Lapatinib ditosylate | CAS#231277-92-2 | CAS#388082-77-7 | EGFR inhibitor | CAT#100490B

MedKoo Cat#: 100946 | Name: Lapatinib ditosylate

Description:

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

Lapatinib is a synthetic, orally-active quinazoline with potential antineoplastic activity. Lapatinib reversibly blocks phosphorylation of the epidermal growth factor receptor (EGFR), ErbB2, and the Erk-1 and-2 and AKT kinases; it also inhibits cyclin D protein levels in human tumor cell lines and xenografts. EGFR and ErbB2 have been implicated in the growth of various tumor types. Check for active clinical trials or closed clinical trials using this agent.

Chemical Structure

Lapatinib ditosylate

CAS#388082-77-7 (ditosylate)

Theoretical Analysis

MedKoo Cat#: 100946

Name: Lapatinib ditosylate

CAS#: 388082-77-7 (ditosylate)

Chemical Formula: C43H42ClFN4O10S3

Exact Mass: 0.0000

Molecular Weight: 925.46

Elemental Analysis: C, 55.81; H, 4.57; Cl, 3.83; F, 2.05; N, 6.05; O, 17.29; S, 10.39

Price and Availability

Size	Price	Availability
500mg	USD 90.00	Ready to ship
1g	USD 150.00	Ready to ship
2g	USD 250.00	Ready to ship
5g	USD 450.00	Ready to ship
10g	USD 750.00	Ready to ship
20g	USD 1,250.00	Ready to ship

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Related CAS #

388082-77-7 (ditosylate) 231277-92-2 (free base)

Synonym

GSK572016; GSK-572016; GSK 572016; GW2016; GW-2016; GW 2016; Lapatinib; Lapatinib ditosylate; Brand name: Tykerb. CAT#100490B.

IUPAC/Chemical Name

N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)furan-2-yl)quinazolin-4-amine ditosylate

InChi Key

UWYXLGUQQFPJRI-UHFFFAOYSA-N

InChi Code

InChI=1S/C29H26ClFN4O4S.2C7H8O3S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19;2*1-6-2-4-7(5-3-6)11(8,9)10/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35);2*2-5H,1H3,(H,8,9,10)

SMILES Code

O=S(CCNCC1=CC=C(C2=CC3=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)N=CN=C3C=C2)O1)(C)=O.OS(=O)(C6=CC=C(C)C=C6)=O.OS(=O)(C7=CC=C(C)C=C7)=O

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, 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

Note: Previously we assigned 100490B for Lapatinib ditosylate. New catalogue# for Lapatinib ditosylat is 100946, which was created on 2/10/2017. CAT#100490B is the same product as CAT#100946.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TZC70216

QC Data

View QC data: current batch, Lot#TZC70216

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Lapatinib ditosylate is an inhibitor of the ErbB-2 and EGFR tyrosine kinase domains with IC50 values against purified EGFR and ErbB-2 of 10.2 and 9.8 nM, respectively.

In vitro activity:

The anti-tumour effect of lapatinib on canine TCC (transitional cell carcinoma) cell lines was examined in vitro. Five canine TCC cell lines (TCCUB, Love, Sora, LCTCC, and MCTCC) were used. Western blotting showed that HER2 protein expression was observed in all of the canine TCC cell lines. Lapatinib inhibited phosphorylation of HER2 and cell growth in a dose-dependent manner. Cell cycle analyses using flow cytometry showed that lapatinib significantly increased the sub-G1 and G0/G1 phase fractions and significantly decreased the S and G2/M phase fractions in the cell lines (Sora and TCCUB). Reference: Vet Comp Oncol. 2018 Dec;16(4):642-649. https://onlinelibrary.wiley.com/doi/abs/10.1111/vco.12434

In vivo activity:

For the in vivo experiments, the canine TCC cells (Sora) were subcutaneously injected into nude mice. Six days after inoculation, lapatinib (100 mg/kg) or vehicle was administered daily via intraperitoneal administration for 14 days. Tumour volume was significantly smaller in the lapatinib group compared with the vehicle control group. Reference: Vet Comp Oncol. 2018 Dec;16(4):642-649. https://onlinelibrary.wiley.com/doi/abs/10.1111/vco.12434

	Solvent	mg/mL	mM
Solubility
	DMSO	125.0	135.07

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 925.46 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.

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. Mu Y, Sun D. Lapatinib, a Dual Inhibitor of Epidermal Growth Factor Receptor (EGFR) and HER-2, Enhances Radiosensitivity in Mouse Bladder Tumor Line-2 (MBT-2) Cells In Vitro and In Vivo. Med Sci Monit. 2018 Aug 20;24:5811-5819. doi: 10.12659/MSM.909865. PMID: 30125265; PMCID: PMC6113922. 2. Sakai K, Maeda S, Saeki K, Nakagawa T, Murakami M, Endo Y, Yonezawa T, Kadosawa T, Mori T, Nishimura R, Matsuki N. Anti-tumour effect of lapatinib in canine transitional cell carcinoma cell lines. Vet Comp Oncol. 2018 Dec;16(4):642-649. doi: 10.1111/vco.12434. Epub 2018 Sep 23. PMID: 30246405.

In vitro protocol:

In vivo protocol:

1: Bowen JM. Development of the rat model of lapatinib-induced diarrhoea. Scientifica (Cairo). 2014;2014:194185. doi: 10.1155/2014/194185. Epub 2014 Jul 7. Review. PubMed PMID: 25126444; PubMed Central PMCID: PMC4121095. 2: Wang H. Lapatinib for the treatment of breast cancer in the People's Republic of China. Onco Targets Ther. 2014 Jul 31;7:1367-73. doi: 10.2147/OTT.S60586. eCollection 2014. Review. PubMed PMID: 25114575; PubMed Central PMCID: PMC4125370. 3: Abdel-Rahman O, Fouad M. Does the use of lapatinib increase the risk of fatigue and hepatic toxicities in patients with solid tumors? A critical literature review and meta-analysis. Expert Opin Drug Saf. 2014 Aug;13(8):999-1008. doi: 10.1517/14740338.2014.921679. Epub 2014 Jun 14. Review. PubMed PMID: 24930544. 4: Nolting M, Schneider-Merck T, Trepel M. Lapatinib. Recent Results Cancer Res. 2014;201:125-43. doi: 10.1007/978-3-642-54490-3_7. Review. PubMed PMID: 24756789. 5: Gandhi MD, Agulnik M. Targeted treatment of head and neck squamous-cell carcinoma: potential of lapatinib. Onco Targets Ther. 2014 Feb 13;7:245-51. doi: 10.2147/OTT.S46933. eCollection 2014. Review. PubMed PMID: 24611017; PubMed Central PMCID: PMC3928467. 6: Bianchi GV, Duca M, Sica L, Mariani G. Metastatic breast cancer treated with lapatinib with a prolonged benefit: a case report and a review of therapeutic options available. Tumori. 2013 Nov-Dec;99(6):269e-72e. doi: 10.1700/1390.15466. Review. PubMed PMID: 24503801. 7: Botrel TE, Paladini L, Clark OA. Lapatinib plus chemotherapy or endocrine therapy (CET) versus CET alone in the treatment of HER-2-overexpressing locally advanced or metastatic breast cancer: systematic review and meta-analysis. Core Evid. 2013;8:69-78. doi: 10.2147/CE.S50474. Epub 2013 Sep 30. Review. PubMed PMID: 24115917; PubMed Central PMCID: PMC3793631. 8: Larsen PB, KÃ¼mler I, Nielsen DL. A systematic review of trastuzumab and lapatinib in the treatment of women with brain metastases from HER2-positive breast cancer. Cancer Treat Rev. 2013 Nov;39(7):720-7. doi: 10.1016/j.ctrv.2013.01.006. Epub 2013 Mar 5. Review. PubMed PMID: 23481218. 9: Gross-Goupil M, Bernhard JC, Ravaud A. Lapatinib and renal cell carcinoma. Expert Opin Investig Drugs. 2012 Nov;21(11):1727-32. doi: 10.1517/13543784.2012.713935. Epub 2012 Aug 9. Review. PubMed PMID: 22876762. 10: Riemsma R, Forbes CA, Amonkar MM, Lykopoulos K, Diaz JR, Kleijnen J, Rea DW. Systematic review of lapatinib in combination with letrozole compared with other first-line treatments for hormone receptor positive(HR+) and HER2+ advanced or metastatic breast cancer(MBC). Curr Med Res Opin. 2012 Aug;28(8):1263-79. doi: 10.1185/03007995.2012.707643. Epub 2012 Jul 16. Review. PubMed PMID: 22738819. 11: Opdam FL, Guchelaar HJ, Beijnen JH, Schellens JH. Lapatinib for advanced or metastatic breast cancer. Oncologist. 2012;17(4):536-42. doi: 10.1634/theoncologist.2011-0461. Epub 2012 Apr 3. Review. PubMed PMID: 22477724; PubMed Central PMCID: PMC3336826. 12: Hurvitz SA, Kakkar R. Role of lapatinib alone or in combination in the treatment of HER2-positive breast cancer. Breast Cancer (Dove Med Press). 2012 Apr 3;4:35-51. doi: 10.2147/BCTT.S29996. Review. PubMed PMID: 24367193; PubMed Central PMCID: PMC3846547. 13: Fleeman N, Bagust A, Boland A, Dickson R, Dundar Y, Moonan M, Oyee J, Blundell M, Davis H, Armstrong A, Thorp N. Lapatinib and trastuzumab in combination with an aromatase inhibitor for the first-line treatment of metastatic hormone receptor-positive breast cancer which over-expresses human epidermal growth factor 2 (HER2): a systematic review and economic analysis. Health Technol Assess. 2011;15(42):1-93, iii-iv. doi: 10.3310/hta15420. Review. PubMed PMID: 22152751. 14: Vrdoljak E, Boban M, Ban M. Lapatinib in the treatment of HER-2 overexpressing breast cancer. J BUON. 2011 Jul-Sep;16(3):393-9. Review. PubMed PMID: 22006739. 15: Kenny LM, Lam EW. Review: lapatinib in metastatic colorectal cancer-another strategy for disease control? Clin Adv Hematol Oncol. 2011 Jun;9(6):500-1. Review. PubMed PMID: 21841752. 16: Bouchalova K, Cizkova M, Cwiertka K, Trojanec R, Friedecky D, Hajduch M. Lapatinib in breast cancer - the predictive significance of HER1 (EGFR), HER2, PTEN and PIK3CA genes and lapatinib plasma level assessment. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2010 Dec;154(4):281-8. Review. PubMed PMID: 21293538. 17: Merriam P, Sikov WM. Clinical utility of the combination of lapatinib and letrozole in the management of hormone receptor-positive and HER2-positive advanced breast cancer. Breast Cancer (Dove Med Press). 2011 Oct 26;3:139-50. doi: 10.2147/BCTT.S12150. Review. PubMed PMID: 24367183; PubMed Central PMCID: PMC3846896. 18: Giampaglia M, Chiuri VE, Tinelli A, De Laurentiis M, Silvestris N, Lorusso V. Lapatinib in breast cancer: clinical experiences and future perspectives. Cancer Treat Rev. 2010 Nov;36 Suppl 3:S72-9. doi: 10.1016/S0305-7372(10)70024-4. Review. PubMed PMID: 21129615. 19: MacFarlane RJ, Gelmon KA. Lapatinib for breast cancer: a review of the current literature. Expert Opin Drug Saf. 2011 Jan;10(1):109-21. doi: 10.1517/14740338.2011.533168. Epub 2010 Nov 20. Review. PubMed PMID: 21091041. 20: Arai H, Yamaki M, Nishimura Y. [Pharmacological profiles and clinical effects of lapatinib tosilate (Tykerb)]. Nihon Yakurigaku Zasshi. 2010 Sep;136(3):175-84. Review. Japanese. PubMed PMID: 20838021.