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gefitinib 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
tyrosine kinase inhibitors	1282	184475-35-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: ZD1839 gefitinib iressa ZD 1839	Gefitinib reversibly inhibits the kinase activity of wild-type and certain activating mutations of EGFR, preventing autophosphorylation of tyrosine residues associated with the receptor, thereby inhibiting further downstream signalling and blocking EGFR-dependent proliferation. Molecular weight: 446.91 Formula: C22H24ClFN4O3 CLOGP: 5.25 LIPINSKI: 1 HAC: 7 HDO: 1 TPSA: 68.74 ALOGS: -4.22 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

ZD1839
gefitinib
iressa
ZD 1839

Gefitinib reversibly inhibits the kinase activity of wild-type and certain activating mutations of EGFR, preventing autophosphorylation of tyrosine residues associated with the receptor, thereby inhibiting further downstream signalling and blocking EGFR-dependent proliferation.

Molecular weight: 446.91
Formula: C22H24ClFN4O3
CLOGP: 5.25
LIPINSKI: 1
HAC: 7
HDO: 1
TPSA: 68.74
ALOGS: -4.22
ROTB: 8

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.25	g	O

ADMET properties:

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Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	8 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	60 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	34 hours	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	23 L/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	2 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	12 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.09 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.00 mg/mL	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
May 5, 2003	FDA

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Malignant neoplasm progression	1178.77	23.83	410	6511	81711	63400390
Drug resistance	730.58	23.83	211	6710	22722	63459379
Acquired gene mutation	429.99	23.83	77	6844	906	63481195
Metastases to central nervous system	310.01	23.83	96	6825	13009	63469092
EGFR gene mutation	288.10	23.83	46	6875	251	63481850
Interstitial lung disease	253.53	23.83	127	6794	61781	63420320
Hepatic function abnormal	238.35	23.83	104	6817	37038	63445063
Disease progression	191.49	23.83	135	6786	122623	63359478
Malignant transformation	184.51	23.83	33	6888	384	63481717
Liver disorder	173.40	23.83	94	6827	53593	63428508

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Malignant neoplasm progression	482.14	24.00	240	4827	87806	34864058
Interstitial lung disease	289.97	24.00	155	4912	65127	34886737
Drug resistance	273.12	24.00	112	4955	25815	34926049
Acquired gene mutation	210.87	24.00	47	5020	1308	34950556
EGFR gene mutation	182.04	24.00	30	5037	147	34951717
Lung disorder	155.33	24.00	83	4984	34613	34917251
Metastases to central nervous system	123.53	24.00	46	5021	8159	34943705
Disease progression	103.62	24.00	101	4966	107976	34843888
Rash	92.93	24.00	136	4931	222616	34729248
Metastases to bone	78.07	24.00	37	5030	11933	34939931

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Malignant neoplasm progression	1253.70	22.18	521	10217	135469	79598181
Drug resistance	887.62	22.18	297	10441	41916	79691734
Acquired gene mutation	587.69	22.18	118	10620	2115	79731535
Interstitial lung disease	468.42	22.18	250	10488	112350	79621300
EGFR gene mutation	442.94	22.18	73	10665	391	79733259
Metastases to central nervous system	366.48	22.18	121	10617	16254	79717396
Hepatic function abnormal	285.87	22.18	156	10582	72951	79660699
Lung disorder	214.42	22.18	134	10604	80423	79653227
Malignant transformation	202.30	22.18	44	10694	1174	79732476
Liver disorder	201.68	22.18	124	10614	72293	79661357

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01EB01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS PROTEIN KINASE INHIBITORS Epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:74440	EGFR antagonoists
FDA EPC	N0000175605	Kinase Inhibitor
FDA MoA	N0000175076	Protein Kinase Inhibitors
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D047428	Protein Kinase Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Non-small cell lung cancer	indication	254637007	DOID:3908
Non-small cell lung cancer, positive for epidermal growth factor receptor expression	indication	426964009
Fibrosis of lung	contraindication	51615001	DOID:3770
Acute nephropathy	contraindication	58574008
Interstitial pneumonia	contraindication	64667001
Disease of liver	contraindication	235856003	DOID:409
Pregnancy, function	contraindication	289908002
Breastfeeding (mother)	contraindication	413712001
Non-small cell lung cancer, negative for epidermal growth factor receptor expression	contraindication	427038005

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.65	Basic
pKa2	5.8	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Epidermal growth factor receptor	Kinase	P00533	EGFR_HUMAN	INHIBITOR	Ki	9.40	CHEMBL	CHEMBL
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	5.96	CHEMBL
Tyrosine-protein kinase ABL1	Kinase	P00519	ABL1_HUMAN		Kd	6.64	CHEMBL
Mast/stem cell growth factor receptor Kit	Kinase	P10721	KIT_HUMAN		Kd	5.74	CHEMBL
Tyrosine-protein kinase Lck	Kinase	P06239	LCK_HUMAN		Kd	6.20	CHEMBL
Serine/threonine-protein kinase B-raf	Kinase	P15056	BRAF_HUMAN		IC50	5.70	CHEMBL
Receptor-type tyrosine-protein kinase FLT3	Kinase	P36888	FLT3_HUMAN		Kd	6	CHEMBL
Proto-oncogene tyrosine-protein kinase receptor Ret	Kinase	P07949	RET_HUMAN		IC50	5.77	CHEMBL
Vascular endothelial growth factor receptor 2	Kinase	P35968	VGFR2_HUMAN		IC50	5.72	CHEMBL
Receptor tyrosine-protein kinase erbB-2	Kinase	P04626	ERBB2_HUMAN		Kd	5.96	CHEMBL

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External reference:

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ID	Source
IRE	PDB_CHEM_ID
009981	NDDF
123631	PUBCHEM_CID
17257	MMSL
256478	MMSL
281883	RXNORM
398685009	SNOMEDCT_US
4021392	VUID
4021392	VANDF
407100002	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Gefitinib	HUMAN PRESCRIPTION DRUG LABEL	1	0480-4053	TABLET, FILM COATED	250 mg	ORAL	ANDA	26 sections
Gefitinib	HUMAN PRESCRIPTION DRUG LABEL	1	50742-366	TABLET, COATED	250 mg	ORAL	ANDA	26 sections
Gefitinib	HUMAN PRESCRIPTION DRUG LABEL	1	60505-4512	TABLET	250 mg	ORAL	ANDA	26 sections
Gefitinib	HUMAN PRESCRIPTION DRUG LABEL	1	67184-0531	TABLET, COATED	250 mg	ORAL	ANDA	26 sections
Gefitinib	Human Prescription Drug Label	1	69339-168	TABLET, FILM COATED	250 mg	ORAL	ANDA	25 sections
IRESSA	HUMAN PRESCRIPTION DRUG LABEL	1	0310-0482	TABLET, COATED	250 mg	ORAL	NDA	28 sections
IRESSA	HUMAN PRESCRIPTION DRUG LABEL	1	0310-0482	TABLET, COATED	250 mg	ORAL	NDA	28 sections
IRESSA	HUMAN PRESCRIPTION DRUG LABEL	1	0310-0482	TABLET, COATED	250 mg	ORAL	NDA	28 sections

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