GW 583340 dihydrochloride
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MedKoo CAT#: 531893

CAS#: 1173023-85-2

Description: GW 583340 dihydrochloride is a potent dual EGFR/ErbB2 tyrosine kinase inhibitor (IC50 values are 0.01 and 0.014 μM respectively). GW 583340 dihydrochloride selectively inhibits growth of human tumor cells overexpressing EGFR and ErbB2 (IC50 values are 0.11 μM for inhibition of HN5, N87 and BT474 tumor cell lines vs. > 30 μM for inhibition of non-tumor cell line HFF).

Chemical Structure

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GW 583340 dihydrochloride
CAS# 1173023-85-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531893
Name: GW 583340 dihydrochloride
CAS#: 1173023-85-2
Chemical Formula: C28H27Cl3FN5O3S2
Exact Mass: 0.00
Molecular Weight: 671.024
Elemental Analysis: C, 50.12; H, 4.06; Cl, 15.85; F, 2.83; N, 10.44; O, 7.15; S, 9.56

Price and Availability

Size Price Availability Quantity
10mg USD 450 2 Weeks
50mg USD 1450
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Synonym: GW 583340 dihydrochloride; GW583340; GW 583340; GW-583340.

IUPAC/Chemical Name: N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(2-{[(2-methanesulfonylethyl)amino]methyl}-1,3-thiazol-4-yl)quinazolin-4-amine dihydrochloride

InChi Key: WIMITXDBYLKRKB-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H25ClFN5O3S2.2ClH/c1-40(36,37)10-9-31-14-27-35-25(16-39-27)19-5-7-24-22(12-19)28(33-17-32-24)34-21-6-8-26(23(29)13-21)38-15-18-3-2-4-20(30)11-18;;/h2-8,11-13,16-17,31H,9-10,14-15H2,1H3,(H,32,33,34);2*1H

SMILES Code: O=S(CCNCC1=NC(C2=CC3=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)N=CN=C3C=C2)=CS1)(C)=O.[H]Cl.[H]Cl

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: >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:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Potent dual EGFR/ErbB2 inhibitor; orally active.
In vitro activity: GW583340 and GW2974 significantly decreased the IC50 values of MX in both ABCG2-482-R2 and ABCG2-482-T7 cell lines in a concentration dependent manner (Table 1). In addition, the reversal effect produced by GW583340 at 5 μM was comparable to the effect produced by 5 μM of lapatinib and 5 μM of FTC (Table 1). Reference: Biochem Pharmacol. 2012 Jun 15;83(12):1613-22. https://pubmed.ncbi.nlm.nih.gov/22414725/
In vivo activity: Using xenograft models of the same cell lines, this study found that the compounds (including GW583340) given orally inhibited in vivo tumor growth significantly compared with control animals. Reference: Bioorg Med Chem Lett. 2003 Feb 24;13(4):637-40. https://pubmed.ncbi.nlm.nih.gov/12639547/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 67.1 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 671.02 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. Sodani K, Tiwari AK, Singh S, Patel A, Xiao ZJ, Chen JJ, Sun YL, Talele TT, Chen ZS. GW583340 and GW2974, human EGFR and HER-2 inhibitors, reverse ABCG2- and ABCB1-mediated drug resistance. Biochem Pharmacol. 2012 Jun 15;83(12):1613-22. doi: 10.1016/j.bcp.2012.02.028. Epub 2012 Mar 7. PMID: 22414725; PMCID: PMC3360928. 2. Aird KM, Allensworth JL, Batinic-Haberle I, Lyerly HK, Dewhirst MW, Devi GR. ErbB1/2 tyrosine kinase inhibitor mediates oxidative stress-induced apoptosis in inflammatory breast cancer cells. Breast Cancer Res Treat. 2012 Feb;132(1):109-19. doi: 10.1007/s10549-011-1568-1. Epub 2011 May 11. PMID: 21559822; PMCID: PMC3734382. 3. Gaul MD, Guo Y, Affleck K, Cockerill GS, Gilmer TM, Griffin RJ, Guntrip S, Keith BR, Knight WB, Mullin RJ, Murray DM, Rusnak DW, Smith K, Tadepalli S, Wood ER, Lackey K. Discovery and biological evaluation of potent dual ErbB-2/EGFR tyrosine kinase inhibitors: 6-thiazolylquinazolines. Bioorg Med Chem Lett. 2003 Feb 24;13(4):637-40. doi: 10.1016/s0960-894x(02)01047-8. PMID: 12639547.
In vitro protocol: 1. Sodani K, Tiwari AK, Singh S, Patel A, Xiao ZJ, Chen JJ, Sun YL, Talele TT, Chen ZS. GW583340 and GW2974, human EGFR and HER-2 inhibitors, reverse ABCG2- and ABCB1-mediated drug resistance. Biochem Pharmacol. 2012 Jun 15;83(12):1613-22. doi: 10.1016/j.bcp.2012.02.028. Epub 2012 Mar 7. PMID: 22414725; PMCID: PMC3360928. 2. Aird KM, Allensworth JL, Batinic-Haberle I, Lyerly HK, Dewhirst MW, Devi GR. ErbB1/2 tyrosine kinase inhibitor mediates oxidative stress-induced apoptosis in inflammatory breast cancer cells. Breast Cancer Res Treat. 2012 Feb;132(1):109-19. doi: 10.1007/s10549-011-1568-1. Epub 2011 May 11. PMID: 21559822; PMCID: PMC3734382.
In vivo protocol: 1. Gaul MD, Guo Y, Affleck K, Cockerill GS, Gilmer TM, Griffin RJ, Guntrip S, Keith BR, Knight WB, Mullin RJ, Murray DM, Rusnak DW, Smith K, Tadepalli S, Wood ER, Lackey K. Discovery and biological evaluation of potent dual ErbB-2/EGFR tyrosine kinase inhibitors: 6-thiazolylquinazolines. Bioorg Med Chem Lett. 2003 Feb 24;13(4):637-40. doi: 10.1016/s0960-894x(02)01047-8. PMID: 12639547.

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1: Sodani K, Tiwari AK, Singh S, Patel A, Xiao ZJ, Chen JJ, Sun YL, Talele TT, Chen ZS. GW583340 and GW2974, human EGFR and HER-2 inhibitors, reverse ABCG2- and ABCB1-mediated drug resistance. Biochem Pharmacol. 2012 Jun 15;83(12):1613-22. doi: 10.1016/j.bcp.2012.02.028. PubMed PMID: 22414725; PubMed Central PMCID: PMC3360928.

2: Yu Z, Cui B, Jin Y, Chen H, Wang X. Novel irreversible EGFR tyrosine kinase inhibitor 324674 sensitizes human colon carcinoma HT29 and SW480 cells to apoptosis by blocking the EGFR pathway. Biochem Biophys Res Commun. 2011 Aug 12;411(4):751-6. doi: 10.1016/j.bbrc.2011.07.019. PubMed PMID: 21782788.

3: Aird KM, Allensworth JL, Batinic-Haberle I, Lyerly HK, Dewhirst MW, Devi GR. ErbB1/2 tyrosine kinase inhibitor mediates oxidative stress-induced apoptosis in inflammatory breast cancer cells. Breast Cancer Res Treat. 2012 Feb;132(1):109-19. doi: 10.1007/s10549-011-1568-1. PubMed PMID: 21559822; PubMed Central PMCID: PMC3734382.

4: Aird KM, Ghanayem RB, Peplinski S, Lyerly HK, Devi GR. X-linked inhibitor of apoptosis protein inhibits apoptosis in inflammatory breast cancer cells with acquired resistance to an ErbB1/2 tyrosine kinase inhibitor. Mol Cancer Ther. 2010 May;9(5):1432-42. doi: 10.1158/1535-7163.MCT-10-0160. PubMed PMID: 20406946; PubMed Central PMCID: PMC2957814.

5: Aird KM, Ding X, Baras A, Wei J, Morse MA, Clay T, Lyerly HK, Devi GR. Trastuzumab signaling in ErbB2-overexpressing inflammatory breast cancer correlates with X-linked inhibitor of apoptosis protein expression. Mol Cancer Ther. 2008 Jan;7(1):38-47. doi: 10.1158/1535-7163.MCT-07-0370. PubMed PMID: 18202008.