Vemurafenib-Analog

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

MedKoo CAT#: 461598

CAS#: 918505-61-0 (analog)

Description: Vemurafenib-Analog is a potent BRAF inhibitor and the isomer of Vemurafenib. Vemurafenib, also known as PLX4032, RG7204 or RO5185426, is an orally bioavailable, ATP-competitive, small-molecule inhibitor of BRAF(V600E) kinase with potential antineoplastic activity. Vemurafenib received FDA approval for the treatment of late-stage melanoma on August 17, 2011.

Chemical Structure

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Vemurafenib-Analog
CAS# 918505-61-0 (analog)
Instruction

Theoretical Analysis

MedKoo Cat#: 461598
Name: Vemurafenib-Analog
CAS#: 918505-61-0 (analog)
Chemical Formula: C22H18F2N4O3S
Exact Mass: 456.11
Molecular Weight: 456.460
Elemental Analysis: C, 57.89; H, 3.97; F, 8.32; N, 12.27; O, 10.51; S, 7.02

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 918505-61-0 (analog)   918504-65-1    

Synonym: PLX4032-analog; PLX 4032 analog; PLX-4032 analog; R7204 analog; RG 7204 analog; RO5185426 analog; Vemurafenib-Analog

IUPAC/Chemical Name: N-(2,4-difluoro-3-(5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)phenyl)propane-2-sulfonamide

InChi Key: SUNCACOTKLUNHD-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H18F2N4O3S/c1-12(2)32(30,31)28-18-6-5-17(23)19(20(18)24)21(29)16-11-27-22-15(16)8-14(10-26-22)13-4-3-7-25-9-13/h3-12,28H,1-2H3,(H,26,27)

SMILES Code: CC(S(=O)(NC1=CC=C(F)C(C(C2=CNC3=NC=C(C4=CC=CN=C4)C=C32)=O)=C1F)=O)C

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 456.46 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:
In vitro protocol:
In vivo protocol:

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1: Yu L, Gao LX, Ma XQ, Hu FX, Li CM, Lu Z. Involvement of superoxide and nitric oxide in BRAF(V600E) inhibitor PLX4032-induced growth inhibition of melanoma cells. Integr Biol (Camb). 2014 Dec;6(12):1211-7. doi: 10.1039/c4ib00170b. Epub 2014 Nov 3. PubMed PMID: 25363644.

2: Li Y, Li Y, Liu Q, Wang A. Tyrphostin AG1296, a platelet-derived growth factor receptor inhibitor, induces apoptosis, and reduces viability and migration of PLX4032-resistant melanoma cells. Onco Targets Ther. 2015 May 14;8:1043-51. doi: 10.2147/OTT.S70691. eCollection 2015. PubMed PMID: 25999739; PubMed Central PMCID: PMC4437616.

3: Michaelis M, Rothweiler F, Nerreter T, van Rikxoort M, Zehner R, Dirks WG, Wiese M, Cinatl J Jr. Association between acquired resistance to PLX4032 (vemurafenib) and ATP-binding cassette transporter expression. BMC Res Notes. 2014 Oct 10;7:710. doi: 10.1186/1756-0500-7-710. PubMed PMID: 25300205; PubMed Central PMCID: PMC4197243.

4: Michaelis M, Rothweiler F, Nerreter T, Van Rikxoort M, Sharifi M, Wiese M, Ghafourian T, Cinatl J. Differential effects of the oncogenic BRAF inhibitor PLX4032 (vemurafenib) and its progenitor PLX4720 on ABCB1 function. J Pharm Pharm Sci. 2014;17(1):154-68. PubMed PMID: 24735766.

5: Choi J, Landrette SF, Wang T, Evans P, Bacchiocchi A, Bjornson R, Cheng E, Stiegler AL, Gathiaka S, Acevedo O, Boggon TJ, Krauthammer M, Halaban R, Xu T. Identification of PLX4032-resistance mechanisms and implications for novel RAF inhibitors. Pigment Cell Melanoma Res. 2014 Mar;27(2):253-62. doi: 10.1111/pcmr.12197. Epub 2014 Jan 6. PubMed PMID: 24283590; PubMed Central PMCID: PMC4065135.

6: Jenkins MH, Croteau W, Mullins DW, Brinckerhoff CE. The BRAF(V600E) inhibitor, PLX4032, increases type I collagen synthesis in melanoma cells. Matrix Biol. 2015 Oct;48:66-77. doi: 10.1016/j.matbio.2015.05.007. Epub 2015 May 16. PubMed PMID: 25989506; PubMed Central PMCID: PMC5048745.

7: Kim SH, Kang JG, Kim CS, Ihm SH, Choi MG, Yoo HJ, Lee SJ. Akt inhibition enhances the cytotoxic effect of apigenin in combination with PLX4032 in anaplastic thyroid carcinoma cells harboring BRAFV600E. J Endocrinol Invest. 2013 Dec;36(11):1099-104. doi: 10.3275/9099. Epub 2013 Sep 27. PubMed PMID: 24084189.

8: Jenkins MH, Steinberg SM, Alexander MP, Fisher JL, Ernstoff MS, Turk MJ, Mullins DW, Brinckerhoff CE. Multiple murine BRaf(V600E) melanoma cell lines with sensitivity to PLX4032. Pigment Cell Melanoma Res. 2014 May;27(3):495-501. doi: 10.1111/pcmr.12220. Epub 2014 Mar 6. PubMed PMID: 24460976; PubMed Central PMCID: PMC3988244.

9: Yang H, Higgins B, Kolinsky K, Packman K, Go Z, Iyer R, Kolis S, Zhao S, Lee R, Grippo JF, Schostack K, Simcox ME, Heimbrook D, Bollag G, Su F. RG7204 (PLX4032), a selective BRAFV600E inhibitor, displays potent antitumor activity in preclinical melanoma models. Cancer Res. 2010 Jul 1;70(13):5518-27. doi: 10.1158/0008-5472.CAN-10-0646. Epub 2010 Jun 15. Erratum in: Cancer Res. 2010 Nov 15;70(22):9527. PubMed PMID: 20551065.

10: Joseph EW, Pratilas CA, Poulikakos PI, Tadi M, Wang W, Taylor BS, Halilovic E, Persaud Y, Xing F, Viale A, Tsai J, Chapman PB, Bollag G, Solit DB, Rosen N. The RAF inhibitor PLX4032 inhibits ERK signaling and tumor cell proliferation in a V600E BRAF-selective manner. Proc Natl Acad Sci U S A. 2010 Aug 17;107(33):14903-8. doi: 10.1073/pnas.1008990107. Epub 2010 Jul 28. PubMed PMID: 20668238; PubMed Central PMCID: PMC2930420.

11: Rohrbeck L, Gong JN, Lee EF, Kueh AJ, Behren A, Tai L, Lessene G, Huang DC, Fairlie WD, Strasser A, Herold MJ. Hepatocyte growth factor renders BRAF mutant human melanoma cell lines resistant to PLX4032 by downregulating the pro-apoptotic BH3-only proteins PUMA and BIM. Cell Death Differ. 2016 Dec;23(12):2054-2062. doi: 10.1038/cdd.2016.96. Epub 2016 Sep 30. PubMed PMID: 27689874; PubMed Central PMCID: PMC5136498.

12: Basile KJ, Abel EV, Aplin AE. Adaptive upregulation of FOXD3 and resistance to PLX4032/4720-induced cell death in mutant B-RAF melanoma cells. Oncogene. 2012 May 10;31(19):2471-9. doi: 10.1038/onc.2011.424. Epub 2011 Sep 26. PubMed PMID: 21996740; PubMed Central PMCID: PMC3262107.

13: 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.

14: Vergani E, Vallacchi V, Frigerio S, Deho P, Mondellini P, Perego P, Cassinelli G, Lanzi C, Testi MA, Rivoltini L, Bongarzone I, Rodolfo M. Identification of MET and SRC activation in melanoma cell lines showing primary resistance to PLX4032. Neoplasia. 2011 Dec;13(12):1132-42. PubMed PMID: 22241959; PubMed Central PMCID: PMC3257188.

15: Xing J, Liu R, Xing M, Trink B. The BRAFT1799A mutation confers sensitivity of thyroid cancer cells to the BRAFV600E inhibitor PLX4032 (RG7204). Biochem Biophys Res Commun. 2011 Jan 28;404(4):958-62. doi: 10.1016/j.bbrc.2010.12.088. Epub 2010 Dec 23. PubMed PMID: 21185263; PubMed Central PMCID: PMC4596240.

16: Robert C, Karaszewska B, Schachter J, Rutkowski P, Mackiewicz A, Stroiakovski D, Lichinitser M, Dummer R, Grange F, Mortier L, Chiarion-Sileni V, Drucis K, Krajsova I, Hauschild A, Lorigan P, Wolter P, Long GV, Flaherty K, Nathan P, Ribas A, Martin AM, Sun P, Crist W, Legos J, Rubin SD, Little SM, Schadendorf D. Improved overall survival in melanoma with combined dabrafenib and trametinib. N Engl J Med. 2015 Jan 1;372(1):30-9. doi: 10.1056/NEJMoa1412690. Epub 2014 Nov 16. PubMed PMID: 25399551.

17: Roukos DH. PLX4032 and melanoma: resistance, expectations and uncertainty. Expert Rev Anticancer Ther. 2011 Mar;11(3):325-8. doi: 10.1586/era.11.3. PubMed PMID: 21417847.

18: Patrawala S, Puzanov I. Vemurafenib (RG67204, PLX4032): a potent, selective BRAF kinase inhibitor. Future Oncol. 2012 May;8(5):509-23. doi: 10.2217/fon.12.31. PubMed PMID: 22646766.

19: Comin-Anduix B, Chodon T, Sazegar H, Matsunaga D, Mock S, Jalil J, Escuin-Ordinas H, Chmielowski B, Koya RC, Ribas A. The oncogenic BRAF kinase inhibitor PLX4032/RG7204 does not affect the viability or function of human lymphocytes across a wide range of concentrations. Clin Cancer Res. 2010 Dec 15;16(24):6040-8. doi: 10.1158/1078-0432.CCR-10-1911. PubMed PMID: 21169256; PubMed Central PMCID: PMC3057460.

20: Liu R, Liu D, Xing M. The Akt inhibitor MK2206 synergizes, but perifosine antagonizes, the BRAF(V600E) inhibitor PLX4032 and the MEK1/2 inhibitor AZD6244 in the inhibition of thyroid cancer cells. J Clin Endocrinol Metab. 2012 Feb;97(2):E173-82. doi: 10.1210/jc.2011-1054. Epub 2011 Nov 16. PubMed PMID: 22090271; PubMed Central PMCID: PMC3275354.