Danuglipron free acid | CAS# 2230198-02-2 | GLP-1R inhibitor

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

MedKoo CAT#: 555705

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

Description: 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

CAS# 2230198-02-2 (free acid)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555705
Name: Danuglipron free acid
CAS#: 2230198-02-2 (free acid)
Chemical Formula: C31H30FN5O4
Exact Mass: 555.23
Molecular Weight: 555.610
Elemental Analysis: C, 67.01; H, 5.44; F, 3.42; N, 12.61; O, 11.52

Price and Availability

Size	Price	Availability
5mg	USD 150	Ready to ship
10mg	USD 250	Ready to ship
25mg	USD 450	Ready to ship
50mg	USD 750	Ready to ship
100mg	USD 1250	Ready to Ship
200mg	USD 2250	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#A22T06K28

QC Data:

View QC data: current batch, Lot#A22T06K28

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	10.0	18.00
	Ethanol	100.0	179.98

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.

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.

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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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.

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