Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00351)
Name
Lapatinib
Synonyms    Click to Show/Hide the Synonyms of This API
Lapatinib; 231277-92-2; Tykerb; GW572016; Lapatinib base; GW 572016; Tyverb; 388082-78-8; Lapatinib tosilate hydrate; Lapatinib free base; UNII-0VUA21238F; Lapatinib (free base); 231277-92-2 (free base); MFCD09264194; CHEMBL554; GW-572016; CHEBI:49603; 0VUA21238F; NSC745750; NCGC00167507-01; C29H26ClFN4O4S; DSSTox_CID_26675; DSSTox_RID_81812; DSSTox_GSID_46675; Lapatinib (INN); GSK 572016; CAS-231277-92-2; GW-2016; Lapatinib [INN:BAN]; GSK572016; GW 282974X; HSDB 8209; Lapatinib Ditosylate/; PubChem7650; nchembio866-comp20; Kinome_3684; Kinome_3685; SCHEMBL8100; BDBM5445; cid_208908; GTPL5692; QCR-63; DTXSID7046675; AOB5254; EX-A402; SYN1052; BCPP000188; BCPP000189; HMS2089H10; HMS3244N06; HMS3244N10; HMS3244N14; HMS3744K11; Tykerb (TN) (Glaxo Smith Kline); BCP01874; ZINC1550477; Tox21_112505; ABP000866; ABP000872; NSC800780; AKOS005145766; Tox21_112505_1; AC-1314; BCP9000837; BCP9000838; CCG-270133; CM14421; DB01259; GSK-572016; GW-572016X; NSC-745750; NSC-800780; SB16918; NCGC00167507-02; NCGC00167507-03; NCGC00167507-04; NCGC00167507-09; 913989-15-8; AK-46487; AS-14065; HY-50898; AB0005824; AM20090641; FT-0659650; SW199101-5; A25184; D08108; J90020; W-3749; 49311-EP2298768A1; 49311-EP2298778A1; 49311-EP2311840A1; AB01273965-01; AB01273965-02; AB01273965-03; AB01273965_04; AB01273965_05; 277L922; Q420323; Q-101353; SR-05000001472-1; BRD-K19687926-001-01-7; BRD-K19687926-379-02-5; GW572016;GW-572016;GW 572016; 1092929-10-6
Clinical Status
Approved
Disease Indication Breast cancer ICD-11: 2C60 [1]
PubChem CID
208908
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
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=208908"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 581.1 Topological Polar Surface Area 115
XlogP 5.1 Complexity 898
Heavy Atom Count 40 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Lapatinib 250 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Polysorbate 80; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols; Povidones; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company GlaxoSmithKline; Novartis Pharmaceuticals Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Lapatinib Ditosylate eq 250mg base tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium Stearate; Microcrystalline Cellulose; Povidone; Sodium Starch Glycolate; Fd&C Yellow No. 6/Sunset Yellow Fcf Aluminum Lake; Hypromellose; Macrogol/Peg 400; Polysorbate 80; Titanium Dioxide
                   Dosage Form Tablet
                   Company Novartis
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [5]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [6]
References
1 FDA label for approved lapatinib from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
6 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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