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Details

Stereochemistry MIXED
Molecular Formula C18H25N3O2
Molecular Weight 315.41
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SAXAGLIPTIN ANHYDROUS

SMILES

N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C34CC5CC(CC(O)(C5)C3)C4

InChI

InChIKey=QGJUIPDUBHWZPV-SGTAVMJGSA-N
InChI=1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10?,11?,12-,13+,14+,15-,17?,18?/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H25N3O2
Molecular Weight 315.41
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry
Defined Stereocenters 4 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Saxagliptin is an orally active hypoglycemic (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. FDA approved on July 31, 2009. Saxagliptin is a dipeptidyl peptidase-4 (DPP-4) inhibitor antidiabetic for the treatment of type 2 diabetes. DPP-4 inhibitors are a class of compounds that work by affecting the action of natural hormones in the body called incretins. Incretins decrease blood sugar by increasing consumption of sugar by the body, mainly through increasing insulin production in the pancreas, and by reducing production of sugar by the liver. [Bristol-Myers Squibb Press Release] DPP-4 is a membrane associated peptidase which is found in many tissues, lymphocytes and plasma. DPP-4 has two main mechanisms of action, an enzymatic function and another mechanism where DPP-4 binds adenosine deaminase, which conveys intracellular signals via dimerization when activated. Saxagliptin forms a reversible, histidine-assisted covalent bond between its nitrile group and the S630 hydroxyl oxygen on DPP-4. The inhibition of DPP-4 increases levels active of glucagon like peptide 1 (GLP-1), which inhibits glucagon production from pancreatic alpha cells and increases production of insulin from pancreatic beta cells.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
30.3 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Onglyza
PubMed

PubMed

TitleDatePubMed
(R)-8-(3-amino-piperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione (BI 1356), a novel xanthine-based dipeptidyl peptidase 4 inhibitor, has a superior potency and longer duration of action compared with other dipeptidyl peptidase-4 inhibitors.
2008 Apr
Antihyperglycemic effects of ASP8497 in streptozotocin-nicotinamide induced diabetic rats: comparison with other dipeptidyl peptidase-IV inhibitors.
2009 Sep-Oct
Patents

Sample Use Guides

In Vivo Use Guide
Diabetes Mellitus Monotherapy Oral 2.5 or 5 mg once daily.1 Higher dosages (e.g., 10 mg once daily) did not provide additional benefit in clinical trials and are not recommended by manufacturer.
Route of Administration: Oral
In Vitro Use Guide
Saxagliptin inhibited rat plasma DPP-IV activity in vitro with an IC(50) value of 2.00 nmol/l
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:10:23 UTC 2019
Edited
by admin
on Mon Oct 21 20:10:23 UTC 2019
Record UNII
8I7IO46IVQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAXAGLIPTIN ANHYDROUS
Common Name English
SAXAGLIPTIN [MI]
Common Name English
SAXAGLIPTIN [INN]
Common Name English
SAXAGLIPTIN [WHO-DD]
Common Name English
BMS-477118
Code English
(1S,3S,5S)-2-((2S)-AMINO(3-HYDROXYTRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YL)ACETYL)-2-AZABICYCLO(3.1.0)HEXANE-3-CARBONITRILE
Systematic Name English
2-AZABICYCLO(3.1.0)HEXANE-3-CARBONITRILE, 2-((2S)-AMINO(3-HYDROXYTRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YL)ACETYL), (1S,3S,5S)-
Common Name English
Classification Tree Code System Code
NDF-RT N0000175913
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
NCI_THESAURUS C98086
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
WHO-ATC A10BH03
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
NDF-RT N0000175912
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
Code System Code Type Description
INN
8577
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY
CAS
361442-04-8
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY
PUBCHEM
11243969
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY
RXCUI
1546030
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C75984
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY
HSDB
361442-04-8
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY
MERCK INDEX
M9795
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY Merck Index
EVMPD
SUB25220
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY
EPA CompTox
361442-04-8
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY
DRUG BANK
DB06335
Created by admin on Mon Oct 21 20:10:23 UTC 2019 , Edited by admin on Mon Oct 21 20:10:23 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
BINDING
Kd
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC ONCE DAILY ADMINISTRATION

Tmax PHARMACOKINETIC ONCE DAILY ADMINISTRATION