rac-Sitagliptin

Modify Date: 2024-01-03 10:18:04

rac-Sitagliptin structure	Common Name	rac-Sitagliptin
	CAS Number	823817-56-7	Molecular Weight	407.31
	Density	1.6±0.1 g/cm3	Boiling Point	529.9±60.0 °C at 760 mmHg
	Molecular Formula	C₁₆H₁₅F₆N₅O	Melting Point	N/A
	MSDS	N/A	Flash Point	274.3±32.9 °C

Use of rac-Sitagliptin

(Rac)-Sitagliptin is an isoform of Sitagliptin (HY-13749), which is a potent and orally active inhibitor of DPP4 with an IC50 of 19 nM in Caco-2 cell extracts[1].

Name	3-Amino-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]p yrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-1-butanone
Synonym	More Synonyms

Description	(Rac)-Sitagliptin is an isoform of Sitagliptin (HY-13749), which is a potent and orally active inhibitor of DPP4 with an IC50 of 19 nM in Caco-2 cell extracts[1].
Related Catalog	Signaling Pathways >> Metabolic Enzyme/Protease >> Dipeptidyl Peptidase Signaling Pathways >> Autophagy >> Autophagy Research Areas >> Metabolic Disease
References	[1]. Beconi, M.G., et al. Disposition of the dipeptidyl peptidase 4 inhibitor sitagliptin in rats and dogs. Drug Metab Dispos, 2007. 35(4): p. 525-32. [2]. Thomas, L., et al. (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. J Pharmacol Exp Ther. 2008 Apr;325(1):175-82. [3]. Kim, S.J., et al., Dipeptidyl peptidase IV inhibition with MK0431 improves islet graft survival in diabetic NOD mice partially via T-cell modulation. Diabetes, 2009. 58(3): p. 641-51. [4]. Sangle, G.V., et al., Novel biological action of the dipeptidylpeptidase-IV inhibitor, sitagliptin, as a GLP-1 secretagogue. Endocrinology, 2012. 153(2): p. 564-73. [5]. Kim, S.J., et al., Inhibition of dipeptidyl peptidase IV with sitagliptin (MK0431) prolongs islet graft survival in streptozotocin-induced diabetic mice. Diabetes, 2008. 57(5): p. 1331-9.

Description

(Rac)-Sitagliptin is an isoform of Sitagliptin (HY-13749), which is a potent and orally active inhibitor of DPP4 with an IC50 of 19 nM in Caco-2 cell extracts[1].

Related Catalog

Signaling Pathways >> Metabolic Enzyme/Protease >> Dipeptidyl Peptidase

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Metabolic Disease

References

[1]. Beconi, M.G., et al. Disposition of the dipeptidyl peptidase 4 inhibitor sitagliptin in rats and dogs. Drug Metab Dispos, 2007. 35(4): p. 525-32.

[2]. Thomas, L., et al. (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. J Pharmacol Exp Ther. 2008 Apr;325(1):175-82.

[3]. Kim, S.J., et al., Dipeptidyl peptidase IV inhibition with MK0431 improves islet graft survival in diabetic NOD mice partially via T-cell modulation. Diabetes, 2009. 58(3): p. 641-51.

[4]. Sangle, G.V., et al., Novel biological action of the dipeptidylpeptidase-IV inhibitor, sitagliptin, as a GLP-1 secretagogue. Endocrinology, 2012. 153(2): p. 564-73.

[5]. Kim, S.J., et al., Inhibition of dipeptidyl peptidase IV with sitagliptin (MK0431) prolongs islet graft survival in streptozotocin-induced diabetic mice. Diabetes, 2008. 57(5): p. 1331-9.

Density	1.6±0.1 g/cm3
Boiling Point	529.9±60.0 °C at 760 mmHg
Molecular Formula	C₁₆H₁₅F₆N₅O
Molecular Weight	407.31
Flash Point	274.3±32.9 °C
Exact Mass	407.118073
PSA	77.04000
LogP	1.30
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.590

Precursor 6
CAS#:847445-81-2 3-AMINO-1-(3-(T... CAS#:1253056-14-2 (R/S)-2-(4-oxo-... CAS#:767340-03-4 (2Z)-4-Oxo-4-[3... CAS#:209995-38-0 2,4,5-Trifluoro...
CAS#:1351564-27-6 3-nitro-1-(3-(t... CAS#:1253056-01-7 (R/S)-3-hydroxy...
DownStream 1
CAS#:486460-32-6 Sitagliptin

7-(1-oxo-3-amino-4-(2,4,5-trifluorophenyl)butyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine

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

3-amino-1-(3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-4-(2,4,5-trifluoro-phenyl)-butan-1-one

(2RS)-2-methyloctan-1-ol

(R/S)-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

2-methyloctanol

1-Butanone, 3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-

2-Methylontan-1-ol

3-Amino-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-1-butanone

2-methyloctan-1-ol

3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

(2RS)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-rifluorophenyl)butan-2-amine

7-[1-Oxo-3-amino-4-(2,4,5-trifluorophenyl)butyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine

Sitagliptin Impurity 1

rac-Sitagliptin

Use of rac-Sitagliptin

Names

rac-Sitagliptin Biological Activity

Chemical & Physical Properties

Synthetic Route

Precursor & DownStream

Synonyms