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Home> Encyclopedia >   /  Antineoplastic Agents  /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Organic Intermediate  /  Pharmaceuticals and Biochemicals
Gefitinib structure
Gefitinib structure


Iupac Name:N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
CAS No.:184475-35-2
Molecular Weight:446.907
Introduction: Gefitinib was introduced in Japan as a daily oral monotherapy for the treatment ofinoperable or recurrent non-small cell lung cancers (NSCLC). This anilinoquinazolinederivative can be synthesized in 6 steps starting from 6,7-dimethoxyquinazolin-4(3H)-oneby successive monodemethylationlacetylation of the 6-hydroxy-group followed bychlorination and reaction with 3-chloro-4-fluoroaniline, finally deacetylation and alkylationwith 3-(4-morpholinyl)propylbromide complete the synthesis. Gefitinib reversibly inhibitsthe activity of the epidermal growth factor receptor tyrosine kinase (EGRF TK). Thisinhibits autophosphorylation of EGRF and blocks the cascade of intracellular events whichhave been implicated in the proliferation, survival and metastasis of cancer cells. Gefitinibdiplays good selectivity for the EGRF TK relative to other growth factors in humanumbilical endothelial cells. It is similarly selective relative to other kinases, for example cerB2.Data from two large phase II studies in patients with pretreated NSCLC have shownthat gefitinib induces a response rate approaching 20% in patients receiving the agent as a second line therapy and approximately 10% in those pretreated with more lines ofchemotherapy. Gefitinib has good bioavailability and is metabolized in the liver via thecytochrome P450 3A4 enzyme system with a mean elimination half life of 28 h. Gefitinibhas been generally well tolerated in cancer patients with predominant side effects beingacne-like skin-rash, diarrhea, nausea, vomiting and mild to moderate myelosuppression..
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(3-chloro-4-fluoro-phenyl)-[7-methoxy-6-(3-morpholin-4-yl-propoxy)-quinazolin-4-yl]-amine (3-chloro-4-fluoro-phenyl)-[7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-yl]amine (3-chloro-4-fluorophenyl)[7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-yl]amine 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 3-chloro-4-fluoro-n-[(4z)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(1h)-ylidene]aniline 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)-quinazoline 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline 4-[(3-chloro-4-fluorophenyl)amino]-7-methoxy-6-(3-morpholinopropoxy)quinazoline 475g352 4CA-0562 4-quinazolinamine, n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)- 4-quinazolinamine, n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-4-morpholin)propoxy)- 4-quinazolinamine, n-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]- 6-(3-morpholinopropoxy)-n-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine 6-(Benzyloxy)-7-methoxyquinazolin-4(3H)-one A812870 AB0000095 AB01273954_04 AB01273954-01 AB01273954-02 AB01273954-03 AB20814 ABP000855 AC-1556 AC1L3X0A AJ-74091 AK-72948 AKOS 91371 AKOS000280752 AM20090619 AMX10169 AN-5192 AOB6917 api0002810 BC215794 BCB03_000781 BCP9000718 BCPP000221 bdbm5447 BIO-0046 BR-72948 c-22438 cas-184475-35-2 cc-28943 CCG-220642 ccris 9011 CG0031 CHEBI:49668 chembl939 cid_123631 CJ-16232 CS-0124 CTK7A0364 CU-00000000396-1 D01977 D09XZB DB00317 DR002765 dsstox_cid_21034 dsstox_gsid_41034 dsstox_rid_79614 DTXSID8041034 EBD446 EN002708 FC0028 FT-0081035 FT-0602325 g-4408 Gefinitib gefitini gefitini iressa GEFITINIB GEFITINIB - IRESSA gefitinib (iressa) Gefitinib (JAN/USAN) gefitinib (jan/usan/inn) gefitinib (zd1839) gefitinib [usan] gefitinib for system suitability, europepharmacopoeia (ep) reference standard Gefitinib N-(3-Chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine GEFITINIB RELATED COMPOUND Gefitinib(TINIBS) gefitinib, >=98% (hplc) Gefitinib, >=99% gefitinib, europepharmacopoeia (ep) reference standard gefitinib, iressa, zd1839 gefitinib,iressa, zd1839 gefitinib,zd-1839,iressa gefitinib/zd-1839,iressa gefitinib gefitinib iressa geftinib GP9843 gtpl4941 H018 HE320284 HE320285 HMS2089B19 HMS3244M21 HMS3244M22 HMS3244N21 HMS3654A07 HY-50895 I01-1227 ire iressa iressa (astrazeneca) iressa (tn) iressa(tm) iressa|||zd 1839 irressa irressat J10250 K00240 KB-52238 KBIOSS_002241 KINOME_3321 KINOME_3322 KS-00000E11 KS-1204 LS-139916 MCULE-6951584187 mfcd04307832 MLS003899193 MOLPORT-000-883-335 N-(3-Chlor-4-fluorophenyl)-7-[methoxy-6-[(3-morpholin-4-yl)propoxyl]-quinazolin-4-yl]amine n-(3-chloranyl-4-fluoranyl-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamide n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamine n-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine N-(3-Chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine Gefitinib n-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine n-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine n-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine n-?(3-?chloro-?4-?fluorophenyl)-?7-?methoxy-?6-?[3-?(4-?morpholinyl)propoxy]-?4-?quinazolinamine NCGC00159455-02 NCGC00159455-03 NCGC00159455-04 NCGC00159455-05 NCGC00159455-06 NCGC00159455-08 NCGC00159455-09 NCHEMBIO866-COMP14 nsc715055 nsc-715055 nsc759856 nsc-759856 pharmakon1600-01502274 Q-201149 QCR-105 RS0033 S1025 S-2176 S65743JHBS SC-18023 SCHEMBL7866 smr002204119 sr-00000000262 SR-00000000262-2 SR-00000000262-3 ST2413546 STK621310 SYN1042 tox21_111683 tox21_111683_1 unii-s65743jhbs XGALLCVXEZPNRQ-UHFFFAOYSA-N Z1551429741 zd 1839 zd1839 zd-1839 zd-1839, iressa, gefitinib ZINC19632614

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C22H24ClFN4O3 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
2. 3D Conformer
3. Properties
3.1 Density
3.2 Melting Point
3.3 Boiling Point
586.8 °C at 760 mmHg
3.4 Vapour
0mmHg at 25°C
3.5 Refractive Index
3.6 Flash Point
308.7 °C
3.7 Appearance
Light-Yellow Crystalline Powder
3.8 Chemical Properties
Light-Yellow Crystalline Powder
3.9 Color/Form
3.10 Physical
3.11 pKa
5.4and 7.2
3.12 StorageTemp
Store at RT
4. Use and Manufacturing
4.1 General Description
Geftinib is available as 250-mg tablets for oral administrationin the treatment of NSCLC for those patients who have failedto respond to platinum-based therapies and docetaxel and hasalso been used against squamous cell cancers of the head andneck. The agent is an inhibitor of the TK of EGF-R and possiblyother TKs as well. Gefitinib is both a substrate and inhibitorof Pgp and BCRP. The agent is absorbed slowly afterbeing administered orally with 60% bioavailability.Metabolism occurs in the liver and is mediated primarily byCYP3A4 to give eight identified metabolites resulting fromdefluorination of the phenyl ring, oxidative-O-demethylation,and multiple products arising as a result of oxidation of themorpholine ring. The O-demethylated product represents thepredominate metabolite and is 14-fold less active comparedwith the parent. The parent and metabolites are eliminated inthe feces with a terminal elimination half-life of 48 hours.The drug appears to be well tolerated with the most commonlyreported side effects being rash and diarrhea. It mayalso cause elevations in blood pressure especially in those patientswith preexisting hypertension, elevation of transaminaselevels, and mild nausea and mucositits.
4.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 32 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
H318 (53.12%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H351 (53.12%): Suspected of causing cancer [Warning Carcinogenicity]
H361 (56.25%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H373 (53.12%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H400 (40.62%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H411 (53.12%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P314, P321, P330, P332+P313, P362, P391, P405, and P501
4.3 Usage
Gefitinib is an antineoplastic target therapy drug with relatively high specificity that was developed by the British pharmaceutical company AstraZeneca; it is the first molecular targeted drug to be used in non-small cell lung cancer treatment. Epidermal growth factors (EGF) are a kind of polypeptide with a relative molecular mass of 6.45x103, and they can bind with epidermal growth factor receptors (EGFR) on target cell membrane surfaces to trigger biological effects. EGFR is a type of tyrosine kinase (TK) type receptor, so when bound with EGF, it will promote TK activation in the receptor. This will cause tyrosine residue in the receptor to autophosphorylate and send continuous dividing signals into the cell, causing cell proliferation and differentiation. EGFR is abundant in human tissue, and it is highly expressed in malign tumors. Gefitinib blocks the signal transduction pathway of cell surface EGFR to prevent tumor growth, metastasis, and growth in blood vessels, and it can induce tumor cell apoptosis. Gefitinib is mainly used to treat non-stem cell lung cancer.
5. Safety and Handling
5.1 Hazard Codes
5.2 Safety Statements
5.3 Hazard Note
H302; H315; H319; H335
5.4 Specification

? Gefitinib ,?its cas register number is 184475-35-2. It also can be called?4-(3'-Chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline ; CCRIS 9011 ; Iressa ; Irressat .?Gefitinib (CAS NO.184475-35-2) is?an light-yellow crystalline Powder.


2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H302 Harmful if swallowed

H400 Very toxic to aquatic life

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P273 Avoid release to the environment.


P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P391 Collect spillage.




P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


10. Computational chemical data
  • Molecular Weight:446.907g/mol
  • Molecular Formula:C22H24ClFN4O3
  • Compound Is Canonicalized:True
  • Exact Mass:446.152
  • Monoisotopic Mass:446.152
  • Complexity:545
  • Rotatable Bond Count:8
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:8
  • Topological Polar Surface Area:68.7A^2
  • Heavy Atom Count:31
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
12. Question & Answer
  • Gefitinib has been shown to be an effective tyrosine kinase inhibitor in a fraction (~ 10 " style="position: relative;" tabindex="0" id="MathJax-Element-2-Frame" class="MathJax" 10 10 %) of non-small cell lung cancer patients. These patients are characterized as having a mutation (usually a deletio...
  • Imatinib mesylate is a novel tyrosine kinase inhibitor and a derivative of phenylpyrimidine. About 95% of patients with chronic myeloid leukemia (CML) are Philadelphia chromosome-positive, that is, the proto-oncogene ABL of chromosome 9 is ectopic to the oncogene of chromosome 22 called the breakpo...
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