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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1422
CHEMBL1422
Compound Name SITAGLIPTIN
ChEMBL Synonyms JANUVIA | SITAGLIPTIN | Sitagliptin phosphate | Janumet Xr | MK-0431
Max Phase 4 (Approved)
Trade Names JANUVIA | Janumet Xr
Molecular Formula C16H15F6N5O

Additional synonyms for CHEMBL1422 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES N[C@@H](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)Cc3cc(F)c(F)cc3F
Standard InChI InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14 ...
Download InChI
Standard InChI Key MFFMDFFZMYYVKS-SECBINFHSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1422

Molecule Features

CHEMBL1422 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Dipeptidyl peptidase IV inhibitor Dipeptidyl peptidase IV DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma1ClinicalTrials
Diabetes MellitusD003920EFO:0000400diabetes mellitus4ClinicalTrials
ATC
ClinicalTrials
Glucose IntoleranceD018149EFO:0002546abnormal glucose tolerance2ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis2ClinicalTrials
Heart FailureD006333EFO:0000373congestive heart failure0ClinicalTrials
Diabetic FootD017719EFO:1001459diabetic foot3ClinicalTrials
Myocardial InfarctionD009203EFO:0000612myocardial infarction3ClinicalTrials
Diabetes Mellitus, Type 1D003922EFO:0001359type I diabetes mellitus2ClinicalTrials
Glucose IntoleranceD018149HP:0000833Glucose intolerance2ClinicalTrials
Prediabetic StateD011236EFO:1001121prediabetes syndrome2ClinicalTrials
Cystic FibrosisD003550Orphanet:586Cystic fibrosis2ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection1ClinicalTrials
Non-alcoholic Fatty Liver DiseaseD065626EFO:0003095non-alcoholic fatty liver disease2ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus4ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
Graft vs Host DiseaseD006086EFO:0004599acute graft vs. host disease2ClinicalTrials
HIV InfectionsD015658EFO:0000180HIV-1 infection2ClinicalTrials
HyperlipidemiasD006949EFO:0003774hyperlipidemia2ClinicalTrials
Renal InsufficiencyD0514371ClinicalTrials

Clinical Data

ClinicalTrials.gov SITAGLIPTIN
The Cochrane Collaboration SITAGLIPTIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1422. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL284 Dipeptidyl peptidase IV Homo sapiens 1.000
CHEMBL4657 Dipeptidyl peptidase VIII Homo sapiens 1.000
CHEMBL4793 Dipeptidyl peptidase IX Homo sapiens 1.000
CHEMBL3976 Dipeptidyl peptidase II Homo sapiens 1.000
CHEMBL4653 Dipeptidyl peptidase IV Rattus norvegicus 1.000
CHEMBL4683 Fibroblast activation protein alpha Homo sapiens 0.658



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL284 Dipeptidyl peptidase IV Homo sapiens 1.000
CHEMBL4657 Dipeptidyl peptidase VIII Homo sapiens 1.000
CHEMBL4793 Dipeptidyl peptidase IX Homo sapiens 1.000
CHEMBL4683 Fibroblast activation protein alpha Homo sapiens 1.000
CHEMBL3976 Dipeptidyl peptidase II Homo sapiens 1.000
CHEMBL4653 Dipeptidyl peptidase IV Rattus norvegicus 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
407.3 407.1181 2.02 4 77.04 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 1 0 6 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 7.2 2.06 1.93 2 28 0.62

Structural Alerts

There are 2 structural alerts for CHEMBL1422. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A10 - DRUGS USED IN DIABETES
A10B - BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
A10BH - Dipeptidyl peptidase 4 (DPP-4) inhibitors
A10BH01 - sitagliptin

ChemSpider ChemSpider:MFFMDFFZMYYVKS-SECBINFHSA-N
DailyMed sitagliptin phosphate
Wikipedia Sitagliptin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1422



ACToR 486460-32-6
BindingDB 11162
Brenda 27125 14136 151478 39010
ChEBI 40237
ChemicalBook CB01449778
DrugBank DB01261
DrugCentral 2448
eMolecules 6755163
EPA CompTox Dashboard DTXSID70197572
FDA SRS QFP0P1DV7Z
Guide to Pharmacology 6286
Human Metabolome Database HMDB0015390
IBM Patent System F45DEBE26B63A3F00209A8E5054852DF
LINCS LSM-5363
Mcule MCULE-2101761133
MolPort MolPort-003-666-756
Nikkaji J2.231.708C
PDBe 715
PharmGKB PA164748978
PubChem 4369359
PubChem: Thomson Pharma 14904024 16466401
SureChEMBL SCHEMBL17783
ZINC ZINC000001489478

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/MFFMDFFZMYYVKS-SECBINFHSA-N spacer
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