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MedKoo Cat#: 584234 | Name: Saxagliptin HCl
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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 HCl
Saxagliptin HCl
CAS#709031-78-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 584234

Name: Saxagliptin HCl

CAS#: 709031-78-7 (HCl)

Chemical Formula: C18H26ClN3O2

Exact Mass: 0.0000

Molecular Weight: 351.88

Elemental Analysis: C, 61.44; H, 7.45; Cl, 10.07; N, 11.94; O, 9.09

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 weeks
250mg USD 550.00 2 Weeks
500mg USD 800.00 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
(1S,3S,5S)-2-((2S)-Amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl)2- azabicyclo(3.1.0)hexane-3-carbonitrile hydrochloride
InChi Key
TUAZNHHHYVBVBR-IGSRIJEQSA-N
InChi Code
InChI=1S/C18H25N3O2.ClH/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;1H/t10-,11+,12-,13+,14+,15-,17+,18-;/m1./s1
SMILES Code
[H]Cl.N#C[C@H]1N(C([C@H]([C@]2(C[C@@H](C3)C4)C[C@]4(O)C[C@@H]3C2)N)=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
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:
Saxagliptin HCl is a high affinity DPP-IV inhibitor (Ki = 0.6 nM) and inhibits plasma DPP-IV (87%).
In vitro activity:
Saxagliptin shows promise as a treatment against diabetes-associated coronary heart disease. Saxagliptin improved cell viability in H9c2 cells. It reduced hypoxia-induced oxidative damage, loss of mitochondrial membrane potential, NOX 4, MMP-2, and MMP-9. Saxagliptin also suppressed hypoxia-induced expression ofHMGB1. Saxagliptin exerted atheroprotective effects by reducing the expression of MyD88 and increasing the expression of Nrf2 and HO-1. Reference: Chem Biol Interact. 2020 Jan 5;315:108864. https://pubmed.ncbi.nlm.nih.gov/31629700/
In vivo activity:
In a dorsal McFarlane flap rat model, saxagliptin promoted random skin flap survival. The saxagliptin group had reduced oxidative stress, NF-κB, TLR4, proinflammatory cytokines, and pyroptosis-related proteins but had increased VEGF levels in a dose-dependent manner. Reference: Int Immunopharmacol. 2023 Jul;120:110364. https://pubmed.ncbi.nlm.nih.gov/37224651/
Solvent mg/mL mM
Solubility
DMSO 35.2 100.00
Water 35.2 100.00
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 351.88 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.

Recalculate based on batch purity %
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. Wang Q, Xie X, Zhang D, Mao F, Wang S, Liao Y. Saxagliptin enhances osteogenic differentiation in MC3T3-E1 cells, dependent on the activation of AMP-activated protein kinase α (AMPKα)/runt-related transcription factor-2 (Runx-2). Bioengineered. 2022 Jan;13(1):431-439. doi: 10.1080/21655979.2021.2008667. PMID: 35258398; PMCID: PMC8805826. 2. Zhang L, Qi X, Zhang G, Zhang Y, Tian J. Saxagliptin protects against hypoxia-induced damage in H9c2 cells. Chem Biol Interact. 2020 Jan 5;315:108864. doi: 10.1016/j.cbi.2019.108864. Epub 2019 Oct 17. PMID: 31629700. 3. Meng Z, Wang K, Lan Q, Zhou T, Lin Y, Jiang Z, Chen J, Lin Y, Liu X, Lin H, Lin D. Saxagliptin promotes random skin flap survival. Int Immunopharmacol. 2023 Jul;120:110364. doi: 10.1016/j.intimp.2023.110364. Epub 2023 May 23. PMID: 37224651. 4. Tang Y, Leng YF, Wang W, Zhang J, Yuan TL, Wang J. Protective effect of Saxagliptin on diabetic rats with renal ischemia reperfusion injury by targeting oxidative stress and mitochondrial apoptosis pathway through activating Nrf-2/HO-1 signaling. Transpl Immunol. 2023 Feb;76:101762. doi: 10.1016/j.trim.2022.101762. Epub 2022 Nov 23. PMID: 36435353.
In vitro protocol:
1. Wang Q, Xie X, Zhang D, Mao F, Wang S, Liao Y. Saxagliptin enhances osteogenic differentiation in MC3T3-E1 cells, dependent on the activation of AMP-activated protein kinase α (AMPKα)/runt-related transcription factor-2 (Runx-2). Bioengineered. 2022 Jan;13(1):431-439. doi: 10.1080/21655979.2021.2008667. PMID: 35258398; PMCID: PMC8805826. 2. Zhang L, Qi X, Zhang G, Zhang Y, Tian J. Saxagliptin protects against hypoxia-induced damage in H9c2 cells. Chem Biol Interact. 2020 Jan 5;315:108864. doi: 10.1016/j.cbi.2019.108864. Epub 2019 Oct 17. PMID: 31629700.
In vivo protocol:
1. Meng Z, Wang K, Lan Q, Zhou T, Lin Y, Jiang Z, Chen J, Lin Y, Liu X, Lin H, Lin D. Saxagliptin promotes random skin flap survival. Int Immunopharmacol. 2023 Jul;120:110364. doi: 10.1016/j.intimp.2023.110364. Epub 2023 May 23. PMID: 37224651. 2. Tang Y, Leng YF, Wang W, Zhang J, Yuan TL, Wang J. Protective effect of Saxagliptin on diabetic rats with renal ischemia reperfusion injury by targeting oxidative stress and mitochondrial apoptosis pathway through activating Nrf-2/HO-1 signaling. Transpl Immunol. 2023 Feb;76:101762. doi: 10.1016/j.trim.2022.101762. Epub 2022 Nov 23. PMID: 36435353.
1: Leiter LA, Teoh H, Braunwald E, Mosenzon O, Cahn A, Kumar KM, Smahelova A, Hirshberg B, Stahre C, Frederich R, Bonnici F, Scirica BM, Bhatt DL, Raz I; SAVOR-TIMI 53 Steering Committee and Investigators. Efficacy and safety of saxagliptin in older participants in the SAVOR-TIMI 53 trial. Diabetes Care. 2015 Jun;38(6):1145-53. doi: 10.2337/dc14-2868. Epub 2015 Mar 10. PubMed PMID: 25758769. 2: Scirica BM, Bhatt DL, Braunwald E, Steg PG, Davidson J, Hirshberg B, Ohman P, Frederich R, Wiviott SD, Hoffman EB, Cavender MA, Udell JA, Desai NR, Mosenzon O, McGuire DK, Ray KK, Leiter LA, Raz I; SAVOR-TIMI 53 Steering Committee and Investigators. Saxagliptin and cardiovascular outcomes in patients with type 2 diabetes mellitus. N Engl J Med. 2013 Oct 3;369(14):1317-26. doi: 10.1056/NEJMoa1307684. Epub 2013 Sep 2. PubMed PMID: 23992601. 3: Schernthaner G, Durán-Garcia S, Hanefeld M, Langslet G, Niskanen L, Östgren CJ, Malvolti E, Hardy E. Efficacy and tolerability of saxagliptin compared with glimepiride in elderly patients with type 2 diabetes: a randomized, controlled study (GENERATION). Diabetes Obes Metab. 2015 Jul;17(7):630-8. doi: 10.1111/dom.12461. Epub 2015 Apr 7. PubMed PMID: 25761977. 4: Udell JA, Bhatt DL, Braunwald E, Cavender MA, Mosenzon O, Steg PG, Davidson JA, Nicolau JC, Corbalan R, Hirshberg B, Frederich R, Im K, Umez-Eronini AA, He P, McGuire DK, Leiter LA, Raz I, Scirica BM; SAVOR-TIMI 53 Steering Committee and Investigators. Saxagliptin and cardiovascular outcomes in patients with type 2 diabetes and moderate or severe renal impairment: observations from the SAVOR-TIMI 53 Trial. Diabetes Care. 2015 Apr;38(4):696-705. doi: 10.2337/dc14-1850. Epub 2014 Dec 31. PubMed PMID: 25552421. 5: Jain R. Utility of Saxagliptin in the Treatment of Type 2 Diabetes: Review of Efficacy and Safety. Adv Ther. 2015 Nov;32(11):1065-84. doi: 10.1007/s12325-015-0262-9. Epub 2015 Nov 17. Review. PubMed PMID: 26578430; PubMed Central PMCID: PMC4662714. 6: Mathieu C, Ranetti AE, Li D, Ekholm E, Cook W, Hirshberg B, Chen H, Hansen L, Iqbal N. Randomized, Double-Blind, Phase 3 Trial of Triple Therapy With Dapagliflozin Add-on to Saxagliptin Plus Metformin in Type 2 Diabetes. Diabetes Care. 2015 Nov;38(11):2009-17. doi: 10.2337/dc15-0779. Epub 2015 Aug 5. PubMed PMID: 26246458. 7: Rosenstock J, Hansen L, Zee P, Li Y, Cook W, Hirshberg B, Iqbal N. Dual add-on therapy in type 2 diabetes poorly controlled with metformin monotherapy: a randomized double-blind trial of saxagliptin plus dapagliflozin addition versus single addition of saxagliptin or dapagliflozin to metformin. Diabetes Care. 2015 Mar;38(3):376-83. doi: 10.2337/dc14-1142. Epub 2014 Oct 28. PubMed PMID: 25352655. 8: Vakkalagadda B, Vetter ML, Rana J, Smith CH, Huang J, Karkas J, Boulton DW, LaCreta F. Bioequivalence of saxagliptin/dapagliflozin fixed-dose combination tablets compared with coadministration of the individual tablets to healthy subjects. Pharmacol Res Perspect. 2016 Jan 12;3(6):e00201. doi: 10.1002/prp2.201. eCollection 2015 Dec. PubMed PMID: 27022473; PubMed Central PMCID: PMC4777251. 9: Sakai M, Uchii M, Myojo K, Kitayama T, Kunori S. Critical role of renal dipeptidyl peptidase-4 in ameliorating kidney injury induced by saxagliptin in Dahl salt-sensitive hypertensive rats. Eur J Pharmacol. 2015 Aug 15;761:109-15. doi: 10.1016/j.ejphar.2015.04.023. Epub 2015 May 1. PubMed PMID: 25936515. 10: Matthaei S, Catrinoiu D, Celiński A, Ekholm E, Cook W, Hirshberg B, Chen H, Iqbal N, Hansen L. Randomized, Double-Blind Trial of Triple Therapy With Saxagliptin Add-on to Dapagliflozin Plus Metformin in Patients With Type 2 Diabetes. Diabetes Care. 2015 Nov;38(11):2018-24. doi: 10.2337/dc15-0811. Epub 2015 Aug 31. PubMed PMID: 26324329. 11: Saine ME, Carbonari DM, Newcomb CW, Nezamzadeh MS, Haynes K, Roy JA, Cardillo S, Hennessy S, Holick CN, Esposito DB, Gallagher AM, Bhullar H, Strom BL, Lo Re V 3rd. Determinants of saxagliptin use among patients with type 2 diabetes mellitus treated with oral anti-diabetic drugs. BMC Pharmacol Toxicol. 2015 Apr 2;16:8. doi: 10.1186/s40360-015-0007-z. PubMed PMID: 25889498; PubMed Central PMCID: PMC4404079. 12: Dhillon S. Saxagliptin: A Review in Type 2 Diabetes. Drugs. 2015 Oct;75(15):1783-96. doi: 10.1007/s40265-015-0473-z. Review. PubMed PMID: 26403305. 13: Leibowitz G, Cahn A, Bhatt DL, Hirshberg B, Mosenzon O, Wei C, Jermendy G, Sheu WH, Sendon JL, Im K, Braunwald E, Scirica BM, Raz I. Impact of treatment with saxagliptin on glycaemic stability and β-cell function in the SAVOR-TIMI 53 study. Diabetes Obes Metab. 2015 May;17(5):487-94. doi: 10.1111/dom.12445. Epub 2015 Feb 25. PubMed PMID: 25656169. 14: Scirica BM, Braunwald E, Raz I, Cavender MA, Morrow DA, Jarolim P, Udell JA, Mosenzon O, Im K, Umez-Eronini AA, Pollack PS, Hirshberg B, Frederich R, Lewis BS, McGuire DK, Davidson J, Steg PG, Bhatt DL; SAVOR-TIMI 53 Steering Committee and Investigators*. Heart failure, saxagliptin, and diabetes mellitus: observations from the SAVOR-TIMI 53 randomized trial. Circulation. 2014 Oct 28;130(18):1579-88. doi: 10.1161/CIRCULATIONAHA.114.010389. Epub 2014 Sep 4. Erratum in: Circulation. 2015 Oct 13;132(15):e198. PubMed PMID: 25189213. 15: Iazzetta N, Garofalo C, Savino M, Sagliocca A, Santangelo S, Pacilio M, Liberti ME, Camocardi A, Ambrosca C, Minutolo R, De Nicola L, Conte G. Nephroprotection with saxagliptin. G Ital Nefrol. 2015 Nov-Dec;32(6). pii: gin/32.6.11. PubMed PMID: 26845214. 16: Mintz ML, Minervini G. Saxagliptin versus glipizide as add-on therapy to metformin: assessment of hypoglycemia. Curr Med Res Opin. 2014 May;30(5):761-70. doi: 10.1185/03007995.2014.880674. Epub 2014 Jan 30. PubMed PMID: 24397584. 17: Davidson JA. Tolerability of saxagliptin in patients with inadequately controlled type 2 diabetes: results from 6 phase III studies. J Manag Care Pharm. 2014 Feb;20(2):120-9. Review. PubMed PMID: 24456313. 18: Keller AC, Knaub LA, Miller MW, Birdsey N, Klemm DJ, Reusch JE. Saxagliptin restores vascular mitochondrial exercise response in the Goto-Kakizaki rat. J Cardiovasc Pharmacol. 2015 Feb;65(2):137-47. doi: 10.1097/FJC.0000000000000170. PubMed PMID: 25264749; PubMed Central PMCID: PMC4320657. 19: Williams DM, Stephens JW. Combination therapy with saxagliptin and dapagliflozin for the treatment of type 2 diabetes. Expert Opin Pharmacother. 2015;16(15):2373-9. doi: 10.1517/14656566.2015.1088830. Review. PubMed PMID: 26389773. 20: Konya H, Yano Y, Matsutani S, Tsunoda T, Ikawa T, Kusunoki Y, Matsuo T, Miuchi M, Katsuno T, Hamaguchi T, Miyagawa J, Namba M. Profile of saxagliptin in the treatment of type 2 diabetes: focus on Japanese patients. Ther Clin Risk Manag. 2014 Jul 11;10:547-58. doi: 10.2147/TCRM.S46076. eCollection 2014. Review. PubMed PMID: 25050065; PubMed Central PMCID: PMC4103926.

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TQB3616

TQB3616