Drug Information

General Information
Drug ID
DR00120
Drug Name
Lapatinib
Synonyms
4-[[3-Chloro-4-(3-fluorobenzyloxy)phenyl]amino]-6-[5-[[(2-methanesulfonylethyl)amino]methyl]furan-2-yl]quinazoline; FMM; GSK 572016; GSK572016; GW 572016; GW 572016X; GW572016; Lapatinib (ERBB2 inhibitor); Lapatinib (INN); Lapatinib Ditosylate; Lapatinib [INN]; Lapatinib tosilate hydrate; Lapatinib, Tykerb, GW572016; N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-((2-methylsulfonylethylamino)methyl)-2-furyl)quinazolin-4-amine; N-(3-Chloro-4-{[(3-fluorophenyl)methyl]oxy}phenyl)-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furanyl]-4-quinazolinamine; N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine; N-{3-CHLORO-4-[(3-FLUOROBENZYL)OXY]PHENYL}-6-[5-({[2-(METHYLSULFONYL)ETHYL]AMINO}METHYL)-2-FURYL]-4-QUINAZOLINAMINE; Tycerb; Tykerb (TN)
Drug Type
Small molecular drug
Indication Breast cancer [ICD11:2C60-2C6Z] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
Formula
C29H26ClFN4O4S
Canonical SMILES
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
InChI
InChI=1S/C29H26ClFN4O4S/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/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35)
InChIKey
BCFGMOOMADDAQU-UHFFFAOYSA-N
CAS Number
CAS 388082-78-8
Pharmaceutical Properties Molecular Weight 581.1 Topological Polar Surface Area 115
Heavy Atom Count 40 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
XLogP
5.1
PubChem CID
208908
PubChem SID
103177479 ,103854383 ,103905567 ,103905568 ,109692966 ,113442073 ,117695459 ,124360113 ,124893335 ,124893336 ,125345521 ,126592984 ,126621155 ,126649062 ,126666978 ,126667073 ,126731332 ,127325943 ,127325944 ,127325945 ,127494626 ,134338132 ,135128225 ,135685383 ,135685387 ,14911387 ,21317859 ,30413551 ,46393564 ,46506302 ,46507141 ,49742619 ,50070568 ,50071307 ,50100107 ,50112760 ,50644701 ,53788364 ,57399558 ,585695 ,7887520 ,8035064 ,85171071 ,85202079 ,91147938 ,92308826 ,92719029 ,93581028 ,9368726 ,96024798
ChEBI ID
ChEBI:49603
TTD Drug ID
D08CDI
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
P-GP Transporter Info P-glycoprotein 1 Substrate [3]
References
1 Lapatinib was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 The role of efflux and uptake transporters in [N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine (GW572016, lapatinib) disposition and drug interactions. Drug Metab Dispos. 2008 Apr;36(4):695-701.
3 Tarascon Pocket Pharmacopoeia 2018 Classic Shirt-Pocket Edition.

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