IPI-549
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MedKoo CAT#: 206618

CAS#: 1693758-51-8

Description: Eganelisib, also known as IPI-549 is a potent and selective phosphoinositide-3-kinase (PI3Kγ) Inhibitor as an Immuno-Oncology Clinical Candidate (Kd = 0.29 nM). Bioactivity data of IPI-549: biochemcial IC50 (nM) for PI3K isoform: 3200 (α); 3500 (β); 16 (γ); and >8400 (δ) respectively. Cellar IC50 (nM) of IPI549 for PI3K isoform: 250 (α); 240 (β); 1.6 (γ); and 180 (δ) respectively. IPI-549 shows >100-fold selectivity over other lipid and protein kinases. IPI-549 demonstrates favorable pharmacokinetic properties and robust inhibition of PI3K-γ mediated neutrophil migration in vivo rs.

Chemical Structure

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IPI-549
CAS# 1693758-51-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 206618
Name: IPI-549
CAS#: 1693758-51-8
Chemical Formula: C30H24N8O2
Exact Mass: 528.20
Molecular Weight: 528.576
Elemental Analysis: C, 68.17; H, 4.58; N, 21.20; O, 6.05

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 400 Ready to ship
100mg USD 650 Ready to ship
200mg USD 1050 Ready to ship
500mg USD 2250 Ready to ship
1g USD 3850 Ready to ship
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Synonym: Eganelisib; IPI-549; IPI 549; IPI549.

IUPAC/Chemical Name: (S)-2-amino-N-(1-(8-((1-methyl-1H-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

InChi Key: XUMALORDVCFWKV-IBGZPJMESA-N

InChi Code: InChI=1S/C30H24N8O2/c1-19(34-29(39)26-27(31)35-37-15-7-14-32-28(26)37)24-16-22-9-6-8-21(13-12-20-17-33-36(2)18-20)25(22)30(40)38(24)23-10-4-3-5-11-23/h3-11,14-19H,1-2H3,(H2,31,35)(H,34,39)/t19-/m0/s1

SMILES Code: O=C1N(C2=CC=CC=C2)C([C@@H](NC(C3=C(N=CC=C4)N4N=C3N)=O)C)=CC5=CC=CC(C#CC6=CN(C)N=C6)=C51

Appearance: Yellow 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:

Biological target: PI3Kγ inhibitor with an IC50 of 85nM.
In vitro activity: In vitro absorption, distribution, metabolism, and excretion (ADME) properties and pharmacokinetic parameters of compound 26 were also determined (summarized in Table 5). In vitro, IPI-549 showed moderate to high cell permeability across Caco-2 cell monolayers, was slowly metabolized in cultured hepatocytes (t1/2 > 360 min), and demonstrated IC50s greater than 20 μM for the CYP isoforms tested (1A2, 2B6, 2C8, 2C9, 2C19, 2D6, 3A4). Reference: ACS Med Chem Lett. 2016 Sep 8; 7(9): 862–867. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5018865/#tbl5
In vivo activity: In vivo (mice, rats, dog, and monkeys), IPI-549 had excellent oral bioavailability, low clearance, and distributed into tissues with a mean volume of distribution of 1.2 L/kg (Table 5). Overall, IPI-549 had a favorable pharmacokinetic profile to allow potent and selective inhibition of PI3K-γ in vivo. Reference: ACS Med Chem Lett. 2016 Sep 8; 7(9): 862–867. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5018865/#tbl5

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 100.0 189.10

Preparing Stock Solutions

The following data is based on the product molecular weight 528.58 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. De Vera AA, Gupta P, Lei Z, Liao D, Narayanan S, Teng Q, Reznik SE, Chen ZS. Immuno-oncology agent IPI-549 is a modulator of P-glycoprotein (P-gp, MDR1, ABCB1)-mediated multidrug resistance (MDR) in cancer: In vitro and in vivo. Cancer Lett. 2019 Feb 1;442:91-103. doi: 10.1016/j.canlet.2018.10.020. Epub 2018 Nov 1. PMID: 30391357; PMCID: PMC6348084. 2. Evans CA, Liu T, Lescarbeau A, Nair SJ, Grenier L, Pradeilles JA, Glenadel Q, Tibbitts T, Rowley AM, DiNitto JP, Brophy EE, O'Hearn EL, Ali JA, Winkler DG, Goldstein SI, O'Hearn P, Martin CM, Hoyt JG, Soglia JR, Cheung C, Pink MM, Proctor JL, Palombella VJ, Tremblay MR, Castro AC. Discovery of a Selective Phosphoinositide-3-Kinase (PI3K)-γ Inhibitor (IPI-549) as an Immuno-Oncology Clinical Candidate. ACS Med Chem Lett. 2016 Jul 22;7(9):862-7. doi: 10.1021/acsmedchemlett.6b00238. PMID: 27660692; PMCID: PMC5018865. 3. Jiang M, He K, Qiu T, Sun J, Liu Q, Zhang X, Zheng H. Tumor-targeted delivery of silibinin and IPI-549 synergistically inhibit breast cancer by remodeling the microenvironment. Int J Pharm. 2020 May 15;581:119239. doi: 10.1016/j.ijpharm.2020.119239. Epub 2020 Mar 16. PMID: 32194211.
In vitro protocol: 1. De Vera AA, Gupta P, Lei Z, Liao D, Narayanan S, Teng Q, Reznik SE, Chen ZS. Immuno-oncology agent IPI-549 is a modulator of P-glycoprotein (P-gp, MDR1, ABCB1)-mediated multidrug resistance (MDR) in cancer: In vitro and in vivo. Cancer Lett. 2019 Feb 1;442:91-103. doi: 10.1016/j.canlet.2018.10.020. Epub 2018 Nov 1. PMID: 30391357; PMCID: PMC6348084.
In vivo protocol: 1. Evans CA, Liu T, Lescarbeau A, Nair SJ, Grenier L, Pradeilles JA, Glenadel Q, Tibbitts T, Rowley AM, DiNitto JP, Brophy EE, O'Hearn EL, Ali JA, Winkler DG, Goldstein SI, O'Hearn P, Martin CM, Hoyt JG, Soglia JR, Cheung C, Pink MM, Proctor JL, Palombella VJ, Tremblay MR, Castro AC. Discovery of a Selective Phosphoinositide-3-Kinase (PI3K)-γ Inhibitor (IPI-549) as an Immuno-Oncology Clinical Candidate. ACS Med Chem Lett. 2016 Jul 22;7(9):862-7. doi: 10.1021/acsmedchemlett.6b00238. PMID: 27660692; PMCID: PMC5018865. 2. Jiang M, He K, Qiu T, Sun J, Liu Q, Zhang X, Zheng H. Tumor-targeted delivery of silibinin and IPI-549 synergistically inhibit breast cancer by remodeling the microenvironment. Int J Pharm. 2020 May 15;581:119239. doi: 10.1016/j.ijpharm.2020.119239. Epub 2020 Mar 16. PMID: 32194211.

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Discovery of a Selective Phosphoinositide-3-Kinase (PI3K)-γ Inhibitor (IPI-549) as an Immuno-Oncology Clinical Candidate
Catherine A. Evans, Tao Liu, André Lescarbeau, Somarajan J. Nair, Louis Grenier, Johan A. Pradeilles, Quentin Glenadel, Thomas Tibbitts, Ann M. Rowley, Jonathan P. DiNitto, Erin E. Brophy, Erin L. O’Hearn, Janid A. Ali, David G. Winkler, Stanley I. Goldstein, Patrick O’Hearn, Christian M. Martin, Jennifer G. Hoyt, John R. Soglia, Culver Cheung, Melissa M. Pink, Jennifer L. Proctor, Vito J. Palombella, Martin R. Tremblay, and Alfredo C. Castro
Publication Date (Web): July 22, 2016 (Letter)
DOI: 10.1021/acsmedchemlett.6b00238