Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H22Cl2FN5O |
Molecular Weight | 450.337 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H](OC1=CC(=CN=C1N)C2=CN(N=C2)C3CCNCC3)C4=C(Cl)C=CC(F)=C4Cl
InChI
InChIKey=KTEIFNKAUNYNJU-GFCCVEGCSA-N
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
DescriptionSources: http://www.fda.gov/Drugs/InformationOnDrugs/ApprovedDrugs/ucm376058.htm?source=govdelivery&utm_medium=email&utm_source=govdeliveryhttps://www.ncbi.nlm.nih.gov/pubmed/24695225Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202570s006lbl.pdf; https://www.mskcc.org/cancer-care/clinical-trials/14-063
Sources: http://www.fda.gov/Drugs/InformationOnDrugs/ApprovedDrugs/ucm376058.htm?source=govdelivery&utm_medium=email&utm_source=govdeliveryhttps://www.ncbi.nlm.nih.gov/pubmed/24695225
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202570s006lbl.pdf; https://www.mskcc.org/cancer-care/clinical-trials/14-063
(S)-crizotinib was discovered as an attractive chemical entity for further pre-clinical evaluation, and small-molecule inhibitors of MTH1 as a promising novel class of anticancer agents.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26628475
Curator's Comment: The CNS is frequently a site of disease progression, where up to 60% of patients develop metastases during treatment with crizotinib.The most likely reason for such isolated CNS failure is incomplete penetration of the blood-brain barrier by crizotinib.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=18089725
Curator's Comment: # Pfizer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4247 |
24.0 nM [IC50] | ||
Target ID: CHEMBL3717 |
11.0 nM [IC50] | ||
Target ID: P36639 Gene ID: 4521.0 Gene Symbol: NUDT1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24695225 |
72.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | XALKORI Approved UseIndicated for the treatment of patients with metastatic non-small cell lung cancer (NSCLC) whose tumors are anaplastic lymphoma kinase (ALK)-positive as detected by an FDA-approved test. Launch Date2011 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
475 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31778074 |
300 mg 2 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CRIZOTINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
99.6 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24990113 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CRIZOTINIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
328 ng/mL |
250 mg 2 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CRIZOTINIB unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
327 ng/mL |
250 mg 2 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CRIZOTINIB unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
87 ng/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CRIZOTINIB unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3240 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31778074 |
300 mg 2 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CRIZOTINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2321 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24990113 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CRIZOTINIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3054 ng × h/mL |
250 mg 2 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CRIZOTINIB unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3084 ng × h/mL |
250 mg 2 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CRIZOTINIB unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1817 ng × h/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CRIZOTINIB unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
29 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/24990113 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CRIZOTINIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
47.1 h |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CRIZOTINIB unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.3% |
CRIZOTINIB plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
300 mg 2 times / day steady, oral Dose: 300 mg, 2 times / day Route: oral Route: steady Dose: 300 mg, 2 times / day Sources: |
unhealthy, 49 years n = 6 Health Status: unhealthy Age Group: 49 years Sex: M+F Population Size: 6 Sources: |
Disc. AE: Fatigue... AEs leading to discontinuation/dose reduction: Fatigue (grade 3, 1 patient) Sources: |
250 mg 2 times / day steady, oral Recommended|MTD Dose: 250 mg, 2 times / day Route: oral Route: steady Dose: 250 mg, 2 times / day Sources: |
unhealthy, 51 years (range: 21-79 years) n = 119 Health Status: unhealthy Condition: Adenocarcinoma | Squamous Cell Carcinoma |Non-small Cell Lung Cancer Age Group: 51 years (range: 21-79 years) Sex: M+F Population Size: 119 Sources: |
Disc. AE: Autoimmune thyroiditis... AEs leading to discontinuation/dose reduction: Autoimmune thyroiditis (1 patient) Sources: |
250 mg 2 times / day steady, oral Recommended|MTD Dose: 250 mg, 2 times / day Route: oral Route: steady Dose: 250 mg, 2 times / day Sources: |
unhealthy, 52 years (range: 29-82 years) n = 136 Health Status: unhealthy Condition: Adenocarcinoma | Adenosquamous Carcinoma|Non-small Cell Lung Cancer Age Group: 52 years (range: 29-82 years) Sex: M+F Population Size: 136 Sources: |
Disc. AE: ALT increased, Pneumonitis... AEs leading to discontinuation/dose reduction: ALT increased (2.2%) Sources: Pneumonitis (1.5%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fatigue | grade 3, 1 patient Disc. AE |
300 mg 2 times / day steady, oral Dose: 300 mg, 2 times / day Route: oral Route: steady Dose: 300 mg, 2 times / day Sources: |
unhealthy, 49 years n = 6 Health Status: unhealthy Age Group: 49 years Sex: M+F Population Size: 6 Sources: |
Autoimmune thyroiditis | 1 patient Disc. AE |
250 mg 2 times / day steady, oral Recommended|MTD Dose: 250 mg, 2 times / day Route: oral Route: steady Dose: 250 mg, 2 times / day Sources: |
unhealthy, 51 years (range: 21-79 years) n = 119 Health Status: unhealthy Condition: Adenocarcinoma | Squamous Cell Carcinoma |Non-small Cell Lung Cancer Age Group: 51 years (range: 21-79 years) Sex: M+F Population Size: 119 Sources: |
Pneumonitis | 1.5% Disc. AE |
250 mg 2 times / day steady, oral Recommended|MTD Dose: 250 mg, 2 times / day Route: oral Route: steady Dose: 250 mg, 2 times / day Sources: |
unhealthy, 52 years (range: 29-82 years) n = 136 Health Status: unhealthy Condition: Adenocarcinoma | Adenosquamous Carcinoma|Non-small Cell Lung Cancer Age Group: 52 years (range: 29-82 years) Sex: M+F Population Size: 136 Sources: |
ALT increased | 2.2% Disc. AE |
250 mg 2 times / day steady, oral Recommended|MTD Dose: 250 mg, 2 times / day Route: oral Route: steady Dose: 250 mg, 2 times / day Sources: |
unhealthy, 52 years (range: 29-82 years) n = 136 Health Status: unhealthy Condition: Adenocarcinoma | Adenosquamous Carcinoma|Non-small Cell Lung Cancer Age Group: 52 years (range: 29-82 years) Sex: M+F Population Size: 136 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
weak [IC50 44 uM] | ||||
weak [IC50 48 uM] | ||||
weak [Inhibition 30 uM] | ||||
yes [IC50 0.83 uM] | ||||
yes [IC50 14.6 uM] | ||||
yes [IC50 22 uM] | ||||
yes [IC50 23 uM] | ||||
yes [IC50 5.79 uM] | ||||
yes [IC50 7.3 uM] | yes (co-administration study) Comment: crizotinib increased AUC of midazolam by 3.7x |
|||
yes [IC50 >30 uM] | ||||
yes [IC50 >30 uM] | ||||
yes [IC50 >30 uM] | ||||
yes [IC50 >30 uM] | ||||
yes | no (co-administration study) Comment: effect is masked by inhibition |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | yes (co-administration study) Comment: ketoconazole increased cmax of crizotinib by 44%, auc by 216% |
|||
major | yes (co-administration study) Comment: ketoconazole increased cmax of crizotinib by 44%, auc by 216% |
|||
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Crizotinib-resistant mutants of EML4-ALK identified through an accelerated mutagenesis screen. | 2011 Dec |
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ALK mutations conferring differential resistance to structurally diverse ALK inhibitors. | 2011 Dec 1 |
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MET amplification identifies a small and aggressive subgroup of esophagogastric adenocarcinoma with evidence of responsiveness to crizotinib. | 2011 Dec 20 |
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Genotype-driven therapies for non-small cell lung cancer: focus on EGFR, KRAS and ALK gene abnormalities. | 2011 May |
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Differential inhibitor sensitivity of anaplastic lymphoma kinase variants found in neuroblastoma. | 2011 Nov 9 |
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Effect of crizotinib on overall survival in patients with advanced non-small-cell lung cancer harbouring ALK gene rearrangement: a retrospective analysis. | 2011 Oct |
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Comprehensive analysis of kinase inhibitor selectivity. | 2011 Oct 30 |
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Personalized therapy of lung cancer. | 2012 |
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Aberrant expression of the transcriptional factor Twist1 promotes invasiveness in ALK-positive anaplastic large cell lymphoma. | 2012 Apr |
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Echinoderm microtubule-associated protein-like 4-anaplastic lymphoma kinase-targeted therapy for advanced non-small cell lung cancer: molecular and clinical aspects. | 2012 Aug |
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Adenocarcinoma of the lung with miliary brain and pulmonary metastases with echinoderm microtubule-associated protein like 4-anaplastic lymphoma kinase translocation treated with crizotinib: a case report. | 2012 Dec |
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Isolated central nervous system progression on Crizotinib: an Achilles heel of non-small cell lung cancer with EML4-ALK translocation? | 2012 Dec |
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Anaplastic Lymphoma Kinase (ALK) regulates initiation of transcription of MYCN in neuroblastoma cells. | 2012 Dec 13 |
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Mechanisms of acquired crizotinib resistance in ALK-rearranged lung Cancers. | 2012 Feb 8 |
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Rapid radiographic and clinical improvement after treatment of a MET-amplified recurrent glioblastoma with a mesenchymal-epithelial transition inhibitor. | 2012 Jan 20 |
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Antitumor action of the MET tyrosine kinase inhibitor crizotinib (PF-02341066) in gastric cancer positive for MET amplification. | 2012 Jul |
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Autocrine activation of the MET receptor tyrosine kinase in acute myeloid leukemia. | 2012 Jul |
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Preclinical rationale for use of the clinically available multitargeted tyrosine kinase inhibitor crizotinib in ROS1-translocated lung cancer. | 2012 Jul |
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Crizotinib (PF-02341066) reverses multidrug resistance in cancer cells by inhibiting the function of P-glycoprotein. | 2012 Jul |
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Paracrine receptor activation by microenvironment triggers bypass survival signals and ALK inhibitor resistance in EML4-ALK lung cancer cells. | 2012 Jul 1 |
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The ALK(F1174L) mutation potentiates the oncogenic activity of MYCN in neuroblastoma. | 2012 Jul 10 |
|
[Management of crizotinib, a new individualized treatment]. | 2012 Jul-Aug |
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Crizotinib in the treatment of non-small-cell lung cancer. | 2012 Jun |
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Development of treatment strategies for advanced neuroblastoma. | 2012 Jun |
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Remarkable tumor response to crizotinib in a 14-year-old girl with ALK-positive non-small-cell lung cancer. | 2012 Jun 1 |
|
A molecular dynamics investigation on the crizotinib resistance mechanism of C1156Y mutation in ALK. | 2012 Jun 29 |
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Pharmacokinetic/pharmacodynamic modeling of crizotinib for anaplastic lymphoma kinase inhibition and antitumor efficacy in human tumor xenograft mouse models. | 2012 Mar |
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Mechanisms of resistance to crizotinib in patients with ALK gene rearranged non-small cell lung cancer. | 2012 Mar 1 |
|
ROS1 rearrangements define a unique molecular class of lung cancers. | 2012 Mar 10 |
|
ALK inhibitor crizotinib combined with intrathecal methotrexate treatment for non-small cell lung cancer with leptomeningeal carcinomatosis. | 2012 May |
|
Targeted therapy for lung cancer. | 2012 Nov |
|
Rapid-onset hypogonadism secondary to crizotinib use in men with metastatic nonsmall cell lung cancer. | 2012 Nov 1 |
|
Antibody targeting of anaplastic lymphoma kinase induces cytotoxicity of human neuroblastoma. | 2012 Nov 15 |
|
Treatment of ALK-positive non-small cell lung cancer. | 2012 Oct |
|
Activity and safety of crizotinib in patients with ALK-positive non-small-cell lung cancer: updated results from a phase 1 study. | 2012 Oct |
|
[Cavitating nodules in a 40-year-old non-smoking woman: a very particular tumour]. | 2012 Sep |
|
Targeting ALK: a promising strategy for the treatment of non-small cell lung cancer, non-Hodgkin's lymphoma, and neuroblastoma. | 2012 Sep |
|
Identifying and targeting ROS1 gene fusions in non-small cell lung cancer. | 2012 Sep 1 |
|
Differential protein stability and ALK inhibitor sensitivity of EML4-ALK fusion variants. | 2012 Sep 1 |
|
Correlations between the percentage of tumor cells showing an anaplastic lymphoma kinase (ALK) gene rearrangement, ALK signal copy number, and response to crizotinib therapy in ALK fluorescence in situ hybridization-positive nonsmall cell lung cancer. | 2012 Sep 15 |
|
Enhancement of the antiproliferative activity of gemcitabine by modulation of c-Met pathway in pancreatic cancer. | 2013 |
|
Prediction of crizotinib-midazolam interaction using the Simcyp population-based simulator: comparison of CYP3A time-dependent inhibition between human liver microsomes versus hepatocytes. | 2013 Feb |
|
Overcoming erlotinib resistance with tailored treatment regimen in patient-derived xenografts from naïve Asian NSCLC patients. | 2013 Jan 15 |
|
Crizotinib for the treatment of non-small-cell lung cancer. | 2013 Jun 1 |
|
Cell culture and Drosophila model systems define three classes of anaplastic lymphoma kinase mutations in neuroblastoma. | 2013 Mar |
|
Targeted agents in the third-/fourth-line treatment of patients with advanced (stage III/IV) non-small cell lung cancer (NSCLC). | 2013 May |
|
Multi-parameter in vitro toxicity testing of crizotinib, sunitinib, erlotinib, and nilotinib in human cardiomyocytes. | 2013 Oct 1 |
|
Stereospecific targeting of MTH1 by (S)-crizotinib as an anticancer strategy. | 2014 Apr 10 |
|
Elucidating mechanisms of toxicity using phenotypic data from primary human cell systems--a chemical biology approach for thrombosis-related side effects. | 2015 Jan 5 |
Sample Use Guides
The recommended dose and schedule for crizotinib is 250 mg orally, twice daily, with or without food.
Route of Administration:
fVal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=18089725
PF-2341066 potently inhibited NPM-ALK phosphorylation in Karpas299 or SU-DHL-1 ALCL cells (mean IC50 value of 24 nmol/L). In biochemical and cellular screens, PF-2341066 was shown to be selective for c-Met and ALK at pharmacologically relevant concentrations across a panel of >120 diverse kinases. PF-2341066 potently inhibited cell proliferation, which was associated with G(1)-S-phase cell cycle arrest and induction of apoptosis in ALK-positive ALCL cells at IC50 values of approximately 30 nmol/L but not ALK-negative lymphoma cells.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QL01XE16
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FDA ORPHAN DRUG |
379812
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WHO-ATC |
L01XE16
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FDA ORPHAN DRUG |
834721
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FDA ORPHAN DRUG |
310610
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NDF-RT |
N0000175605
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FDA ORPHAN DRUG |
379712
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NCI_THESAURUS |
C141136
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LIVERTOX |
NBK548638
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NCI_THESAURUS |
C129825
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m3847
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PRIMARY | Merck Index | ||
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DB08865
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CHEMBL601719
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53AH36668S
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N0000182139
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PRIMARY | Cytochrome P450 2B6 Inhibitors [MoA] | ||
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4903
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877399-52-5
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WW-148
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N0000185503
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PRIMARY | P-Glycoprotein Inhibitors [MoA] | ||
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Crizotinib
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SUB32267
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N0000190114
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PRIMARY | Cytochrome P450 3A Inhibitors [MoA] | ||
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XALKORI
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PRIMARY | APPROVED MARCH 2012 | ||
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9301
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N0000191265
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PRIMARY | Organic Cation Transporter 1 Inhibitors [MoA] | ||
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N0000187061
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PRIMARY | Organic Cation Transporter 2 Inhibitors [MoA] | ||
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C74061
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C551994
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N0000020000
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PRIMARY | Receptor Tyrosine Kinase Inhibitors [MoA] | ||
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11626560
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DTXSID701009329
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1148495
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4187
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53AH36668S
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CRIZOTINIB
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ACTIVE MOIETY
METABOLITE LESS ACTIVE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)