sitagliptin

Trade name: januvia

Small moleculeapproved

Approved

Oct 16, 2006

Sitagliptin (MK-0431), chemically (2R)-4-Oxo-4-[3- (trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin- 7(8H)-yl]-1-(2,4,5-trifl uorophenyl)butan-2-amine has a very high selectivity towards DPP-4, with an IC(50) of 18 nM. There is no affinity towards other DDP enzymes (DPP- 8 and DPP-9). It has been approved for the treatment of type 2 diabetes in the USA and Europe and is registered by the name Januvia (Merck Pharmaceuticals, Whitehouse Station, NJ, USA). In healthy volunteers and in patients with type 2 diabetes of different ethnic background, the tolerability of different doses given once or twice daily is good. The drug works to competitively inhibit a protein/enzyme, dipeptidyl peptidase 4 (DPP-4), that results in an increased amount of active incretins (GLP-1 and GIP), reduced amount of release of glucagon (diminishes its release) and increased release of insulin. Sitagliptin is an incretin enhancer and the first marketed medication belonging to the gliptin class. In fact, no published literature exists regarding incidence or severity of hypoglycemia when sitagliptin is used off-label in combined with insulin therapy. However, is recommended to use methods to avoid hypoglycemia when using this off-label combination. Approximately 79% of sitagliptin is excreted unchanged in the urine with metabolism being a minor pathway of elimination. Elimination of sitagliptin occurs primarily via renal excretion and involves active tubular secretion. Sitagliptin is a substrate for human organic anion transporter-3 (hOAT-3), which may be involved in the renal elimination of sitagliptin — NCATS

Clinical trial activity

1,778 trials · 840 clinical orgs · 30 marketing orgs

Phase 1
381
Phase 2
726
Phase 3
452
Phase 4
439

Earliest trial started Dec 1, 1997 (NCT00413179)

Timeline

1990s

  1. Jan 1, 1997

    Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 1999

    Earliest Phase 1 Sponsor(trial)

  3. Jan 1, 1999

    Earliest Phase 2 Sponsor(trial)

  4. May 25, 1999

    SmithKline Beecham — NDA Secondary Org

2000s

  1. Oct 16, 2006

    Merck — Earliest FDA Approval

  2. Oct 16, 2006

    Merck — NDA Organization

  3. Oct 16, 2006

    Merck — NDA Secondary Org

  4. Oct 16, 2006

    Merck — Marketing Organization

  5. Jan 31, 2007

    Watson Pharmaceuticals — Marketing Organization

  6. Mar 10, 2008

    Roxane Laboratories — Marketing Organization

  7. Dec 2, 2008

    Mylan — Marketing Organization

  8. Mar 9, 2009

    Sandoz — Marketing Organization

  9. Dec 8, 2009

    Hikma — Marketing Organization

2010s

  1. Jan 25, 2013

    Ani Pharmaceuticals — Marketing Organization

  2. Jan 25, 2013

    Teva — Marketing Organization

  3. Apr 11, 2013

    Sun Pharmaceuticals — Marketing Organization

  4. Jul 30, 2013

    Novartis — Marketing Organization

  5. Feb 18, 2014

    Apotex — Marketing Organization

  6. Apr 15, 2014

    Actavis — Marketing Organization

  7. Apr 21, 2015

    Anchen Pharmaceuticals, Inc — Marketing Organization

  8. Apr 21, 2015

    Par Pharmaceuticals — Marketing Organization

  9. Oct 30, 2015

    Allergan PLC (2015) — Marketing Organization

  10. Apr 29, 2016

    Dr. Reddy's Laboratories — Marketing Organization

  11. Jul 3, 2017

    Zydus Discovery DMCC — Marketing Organization

2020s

  1. Jan 5, 2021

    Ajanta Pharma Ltd — Marketing Organization

  2. Jul 9, 2021

    Unichem — Marketing Organization

  3. Sep 2, 2021

    Zydus Discovery DMCC — NDA Secondary Org

  4. Apr 8, 2022

    Alkem Labs Ltd — Marketing Organization

  5. Jan 2, 2024

    Mankind Pharma — Marketing Organization

  6. Jan 16, 2025

    Azurity — Marketing Organization

  7. Mar 6, 2025

    Sciegen Pharmaceticals — Marketing Organization

  8. Apr 2, 2025

    Macleods Pharmaceuticals, Ltd — Marketing Organization

  9. Jun 4, 2025

    PH HEALTH — Marketing Organization

  10. Jul 23, 2025

    MSN Laboratories — Marketing Organization

  11. Aug 25, 2025

    Biocon Limited — Marketing Organization

  12. Nov 12, 2025

    Laurus Labs Ltd — Marketing Organization

  13. Jan 26, 2026

    Fosun — Marketing Organization

Indications

Studied for

Mechanism of action

Combination products

Approval history

  • approvedOct 16, 2006

Chemistry & pharmacology

Loading structure…

SMILES

N[C@@H](CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F
Mol. weight
407.32 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 1,1-dimethylbiguanide
  • 1,1-dimethylbiguanide
  • 1,1-dimethylbiguanide
  • 2,4-thiazolidinedione, 5-004-02-((((methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-
  • (2r)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine
  • (2r)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine
  • 5-((4-(2-methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioate
  • (±)-5-[p-[2-(methyl-2-pyridylamino)ethoxy]benzyl]-2,4-thiazolidinedione
  • (±)-5-[p-[2-(methyl-2-pyridylamino)ethoxy]benzyl]-2,4-thiazolidinedione
  • dimethylbiguanid
  • dimethylbiguanid
  • dimethyldiguanide
  • dimethyldiguanide
  • ertugliflozin l-pyroglutamic acid / sitagliptin phosphate monohydrate
  • glaxosmithkline brand of rosiglitazone maleate
  • glaxo wellcome brand of rosiglitazone maleate
  • januvia
  • januvia
  • januvia
  • januvia
  • mk0431
  • mk0431
  • mk 0431
  • mk-0431
  • mk-0431
  • mk-0431
  • mk-0431
  • mk-0431
  • n,n-dimethylguanylguanidine
  • ono-5435
  • ono-5435
  • ristaben
  • (rs)-5-{4-[2-(methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedion
  • (rs)-5-{4-[2-(methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedion
  • sitagliptan
  • sitagliptan
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptin
  • sitagliptina
  • sitagliptina
  • sitagliptine
  • sitagliptine
  • sitagliptin / metformin hydrochloride
  • sitagliptin monophosphate monohydrate
  • sitagliptin phosphate
  • sitagliptin phosphate
  • sitagliptin phosphate
  • sitagliptin phosphate
  • sitagliptin phosphate
  • sitagliptin phosphate
  • sitagliptin phosphate anhydrous
  • sitagliptin phosphate hydrate
  • sitagliptin phosphate monohydrate
  • sitagliptinum
  • sitagliptinum
  • smithkline beecham brand of rosiglitazone maleate

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06560333Phase 3Nov 30, 2026Eurofarma Laboratorios S.A.
NCT07241897Phase 3Dec 15, 2025Soochow University
NCT07003542Phase 2Aug 8, 2025Case Western Reserve University
NCT07073768Phase 3Jul 1, 2025Khyber Medical University Peshawar, Khyber Medical University Peshawer
NCT06972732Phase 4Jun 11, 2025Boryung Pharmaceutical Company
NCT06851962Phase 4Apr 30, 2025University of Valencia
NCT06759922Phase 4Jan 1, 2025Bahria University
NCT06246799Phase 3Nov 30, 2024National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK), University of Texas, San Antonio
NCT07083232Phase 4Oct 30, 2024Al Azhar University
NCT07172269N/ASep 15, 2024Al-Mustansiriyah University
NCT06587698N/AAug 21, 2024Peking University
NCT06233201Phase 1Jun 4, 2024Bio-innova Co., Ltd
NCT06613750Phase 4Jun 1, 2024Guangzhou Medical University, Southern Medical University
NCT06952231Phase 3May 21, 2024University of Health Sciences Lahore
NCT06263673Phase 4May 7, 2024Mayo Clinic
NCT06233240Phase 1Apr 30, 2024Bio-innova Co., Ltd
NCT06329882Phase 1/Phase 2 (Phase 2)Mar 30, 2024Tanta University
NCT05833958Phase 2Jan 31, 2024George Medicines PTY Limited, University of New South Wales
NCT06187285N/AJan 1, 2024Diabetes & Endocrinology Foundation, Medanta - The Medicity
NCT06164535Phase 4Dec 30, 2023Beni Suef University, Minia University
Showing 20 of 1,778 trials
Page 1 / 89

Organizations

Research & Development (840)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
MerckFor profit15911051998
GlaxoSmithKlineFor profit976652000
AstraZenecaFor profit847452004
Novo NordiskFor profit715751998
SanofiFor profit635842001
Bristol-Myers SquibbFor profit57842001
Boehringer IngelheimFor profit525242005
Eli LillyFor profit481352000
Johnson and JohnsonFor profit403852007
National Cancer Institute (NCI)Government36941999
NovartisFor profit353142004
National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK)Government29851999
TakedaFor profit292451998
Seoul National UniversityAcademic/Hospital271852008
University of TorontoAcademic/Hospital241842003
Harvard UniversityAcademic/Hospital231851999
National Institutes of Health (NIH)Government23752000
University of CopenhagenAcademic/Hospital201752004
People's Liberation Army of ChinaGovernment181342007
PfizerFor profit17742001
840 organizations
Page 1 / 42

Marketing (44)

OrganizationOrg typeRelationshipDate
ActavisFor profitMKTGApr 15, 2014
Ajanta Pharma LtdFor profitMKTGJan 5, 2021
Alkem Labs LtdFor profitMKTGApr 8, 2022
Allergan PLC (2015)For profitMKTGOct 30, 2015
Anchen Pharmaceuticals, IncFor profitMKTGApr 21, 2015
Ani PharmaceuticalsFor profitMKTGJan 25, 2013
ApotexFor profitMKTGFeb 18, 2014
ApotexFor profitSYNJan 20, 2026
AzurityFor profitMKTGJan 16, 2025
Biocon LimitedFor profitMKTGAug 25, 2025
Dr. Reddy's LaboratoriesFor profitMKTGApr 29, 2016
Dr. Reddy's LaboratoriesFor profitSYNMay 12, 2025
FosunFor profitMKTGJan 26, 2026
HikmaFor profitMKTGDec 8, 2009
Laurus Labs LtdFor profitMKTGNov 12, 2025
MSN LaboratoriesFor profitMKTGJul 23, 2025
Macleods Pharmaceuticals, LtdFor profitMKTGApr 2, 2025
Mankind PharmaFor profitMKTGJan 2, 2024
MerckFor profitNDAOct 16, 2006
MerckFor profitNDA2Oct 16, 2006
MerckFor profitSYNMar 30, 2007
MerckFor profitMKTGOct 16, 2006
MylanFor profitMKTGDec 2, 2008
MylanFor profitSYNOct 10, 2012
NovartisFor profitMKTGJul 30, 2013
PH HEALTHFor profitMKTGJun 4, 2025
Par PharmaceuticalsFor profitMKTGApr 21, 2015
Roxane LaboratoriesFor profitMKTGMar 10, 2008
SandozFor profitMKTGMar 9, 2009
SandozFor profitSYNJan 30, 2013
Sciegen PharmaceticalsFor profitMKTGMar 6, 2025
SmithKline BeechamFor profitNDA2May 25, 1999
Sun PharmaceuticalsFor profitMKTGApr 11, 2013
TevaFor profitMKTGJan 25, 2013
TevaFor profitSYNFeb 23, 2015
TevaFor profitSYNSep 29, 2015
UnichemFor profitMKTGJul 9, 2021
Watson PharmaceuticalsFor profitMKTGJan 31, 2007
Watson PharmaceuticalsFor profitSYNApr 15, 2014
Zydus Discovery DMCCFor profitSYNOct 18, 2023
Zydus Discovery DMCCFor profitMKTGJul 3, 2017
Zydus Discovery DMCCFor profitMKTGSep 2, 2021
Zydus Discovery DMCCFor profitNDA2Sep 2, 2021
Zydus Discovery DMCCFor profitSYNOct 18, 2023