Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H27FN4O2.ClH |
Molecular Weight | 434.935 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C
InChI
InChIKey=WDCRLQNNJFZOIA-HBPAQXCTSA-N
InChI=1S/C22H27FN4O2.ClH/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28;/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28);1H/b17-12-;
Molecular Formula | C22H27FN4O2 |
Molecular Weight | 398.4738 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01268 | http://reference.medscape.com/drug/sutent-sunitinib-342201 | https://www.drugs.com/cdi/sunitinib.html | https://www.ncbi.nlm.nih.gov/pubmed/25272897 | https://www.ncbi.nlm.nih.gov/pubmed/28413468
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01268 | http://reference.medscape.com/drug/sutent-sunitinib-342201 | https://www.drugs.com/cdi/sunitinib.html | https://www.ncbi.nlm.nih.gov/pubmed/25272897 | https://www.ncbi.nlm.nih.gov/pubmed/28413468
Sunitinib (marketed as Sutent by Pfizer, and previously known as SU11248) is an oral, small-molecule, multi-targeted receptor tyrosine kinase inhibitor that was approved by the FDA for the treatment of renal cell carcinoma (RCC) and imatinib-resistant gastrointestinal stromal tumor. Sunitinib was evaluated for its inhibitory activity against a variety of kinases and was identified as an inhibitor of platelet-derived growth factor receptors (PDGFRa and PDGFRb), vascular endothelial growth factor receptors (VEGFR1, VEGFR2, and VEGFR3), stem cell factor receptor (KIT), Fms-like tyrosine kinase-3 (FLT3), colony-stimulating factor receptor Type 1 (CSF-1R), and the glial cell-line derived neurotrophic factor receptor (RET). Sunitinib adverse events are considered somewhat manageable and the incidence of serious adverse events low. The most common adverse events associated with sunitinib therapy are fatigue, diarrhea, nausea, anorexia, hypertension, yellow skin discoloration, hand-foot skin reaction, and stomatitis. In the placebo-controlled Phase III GIST study, adverse events which occurred more often with sunitinib than placebo included diarrhea, anorexia, skin discoloration, mucositis/stomatitis, asthenia, altered taste, and constipation. Dose reductions were required in 50% of the patients studied in RCC in order to manage the significant toxicities of this agent.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22037378 |
0.79 nM [Kd] | ||
Target ID: CHEMBL1913 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25882519 |
83.1 nM [IC50] | ||
Target ID: CHEMBL1868 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22765894 |
1.0 nM [IC50] | ||
Target ID: CHEMBL279 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23583911 |
18.0 nM [IC50] | ||
Target ID: CHEMBL1955 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22037378 |
50.0 nM [Kd] | ||
Target ID: CHEMBL1936 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22221201 |
8.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SUTENT Approved UseSUTENT is a kinase inhibitor indicated for the treatment of: Gastrointestinal stromal tumor (GIST) after disease progression on or intolerance to imatinib mesylate. (1.1) Advanced renal cell carcinoma (RCC). (1.2) Progressive, well-differentiated pancreatic neuroendocrine tumors (pNET) in patients with unresectable locally advanced or metastatic disease. (1.3) 1.1 Gastrointestinal Stromal Tumor (GIST) SUTENT is indicated for the treatment of gastrointestinal stromal tumor after disease progression on or intolerance to imatinib mesylate. 1.2 Advanced Renal Cell Carcinoma (RCC) SUTENT is indicated for the treatment of advanced renal cell carcinoma. 1.3 Advanced Pancreatic Neuroendocrine Tumors (pNET) SUTENT is indicated for the treatment of progressive, well-differentiated pancreatic neuroendocrine tumors in patients with unresectable locally advanced or metastatic disease. Launch Date1.13823357E12 |
|||
Primary | SUTENT Approved UseSUTENT is a kinase inhibitor indicated for the treatment of: Gastrointestinal stromal tumor (GIST) after disease progression on or intolerance to imatinib mesylate. (1.1) Advanced renal cell carcinoma (RCC). (1.2) Progressive, well-differentiated pancreatic neuroendocrine tumors (pNET) in patients with unresectable locally advanced or metastatic disease. (1.3) 1.1 Gastrointestinal Stromal Tumor (GIST) SUTENT is indicated for the treatment of gastrointestinal stromal tumor after disease progression on or intolerance to imatinib mesylate. 1.2 Advanced Renal Cell Carcinoma (RCC) SUTENT is indicated for the treatment of advanced renal cell carcinoma. 1.3 Advanced Pancreatic Neuroendocrine Tumors (pNET) SUTENT is indicated for the treatment of progressive, well-differentiated pancreatic neuroendocrine tumors in patients with unresectable locally advanced or metastatic disease. Launch Date1.13823357E12 |
|||
Primary | SUTENT Approved UseSUTENT is a kinase inhibitor indicated for the treatment of: Gastrointestinal stromal tumor (GIST) after disease progression on or intolerance to imatinib mesylate. (1.1) Advanced renal cell carcinoma (RCC). (1.2) Progressive, well-differentiated pancreatic neuroendocrine tumors (pNET) in patients with unresectable locally advanced or metastatic disease. (1.3) 1.1 Gastrointestinal Stromal Tumor (GIST) SUTENT is indicated for the treatment of gastrointestinal stromal tumor after disease progression on or intolerance to imatinib mesylate. 1.2 Advanced Renal Cell Carcinoma (RCC) SUTENT is indicated for the treatment of advanced renal cell carcinoma. 1.3 Advanced Pancreatic Neuroendocrine Tumors (pNET) SUTENT is indicated for the treatment of progressive, well-differentiated pancreatic neuroendocrine tumors in patients with unresectable locally advanced or metastatic disease. Launch Date1.13823357E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.35 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20049443 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
N-DESETHYL SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
51.1 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22743295 |
37.5 mg 1 times / day steady-state, oral dose: 37.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ERLOTINIB |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20049443 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
21.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22179104 |
15 mg/m² 1 times / day steady-state, oral dose: 15 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
559 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20049443 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
N-DESETHYL SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1056 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22743295 |
37.5 mg 1 times / day steady-state, oral dose: 37.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ERLOTINIB |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1369 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20049443 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
791 ng × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22179104 |
15 mg/m² 1 times / day steady-state, oral dose: 15 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
111 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20049443 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
N-DESETHYL SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
63.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20049443 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
22.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22179104 |
15 mg/m² 1 times / day steady-state, oral dose: 15 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered: |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20049443 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
N-DESETHYL SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20049443 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUNITINIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5% |
SUNITINIB plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, 52-77 years n = 5 Health Status: unhealthy Condition: Renal Cell Carcinoma Age Group: 52-77 years Sex: M+F Population Size: 5 Sources: |
Disc. AE: Thrombocytopenia, Fever... AEs leading to discontinuation/dose reduction: Thrombocytopenia (1 patient) Sources: Fever (1 patient) Fatigue (1 patient) Nausea (1 patient) Vomiting (1 patient) |
25 mg 1 times / day steady, oral Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, 74 years n = 1 Health Status: unhealthy Condition: Renal Cell Carcinoma Age Group: 74 years Sex: M Population Size: 1 Sources: |
Disc. AE: Fever... AEs leading to discontinuation/dose reduction: Fever (1 patient) Sources: |
350 mg 1 times / day steady, oral Highest studied dose Dose: 350 mg, 1 times / day Route: oral Route: steady Dose: 350 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
175 mg steady, oral Studied dose Dose: 175 mg Route: oral Route: steady Dose: 175 mg Sources: |
unhealthy Health Status: unhealthy Condition: advanced solid tumors Sources: |
|
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 202 Health Status: unhealthy Population Size: 202 Sources: |
Disc. AE: Anemia, Liver failure... AEs leading to discontinuation/dose reduction: Anemia (4 patients) Sources: Liver failure (2 patients) Metabolic disorder (3 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fatigue | 1 patient Disc. AE |
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, 52-77 years n = 5 Health Status: unhealthy Condition: Renal Cell Carcinoma Age Group: 52-77 years Sex: M+F Population Size: 5 Sources: |
Fever | 1 patient Disc. AE |
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, 52-77 years n = 5 Health Status: unhealthy Condition: Renal Cell Carcinoma Age Group: 52-77 years Sex: M+F Population Size: 5 Sources: |
Nausea | 1 patient Disc. AE |
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, 52-77 years n = 5 Health Status: unhealthy Condition: Renal Cell Carcinoma Age Group: 52-77 years Sex: M+F Population Size: 5 Sources: |
Thrombocytopenia | 1 patient Disc. AE |
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, 52-77 years n = 5 Health Status: unhealthy Condition: Renal Cell Carcinoma Age Group: 52-77 years Sex: M+F Population Size: 5 Sources: |
Vomiting | 1 patient Disc. AE |
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy, 52-77 years n = 5 Health Status: unhealthy Condition: Renal Cell Carcinoma Age Group: 52-77 years Sex: M+F Population Size: 5 Sources: |
Fever | 1 patient Disc. AE |
25 mg 1 times / day steady, oral Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy, 74 years n = 1 Health Status: unhealthy Condition: Renal Cell Carcinoma Age Group: 74 years Sex: M Population Size: 1 Sources: |
Liver failure | 2 patients Disc. AE |
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 202 Health Status: unhealthy Population Size: 202 Sources: |
Metabolic disorder | 3 patients Disc. AE |
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 202 Health Status: unhealthy Population Size: 202 Sources: |
Anemia | 4 patients Disc. AE |
50 mg 1 times / day steady, oral (starting) Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Sources: |
unhealthy n = 202 Health Status: unhealthy Population Size: 202 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
yes [IC50 39 uM] | ||||
yes [Ki 110 uM] | ||||
yes [Ki 140 uM] | ||||
yes [Ki 24 uM] | ||||
yes [Ki 28 uM] | ||||
yes [Ki 5.4 uM] | ||||
yes [Ki 54 uM] | ||||
yes [Ki >150 uM] | ||||
yes [Ki >150 uM] | ||||
yes [Ki >150 uM] | ||||
yes [Ki >150 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
minor | ||||
minor | ||||
minor | ||||
minor | ||||
moderate | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | yes (co-administration study) Comment: ketoconazole increased auc of sunitinib by 51% |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Sequential sorafenib and sunitinib for renal cell carcinoma. | 2009 Jul |
|
The cardiotoxicity and myocyte damage caused by small molecule anticancer tyrosine kinase inhibitors is correlated with lack of target specificity. | 2010 Apr 15 |
|
Can angiogenesis be a target of treatment for ribavirin associated hemolytic anemia? | 2010 May-Jun |
|
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry. | 2010 Nov 24 |
|
Autophagy plays an important role in sunitinib-mediated cell death in H9c2 cardiac muscle cells. | 2010 Oct 1 |
|
Potent activity of ponatinib (AP24534) in models of FLT3-driven acute myeloid leukemia and other hematologic malignancies. | 2011 Jun |
|
Sunitinib improves chemotherapeutic efficacy and ameliorates cisplatin-induced nephrotoxicity in experimental animals. | 2011 May |
|
Comprehensive analysis of kinase inhibitor selectivity. | 2011 Oct 30 |
|
Modulation of Akt/mTOR signaling overcomes sunitinib resistance in renal and prostate cancer cells. | 2012 Jul |
|
A novel chordoma xenograft allows in vivo drug testing and reveals the importance of NF-κB signaling in chordoma biology. | 2013 |
|
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery. | 2013 Apr 15 |
|
Sunitinib, a tyrosine kinase inhibitor, induces cytochrome P450 1A1 gene in human breast cancer MCF7 cells through ligand-independent aryl hydrocarbon receptor activation. | 2013 May |
|
Multi-parameter in vitro toxicity testing of crizotinib, sunitinib, erlotinib, and nilotinib in human cardiomyocytes. | 2013 Oct 1 |
|
A high-throughput screen for teratogens using human pluripotent stem cells. | 2014 Jan |
|
Chloroquine synergizes sunitinib cytotoxicity via modulating autophagic, apoptotic and angiogenic machineries. | 2014 Jun 25 |
|
Development of cardiac hypertrophy by sunitinib in vivo and in vitro rat cardiomyocytes is influenced by the aryl hydrocarbon receptor signaling pathway. | 2014 Mar |
|
Association of single nucleotide polymorphisms in IL8 and IL13 with sunitinib-induced toxicity in patients with metastatic renal cell carcinoma. | 2015 Dec |
|
Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs. | 2015 Jun |
|
Bridging Functional and Structural Cardiotoxicity Assays Using Human Embryonic Stem Cell-Derived Cardiomyocytes for a More Comprehensive Risk Assessment. | 2015 Nov |
|
Identification of a Mitochondrial DNA Polymerase Affecting Cardiotoxicity of Sunitinib Using a Genome-Wide Screening on S. pombe Deletion Library. | 2016 Jan |
|
Inflammatory and fibrotic processes are involved in the cardiotoxic effect of sunitinib: Protective role of L-carnitine. | 2016 Jan 22 |
Patents
Sample Use Guides
GIST: 50 mg orally once daily, with or without food, 4 weeks on treatment
followed by 2 weeks off.
pNET: 37.5 mg orally once daily, with or without food, continuously without a
scheduled off-treatment period
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28413468
Cell viability assays following suni¬tinib treatment were performed using a cell counting kit 8 (CCK 8; Dojindo Molecular Technologies, Inc., Kumamoto, Japan). PC 3 and LNCaP cells were seeded in 96 well plates (1x104 cells/well) with culture medium supplemented with 10% FBS and were incubated at 37˚C in incubator with an atmosphere of 5% CO2 for 12 h to allow adherence. Cells were treated with 10 μl culture medium containing 0, 5, 10 or 20 μmol/l of sunitinib for 24 h. A total of 10 μl CCK 8 was added to the cells, following sunitinib treatment, and the cells were incubated for a further 2 h at 37˚C. A microplate reader was used to measure the absorbance of each well at 450 nm
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 19:10:16 UTC 2023
by
admin
on
Sat Dec 16 19:10:16 UTC 2023
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Record UNII |
J48Z6FW33H
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Record Status |
Validated (UNII)
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Record Version |
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1327155-72-5
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300000020291
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86691060
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