Omarigliptin | MK3102 | 1226781-44-7 | DPP-4 inhibitor

MedKoo Cat#: 510312 | Name: Omarigliptin

Description:

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

Omarigliptin, also known as MK-3102, is a potent and long-acting DPP-4 inhibitor for once-weekly treatment of type 2 diabetes. MK-3102 (omarigliptin), was identified as a potent and selective dipeptidyl peptidase 4 (DPP-4) inhibitor with an excellent pharmacokinetic profile amenable for once-weekly human dosing and selected as a clinical development candidate. Omarigliptin is currently in phase 3 clinical development.

Chemical Structure

Omarigliptin

CAS#1226781-44-7

Theoretical Analysis

MedKoo Cat#: 510312

Name: Omarigliptin

CAS#: 1226781-44-7

Chemical Formula: C17H20F2N4O3S

Exact Mass: 398.1224

Molecular Weight: 398.43

Elemental Analysis: C, 51.25; H, 5.06; F, 9.54; N, 14.06; O, 12.05; S, 8.05

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 425.00	Ready to ship
100mg	USD 700.00	Ready to ship
200mg	USD 1,150.00	Ready to ship
500mg	USD 2,050.00	Ready to ship
1g	USD 3,450.00	2 weeks
2g	USD 4,950.00	2 weeks
5g	USD 6,950.00	2 weeks

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Related CAS #

No Data

Synonym

MK3102; MK-3102; MK 3102; Omarigliptin

IUPAC/Chemical Name

(2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-(methylsulfonyl)pyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-yl)tetrahydro-2H-pyran-3-amine

InChi Key

MKMPWKUAHLTIBJ-ISTRZQFTSA-N

InChi Code

InChI=1S/C17H20F2N4O3S/c1-27(24,25)23-7-10-6-22(8-16(10)21-23)12-5-15(20)17(26-9-12)13-4-11(18)2-3-14(13)19/h2-4,7,12,15,17H,5-6,8-9,20H2,1H3/t12-,15+,17-/m1/s1

SMILES Code

N[C@@H]1[C@@H](C2=CC(F)=CC=C2F)OC[C@H](N3CC4=NN(S(=O)(C)=O)C=C4C3)C1

Appearance

White to off-white 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, DMF, and EtOH

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

Certificate of Analysis

View CoA: current batch, Lot#CRB50421

View CoA: current batch, Lot#CRB41222.

QC Data

View QC data: current batch, Lot#CRB50421

View QC data: current batch, Lot#CRB41222.

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Omarigliptin (MK-3102) is a long-acting DPP-4 inhibitor with IC50 of 1.6 nM.

In vitro activity:

To evaluate the effects of Omarigliptin on the inflammation induced by LPS stimulation, the bEnd.3 brain endothelial cells were incubated with 10 and 20 μM Omarigliptin following stimulation with 1 μg/mL LPS for 24 h. As shown in Figure 5, HMGB-1 was found to be significantly up-regulated by stimulation with LPS but was greatly down-regulated by the introduction of Omarigliptin in a dose-dependent manner. Reference: ACS Chem Neurosci. 2020 Dec 16;11(24):4262-4269. https://pubmed.ncbi.nlm.nih.gov/33237730/

In vivo activity:

The lead candidate 23 (Omarigliptin) was assessed for its ability to improve glucose tolerance in lean mice. In lean animals, 23, orally administered 1 h prior to dextrose challenge in an oral glucose tolerance test (OGTT), significantly reduced blood glucose excursion in a dose-dependent manner from 0.1 mg/kg (27% reduction in glucose AUC) to 3 mg/kg (47% reduction). Reference: Bioorg Med Chem Lett. 2013 Oct 1;23(19):5361-6. https://pubmed.ncbi.nlm.nih.gov/23972441/

	Solvent	mg/mL	mM
Solubility
	DMSO	31.0	77.80

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 398.43 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. Du H, Wang S. Omarigliptin Mitigates Lipopolysaccharide-Induced Neuroinflammation and Dysfunction of the Integrity of the Blood-Brain Barrier. ACS Chem Neurosci. 2020 Dec 16;11(24):4262-4269. doi: 10.1021/acschemneuro.0c00537. Epub 2020 Nov 25. PMID: 33237730. 2. Biftu T, Qian X, Chen P, Feng D, Scapin G, Gao YD, Cox J, Roy RS, Eiermann G, He H, Lyons K, Salituro G, Patel S, Petrov A, Xu F, Xu SS, Zhang B, Caldwell C, Wu JK, Lyons K, Weber AE. Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2- (2,5-difluorophenyl)-5-(4,6-dihydropyrrolo [3,4-c]pyrazol-5-(1H)-yl)tetrahydro-2H-pyran-3-amine (23) [corrected]. Bioorg Med Chem Lett. 2013 Oct 1;23(19):5361-6. doi: 10.1016/j.bmcl.2013.07.061. Epub 2013 Aug 5. Erratum in: Bioorg Med Chem Lett. 2014 Jun 1;24(11):2590. PMID: 23972441.

In vitro protocol:

In vivo protocol:

1: Abd Elmaaboud MA, Kabel AM, Borg HM, Magdy AA, Kabel SM, Arafa EA, Alsufyani SE, Arab HH. Omarigliptin/rosinidin combination ameliorates cyclophosphamide- induced lung toxicity in rats: The interaction between glucagon-like peptide-1, TXNIP/NLRP3 inflammasome signaling, and PI3K/Akt/FoxO1 axis. Biomed Pharmacother. 2024 Aug;177:117026. doi: 10.1016/j.biopha.2024.117026. Epub 2024 Jun 26. PMID: 38936197. 2: Mohr A, de Souza Barbosa F, Wingert NR, Takeuchi CK, Garcia L, Ribeiro MFN, Arbo MD, de Oliveira TF, Steppe M. Analysis of omarigliptin forced degradation products by ultra-fast liquid chromatography, mass spectrometry, and in vitro toxicity assay. Biomed Chromatogr. 2024 Aug;38(8):e5904. doi: 10.1002/bmc.5904. Epub 2024 May 29. PMID: 38811368. 3: Kamrul-Hasan ABM, Alam MS, Talukder SK, Dutta D, Selim S. Efficacy and Safety of Omarigliptin, a Novel Once-Weekly Dipeptidyl Peptidase-4 Inhibitor, in Type 2 Diabetes Mellitus: A Systematic Review and Meta-Analysis. Endocrinol Metab (Seoul). 2024 Feb;39(1):109-126. doi: 10.3803/EnM.2023.1839. Epub 2024 Jan 23. PMID: 38417828; PMCID: PMC10901664. 4: Zhang Y, Liu Y, Yong VW, Xue M. Omarigliptin inhibits brain cell ferroptosis after intracerebral hemorrhage. Sci Rep. 2023 Sep 1;13(1):14339. doi: 10.1038/s41598-023-41635-y. PMID: 37658227; PMCID: PMC10474264. 5: Mathur V, Alam O, Siddiqui N, Jha M, Manaithiya A, Bawa S, Sharma N, Alshehri S, Alam P, Shakeel F. Insight into Structure Activity Relationship of DPP-4 Inhibitors for Development of Antidiabetic Agents. Molecules. 2023 Aug 3;28(15):5860. doi: 10.3390/molecules28155860. PMID: 37570832; PMCID: PMC10420935. 6: Ishii H, Kamei N, Shimono D, Niiya T, Tosaki T, Kitazawa T, Suzuki D, Wakasa Y, Seino H, Oishi M, Ohashi H, Higami K, Akai H; ONWARD-DPP4 study investigators. Treatment Burden on Once-Weekly Omarigliptin Versus Daily Dipeptidyl Peptidase-4 Inhibitors in Patients with Type 2 Diabetes: Randomized Controlled Trial (ONWARD-DPP4 Study). Diabetes Ther. 2023 Oct;14(10):1639-1658. doi: 10.1007/s13300-023-01442-0. Epub 2023 Jul 19. PMID: 37468684; PMCID: PMC10499707. 7: Zhang Y, Liu Y, Zhang X, Yong VW, Xue M. Omarigliptin Protects the Integrity of the Blood-Brain Barrier After Intracerebral Hemorrhage in Mice. J Inflamm Res. 2023 Jun 15;16:2535-2548. doi: 10.2147/JIR.S411017. PMID: 37342770; PMCID: PMC10278948. 8: Magdy G, Al-Enna AA, Belal F, El-Domany RA, Abdel-Megied AM. Analytical quality-by-design approach for development and validation of HPLC method for the simultaneous estimation of omarigliptin, metformin, and ezetimibe: application to human plasma and dosage forms. BMC Chem. 2023 May 5;17(1):45. doi: 10.1186/s13065-023-00955-w. PMID: 37147652; PMCID: PMC10163694. 9: Ogura T, Shiraishi C. Comparison of Adverse Events Occurred During Administration of Dipeptidyl Peptidase-4 Inhibitor in Patients with Diabetes Using FDA Adverse Event Reporting System. Clin Drug Investig. 2023 Feb;43(2):129-140. doi: 10.1007/s40261-022-01242-7. Epub 2023 Jan 13. PMID: 36637688. 10: Gouda NA, Cho J. Omarigliptin Mitigates 6-Hydroxydopamine- or Rotenone- Induced Oxidative Toxicity in PC12 Cells by Antioxidant, Anti-Inflammatory, and Anti-Apoptotic Actions. Antioxidants (Basel). 2022 Sep 28;11(10):1940. doi: 10.3390/antiox11101940. PMID: 36290663; PMCID: PMC9598347. 11: Heo R, Kang M, Mun SY, Park M, Han ET, Han JH, Chun W, Park H, Jung WK, Choi IW, Park WS. Antidiabetic omarigliptin dilates rabbit aorta by activating voltage-dependent K+ channels and the sarco/endoplasmic reticulum Ca2+ -ATPase pump. Fundam Clin Pharmacol. 2023 Feb;37(1):75-84. doi: 10.1111/fcp.12831. Epub 2022 Sep 26. PMID: 36093990. 12: Wu C, Liu H, Yu S, Ren C, Zhang J, Wang G, Li B, Liu Y. Prediction of pharmacokinetics and pharmacodynamics of trelagliptin and omarigliptin in healthy humans and in patients with renal impairment using physiologically based pharmacokinetic combined DPP-4 occupancy modeling. Biomed Pharmacother. 2022 Sep;153:113509. doi: 10.1016/j.biopha.2022.113509. Epub 2022 Aug 4. PMID: 36076596. 13: Zhang X, Yuan J, Zhou N, Shen K, Wang Y, Wang K, Zhu H. Retraction of "Omarigliptin Prevents TNF-α-Induced Cellular Senescence in Rat Aorta Vascular Smooth Muscle Cells". Chem Res Toxicol. 2022 Jun 20;35(6):1125. doi: 10.1021/acs.chemrestox.2c00134. Epub 2022 Jun 2. PMID: 35652536. 14: Khayat MT, Abbas HA, Ibrahim TS, Khayyat AN, Alharbi M, Darwish KM, Elhady SS, Khafagy ES, Safo MK, Hegazy WAH. Anti-Quorum Sensing Activities of Gliptins against Pseudomonas aeruginosa and Staphylococcus aureus. Biomedicines. 2022 May 18;10(5):1169. doi: 10.3390/biomedicines10051169. PMID: 35625906; PMCID: PMC9138634. 15: Michel HE, Tadros MM, Hendy MS, Mowaka S, Ayoub BM. Omarigliptin attenuates rotenone-induced Parkinson's disease in rats: Possible role of oxidative stress, endoplasmic reticulum stress and immune modulation. Food Chem Toxicol. 2022 Jun;164:113015. doi: 10.1016/j.fct.2022.113015. Epub 2022 Apr 16. PMID: 35439590. 16: Li X, Yin Y, Li W, Li S, Zhang D, Liu Z. Omarigliptin alleviates cognitive dysfunction in Streptozotocin-induced diabetic mouse. Bioengineered. 2022 Apr;13(4):9387-9396. doi: 10.1080/21655979.2022.2055699. PMID: 35389830; PMCID: PMC9161942. 17: Lin C, Kong Y, Wang F, Rong R, Li X, Xiao R, Wu Z, Zhang Q, Wang L. Design, synthesis and evaluation of a series of novel long-acting dipeptidyl peptidase-4 inhibitors for the treatment of type 2 diabetes. Bioorg Chem. 2022 Jun;123:105767. doi: 10.1016/j.bioorg.2022.105767. Epub 2022 Mar 26. PMID: 35381556. 18: Kabel AM, Arab HH, Atef A, Estfanous RS. Omarigliptin/galangin combination mitigates lipopolysaccharide-induced neuroinflammation in rats: Involvement of glucagon-like peptide-1, toll-like receptor-4, apoptosis and Akt/GSK-3β signaling. Life Sci. 2022 Apr 15;295:120396. doi: 10.1016/j.lfs.2022.120396. Epub 2022 Feb 11. PMID: 35157909. 19: Kawasaki E, Nakano Y, Fukuyama T, Uchida A, Sagara Y, Tamai H, Tojikubo M, Hiromatsu Y, Koga N. Efficacy of omarigliptin, once-weekly dipeptidyl peptidase-4 inhibitor, in patients with type 2 diabetes. World J Diabetes. 2021 Dec 15;12(12):2087-2095. doi: 10.4239/wjd.v12.i12.2087. PMID: 35047122; PMCID: PMC8696643. 20: Kelani KM, Hegazy MA, Hassan AM, Tantawy MA. Univariate versus multivariate spectrophotometric methods for the simultaneous determination of omarigliptin and two of its degradation products. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Apr 15;271:120880. doi: 10.1016/j.saa.2022.120880. Epub 2022 Jan 10. PMID: 35032731.