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Chemistry

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Also known as: 388082-77-7, Tykerb, Tykerb ditosylate, Lapatinib (gw-572016) ditosylate, Tyverb, Lapatinib (ditosylate)
Molecular Formula
C43H42ClFN4O10S3
Molecular Weight
925.5  g/mol
InChI Key
UWYXLGUQQFPJRI-UHFFFAOYSA-N
FDA UNII
4WK72K94MC

Lapatinib Ditosylate
A quinazoline derivative that inhibits EPIDERMAL GROWTH FACTOR RECEPTOR and HER2 (RECEPTOR, ERBB-2) tyrosine kinases. It is used for the treatment of advanced or metastatic breast cancer, where tumors overexpress HER2.
1 2D Structure

Lapatinib Ditosylate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine;4-methylbenzenesulfonic acid
2.1.2 InChI
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)
2.1.3 InChI Key
UWYXLGUQQFPJRI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)O.CC1=CC=C(C=C1)S(=O)(=O)O.CS(=O)(=O)CCNCC1=CC=C(O1)C2=CC3=C(C=C2)N=CN=C3NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl
2.2 Other Identifiers
2.2.1 UNII
4WK72K94MC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gw 282974x

2. Gw 572016

3. Gw-282974x

4. Gw-572016

5. Gw282974x

6. Gw572016

7. Lapatinib

8. N-(3-chloro-4-(((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-methylsulfonyl)ethyl)amino)methyl) -2-furyl)-4-quinazolinamine

9. Tykerb

2.3.2 Depositor-Supplied Synonyms

1. 388082-77-7

2. Tykerb

3. Tykerb Ditosylate

4. Lapatinib (gw-572016) Ditosylate

5. Tyverb

6. Lapatinib (ditosylate)

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

8. 388082-78-8

9. Lapatinib Ditosylate Anhydrous

10. 4wk72k94mc

11. 388082-77-7 (ditosylate)

12. Bis(4-methylbenzene-1-sulfonic Acid); N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-amine

13. Gw-572016

14. 4-quinazolinamine, N-(3-chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-, Bis(4-methylbenzenesulfonate)

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

16. Sr-05000001472

17. N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine;4-methylbenzenesulfonic Acid

18. S1028

19. Unii-4wk72k94mc

20. Gw 572016f

21. Gw-572016 Ditosylate

22. Lapatinib Ditosylate,tykerb

23. Schembl93590

24. Quinazolin-4-amine Ditosylate

25. Chembl1201183

26. Dtxsid60959606

27. Hms3265i13

28. Hms3265i14

29. Hms3265j13

30. Hms3265j14

31. Hms3654e07

32. Hy-50898a

33. Mfcd09264195

34. Akos015888607

35. Ac-5247

36. Ccg-264661

37. Cs-0831

38. Gs-3661

39. Db-119273

40. Ft-0670728

41. Lapatinib Ditoluenesulfonate Anhydrous

42. Sw199101-4

43. Ec-000.2339

44. Lapatinib Ditosylate Anhydrous [who-dd]

45. Gw 572016 Ditosylate;gw-572016 Ditosylate

46. Lapatinib Ditoluenesulfonate Anhydrous [mi]

47. Sr-05000001472-2

48. Sr-05000001472-5

49. Q27260601

50. Z1692482592

51. 4-methylbenzene-1-sulfonic Acid--n-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-[5-({[2-(methanesulfonyl)ethyl]amino}methyl)furan-2-yl]quinazolin-4-amine (2/1)

52. 4-quinazolinamine, N-(3-chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-, 4-methylbenzenesulfonate (1:2)

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

54. N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl) Ethylamino)methyl)furan-2-yl)quinazolin-4-amine Ditosylate

55. N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl)ethylamino)methyl)furan-2-yl)quinazolin-4-amine Ditosylate

56. N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2-furyl]

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 925.5 g/mol
Molecular Formula C43H42ClFN4O10S3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count15
Rotatable Bond Count13
Exact Mass924.1735629 g/mol
Monoisotopic Mass924.1735629 g/mol
Topological Polar Surface Area240 Ų
Heavy Atom Count62
Formal Charge0
Complexity1100
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameTykerb
PubMed HealthLapatinib (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelLapatinib is a small molecule and a member of the 4-anilinoquinazoline class of kinase inhibitors. It is present as the monohydrate of the ditosylate salt, with chemical name N-(3-chloro-4-{[(3-fluorophenyl)methyl]oxy}phenyl)-6-[5-({[2-(methylsulfony...
Active IngredientLapatinib ditosylate
Dosage FormTablet
RouteOral
Strengtheq 250mg base
Market StatusPrescription
CompanySmithkline Beecham

2 of 2  
Drug NameTykerb
PubMed HealthLapatinib (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelLapatinib is a small molecule and a member of the 4-anilinoquinazoline class of kinase inhibitors. It is present as the monohydrate of the ditosylate salt, with chemical name N-(3-chloro-4-{[(3-fluorophenyl)methyl]oxy}phenyl)-6-[5-({[2-(methylsulfony...
Active IngredientLapatinib ditosylate
Dosage FormTablet
RouteOral
Strengtheq 250mg base
Market StatusPrescription
CompanySmithkline Beecham

4.2 Drug Indication

Tyverb is indicated for the treatment of patients with breast cancer , whose tumours overexpress HER2 (ErbB2):

- in combination with capecitabine for patients with advanced or metastatic disease with progression following prior therapy, which must have included anthracyclines and taxanes and therapy with trastuzumab in the metastatic setting;

- in combination with trastuzumab for patients with hormone-receptor-negative metastatic disease that has progressed on prior trastuzumab therapy or therapies in combination with chemotherapy;

- in combination with an aromatase inhibitor for post-menopausal women with hormone-receptor-positive metastatic disease, not currently intended for chemotherapy. The patients in the registration study had not previously been treated with trastuzumab or an aromatase inhibitor. No data are available on the efficacy of this combination relative to trastuzumab in combination with an aromatase inhibitor in this patient population.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Protein Kinase Inhibitors

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)


5.2 ATC Code

L01EH01


API Reference Price

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