Details of the Drug

General Information of Drug (ID: DMLK2QH)

• Drug Name: Nateglinide
• Synonyms: Fastic; IPCCPA; Senaglinide; Starlix; Starsis; Trazec; Nateglinide [INN]; Novartis brand of nateglinide; DJN 608; A-4166; AY-4166; DJN-608; Nate-glinide; Starlix (TN); YM-026; SDZ-DJN-608; N-((4-isopropylcyclohexyl)carbonyl)phenylalanine; Nateglinide, (D-Phe)-isomer; Nateglinide, (cis,D-Phe)-isomer; N-{[4-(propan-2-yl)cyclohexyl]carbonyl}phenylalanine; N-{[trans-4-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine; (2R)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic acid; 3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic acid

Indication

Disease Entry	ICD 11	Status	REF
Diabetic complication	5A2Y	Approved	[1]

• Therapeutic Class: Hypoglycemic Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 317.4
  Logarithm of the Partition Coefficient (xlogp); 3.2
  Rotatable Bond Count (rotbonds); 6
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 3
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
  Bioavailability: 73% of drug becomes completely available to its intended biological destination(s) [3]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 1.8 mL/min/kg [4]
  Elimination: 13% of drug is excreted from urine in the unchanged form [2]
  Half-life: The concentration or amount of drug in body reduced by one-half in 1.5 hours [4]
  Metabolism: The drug is metabolized via the hepatic []
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 16.2 micromolar/kg/day [5]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.029% [4]
  Vd: The volume of distribution (Vd) of drug is 10 L []
  Water Solubility: The ability of drug to dissolve in water is measured as 0.322 mg/mL [2]
• Chemical Identifiers:
  Formula: C19H27NO3
  IUPAC Name: (2R)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic acid
  Canonical SMILES: CC(C)C1CCC(CC1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)O
  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
  InChIKey: OELFLUMRDSZNSF-OFLPRAFFSA-N
• Cross-matching ID:
  PubChem CID: 5311309
  ChEBI ID: CHEBI:31897
  CAS Number: 105816-04-4
  DrugBank ID: DB00731
  TTD ID: D06PSS
  VARIDT ID: DR00407
  INTEDE ID: DR1132
  ACDINA ID: D00458

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Potassium channel unspecific (KC)	TT1VOHK	NOUNIPROTAC	Modulator	[6]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Monocarboxylate transporter 6 (SLC16A5)	DT3I124	MOT6_HUMAN	Substrate	[7]
Organic anion transporting polypeptide 1B1 (SLCO1B1)	DT3D8F0	SO1B1_HUMAN	Substrate	[8]
Organic anion transporting polypeptide 1B3 (SLCO1B3)	DT9C1TS	SO1B3_HUMAN	Substrate	[9]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[10]
Cytochrome P450 2D6 (CYP2D6)	DECB0K3	CP2D6_HUMAN	Substrate	[11]
Cytochrome P450 2C9 (CYP2C9) Main DME	DE5IED8	CP2C9_HUMAN	Substrate	[10]
Cytochrome P450 3A5 (CYP3A5)	DEIBDNY	CP3A5_HUMAN	Substrate	[12]
Cytochrome P450 3A7 (CYP3A7)	DERD86B	CP3A7_HUMAN	Substrate	[12]
Prostaglandin G/H synthase 1 (COX-1)	DE073H6	PGH1_HUMAN	Substrate	[13]
UDP-glucuronosyltransferase 1A9 (UGT1A9)	DE85D2P	UD19_HUMAN	Substrate	[13]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP-binding cassette sub-family C member 4 (ABCC4)	OTO27PAL	MRP4_HUMAN	Drug Response	[14]
Insulin (INS)	OTZ85PDU	INS_HUMAN	Protein Interaction/Cellular Processes	[15]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Nateglinide

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Glibenclamide	DM8JXPZ	Moderate	Decreased metabolism of Nateglinide caused by Glibenclamide mediated inhibition of CYP450 enzyme.	Acute diabete complication [5A2Y]	[16]
Tolazamide	DMIHRNA	Moderate	Decreased metabolism of Nateglinide caused by Tolazamide mediated inhibition of CYP450 enzyme.	Acute diabete complication [5A2Y]	[16]
Glipizide	DMZA5PQ	Moderate	Decreased metabolism of Nateglinide caused by Glipizide mediated inhibition of CYP450 enzyme.	Acute diabete complication [5A2Y]	[16]

Coadministration of a Drug Treating the Disease Different from Nateglinide (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Metronidazole	DMTIVEN	Moderate	Decreased metabolism of Nateglinide caused by Metronidazole mediated inhibition of CYP450 enzyme.	Amoebiasis [1A36]	[16]
Oxymetholone	DMFXUT8	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Oxymetholone.	Aplastic anaemia [3A70]	[17]
Alpelisib	DMEXMYK	Moderate	Increased metabolism of Nateglinide caused by Alpelisib mediated induction of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[18]
Fluoxymesterone	DMUHCF1	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Fluoxymesterone.	Breast cancer [2C60-2C6Y]	[17]
Fenofibric acid	DMGO2MC	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Fenofibric acid.	Cardiovascular disease [BA00-BE2Z]	[17]
Phenylbutazone	DMAYL0T	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Phenylbutazone.	Chronic pain [MG30]	[17]
Ketoprofen	DMRKXPT	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Ketoprofen.	Chronic pain [MG30]	[17]
Ardeparin	DMYRX8B	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Ardeparin.	Coronary thrombosis [BA43]	[17]
Mifepristone	DMGZQEF	Moderate	Decreased metabolism of Nateglinide caused by Mifepristone mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[19]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Nateglinide caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[20]
Sertraline	DM0FB1J	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Sertraline.	Depression [6A70-6A7Z]	[17]
Vilazodone	DM4LECQ	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Vilazodone.	Depression [6A70-6A7Z]	[17]
Selegiline	DM6034S	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Selegiline.	Depression [6A70-6A7Z]	[17]
Vortioxetine	DM6F1PU	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Vortioxetine.	Depression [6A70-6A7Z]	[17]
Isocarboxazid	DMAF1NB	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Isocarboxazid.	Depression [6A70-6A7Z]	[17]
Escitalopram	DMFK9HG	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Escitalopram.	Depression [6A70-6A7Z]	[17]
Tranylcypromine	DMGB5RE	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Tranylcypromine.	Depression [6A70-6A7Z]	[17]
PMID28870136-Compound-49	DMTUC9E	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and PMID28870136-Compound-49.	Discovery agent [N.A.]	[17]
Mefenamic acid	DMK7HFI	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Mefenamic acid.	Female pelvic pain [GA34]	[17]
Miconazole	DMPMYE8	Moderate	Decreased metabolism of Nateglinide caused by Miconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[21]
Sunitinib	DMCBJSR	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Sunitinib.	Gastrointestinal stromal tumour [2B5B]	[17]
Sulfinpyrazone	DMEV954	Minor	Decreased metabolism of Nateglinide caused by Sulfinpyrazone mediated inhibition of CYP450 enzyme.	Gout [FA25]	[22]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Nateglinide caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[23]
Etravirine	DMGV8QU	Moderate	Decreased metabolism of Nateglinide caused by Etravirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[24]
Fluvastatin	DM4MDJY	Moderate	Decreased metabolism of Nateglinide caused by Fluvastatin mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[25]
Gemfibrozil	DMD8Q3J	Moderate	Decreased metabolism of Nateglinide caused by Gemfibrozil mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[16]
Fenofibrate	DMFKXDY	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Fenofibrate.	Hyper-lipoproteinaemia [5C80]	[17]
Captopril	DM458UM	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Captopril.	Hypertension [BA00-BA04]	[17]
Perindopril	DMOPZDT	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Perindopril.	Hypertension [BA00-BA04]	[17]
Quinapril	DMR8H31	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Quinapril.	Hypertension [BA00-BA04]	[17]
Irbesartan	DMTP1DC	Moderate	Decreased metabolism of Nateglinide caused by Irbesartan mediated inhibition of CYP450 enzyme.	Hypertension [BA00-BA04]	[16]
Probenecid	DMMFWOJ	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Probenecid.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[17]
Balsalazide	DM7I1T9	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Balsalazide.	Indeterminate colitis [DD72]	[17]
Ramelteon	DM7IW9J	Moderate	Decreased metabolism of Nateglinide caused by Ramelteon mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[16]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Nateglinide caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[25]
Hydroxychloroquine	DMSIVND	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Hydroxychloroquine.	Malaria [1F40-1F45]	[17]
Sulphadoxine	DMZI2UF	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Sulphadoxine.	Malaria [1F40-1F45]	[17]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Nateglinide caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[25]
Mecasermin	DM1O3BY	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Mecasermin.	Multiple structural anomalies syndrome [LD2F]	[17]
Nilotinib	DM7HXWT	Moderate	Decreased metabolism of Nateglinide caused by Nilotinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[26]
Naproxen	DMZ5RGV	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Naproxen.	Osteoarthritis [FA00-FA05]	[17]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Nateglinide caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[27]
Aspirin	DM672AH	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Aspirin.	Pain [MG30-MG3Z]	[28]
Etodolac	DM6WJO9	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Etodolac.	Pain [MG30-MG3Z]	[17]
Ibuprofen	DM8VCBE	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Ibuprofen.	Pain [MG30-MG3Z]	[17]
Safinamide	DM0YWJC	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Safinamide.	Parkinsonism [8A00]	[17]
Rasagiline	DM3WKQ4	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Rasagiline.	Parkinsonism [8A00]	[17]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Nateglinide caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[29]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Nateglinide caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[30]
Bromfenac	DMKB79O	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Bromfenac.	Postoperative inflammation [1A00-CA43]	[17]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Nateglinide caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[31]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Nateglinide caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[32]
Salsalate	DM13P4C	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Salsalate.	Rheumatoid arthritis [FA20]	[17]
Meloxicam	DM2AR7L	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Meloxicam.	Rheumatoid arthritis [FA20]	[17]
Oxaprozin	DM9UB0P	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Oxaprozin.	Rheumatoid arthritis [FA20]	[17]
Sulfasalazine	DMICA9H	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Sulfasalazine.	Rheumatoid arthritis [FA20]	[17]
Leflunomide	DMR8ONJ	Moderate	Decreased metabolism of Nateglinide caused by Leflunomide mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[16]
Salicyclic acid	DM2F8XZ	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Salicyclic acid.	Seborrhoeic dermatitis [EA81]	[28]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Nateglinide caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[25]
Ifosfamide	DMCT3I8	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Ifosfamide.	Solid tumour/cancer [2A00-2F9Z]	[17]
Methyltestosterone	DMWLFGO	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Methyltestosterone.	Solid tumour/cancer [2A00-2F9Z]	[17]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Nateglinide caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[33]
Tolbutamide	DM02AWV	Moderate	Decreased metabolism of Nateglinide caused by Tolbutamide mediated inhibition of CYP450 enzyme.	Type 2 diabetes mellitus [5A11]	[16]
Pramlintide	DM0EZ9Q	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Pramlintide.	Type-1/2 diabete [5A10-5A11]	[17]
Olsalazine	DMZW9HA	Moderate	Increased risk of hypoglycemia by the combination of Nateglinide and Olsalazine.	Ulcerative colitis [DD71]	[17]
Amiodarone	DMUTEX3	Moderate	Decreased metabolism of Nateglinide caused by Amiodarone mediated inhibition of CYP450 enzyme.	Ventricular tachyarrhythmia [BC71]	[16]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Fumaric acid	E00420	444972	Acidulant; Antioxidant; Complexing agent; Flavoring agent; Solubilizing agent
Kyselina citronova	E00014	311	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium stearyl fumarate	E00545	23665634	lubricant
Sunset yellow FCF	E00255	17730	Colorant
Carmellose sodium	E00625	Not Available	Disintegrant
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Nateglinide 120 mg tablet	120 mg	Oral Tablet	Oral
Nateglinide 60 mg tablet	60 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6833).
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• [6] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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• [8] Organic Anion Transporter 2-Mediated Hepatic Uptake Contributes to the Clearance of High-Permeability-Low-Molecular-Weight Acid and Zwitterion Drugs: Evaluation Using 25 Drugs. J Pharmacol Exp Ther. 2018 Nov;367(2):322-334.
• [9] FDA Drug Development and Drug Interactions
• [10] Drug-drug and food-drug pharmacokinetic interactions with new insulinotropic agents repaglinide and nateglinide. Clin Pharmacokinet. 2007;46(2):93-108.
• [11] Influence of CYP2C9 and CYP2D6 polymorphisms on the pharmacokinetics of nateglinide in genotyped healthy volunteers. Clin Pharmacokinet. 2004;43(4):267-78.
• [12] Drug Interactions Flockhart Table
• [13] Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
• [14] Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter. Pharm Res. 2007 Dec;24(12):2281-96.
• [15] Purification by p-aminobenzoic acid (PABA)-affinity chromatography and the functional reconstitution of the nateglinide/H+ cotransport system in the rat intestinal brush-border membrane. Biochem Biophys Res Commun. 2006 Feb 17;340(3):879-86. doi: 10.1016/j.bbrc.2005.12.092. Epub 2005 Dec 27.
• [16] Product Information. Starlix (nateglinide) Novartis Pharmaceuticals, East Hanover, NJ.
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• [29] Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
• [30] Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
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