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MedKoo Cat#: 206618 | Name: IPI-549
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Description:

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

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

IPI-549
IPI-549
CAS#1693758-51-8

Theoretical Analysis

MedKoo Cat#: 206618

Name: IPI-549

CAS#: 1693758-51-8

Chemical Formula: C30H24N8O2

Exact Mass: 528.2022

Molecular Weight: 528.58

Elemental Analysis: C, 68.17; H, 4.58; N, 21.20; O, 6.05

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 400.00 Ready to ship
100mg USD 650.00 Ready to ship
200mg USD 1,050.00 Ready to ship
500mg USD 2,250.00 Ready to ship
1g USD 3,850.00 Ready to ship
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Related CAS #
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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
Solvent mg/mL mM
Solubility
Soluble in DMSO 100.0 189.10
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 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.
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