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Crizotinib

HCID 11626560
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
877399-52-5
Standard SMILES
C[C@@H](Oc1cc(-c2cnn(C3CCNCC3)c2)cnc1N)c1c(Cl)ccc(F)c1Cl
InChIKey
KTEIFNKAUNYNJU-GFCCVEGCSA-N
Molecular formula
C21H22Cl2FN5O
Average molar mass
450.3 g/mol
Monoisotopic mass
449.1185439

Overview

Crizotinib is a 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine that has R configuration at the chiral centre. The active enantiomer, it acts as a kinase inhibitor and is used for the treatment of patients with locally advanced or metastatic non-small cell lung cancer (NSCLC). It has a role as an antineoplastic agent, a biomarker and an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor. It is an enantiomer of an ent-crizotinib.

Names & identifiers

Preferred name
Crizotinib
IUPAC
3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine
English name
Crizotinib
Molecular formula
C21H22Cl2FN5O
Molecular weight
450.34

Names & synonyms

Crizotinib877399-52-5PF-02341066(R)-crizotinibPF-2341066XalkoriPF 2341066(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-aminePF 02341066crizotinibumCHEBI:64310PF2341066
Show more names
Crizotini3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine3-[(1R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-2-aMinopyridineCS-164CrozotinibCrizotanib
3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]pyridin-2-amine53AH36668SNSC-756645PF02341066DTXSID7010093292-Pyridinamine, 3-((1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(4-piperidinyl)-1H-pyrazol-4-yl)-2-PYRIDINAMINE, 3-[(1R)-1-(2,6-DICHLORO-3-FLUOROPHENYL)ETHOXY]-5-[1-(4-PIPERIDINYL)-1H-PYRAZOL-4-YL]-3-((1R)-1-(2,6-DICHLORO-3-FLUOROPHENYL)ETHOXY)-5-(1-(PIPERIDIN-4-YL)-1H-PYRAZOL-4-YL)PYRIDIN-2-AMINE

Database identifiers

CAS

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
78 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
30
Formal charge
0
Complexity
557

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agents

Pharmaceuticals -> Listed in ZINC15

SolubilityInsoluble
Human Drugs · 4 items

Breast Feeding; Lactation; Antineoplastic Agents; Enzyme Inhibitors; Protein Kinase Inhibitors; Signal Transduction Inhibitors; Tyrosine Kinase Inhibitors;

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Dissociation Constants9.4 and 5.6

Physicochemical properties

Melting point
192 °C · 192 °C
Boiling point
599.2 · 599.2±50.0 °C(Predicted)
Density
1.47 · 1.47±0.1 g/cm3(Predicted)
storage temp.
room temp

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P305+P354+P338, P317, P318, P321, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 75 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Sens. 1 (100%)

Toxicology

Hepatotoxicity · 1 item

In large early clinical trials, elevations in serum aminotransferase levels occurred in up to 57% of patients treated with standard doses of crizotinib, were greater than 5 times ULN in 6% of patients, and led to early discontinuation of therapy in 2% to 4% of patients. Serum aminotransferase elevations typically arose after 4 to 12 weeks of treatment, but usually without jaundice or alkaline phosphatase elevations. Restarting crizotinib after resolution of the aminotransferase abnormalities can be done starting with a reduced dose. Most cases of liver injury due to crizotinib have been minimally or not symptomatic, and the injury resolved within 1 to 2 months of stopping the drug (Case 1). However, cases with jaundice and symptoms during crizotinib therapy have been reported which were fatal in 0.1% of treated patients (Case 2). The severe cases of liver injury due to crizotinib typically arose within 2 to 6 weeks of starting therapy and presented with marked elevations in serum aminotransferase levels followed by jaundice, progressive hepatic dysfunction, coagulopathy, encephalopathy and death. For these reasons, routine periodic monitoring of liver tests at 2 to 4 week intervals during therapy is recommended.

Chemistry & industry

Pharmacology

ATC Code · 3 items

L01XE16

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein BindingCrizotinib is 91% bound to plasma protein. _In vitro_ studies suggest that this is not affected by drug concentration.
Pharmacodynamics · 1 item

In a phase I study, 37 patients with a variety of solid-tumor cancers refractory to therapy received 50 to 300 mg of crizotinib daily or twice daily. In this group, two patients with non-small cell lung cancer (NSCLC) exhibiting echinoderm microtubule-associated protein-like 4 (EML4)-anaplastic lymphoma kinase (ALK) mutations responded to therapy; therefore, following studies focused on patients with advanced ALK-positive disease. In this group of patients, the 6-month progression-free survival among crizotinib users was approximately 72%. When compared to ALK mutation-positive patients that did not receive crizotinib, ALK mutation-positive patients treated with crizotinib had a higher two-year overall survival rate (54% vs 36%). The use of crizotinib may lead to hepatotoxicity, interstitial lung disease (ILD), pneumonitis, QT interval prolongation, bradycardia, severe visual loss, ​​embryo-fetal toxicity and gastrointestinal toxicity in pediatric and young adult patients with anaplastic large cell lymphoma (ALCL) or pediatric patients with inflammatory myofibroblastic tumor (IMT).

Mechanism of Action · 1 item

Crizotinib is a tyrosine kinase receptor inhibitor that targets anaplastic lymphoma kinase (ALK), hepatocyte growth factor receptor (HGFR, c-MET), ROS1 (c-ros), and Recepteur d'Origine Nantais (RON). When activated, ALK inhibits apoptosis and promotes cell proliferation, and ALK-gene translocations can lead to the expression of oncogenic fusion proteins. A small portion of non-small cell lung cancer (NSCLC) patients have ALK-positive tumors. Most of these cases are characterized by the fusion of ALK with the chimeric protein echinoderm microtubule-associated protein-like 4 (EML4), resulting in increased kinase activity. Crizotinib inhibits ALK by inhibiting its phosphorylation and creating an inactive protein conformation. This ultimately lowers the proliferation of cells carrying this genetic mutation and tumour survivability. _In vitro_ assays on tumor cell lines demonstrated that crizotinib inhibits ALK, ROS1, and c-Met phosphorylation in a concentration-dependent manner. _In vivo_ studies in mice with tumor xenografts that expressed EML4- or nucleophosmin (NPM)-ALK fusion proteins or c-Met showed that crizotinib has antitumor activity.

Related reactions

4 records
New reaction record
HRID 1169707 reaction equation
HRID 1169707As productuspto-grants-2010_11
HRID 1512085 reaction equation
HRID 1512085As productuspto-grants-2012_07
HRID 1627584 reaction equation
HRID 1627584As productuspto-grants-2014_07
HRID 2266717 reaction equation
HRID 2266717As productuspto-grants-2010_12

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
877399-52-5
PubChem CID
11626560
DTXSID
DTXSID701009329
ChEMBL
CHEMBL601719
ChEBI
CHEBI:64310
UNII
53AH36668S
EC Number
638-814-9
Nikkaji
J2.735.431I
solubility
Soluble in DMSO (up to 25 mg/ml with warming) or in Ethanol (up to 25 mg/ml with warming)
form
powder
pka
9.81 · 9.81±0.10(Predicted)
color
white to tan
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
InChI
1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1
InChIKey
KTEIFNKAUNYNJU-GFCCVEGCSA-N
SMILES
C1(N)=NC=C(C2=CN(C3CCNCC3)N=C2)C=C1O[C@@H](C1=C(Cl)C=CC(F)=C1Cl)C
CAS DataBase Reference
877399 · 877399-52-5
FDA UNII
53 AH36668S · 53AH36668S
NCI Dictionary of Cancer Terms
crizotinib; Xalkori
NCI Drug Dictionary
crizotinib
ATC code
1 ED01 · L01ED01
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Protein binding
91 % · 91%
Excreted unchanged in urine
2.3 % · 2.3%
Volume of distribution
1772 Litres · 1772 Litres
Biological half-life
42 · 42 / -
Symbol(GHS)
7 · GHS07,GHS08,GHS09
Signal word
Warning
Hazard statements
317 · H317-H319-H341-H400
Precautionary statements
201 · P201-P273-P280-P302+P352-P305+P351+P338-P308+P313
Safety Statements
24 · 24/25
RIDADR
3077 · UN 3077 9 / PGIII
WGK Germany
3 · 3
HazardClass
IRRITANT
HS Code
29333990 · 29333990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
1 Eye · Aquatic Acute 1Eye Irrit. 2Muta. 2Skin Sens. 1
Limited Quantities
5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Crizotinib

vMost-DILI-concern

8

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
3
ridadr
UN 3077 9 / PGIII
hs_code
29333990
Signal word
Warning
Symbol(GHS)
GHS07,GHS08,GHS09
safety_code
24/25
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids
Hazard statements
H317-H319-H341-H400
Limited Quantities
5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications
Aquatic Acute 1Eye Irrit. 2Muta. 2Skin Sens. 1
Precautionary statements
P201-P273-P280-P302+P352-P305+P351+P338-P308+P313
Biological Half-LifeFollowing single doses of crizotinib, the plasma terminal half-life was 42 hours.
Metabolism/Metabolites · 1 item

Crizotinib is mainly metabolized in the liver by CYP3A4 and CYP3A5, and undergoes an O-dealkylation, with subsequent phase 2 conjugation. Non-metabolic elimination, such as biliary excretion, can not be excluded. PF-06260182 (with two constituent diastereomers, PF-06270079 and PF-06270080) is the only active metabolite of crizotinib that has been identified. _In vitro_ studies suggest that, compared to crizotinib, PF-06270079 and PF-06270080 are approximately 3- to 8-fold less potent against anaplastic lymphoma kinase (ALK) and 2.5- to 4-fold less potent against Hepatocyte Growth Factor Receptor (HGFR, c-Met).

FDA Pharmacological Classification · 6 items

53AH36668S

CRIZOTINIB

Established Pharmacologic Class [EPC] - Kinase Inhibitor

Mechanisms of Action [MoA] - Cytochrome P450 3A Inhibitors

Mechanisms of Action [MoA] - Receptor Tyrosine Kinase Inhibitors

Mechanisms of Action [MoA] - Cytochrome P450 2B6 Inhibitors

MeSH Pharmacological Classification · 2 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Protein kinase inhibitors that inhibit TYROSINE PROTEIN KINASES.

Absorption, Distribution and Excretion · 4 items

In patients with pancreatic, colorectal, sarcoma, anaplastic large-cell lymphoma and non-small cell lung cancer (NSCLC) treated with crizotinib doses ranging from 100 mg once a day to 300 mg twice a day, the mean AUC and Cmax increased in a dose-proportional manner. A single crizotinib dose of crizotinib is absorbed with a median tmax 4 to 6 hours. In patients receiving multiple doses of crizotinib 250 mg twice daily (n=167), the mean AUC was is 2321.00 ng⋅hr/mL, the mean Cmax was 99.60 ng/mL, and the median tmax was 5.0 hours. The mean absolute bioavailability of crizotinib is 43%, ranging from 32% to 66%. High-fat meals reduce the AUC0-INF and Cmax of crizotinib by approximately 14%. Age, sex at birth, and ethnicity (Asian vs non-Asian patients) did not have a clinically significant effect on crizotinib pharmacokinetics. In patients less than 18 years old, higher body weight was associated with a lower crizotinib exposure.

After administering a single 250 mg radiolabeled crizotinib dose to healthy subjects, 63% and 22% of the administered dose were recovered in feces and urine. Unchanged crizotinib represented approximately 53% and 2.3% of the administered dose in feces and urine, respectively.

Following a single intravenous dose, the mean volume of distribution (Vss) of crizotinib was 1772 L.

At steady-state (250 mg twice daily), crizotinib has a mean apparent clearance (CL/F) of 60 L/hr. This value is lower than the one detected after a single 250 mg oral dose (100 L/hr),, possibly due to CYP3A auto-inhibition.

Applications · 3 items

DescriptionCrizotinib is an oral ALK/ROS1/MET/RON inhibitor approved by the U.S. Food and Drug Administration. Crizotinib is not only used for the treatment of ALK- or ROS1-positive metastatic non-small cell lung cancer (NSCLC), but also for the treatment of adult and paediatric patients 1 year of age and older with unresectable, relapsed or refractory inflammatory anaplastic lymphoma kinase (ALK)-positive interstitial myofibroblastic tumours (IMT). In addition, crizotinib has preclinical efficacy in the Philadelphia-chromosome negative myeloproliferative neoplasms (MPNs) patient cells, JAK2 mutant cell lines, and JAK2 mutant mouse models. Crizotinib is recommended for the treatment of patients with MPN, particularly in the setting of JAK inhibitor resistance[1].

UsesCrizotinib is a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK). Crizotinib is a potential antitumor agent. In August 2011, the United States FDA approved crizotinib for the treatment of anaplastic lymphoma kinase (ALK) rearranged non-small-cell lung cancer (NSCLC).

General DescriptionClass: receptor tyrosine kinase; Treatment: NSCLC; Oral bioavailability = 43%; Elimination half-life = 42 h; Protein binding = 90%

Upstream & downstream products

Upstream raw materials

2,6-Dichloro-3-fluoroacetophenoneDiisopropyl azodicarboxylateTriphenylphosphine3-Hydroxy-2-nitropyridine

Suppliers122 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
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艾吉析科技(上海)有限公司17717235263 · [email protected]
Aladdin Scientific[email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海波以尔化工有限公司[email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
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China Kouting Group Limited+86 (21) 5811-6473 5811-6475 · [email protected]
安徽联创生物医药股份有限公司0551-68779238 18056025720 · [email protected]
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VDM Biochemicals0330-2528181 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
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武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
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Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
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广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
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ApexBio Technology LLC+1-832-696-8203 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Crizotinib is a 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine that has R configuration at the chiral centre. The active enantiomer, it acts as a kinase inhibitor and is used for the treatment of patients with locally advanced or metastatic non-small cell lung cancer (NSCLC) It has a role as an antineoplastic agent, a biomarker and an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor. It is an enantiomer of an ent-crizotinib.