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MedKoo Cat#: 555705 | Name: Danuglipron free acid
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Description:

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

Danuglipron, also known as PF-06882961 is a potent, orally bioavailable agonist of the glucagon-like peptide-1 receptor agonist (GLP-1R). WO 2019148044 (2019).

Chemical Structure

Danuglipron free acid
Danuglipron free acid
CAS#2230198-02-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 555705

Name: Danuglipron free acid

CAS#: 2230198-02-2 (free acid)

Chemical Formula: C31H30FN5O4

Exact Mass: 555.2282

Molecular Weight: 555.61

Elemental Analysis: C, 67.01; H, 5.44; F, 3.42; N, 12.61; O, 11.52

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 750.00 Ready to ship
100mg USD 1,250.00 Ready to Ship
200mg USD 2,250.00 Ready to ship
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Related CAS #
2230198-02-2 (free acid) 2230198-03-3 (tris)
Synonym
Danuglipron; PF-06882961; PF 06882961; PF06882961; Danuglipron free acid
IUPAC/Chemical Name
(S)-2-((4-(6-((4-cyano-2-fluorobenzyl)oxy)pyridin-2-yl)piperidin-1-yl)methyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid
InChi Key
HYBAKUMPISVZQP-DEOSSOPVSA-N
InChi Code
InChI=1S/C31H30FN5O4/c32-25-14-20(16-33)4-5-23(25)19-41-30-3-1-2-26(35-30)21-8-11-36(12-9-21)18-29-34-27-7-6-22(31(38)39)15-28(27)37(29)17-24-10-13-40-24/h1-7,14-15,21,24H,8-13,17-19H2,(H,38,39)/t24-/m0/s1
SMILES Code
OC(C1=CC=C(N=C(CN2CCC(C3=NC(OCC4=CC=C(C#N)C=C4F)=CC=C3)CC2)N5C[C@H]6OCC6)C5=C1)=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
>3 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:
Danuglipron (PF-06882961), a non-peptide agonist, activates the canonical G protein signaling activity only in the Glucagon-like peptide-1 (GLP-1) receptor with Trp33ECD.
In vitro activity:
For example, a methylene-linked oxetane increased potency ∼100-fold relative to the methyl substituent of 5, leading to the identification of PF-06882961, which is a full agonist (EC50 = 13 nM) in the CS cAMP assay (Fig. 3A, Table S2). PF-06882961 also incorporates a nitrile replacement for the chloride in the benzyl ether region, which served to reduce CLint in HLM as well as in human hepatocytes (Table S4). Reference: J Med Chem. 2022 Jun 23;65(12):8208-8226. https://pubmed.ncbi.nlm.nih.gov/35647711/
In vivo activity:
Intravenous infusion of PF-06882961 during the IVGTT led to an increase in insulin secretion and the rate of glucose disappearance (K-value) (Fig. 5B–D). Enhancement of glucose-stimulated insulin secretion by PF-06882961 was concentration-dependent and was also observed following oral dosing with similar efficacy when compared to administration by IV infusion (Fig. 5E). Once-daily administration of PF-06882961 for 2 days also inhibited food intake compared to vehicle-treated monkeys (Fig. 5F). Reference: J Med Chem. 2022 Jun 23;65(12):8208-8226. https://pubmed.ncbi.nlm.nih.gov/35647711/
Solvent mg/mL mM
Solubility
DMSO 10.0 18.00
Ethanol 100.0 179.98
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 555.61 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. Griffith DA, Edmonds DJ, Fortin JP, Kalgutkar AS, Kuzmiski JB, Loria PM, Saxena AR, Bagley SW, Buckeridge C, Curto JM, Derksen DR, Dias JM, Griffor MC, Han S, Jackson VM, Landis MS, Lettiere D, Limberakis C, Liu Y, Mathiowetz AM, Patel JC, Piotrowski DW, Price DA, Ruggeri RB, Tess DA. A Small-Molecule Oral Agonist of the Human Glucagon-like Peptide-1 Receptor. J Med Chem. 2022 Jun 23;65(12):8208-8226. doi: 10.1021/acs.jmedchem.1c01856. Epub 2022 Jun 1. PMID: 35647711; PMCID: PMC9234956.
In vitro protocol:
1. Griffith DA, Edmonds DJ, Fortin JP, Kalgutkar AS, Kuzmiski JB, Loria PM, Saxena AR, Bagley SW, Buckeridge C, Curto JM, Derksen DR, Dias JM, Griffor MC, Han S, Jackson VM, Landis MS, Lettiere D, Limberakis C, Liu Y, Mathiowetz AM, Patel JC, Piotrowski DW, Price DA, Ruggeri RB, Tess DA. A Small-Molecule Oral Agonist of the Human Glucagon-like Peptide-1 Receptor. J Med Chem. 2022 Jun 23;65(12):8208-8226. doi: 10.1021/acs.jmedchem.1c01856. Epub 2022 Jun 1. PMID: 35647711; PMCID: PMC9234956.
In vivo protocol:
1. Griffith DA, Edmonds DJ, Fortin JP, Kalgutkar AS, Kuzmiski JB, Loria PM, Saxena AR, Bagley SW, Buckeridge C, Curto JM, Derksen DR, Dias JM, Griffor MC, Han S, Jackson VM, Landis MS, Lettiere D, Limberakis C, Liu Y, Mathiowetz AM, Patel JC, Piotrowski DW, Price DA, Ruggeri RB, Tess DA. A Small-Molecule Oral Agonist of the Human Glucagon-like Peptide-1 Receptor. J Med Chem. 2022 Jun 23;65(12):8208-8226. doi: 10.1021/acs.jmedchem.1c01856. Epub 2022 Jun 1. PMID: 35647711; PMCID: PMC9234956.
1: Saxena AR, Gorman DN, Esquejo RM, Bergman A, Chidsey K, Buckeridge C, Griffith DA, Kim AM. Danuglipron (PF-06882961) in type 2 diabetes: a randomized, placebo-controlled, multiple ascending-dose phase 1 trial. Nat Med. 2021 Jun;27(6):1079-1087. doi: 10.1038/s41591-021-01391-w. Epub 2021 Jun 14. PMID: 34127852. 2: Ono R, Furihata K, Ichikawa Y, Nakazuru Y, Bergman A, Gorman DN, Saxena AR. A phase 1 study to evaluate the safety, tolerability, pharmacokinetics and pharmacodynamics of danuglipron (PF-06882961), an oral small-molecule glucagon- like peptide-1 receptor agonist, in Japanese adults with type 2 diabetes mellitus. Diabetes Obes Metab. 2023 Mar;25(3):805-814. doi: 10.1111/dom.14928. Epub 2022 Dec 19. PMID: 36433713; PMCID: PMC10107991. 3: Griffith DA, Edmonds DJ, Fortin JP, Kalgutkar AS, Kuzmiski JB, Loria PM, Saxena AR, Bagley SW, Buckeridge C, Curto JM, Derksen DR, Dias JM, Griffor MC, Han S, Jackson VM, Landis MS, Lettiere D, Limberakis C, Liu Y, Mathiowetz AM, Patel JC, Piotrowski DW, Price DA, Ruggeri RB, Tess DA. A Small-Molecule Oral Agonist of the Human Glucagon-like Peptide-1 Receptor. J Med Chem. 2022 Jun 23;65(12):8208-8226. doi: 10.1021/acs.jmedchem.1c01856. Epub 2022 Jun 1. PMID: 35647711; PMCID: PMC9234956. 4: Saxena AR, Frias JP, Brown LS, Gorman DN, Vasas S, Tsamandouras N, Birnbaum MJ. Efficacy and Safety of Oral Small Molecule Glucagon-Like Peptide 1 Receptor Agonist Danuglipron for Glycemic Control Among Patients With Type 2 Diabetes: A Randomized Clinical Trial. JAMA Netw Open. 2023 May 1;6(5):e2314493. doi: 10.1001/jamanetworkopen.2023.14493. PMID: 37213102; PMCID: PMC10203889. 5: Kalra S, Arora S, Kapoor N. Person-centered choice of anti-obesity pharmacotherapy. J Pak Med Assoc. 2022 Jul;72(7):1449-1450. doi: 10.47391/JPMA.22-80. PMID: 36156581. 6: Saxena AR, Frias JP, Gorman DN, Lopez RN, Andrawis N, Tsamandouras N, Birnbaum MJ. Tolerability, safety and pharmacodynamics of oral, small-molecule glucagon-like peptide-1 receptor agonist danuglipron for type 2 diabetes: A 12-week, randomized, placebo-controlled, Phase 2 study comparing different dose- escalation schemes. Diabetes Obes Metab. 2023 Oct;25(10):2805-2814. doi: 10.1111/dom.15168. Epub 2023 Jun 13. PMID: 37311722. 7: Chen L, Yun Y, Guo S, Wang X, Xiong M, Zhao T, Xu T, Shen J, Xie X, Wang K. Discovery of Novel 5,6-Dihydro-1,2,4-triazine Derivatives as Efficacious Glucagon-Like Peptide-1 Receptor Agonists. J Med Chem. 2023 Jun 22;66(12):7988-8010. doi: 10.1021/acs.jmedchem.3c00320. Epub 2023 Jun 7. PMID: 37286364. 8: Aspnes GE, Bagley SW, Coffey SB, Conn EL, Curto JM, Edmonds DJ, Genovino J, Griffith DA, Ingle G, Jiao W, Limberakis C, Mathiowetz AM, Piotrowski DW, Rose CR, Ruggeri RB, Wei L. 6-Azaspiro[2.5]octanes as small molecule agonists of the human glucagon-like peptide-1 receptor. Bioorg Med Chem Lett. 2023 Aug 15;94:129454. doi: 10.1016/j.bmcl.2023.129454. Epub ahead of print. PMID: 37591316. 9: Kalra S, Bhattacharya S, Kapoor N. Contemporary Classification of Glucagon- Like Peptide 1 Receptor Agonists (GLP1RAs). Diabetes Ther. 2021 Aug;12(8):2133-2147. doi: 10.1007/s13300-021-01113-y. Epub 2021 Jul 15. PMID: 34268675; PMCID: PMC8342688.