IUPAC/Chemical Name
(R)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile
InChi Key
ZSBOMTDTBDDKMP-OAHLLOKOSA-N
InChi Code
1S/C18H21N5O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3/t15-/m1/s1
SMILES Code
n1(c(=O)cc(n(c1=O)Cc1c(cccc1)C#N)N1C[C@@H](CCC1)N)C
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
>3 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
Biological target:
Alogliptin (SYR-322 free base) is an inhibitor of DPP-4 with an IC50 of <10 nM.
In vitro activity:
As shown in Fig. 5, time course fluorescence tracking showed that OGD/R exposure increased FITC-dextran permeation as compared to the control, which was prevented by treatment with alogliptin in a dose-dependent manner. These data indicate that alogliptin could ameliorate OGD/R-induced increased permeability in human brain vascular cells.
Reference: Biomed Pharmacother. 2019 Jan;109:181-187. https://pubmed.ncbi.nlm.nih.gov/30396075/
In vivo activity:
Representative histological sections from the left ventricle are shown in Fig. 3A–C. Extensive interstitial fibrosis was observed in the diabetic rabbit group compared to controls, which was attenuated by alogliptin treatment. The ultrastructure of left ventricular cardiomyocytes under the different conditions are shown in Fig. 4A–C. There were regular sarcomere organization and uniformly-sized mitochondria in the control group. Under the diabetic condition, swelling mitochondria between sarcomeres were observed. These changes were prevented by alogliptin treatment.
Reference: Cardiovasc Diabetol. 2018; 17: 160. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6307280/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
67.0 |
197.41 |
| Ethanol |
67.0 |
197.41 |
| Water |
18.0 |
53.03 |
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
339.40
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. Shigematsu N, Kawashiri T, Kobayashi D, Shimizu S, Mine K, Hiromoto S, Uchida M, Egashira N, Shimazoe T. Neuroprotective effect of alogliptin on oxaliplatin-induced peripheral neuropathy in vivo and in vitro. Sci Rep. 2020 Apr 21;10(1):6734. doi: 10.1038/s41598-020-62738-w. PMID: 32317735; PMCID: PMC7174301.
2. Hao FL, Han XF, Wang XL, Zhao ZR, Guo AH, Lu XJ, Zhao XF. The neurovascular protective effect of alogliptin in murine MCAO model and brain endothelial cells. Biomed Pharmacother. 2019 Jan;109:181-187. doi: 10.1016/j.biopha.2018.10.064. Epub 2018 Nov 2. PMID: 30396075.
3. Zhang X, Zhang Z, Yang Y, Suo Y, Liu R, Qiu J, Zhao Y, Jiang N, Liu C, Tse G, Li G, Liu T. Alogliptin prevents diastolic dysfunction and preserves left ventricular mitochondrial function in diabetic rabbits. Cardiovasc Diabetol. 2018 Dec 27;17(1):160. doi: 10.1186/s12933-018-0803-z. PMID: 30591063; PMCID: PMC6307280.
4. Ta NN, Schuyler CA, Li Y, Lopes-Virella MF, Huang Y. DPP-4 (CD26) inhibitor alogliptin inhibits atherosclerosis in diabetic apolipoprotein E-deficient mice. J Cardiovasc Pharmacol. 2011 Aug;58(2):157-66. doi: 10.1097/FJC.0b013e31821e5626. PMID: 21558879; PMCID: PMC3155015.
In vitro protocol:
1. Shigematsu N, Kawashiri T, Kobayashi D, Shimizu S, Mine K, Hiromoto S, Uchida M, Egashira N, Shimazoe T. Neuroprotective effect of alogliptin on oxaliplatin-induced peripheral neuropathy in vivo and in vitro. Sci Rep. 2020 Apr 21;10(1):6734. doi: 10.1038/s41598-020-62738-w. PMID: 32317735; PMCID: PMC7174301.
2. Hao FL, Han XF, Wang XL, Zhao ZR, Guo AH, Lu XJ, Zhao XF. The neurovascular protective effect of alogliptin in murine MCAO model and brain endothelial cells. Biomed Pharmacother. 2019 Jan;109:181-187. doi: 10.1016/j.biopha.2018.10.064. Epub 2018 Nov 2. PMID: 30396075.
In vivo protocol:
1. Zhang X, Zhang Z, Yang Y, Suo Y, Liu R, Qiu J, Zhao Y, Jiang N, Liu C, Tse G, Li G, Liu T. Alogliptin prevents diastolic dysfunction and preserves left ventricular mitochondrial function in diabetic rabbits. Cardiovasc Diabetol. 2018 Dec 27;17(1):160. doi: 10.1186/s12933-018-0803-z. PMID: 30591063; PMCID: PMC6307280.
2. Ta NN, Schuyler CA, Li Y, Lopes-Virella MF, Huang Y. DPP-4 (CD26) inhibitor alogliptin inhibits atherosclerosis in diabetic apolipoprotein E-deficient mice. J Cardiovasc Pharmacol. 2011 Aug;58(2):157-66. doi: 10.1097/FJC.0b013e31821e5626. PMID: 21558879; PMCID: PMC3155015.
1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Alogliptin. 2021 Jun 21. PMID: 29999685.
2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Alogliptin. 2018 Jan 3. PMID: 31643598.
3: White WB, Cannon CP, Heller SR, Nissen SE, Bergenstal RM, Bakris GL, Perez AT, Fleck PR, Mehta CR, Kupfer S, Wilson C, Cushman WC, Zannad F; EXAMINE Investigators. Alogliptin after acute coronary syndrome in patients with type 2 diabetes. N Engl J Med. 2013 Oct 3;369(14):1327-35. doi: 10.1056/NEJMoa1305889. Epub 2013 Sep 2. PMID: 23992602.
4: Terrell JM, Jacobs TF. Alogliptin. 2023 May 1. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2023 Jan–. PMID: 29939586.
5: Ganesan D, Grewal H, Bilal H, Goodman A, Kumar R. Alogliptin-Associated Pancreatitis. Am J Ther. 2020 Dec 29. doi: 10.1097/MJT.0000000000001270. Epub ahead of print. PMID: 33416238.
6: Yeddi A, Abdelhai M, Mohamed AB, Yeddi O, Salih L, Ali M, Yeddi M. Alogliptin-Associated Angioedema: Case Report and Review of the Literature. Am J Ther. 2022 Nov-Dec 01;29(6):e748-e749. doi: 10.1097/MJT.0000000000001214. Epub 2020 Aug 3. PMID: 32769388.
7: Cada DJ, Levien TL, Baker DE. Alogliptin. Hosp Pharm. 2013 Jul;48(7):580-92. doi: 10.1310/hpj4807-580. PMID: 24421524; PMCID: PMC3839527.
8: Marino AB, Cole SW. Alogliptin: safety, efficacy, and clinical implications. J Pharm Pract. 2015 Feb;28(1):99-106. doi: 10.1177/0897190014522063. Epub 2014 Feb 13. PMID: 24532820.
9: Keating GM. Alogliptin: a review of its use in patients with type 2 diabetes mellitus. Drugs. 2015 May;75(7):777-96. doi: 10.1007/s40265-015-0385-y. PMID: 25855222.
10: Rendell M, Drincic A, Andukuri R. Alogliptin benzoate for the treatment of type 2 diabetes. Expert Opin Pharmacother. 2012 Mar;13(4):553-63. doi: 10.1517/14656566.2012.656088. Epub 2012 Feb 1. PMID: 22296609.
11: Scott LJ. Alogliptin: a review of its use in the management of type 2 diabetes mellitus. Drugs. 2010 Oct 22;70(15):2051-72. doi: 10.2165/11205080-000000000-00000. Erratum in: Drugs. 2010 Dec 24;70(18):2475. PMID: 20883057.
12: Zafar M, Shahbaz M, Hawley I, Rahmani MJ. Alogliptin-induced bullous pemphigoid. Br J Hosp Med (Lond). 2020 Jul 2;81(7):1-3. doi: 10.12968/hmed.2020.0043. Epub 2020 Jul 29. PMID: 32730152.
13: Tanabe A, Kaku K. [Alogliptin]. Nihon Rinsho. 2011 May;69(5):871-6. Japanese. PMID: 21595274.
14: White JR. Alogliptin for the treatment of type 2 diabetes. Drugs Today (Barc). 2011 Feb;47(2):99-107. doi: 10.1358/dot.2011.47.2.1583163. PMID: 21431099.
15: Yabe D, Seino Y. Alogliptin for the treatment of type 2 diabetes: a drug safety evaluation. Expert Opin Drug Saf. 2016;15(2):249-64. doi: 10.1517/14740338.2016.1125467. PMID: 26607297.
16: Jarvis CI, Cabrera A, Charron D. Alogliptin: a new dipeptidyl peptidase-4 inhibitor for type 2 diabetes mellitus. Ann Pharmacother. 2013 Nov;47(11):1532-9. doi: 10.1177/1060028013504076. PMID: 24285765.
17: Saisho Y. Alogliptin benzoate for management of type 2 diabetes. Vasc Health Risk Manag. 2015 Apr 10;11:229-43. doi: 10.2147/VHRM.S68564. PMID: 25914541; PMCID: PMC4401208.
18: Alogliptin (Nesina) for Type 2 Diabetes Mellitus [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2015 Aug. PMID: 26962596.
19: Terry D, Eads AV. Alogliptin Induced Stomatitis: An Adverse Drug Event Case Report. J Pharm Pract. 2022 Jun 15:8971900221108721. doi: 10.1177/08971900221108721. Epub ahead of print. PMID: 35702931.
20: Ndefo UA, Okoli O, Erowele G. Alogliptin: A new dipeptidyl peptidase-4 inhibitor for the management of type 2 diabetes mellitus. Am J Health Syst Pharm. 2014 Jan 15;71(2):103-9. doi: 10.2146/ajhp130131. PMID: 24375601.
