Sitagliptin free base | CAS#486460-32-6 | DPP4 inhibitor

MedKoo Cat#: 596121 | Name: Sitagliptin free base

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sitagliptin, also known as MK-0431, is a potent inhibitor of DPP4. Sitagliptin is believed to exert its actions in patients with type 2 diabetes mellitus by slowing the inactivation of incretin hormones. By increasing and prolonging active incretin levels, sitagliptin increases insulin release and decreases glucagon levels in the circulation in a glucose-dependent manner. Sitagliptin demonstrates selectivity for DPP-4 and does not inhibit DPP-8 or DPP-9 activity in vitro at concentrations approximating those from therapeutic doses.

Chemical Structure

Sitagliptin free base

CAS#486460-32-6 (free base)

Theoretical Analysis

MedKoo Cat#: 596121

Name: Sitagliptin free base

CAS#: 486460-32-6 (free base)

Chemical Formula: C16H15F6N5O

Exact Mass: 407.1181

Molecular Weight: 407.32

Elemental Analysis: C, 47.18; H, 3.71; F, 27.99; N, 17.19; O, 3.93

Price and Availability

Size	Price	Availability
1g	USD 90.00	2 Weeks
2g	USD 150.00	2 Weeks
5g	USD 350.00	2 Weeks
10g	USD 550.00	2 Weeks
20g	USD 950.00	2 Weeks
50g	USD 1,850.00	2 Weeks
100g	USD 2,950.00	2 Weeks

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Related CAS #

654671-77-9 (phosphate hydrate) 486460-32-6 (free base) 654671-78-0 (phosphate)

Synonym

Sitagliptin; LEZ 763; LEZ-763; LEZ763; MK0431; MK 0431; MK-0431;

IUPAC/Chemical Name

(R)-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

InChi Key

MFFMDFFZMYYVKS-SECBINFHSA-N

InChi Code

InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1

SMILES Code

FC(C1=NN=C2CN(C(C[C@H](N)CC3=CC(F)=C(F)C=C3F)=O)CCN21)(F)F

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sitagliptin is a potent and orally active inhibitor of DPP4 with an IC50 of 19 nM in Caco-2 cell extracts.

In vitro activity:

Sitagliptin induces differentiation of tolerogenic dendritic cells, and the effect is important when considering sitagliptin for treating autoimmune diseases and allotransplant rejection. Sitagliptin impaired differentiation and maturation of human dendritic cells generated from monocytes (MoDCs), while the expression of CD26, tolerogenic DC markers, and production of immunoregulatory cytokines increased. Sitagliptin inhibited p65 expression of NF-kB and p38MAPK during the maturation of MoDCs. Reference: Int J Mol Sci. 2023 Nov 27;24(23):16829. https://pubmed.ncbi.nlm.nih.gov/38069152/

In vivo activity:

Sitagliptin showed significant antinociceptive and anti-inflammatory effects. In the carrageenan test, sitagliptin significantly reduced paw thickness in male Wistar rats. Pretreatment with yohimbine, prazosin, propranolol, naloxone, and cyproheptadine could not reverse the antinociceptive effect of sitagliptin, which indicates that adrenergic, opioid, and serotonin receptors are not involved in the antinociceptive effects. L-NAME, methylene blue, glibenclamide, ondansetron, and sulpiride were able to reverse this effect. Reference: Korean J Pain. 2023 Dec 21. https://pubmed.ncbi.nlm.nih.gov/38123184/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	50.0	122.76

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 407.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Drakul M, Tomić S, Bekić M, Mihajlović D, Vasiljević M, Rakočević S, Đokić J, Popović N, Bokonjić D, Čolić M. Sitagliptin Induces Tolerogenic Human Dendritic Cells. Int J Mol Sci. 2023 Nov 27;24(23):16829. doi: 10.3390/ijms242316829. PMID: 38069152; PMCID: PMC10706581. 2. Kosowska A, Garczorz W, Kłych-Ratuszny A, Aghdam MRF, Kimsa-Furdzik M, Simka-Lampa K, Francuz T. Sitagliptin Modulates the Response of Ovarian Cancer Cells to Chemotherapeutic Agents. Int J Mol Sci. 2020 Nov 26;21(23):8976. doi: 10.3390/ijms21238976. PMID: 33256016; PMCID: PMC7731375. 3. Hajhashemi V, Sadeghi H, Karimi Madab F. Anti-inflammatory and antinociceptive effects of sitagliptin in animal models and possible mechanisms involved in the antinociceptive activity. Korean J Pain. 2023 Dec 21. doi: 10.3344/kjp.23262. Epub ahead of print. PMID: 38123184. 4. Zong Y, Wang X, Zhang Y, Tan N, Zhang Y, Li L, Liu L. Sitagliptin Ameliorates Creb5/lncRNA ENSMUST00000213271-Mediated Vascular Endothelial Dysfunction in Obese Mice. Cardiovasc Drugs Ther. 2023 Feb 4. doi: 10.1007/s10557-023-07436-1. Epub ahead of print. PMID: 36738369.

In vitro protocol:

In vivo protocol:

1. Hajhashemi V, Sadeghi H, Karimi Madab F. Anti-inflammatory and antinociceptive effects of sitagliptin in animal models and possible mechanisms involved in the antinociceptive activity. Korean J Pain. 2023 Dec 21. doi: 10.3344/kjp.23262. Epub ahead of print. PMID: 38123184. 2. Zong Y, Wang X, Zhang Y, Tan N, Zhang Y, Li L, Liu L. Sitagliptin Ameliorates Creb5/lncRNA ENSMUST00000213271-Mediated Vascular Endothelial Dysfunction in Obese Mice. Cardiovasc Drugs Ther. 2023 Feb 4. doi: 10.1007/s10557-023-07436-1. Epub ahead of print. PMID: 36738369.

1: Zeng DK, Xiao Q, Li FQ, Tang YZ, Jia CL, Tang XW. Cardiovascular risk of sitagliptin in treating patients with type 2 diabetes mellitus. Biosci Rep. 2019 Jul 15;39(7):BSR20190980. doi: 10.1042/BSR20190980. PMID: 31262972; PMCID: PMC6629947. 2: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Sitagliptin. 2019 Feb 7. PMID: 30000709. 3: Wiciński M, Wódkiewicz E, Słupski M, Walczak M, Socha M, Malinowski B, Pawlak-Osińska K. Neuroprotective Activity of Sitagliptin via Reduction of Neuroinflammation beyond the Incretin Effect: Focus on Alzheimer's Disease. Biomed Res Int. 2018 Aug 16;2018:6091014. doi: 10.1155/2018/6091014. PMID: 30186862; PMCID: PMC6116461. 4: Zhou Y, Guo Z, Yan W, Wang W. Cardiovascular effects of sitagliptin - An anti-diabetes medicine. Clin Exp Pharmacol Physiol. 2018 Jul;45(7):628-635. doi: 10.1111/1440-1681.12953. Epub 2018 May 20. PMID: 29679391. 5: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Sitagliptin. 2018 Jan 3. PMID: 31643413. 6: Mega C, Teixeira-de-Lemos E, Fernandes R, Reis F. Renoprotective Effects of the Dipeptidyl Peptidase-4 Inhibitor Sitagliptin: A Review in Type 2 Diabetes. J Diabetes Res. 2017;2017:5164292. doi: 10.1155/2017/5164292. Epub 2017 Aug 27. PMID: 29098166; PMCID: PMC5643039. 7: Sharma M, Beckley N, Nazareth I, Petersen I. Effectiveness of sitagliptin compared to sulfonylureas for type 2 diabetes mellitus inadequately controlled on metformin: a systematic review and meta-analysis. BMJ Open. 2017 Oct 30;7(10):e017260. doi: 10.1136/bmjopen-2017-017260. PMID: 29084794; PMCID: PMC5665259. 8: Keshavarz K, Lotfi F, Sanati E, Salesi M, Hashemi-Meshkini A, Jafari M, Mojahedian MM, Najafi B, Nikfar S. Linagliptin versus sitagliptin in patients with type 2 diabetes mellitus: a network meta-analysis of randomized clinical trials. Daru. 2017 Oct 25;25(1):23. doi: 10.1186/s40199-017-0189-6. PMID: 29070077; PMCID: PMC5655990. 9: Li M, Yang Y, Jiang D, Ying M, Wang Y, Zhao R. Efficacy and safety of liraglutide versus sitagliptin both in combination with metformin in patients with type 2 diabetes: A systematic review and meta-analysis. Medicine (Baltimore). 2017 Sep;96(39):e8161. doi: 10.1097/MD.0000000000008161. PMID: 28953663; PMCID: PMC5626306. 10: Scott LJ. Sitagliptin: A Review in Type 2 Diabetes. Drugs. 2017 Feb;77(2):209-224. doi: 10.1007/s40265-016-0686-9. PMID: 28078647. 11: Hayes J, Anderson R, Stephens JW. Sitagliptin/metformin fixed-dose combination in type 2 diabetes mellitus: an evidence-based review of its place in therapy. Drug Des Devel Ther. 2016 Jul 19;10:2263-70. doi: 10.2147/DDDT.S93076. PMID: 27486305; PMCID: PMC4958358. 12: Alshali KZ, Karawagh AM. A review of glycemic efficacy of liraglutide once daily in achieving glycated hemoglobin targets compared with exenatide twice daily, or sitagliptin once daily in the treatment of type 2 diabetes. Saudi Med J. 2016 Aug;37(8):834-42. doi: 10.15537/smj.2016.8.15800. PMID: 27464858; PMCID: PMC5018698. 13: Suresh PS, Srinivas NR, Mullangi R. A concise review of the bioanalytical methods for the quantitation of sitagliptin, an important dipeptidyl peptidase-4 (DPP4) inhibitor, utilized for the characterization of the drug. Biomed Chromatogr. 2016 May;30(5):749-71. doi: 10.1002/bmc.3705. Epub 2016 Mar 14. PMID: 26873580. 14: Fan M, Li Y, Zhang S. Effects of Sitagliptin on Lipid Profiles in Patients With Type 2 Diabetes Mellitus: A Meta-analysis of Randomized Clinical Trials. Medicine (Baltimore). 2016 Jan;95(2):e2386. doi: 10.1097/MD.0000000000002386. PMID: 26765417; PMCID: PMC4718243. 15: Lee M, Rhee MK. Sitagliptin for Type 2 diabetes: a 2015 update. Expert Rev Cardiovasc Ther. 2015 Jun;13(6):597-610. doi: 10.1586/14779072.2015.1046840. PMID: 26000559. 16: Cornell S. Review of empagliflozin monotherapy for previously untreated patients with type 2 diabetes mellitus: Comparison with sitagliptin. Postgrad Med. 2015 Apr;127(3):277-81. doi: 10.1080/00325481.2015.1018798. Epub 2015 Feb 27. PMID: 25724655. 17: Ramadan WH, Kabbara WK. Sitagliptin/Simvastatin: a first combination tablet to treat type 2 diabetes and hypercholesterolemia--a review of its characteristics. Vasc Health Risk Manag. 2015 Feb 11;11:125-32. doi: 10.2147/VHRM.S79198. PMID: 25709467; PMCID: PMC4334171. 18: Du Q, Wang YJ, Yang S, Han P. Clinical utility and patient considerations in the use of the sitagliptin-metformin combination in Chinese patients. Patient Prefer Adherence. 2015 Feb 9;9:281-7. doi: 10.2147/PPA.S64691. PMID: 25709414; PMCID: PMC4332288. 19: Chang MW, Chen CH, Chen YC, Wu YC, Zhen YY, Leu S, Tsai TH, Ko SF, Sung PH, Yang CC, Chiang HJ, Chang HW, Chen YT, Yip HK. Sitagliptin protects rat kidneys from acute ischemia-reperfusion injury via upregulation of GLP-1 and GLP-1 receptors. Acta Pharmacol Sin. 2015 Jan;36(1):119-30. doi: 10.1038/aps.2014.98. Epub 2014 Dec 15. PMID: 25500876; PMCID: PMC4571325. 20: Wang T, Gou Z, Wang F, Ma M, Zhai SD. Comparison of GLP-1 analogues versus sitagliptin in the management of type 2 diabetes: systematic review and meta- analysis of head-to-head studies. PLoS One. 2014 Aug 4;9(8):e103798. doi: 10.1371/journal.pone.0103798. PMID: 25089625; PMCID: PMC4121242.