1 75834-206 TABLET, COATED 120 mg ORAL ANDA 28 sections