WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H510312
CAS#: 1226781-44-7
Description: 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.
Hodoodo Cat#: H510312
Name: Omarigliptin
CAS#: 1226781-44-7
Chemical Formula: C17H20F2N4O3S
Exact Mass: 398.12
Molecular Weight: 398.430
Elemental Analysis: C, 51.25; H, 5.06; F, 9.54; N, 14.06; O, 12.05; S, 8.05
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:
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 | Max Conc. mg/mL | Max Conc. mM | |
---|---|---|---|
Solubility | |||
DMSO | 31.0 | 77.80 |
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: | 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. |
In vivo 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. |
1: Biftu T, Sinha-Roy R, Chen P, Qian X, Feng D, Kuethe JT, Scapin G, Gao YD, Yan Y, Krueger D, Bak A, Eiermann G, He J, Cox J, Hicks J, Lyons K, He H, Salituro G, Tong S, Patel S, Doss G, Petrov A, Wu J, Xu SS, Sewall C, Zhang X, Zhang B, Thornberry NA, Weber AE. Omarigliptin (MK-3102): a novel long-acting DPP-4 inhibitor for once-weekly treatment of type 2 diabetes. J Med Chem. 2014 Apr 24;57(8):3205-12. doi: 10.1021/jm401992e. Epub 2014 Apr 2. PubMed PMID: 24660890.
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. PubMed PMID: 23972441.