Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00299)
Name
Gefitinib
Synonyms    Click to Show/Hide the Synonyms of This API
Gefitinib; 184475-35-2; Iressa; ZD1839; N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine; Irressat; gefitinib (zd1839); ZD 1839; ZD-1839; UNII-S65743JHBS; 4-(3'-Chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline; MFCD04307832; CHEMBL939; S65743JHBS; CHEBI:49668; NCGC00159455-02; DSSTox_CID_21034; DSSTox_RID_79614; DSSTox_GSID_41034; Iressa(TM); Iressa (TN); CCRIS 9011; CAS-184475-35-2; SR-00000000262; gefitinibum; Gefitinib (JAN/USAN/INN); Gefitinib [USAN:INN:BAN]; Gefitini; Iressa; gefitinib (iressa); Gefitinib - Iressa; IRRESSA; Iressa (AstraZeneca); nchembio866-comp14; Kinome_3321; Kinome_3322; Iressa; ZD 1839; SCHEMBL7866; Gefitinib,ZD-1839,Iressa; Gefitinib/ZD-1839,Iressa; KBioSS_002241; cc-596; MLS003899193; CU-00000000396-1; BDBM5447; cid_123631; EBD446; GTPL4941; DTXSID8041034; Gefitinib, >=98% (HPLC); AOB6917; QCR-105; SYN1042; BCPP000221; HMS2089B19; HMS3244M21; HMS3244M22; HMS3244N21; HMS3295A21; HMS3413H08; HMS3654A07; HMS3677H08; HMS3714A05; HMS3748E17; Pharmakon1600-01502274; BCP01365; Tox21_111683; ABP000855; CG0031; NSC715055; NSC759856; NSC800105; STK621310; ZINC19632614; AKOS000280752; Tox21_111683_1; AB20814; AC-1556; BCP9000718; CCG-220642; CS-0124; DB00317; KS-1204; MCULE-6951584187; NSC-715055; NSC-759856; NSC-800105; 4-[(3-Chloro-4-fluorophenyl)amino]-7-methoxy-6-(3-morpholinopropoxy)quinazoline; 6-(3-morpholinopropoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine; N-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine; NCGC00159455-03; NCGC00159455-04; NCGC00159455-05; NCGC00159455-06; NCGC00159455-08; NCGC00159455-09; NCGC00159455-14; AK-72948; BCB03_000781; BR-72948; HY-50895; SMR002204119; SY002154; AB0000095; AM20090619; FT-0602325; SW199108-4; EC-000.2409; D01977; G-4408; J10250; K00240; S-2176; 15215-EP2269994A1; 15215-EP2272827A1; 15215-EP2272832A1; 15215-EP2275413A1; 15215-EP2277865A1; 15215-EP2280006A1; 15215-EP2281813A1; 15215-EP2281815A1; 15215-EP2287156A1; 15215-EP2292234A1; 15215-EP2292615A1; 15215-EP2298768A1; 15215-EP2298778A1; 15215-EP2301533A1; 15215-EP2301933A1; 15215-EP2305640A2; 15215-EP2305671A1; 15215-EP2311807A1; 15215-EP2311827A1; 15215-EP2311840A1; 15215-EP2316832A1; 15215-EP2316833A1; 32333-EP2281815A1; 32333-EP2292615A1; 32333-EP2301933A1; 32333-EP2305640A2; 32333-EP2305671A1; 32333-EP2311827A1; AB01273954-01; AB01273954-02; AB01273954-03; AB01273954_04; 475G352; A812870; Q417824; Q-201149; SR-00000000262-2; SR-00000000262-3; Gefitinib, EuropePharmacopoeia (EP) Reference Standard; Z1551429741; (3-chloro-4-fluorophenyl)[7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-yl]amine; 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)-quinazoline; Gefitinib for system suitability, EuropePharmacopoeia (EP) Reference Standard
Clinical Status
Approved
Disease Indication Lung cancer ICD-11: 2C25 [1]
PubChem CID
123631
Formula
C22H24ClFN4O3
Canonical SMILES
COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
InChI
1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)
InChIKey
XGALLCVXEZPNRQ-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=123631"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 446.9 Topological Polar Surface Area 68.7
XlogP 4.1 Complexity 545
Heavy Atom Count 31 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Full List of Drug Formulations (DFMs) Containing This API
          Gefitinib 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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Titanium dioxide; Croscarmellose sodium; Polyethylene glycol 300; Cellulose, microcrystalline; Hypromelloses; Povidones
                   Dosage Form Oral Tablet
                   Company AstraZeneca
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Polyethylene glycol 300 DIG Info Multidrug resistance protein 1 (Inhibition ratio = 54 %) [4]
References
1 FDA label for approved gefitinib 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 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 The effect of polyoxyethylene polymers on the transport of ranitidine in Caco-2 cell monolayers. Int J Pharm. 2011 May 16;409(1-2):164-8.

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