Alogliptin benzoate | 850649-62-6 | DPP-4 inhibitor

MedKoo Cat#: 314210 | Name: Alogliptin benzoate

Description:

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

Alogliptin benzoate is a DPP-4 inhibitor used for the treatment of Type 2 diabetes. Like other members of the gliptin class, it causes little or no weight gain, exhibits relatively little risk of causing hypoglycemia, and exhibits relatively modest glucose-lowering activity. Alogliptin and other gliptins are commonly used in combination with metformin in patients whose diabetes cannot adequately be controlled with metformin alone.

Chemical Structure

Alogliptin benzoate

CAS#850649-62-6 (benzoate)

Theoretical Analysis

MedKoo Cat#: 314210

Name: Alogliptin benzoate

CAS#: 850649-62-6 (benzoate)

Chemical Formula: C25H27N5O4

Exact Mass: 0.0000

Molecular Weight: 461.52

Elemental Analysis: C, 65.06; H, 5.90; N, 15.17; O, 13.87

Price and Availability

Size	Price	Availability
1g	USD 90.00	Ready to ship
2g	USD 150.00	Ready to ship
5g	USD 350.00	Ready to ship
10g	USD 550.00	Ready to ship
20g	USD 850.00	Ready to ship
50g	USD 1,450.00	Ready to ship
100g	USD 2,250.00	Ready to ship

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Related CAS #

850649-61-5 (free base) 850649-62-6 (benzoate)

Synonym

SYR322, SYR 322, SYR-322, Nesina, Kazano, Oseni, Alogliptin benzoate.

IUPAC/Chemical Name

(R)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile benzoate

InChi Key

KEJICOXJTRHYAK-XFULWGLBSA-N

InChi Code

InChI=1S/C18H21N5O2.C7H6O2/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;8-7(9)6-4-2-1-3-5-6/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3;1-5H,(H,8,9)/t15-;/m1./s1

SMILES Code

O=C(O)C1=CC=CC=C1.N#CC2=CC=CC=C2CN(C(N3C)=O)C(N4C[C@H](N)CCC4)=CC3=O

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

Related: 850649-62-6 (Alogliptin benzoate) 850649-61-5 (Alogliptin free base).

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C7R12B11

QC Data

View QC data: current batch, Lot#C7R12B11

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Alogliptin Benzoate (SYR-322) 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	39.4	85.30
	DMF	0.1	0.22
	PBS (pH 7.2)	10.0	21.67
	Water	2.0	4.33

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 461.52 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:

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: Capuano A, Sportiello L, Maiorino MI, Rossi F, Giugliano D, Esposito K. Dipeptidyl peptidase-4 inhibitors in type 2 diabetes therapy--focus on alogliptin. Drug Des Devel Ther. 2013 Sep 17;7:989-1001. doi: 10.2147/DDDT.S37647. eCollection 2013. Review. PubMed PMID: 24068868; PubMed Central PMCID: PMC3782406. 2: Agrawal R, Bahare RS, Jain P, Dikshit SN, Ganguly S. Novel serine protease dipeptidyl peptidase IV inhibitor: alogliptin. Mini Rev Med Chem. 2012 Nov;12(13):1345-58. Review. PubMed PMID: 22512582. 3: 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. Review. PubMed PMID: 22296609. 4: Ueki K. [A compounding agent of alogliptin and pioglitazone]. Nihon Rinsho. 2011 May;69(5):877-82. Review. Japanese. PubMed PMID: 21595275. 5: Tanabe A, Kaku K. [Alogliptin]. Nihon Rinsho. 2011 May;69(5):871-6. Review. Japanese. PubMed PMID: 21595274. 6: 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. Review. PubMed PMID: 21431099. 7: Takeuchi K, Fujita T, Hiroi S. [Pharmacological and clinical profile of alogliptin benzoate (NESINAÂ®)]. Nihon Yakurigaku Zasshi. 2011 Jan;137(1):43-50. Review. Japanese. PubMed PMID: 21233588. 8: 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. Review. Erratum in: Drugs. 2010 Dec 24;70(18):2475. PubMed PMID: 20883057.