Saxagliptin | CAS# 361442-04-8 | putative antidiabetic agent | DPP-4 inhibitor

MedKoo Cat#: 414578 | Name: Saxagliptin

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Description:

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

Saxagliptin, also known as BMS-477118, is a new oral hypoglycemic (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Saxagliptin was approved in 2008 for the treatment of type 2 diabetes. Saxagliptin is a competitive DPP4 inhibitor that slows the inactivation of the incretin hormones, thereby increasing their bloodstream concentrations and reducing fasting and postprandial glucose concentrations in a glucose-dependent manner in patients with type 2 diabetes mellitus.

Chemical Structure

Saxagliptin

CAS#361442-04-8 (free base)

Theoretical Analysis

MedKoo Cat#: 414578

Name: Saxagliptin

CAS#: 361442-04-8 (free base)

Chemical Formula: C18H25N3O2

Exact Mass: 315.1947

Molecular Weight: 315.42

Elemental Analysis: C, 68.54; H, 7.99; N, 13.32; O, 10.14

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
250mg	USD 450.00	2 Weeks
1g	USD 950.00	2 Weeks

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Related CAS #

945667-22-1 (hydrate) 709031-78-7 (HCl) 361442-04-8 (free base) 1073057-20-1 (HCl hydrate) 1073057-33-6 (benzoate hydrate)

Synonym

Saxagliptin; Saxagliptine; HSDB8199; HSDB-8199; HSDB 8199; OPC262; OPC-262; OPC 262; Onglyza; BMS477118; BMS 477118; BMS-477118;

IUPAC/Chemical Name

2-Azabicyclo(3.1.0)hexane-3-carbonitrile, 2-((2S)-amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl) , (1S,3S,5S)-

InChi Key

QGJUIPDUBHWZPV-SGTAVMJGSA-N

InChi Code

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

SMILES Code

N#C[C@H]1N(C([C@@H](N)C2(C3)CC4(O)CC3CC(C4)C2)=O)[C@@]5([H])C[C@@]5([H])C1

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 315.42 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

1: Elmorsy EA, Youssef ME, Abdel-Hamed MR, Amer MM, Elghandour SR, Alkhamiss AS, Mohamed NB, Khodeir MM, Elsisi HA, Alsaeed TS, Kamal MM, Ellethy AT, Elesawy BH, Saber S. Activation of AMPK/SIRT1/FOXO3a signaling by BMS-477118 (saxagliptin) mitigates chronic colitis in rats: uncovering new anti-inflammatory and antifibrotic roles. Front Pharmacol. 2024 Sep 18;15:1456058. doi: 10.3389/fphar.2024.1456058. PMID: 39359253; PMCID: PMC11445602. 2: Pham Nguyen TP, Leonard CE, Brensinger CM, Bilker WB, Chung SP, Horn JR, Bogar K, Miano TA, Hennessy S. Concomitant Use of Oral Anticoagulants with Oral Dipeptidyl Peptidase-4 Inhibitors and Serious Bleeding Events. Clin Pharmacol Ther. 2024 Sep 11. doi: 10.1002/cpt.3442. Epub ahead of print. PMID: 39262110. 3: Huang KH, Yang Y, Gau SY, Tsai TH, Lee CY. Association between dipeptidyl peptidase-4 inhibitor use and risk of Parkinson's disease among patients with diabetes mellitus: a retrospective cohort study. Aging (Albany NY). 2024 Aug 22;16(16):11994-12007. doi: 10.18632/aging.206074. Epub 2024 Aug 22. PMID: 39177655; PMCID: PMC11386917. 4: Wang T, Tao T, Liu Y, Dong J, Ni S, Liu Y, Li Y, Xu N, Sun Z. Pharmacokinetic/Pharmacodynamic modelling of Saxagliptin and its active metabolite, 5-hydroxy Saxagliptin in rats with Type 2 Diabetes Mellitus. BMC Pharmacol Toxicol. 2024 Jun 26;25(1):35. doi: 10.1186/s40360-024-00757-3. PMID: 39103956; PMCID: PMC11299271. 5: Li X, Zhou X, Gao L. Diabetes and Heart Failure: A Literature Review, Reflection and Outlook. Biomedicines. 2024 Jul 15;12(7):1572. doi: 10.3390/biomedicines12071572. PMID: 39062145; PMCID: PMC11274420. 6: Olivares M, Hernández-Calderón P, Cárdenas-Brito S, Liébana-García R, Sanz Y, Benítez-Páez A. Gut microbiota DPP4-like enzymes are increased in type-2 diabetes and contribute to incretin inactivation. Genome Biol. 2024 Jul 3;25(1):174. doi: 10.1186/s13059-024-03325-4. PMID: 38961511; PMCID: PMC11221189. 7: Atănăsoie AM, Ancuceanu RV, Krajnović D, Waszyk-Nowaczyk M, Skotnicki M, Tondowska D, Petrova G, Niculae AM, Tăerel AE. Approved and Commercialized Antidiabetic Medicines (Excluding Insulin) in Seven European Countries-A Cross- Sectional Comparison. Pharmaceuticals (Basel). 2024 Jun 17;17(6):793. doi: 10.3390/ph17060793. PMID: 38931460; PMCID: PMC11207096. 8: Abdelhamid AH, Mantawy EM, Said RS, El-Demerdash E. Neuroprotective effects of saxagliptin against radiation-induced cognitive impairment: Insights on Akt/CREB/SIRT1/BDNF signaling pathway. Toxicol Appl Pharmacol. 2024 Aug;489:116994. doi: 10.1016/j.taap.2024.116994. Epub 2024 Jun 8. PMID: 38857790. 9: Kim NH, Moon JS, Lee YH, Cho HC, Kwak SH, Lim S, Moon MK, Kim DL, Kim TH, Ko E, Lee J, Kim SG. Efficacy and tolerability of initial triple combination therapy with metformin, dapagliflozin and saxagliptin compared with stepwise add-on therapy in drug-naïve patients with type 2 diabetes (TRIPLE-AXEL study): A multicentre, randomized, 104-week, open-label, active-controlled trial. Diabetes Obes Metab. 2024 Sep;26(9):3642-3652. doi: 10.1111/dom.15705. Epub 2024 Jun 10. PMID: 38853720. 10: Makram TS, Eid SM, Abu-Dahab M, AbouGhaly MHH, Elnahas OS. Formulation of Saxagliptin Oral Films: Optimization, Physicochemical Characterization, In-Vivo Assessment, and In-Vitro Real-Time Release Monitoring via a Novel Polyaniline Nanoparticles-Based Solid-Contact Screen Printed Ion-Selective Electrode. AAPS PharmSciTech. 2024 May 20;25(5):116. doi: 10.1208/s12249-024-02828-4. PMID: 38769223. 11: Tang Y, Yan M, Fang Z, Jin S, Xu T. Effects of metformin, saxagliptin and repaglinide on gut microbiota in high-fat diet/streptozocin-induced type 2 diabetic mice. BMJ Open Diabetes Res Care. 2024 May 6;12(3):e003837. doi: 10.1136/bmjdrc-2023-003837. PMID: 38719505; PMCID: PMC11085777. 12: Dai GX, Tan W, Shen Y, Lin D, Xu RA, Lin Q, Wei Z. Differential inhibition of sildenafil and macitentan on saxagliptin metabolism. Toxicol Appl Pharmacol. 2024 May;486:116934. doi: 10.1016/j.taap.2024.116934. Epub 2024 Apr 24. PMID: 38663673. 13: Daniele G, Tura A, Brocchi A, Saba A, Campi B, Sancho-Bornez V, Dardano A, Del Prato S. β-Cell Function, Incretin Effect, and Glucose Kinetics in Response to a Mixed Meal in Patients With Type 2 Diabetes Treated With Dapagliflozin Plus Saxagliptin. Diabetes Care. 2024 Jul 1;47(7):1131-1139. doi: 10.2337/dc23-2051. PMID: 38652656. 14: Yoosuf BT, Favas Kt M, Dutta P, Bansal D. Comprehensive safety profile of dipeptidyl peptidase-4 inhibitors: a post-marketing study based on FAERS database using signal detection algorithms. Expert Opin Drug Saf. 2024 Apr 23:1-13. doi: 10.1080/14740338.2024.2343015. Epub ahead of print. PMID: 38626310. 15: Rahim K, Shan M, Ul Haq I, Nawaz MN, Maryam S, Alturki MS, Al Khzem AH, Metwally K, Cavalu S, Alqifari SF, Yahya G. Revolutionizing Treatment Strategies for Autoimmune and Inflammatory Disorders: The Impact of Dipeptidyl-Peptidase 4 Inhibitors. J Inflamm Res. 2024 Mar 23;17:1897-1917. doi: 10.2147/JIR.S442106. PMID: 38544813; PMCID: PMC10968008. 16: Tasnim J, Hashim NM, Han HC. A comprehensive review on potential drug-drug interactions of proton pump inhibitors with antidiabetic drugs metformin and DPP-4 inhibitors. Cell Biochem Funct. 2024 Mar;42(2):e3967. doi: 10.1002/cbf.3967. PMID: 38480622. 17: Sivadas A, Sahana S, Jolly B, Bhoyar RC, Jain A, Sharma D, Imran M, Senthivel V, Divakar MK, Mishra A, Mukhopadhyay A, Gibson G, Narayan KV, Sivasubbu S, Scaria V, Kurpad AV. Landscape of pharmacogenetic variants associated with non-insulin antidiabetic drugs in the Indian population. BMJ Open Diabetes Res Care. 2024 Mar 12;12(2):e003769. doi: 10.1136/bmjdrc-2023-003769. PMID: 38471670; PMCID: PMC10936492. 18: Huršidić Radulović A, Babić Ž, Macan M, Macan J. Contact allergy to olanzapine and saxagliptin in a pharmaceutical industrial worker: A case report. Contact Dermatitis. 2024 Jun;90(6):628-630. doi: 10.1111/cod.14534. Epub 2024 Mar 6. PMID: 38448210. 19: Simonson DC, Testa MA, Ekholm E, Su M, Vilsbøll T, Jabbour SA, Lind M. Continuous Glucose Monitoring Profiles and Health Outcomes after Dapagliflozin Plus Saxagliptin vs Insulin Glargine. J Clin Endocrinol Metab. 2024 Feb 27:dgae105. doi: 10.1210/clinem/dgae105. Epub ahead of print. PMID: 38412282. 20: Lee JM, Yoon JH, Maeng HJ, Kim YC. Physiologically Based Pharmacokinetic (PBPK) Modeling to Predict CYP3A-Mediated Drug Interaction between Saxagliptin and Nicardipine: Bridging Rat-to-Human Extrapolation. Pharmaceutics. 2024 Feb 16;16(2):280. doi: 10.3390/pharmaceutics16020280. PMID: 38399334; PMCID: PMC10892660.