Pimasertib | CAS# 1236699-92-5 (free base) | small-molecule inhibitor of MEK1 and MEK2

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

MedKoo CAT#: 200297

CAS#: 1236699-92-5 (free base)

Description: Pimasertib, also known as AS703026, SAR245509, MSC1936369B, is an orally bioavailable small-molecule inhibitor of MEK1 and MEK2 (MEK1/2) with potential antineoplastic activity. MEK inhibitor AS703026 selectively binds to and inhibits the activity of MEK1/2, preventing the activation of MEK1/2-dependent effector proteins and transcription factors, which may result in the inhibition of growth factor-mediated cell signaling and tumor cell proliferation.

Chemical Structure

Pimasertib

CAS# 1236699-92-5 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 200297
Name: Pimasertib
CAS#: 1236699-92-5 (free base)
Chemical Formula: C15H15FIN3O3
Exact Mass: 431.01
Molecular Weight: 431.206
Elemental Analysis: C, 41.78; H, 3.51; F, 4.41; I, 29.43; N, 9.74; O, 11.13

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 450
100mg	USD 750
200mg	USD 1250
500mg	USD 1950
1g	USD 2950
2g	USD 5450
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 #: 1236361-78-6 (HCl); 1236699-92-5 (free base)

Synonym: SAR245509; SAR-245509; SAR 245509; MSC1936369B; AS703026; AS 703026; AS-703026; Pimasertib

IUPAC/Chemical Name: (S)-N-(2,3-dihydroxypropyl)-3-((2-fluoro-4-iodophenyl)amino)isonicotinamide.

InChi Key: VIUAUNHCRHHYNE-JTQLQIEISA-N

InChi Code: InChI=1S/C15H15FIN3O3/c16-12-5-9(17)1-2-13(12)20-14-7-18-4-3-11(14)15(23)19-6-10(22)8-21/h1-5,7,10,20-22H,6,8H2,(H,19,23)/t10-/m0/s1

SMILES Code: O=C(NC[C@H](O)CO)C1=CC=NC=C1NC2=CC=C(I)C=C2F

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, not in water

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: Related CAS# 1236699-92-5 (Pimasertib) 1236361-78-6 (Pimasertib Hydrochloride)

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Pimasertib (AS703026) is a highly selective, ATP non-competitive allosteric orally available MEK1/2 inhibitor.
In vitro activity:	AS703026 and AZD6244 were tested in various cell-based assays and tumor xenograft studies, focusing on isogenic human colorectal tumor cell lines that expressed only WT or mutant K-Ras (D-WT or D-MUT). The EGFR mAb cetuximab inhibited the Ras-ERK pathway and proliferation of D-WT cells in vitro and in vivo, but it did not inhibit proliferation of D-MUT cells in either setting. In contrast, AS703026 and AZD6244 effectively inhibited the growth of D-MUT cells in vitro and in vivo by specific inhibition of the key MEK downstream target kinase ERK. Inhibition of MEK by AS703026 or AZD6244 also suppressed cetuximab-resistant colorectal cancer cells attributed to K-ras mutation both in vitro and in vivo. Reference: Cancer Res. 2011 Jan 15;71(2):445-53. https://pubmed.ncbi.nlm.nih.gov/21118963/
In vivo activity:	AS703026 inhibited growth and survival of MM cells and cytokine-induced osteoclast differentiation more potently (9- to 10-fold) than AZD6244. Inhibition of proliferation induced by AS703026 was mediated by G0-G1 cell cycle arrest and was accompanied by reduction of MAF oncogene expression. AS703026 further induced apoptosis via caspase 3 and Poly ADP ribose polymerase (PARP) cleavage in MM cells, both in the presence or absence of bone marrow stromal cells (BMSCs). Importantly, AS703026 sensitized MM cells to a broad spectrum of conventional (dexamethasone, melphalan), novel or emerging (lenalidomide, perifosine, bortezomib, rapamycin) anti-MM therapies. Significant tumour growth reduction in AS703026- vs. vehicle-treated mice bearing H929 MM xenograft tumours correlated with downregulated pERK1/2, induced PARP cleavage, and decreased microvessels in vivo. Reference: Br J Haematol. 2010 May;149(4):537-49. https://pubmed.ncbi.nlm.nih.gov/20331454/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	69.57
	DMSO	72.0	166.97
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.16
	Ethanol	1.0	2.32

Preparing Stock Solutions

The following data is based on the product molecular weight 431.21 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. Yoon J, Koo KH, Choi KY. MEK1/2 inhibitors AS703026 and AZD6244 may be potential therapies for KRAS mutated colorectal cancer that is resistant to EGFR monoclonal antibody therapy. Cancer Res. 2011 Jan 15;71(2):445-53. doi: 10.1158/0008-5472.CAN-10-3058. Epub 2010 Nov 30. PMID: 21118963. 2. Kim K, Kong SY, Fulciniti M, Li X, Song W, Nahar S, Burger P, Rumizen MJ, Podar K, Chauhan D, Hideshima T, Munshi NC, Richardson P, Clark A, Ogden J, Goutopoulos A, Rastelli L, Anderson KC, Tai YT. Blockade of the MEK/ERK signalling cascade by AS703026, a novel selective MEK1/2 inhibitor, induces pleiotropic anti-myeloma activity in vitro and in vivo. Br J Haematol. 2010 May;149(4):537-49. doi: 10.1111/j.1365-2141.2010.08127.x. Epub 2010 Mar 12. PMID: 20331454; PMCID: PMC3418597. 3. Yoon J, Koo KH, Choi KY. MEK1/2 inhibitors AS703026 and AZD6244 may be potential therapies for KRAS mutated colorectal cancer that is resistant to EGFR monoclonal antibody therapy. Cancer Res. 2011 Jan 15;71(2):445-53. doi: 10.1158/0008-5472.CAN-10-3058. Epub 2010 Nov 30. PMID: 21118963. 4. Kim K, Kong SY, Fulciniti M, Li X, Song W, Nahar S, Burger P, Rumizen MJ, Podar K, Chauhan D, Hideshima T, Munshi NC, Richardson P, Clark A, Ogden J, Goutopoulos A, Rastelli L, Anderson KC, Tai YT. Blockade of the MEK/ERK signalling cascade by AS703026, a novel selective MEK1/2 inhibitor, induces pleiotropic anti-myeloma activity in vitro and in vivo. Br J Haematol. 2010 May;149(4):537-49. doi: 10.1111/j.1365-2141.2010.08127.x. Epub 2010 Mar 12. PMID: 20331454; PMCID: PMC3418597.
In vitro protocol:	1. Yoon J, Koo KH, Choi KY. MEK1/2 inhibitors AS703026 and AZD6244 may be potential therapies for KRAS mutated colorectal cancer that is resistant to EGFR monoclonal antibody therapy. Cancer Res. 2011 Jan 15;71(2):445-53. doi: 10.1158/0008-5472.CAN-10-3058. Epub 2010 Nov 30. PMID: 21118963. 2. Kim K, Kong SY, Fulciniti M, Li X, Song W, Nahar S, Burger P, Rumizen MJ, Podar K, Chauhan D, Hideshima T, Munshi NC, Richardson P, Clark A, Ogden J, Goutopoulos A, Rastelli L, Anderson KC, Tai YT. Blockade of the MEK/ERK signalling cascade by AS703026, a novel selective MEK1/2 inhibitor, induces pleiotropic anti-myeloma activity in vitro and in vivo. Br J Haematol. 2010 May;149(4):537-49. doi: 10.1111/j.1365-2141.2010.08127.x. Epub 2010 Mar 12. PMID: 20331454; PMCID: PMC3418597.
In vivo protocol:	1. Yoon J, Koo KH, Choi KY. MEK1/2 inhibitors AS703026 and AZD6244 may be potential therapies for KRAS mutated colorectal cancer that is resistant to EGFR monoclonal antibody therapy. Cancer Res. 2011 Jan 15;71(2):445-53. doi: 10.1158/0008-5472.CAN-10-3058. Epub 2010 Nov 30. PMID: 21118963. 2. Kim K, Kong SY, Fulciniti M, Li X, Song W, Nahar S, Burger P, Rumizen MJ, Podar K, Chauhan D, Hideshima T, Munshi NC, Richardson P, Clark A, Ogden J, Goutopoulos A, Rastelli L, Anderson KC, Tai YT. Blockade of the MEK/ERK signalling cascade by AS703026, a novel selective MEK1/2 inhibitor, induces pleiotropic anti-myeloma activity in vitro and in vivo. Br J Haematol. 2010 May;149(4):537-49. doi: 10.1111/j.1365-2141.2010.08127.x. Epub 2010 Mar 12. PMID: 20331454; PMCID: PMC3418597.

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1: Zhang Y, Xue D, Wang X, Lu M, Gao B, Qiao X. Screening of kinase inhibitors targeting BRAF for regulating autophagy based on kinase pathways. Mol Med Rep. 2014 Jan;9(1):83-90. doi: 10.3892/mmr.2013.1781. Epub 2013 Nov 7. PubMed PMID: 24213221.

2: Park SJ, Hong SW, Moon JH, Jin DH, Kim JS, Lee CK, Kim KP, Hong YS, Choi EK, Lee JS, Lee JL, Kim TW. The MEK1/2 inhibitor AS703026 circumvents resistance to the BRAF inhibitor PLX4032 in human malignant melanoma cells. Am J Med Sci. 2013 Dec;346(6):494-8. doi: 10.1097/MAJ.0b013e318298a185. PubMed PMID: 24051957.

3: Sarris EG, Syrigos KN, Saif MW. Novel agents and future prospects in the treatment of pancreatic adenocarcinoma. JOP. 2013 Jul 10;14(4):395-400. doi: 10.6092/1590-8577/1654. PubMed PMID: 23846936.

4: Yoon J, Koo KH, Choi KY. MEK1/2 inhibitors AS703026 and AZD6244 may be potential therapies for KRAS mutated colorectal cancer that is resistant to EGFR monoclonal antibody therapy. Cancer Res. 2011 Jan 15;71(2):445-53. doi: 10.1158/0008-5472.CAN-10-3058. Epub 2010 Nov 30. PubMed PMID: 21118963.

5: Kim K, Kong SY, Fulciniti M, Li X, Song W, Nahar S, Burger P, Rumizen MJ, Podar K, Chauhan D, Hideshima T, Munshi NC, Richardson P, Clark A, Ogden J, Goutopoulos A, Rastelli L, Anderson KC, Tai YT. Blockade of the MEK/ERK signalling cascade by AS703026, a novel selective MEK1/2 inhibitor, induces pleiotropic anti-myeloma activity in vitro and in vivo. Br J Haematol. 2010 May;149(4):537-49. doi: 10.1111/j.1365-2141.2010.08127.x. Epub 2010 Mar 12. PubMed PMID: 20331454; PubMed Central PMCID: PMC3418597.

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