Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H15ClN4 |
| Molecular Weight | 346.813 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC=C(NC2=NN=C(CC3=CC=NC=C3)C4=C2C=CC=C4)C=C1
InChI
InChIKey=YCOYDOIWSSHVCK-UHFFFAOYSA-N
InChI=1S/C20H15ClN4/c21-15-5-7-16(8-6-15)23-20-18-4-2-1-3-17(18)19(24-25-20)13-14-9-11-22-12-10-14/h1-12H,13H2,(H,23,25)
| Molecular Formula | C20H15ClN4 |
| Molecular Weight | 346.813 |
| 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:
http://www.drugbank.ca/drugs/DB04879
https://en.wikipedia.org/wiki/Vatalanib
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB04879
https://en.wikipedia.org/wiki/Vatalanib
Vatalanib a potent oral tyrosine kinase inhibitor with a selective range of molecular targets, has been extensively investigated and has shown promising results in patients with solid tumors in early trials. Vatalanib selectively inhibits the tyrosine kinase domains of vascular endothelial growth factor (VEGF) receptor tyrosine kinases (important enzymes in the formation of new blood vessels that contribute to tumor growth and metastasis), platelet-derived growth factor (PDGF) receptor, and c-KIT. The adverse effects of vatalanib appear similar to those of other VEGF inhibitors. In the CONFIRM trials, the most common side effects were high blood pressure, gastrointestinal upset (diarrhea, nausea, and vomiting), fatigue, and dizziness.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 77.0 nM [IC50] | |||
| 37.0 nM [IC50] | |||
Target ID: CHEMBL1955 |
660.0 nM [IC50] | ||
Target ID: CHEMBL1936 |
730.0 nM [IC50] | ||
Target ID: CHEMBL1913 |
580.0 nM [IC50] | ||
Target ID: CHEMBL1844 |
1.4 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Doses
| Dose | Population | Adverse events |
|---|---|---|
750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
Other AEs: elevated transaminases, hypertension... Other AEs: elevated transaminases (3.2%) Sources: hypertension (6.5%) hyperbilirubinemia (3.2%) Anorexia (3.2%) eructation (3.2%) Proteinuria (3.2%) Asthenia (6.5%) rash (3.2%) thrombocytopenia (3.2%) nausea (6.5%) Fatigue (6.5%) lethargy (3.2%) dizziness (3.2%) emesis (9.7%) |
1000 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: |
unhealthy, ADULT n = 18 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 18 Sources: |
DLT: Lethargy, hypertension... Dose limiting toxicities: Lethargy (1 pt) Sources: hypertension (1 pt) |
1000 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: myelodysplastic syndrome Sex: M+F Food Status: UNKNOWN Population Size: 35 Sources: |
DLT: Nausea, emesis... Dose limiting toxicities: Nausea (3 patients) Sources: emesis (2 patients) Anorexia (1 pt) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Anorexia | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| Proteinuria | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| dizziness | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| elevated transaminases | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| eructation | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| hyperbilirubinemia | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| lethargy | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| rash | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| thrombocytopenia | 3.2% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| Asthenia | 6.5% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| Fatigue | 6.5% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| hypertension | 6.5% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| nausea | 6.5% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| emesis | 9.7% | 750 mg 2 times / day multiple, oral (unknown) MTD Dose: 750 mg, 2 times / day Route: oral Route: multiple Dose: 750 mg, 2 times / day Sources: |
unhealthy, ADULT n = 31 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 31 Sources: |
| Lethargy | 1 pt DLT |
1000 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: |
unhealthy, ADULT n = 18 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 18 Sources: |
| hypertension | 1 pt DLT |
1000 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: |
unhealthy, ADULT n = 18 Health Status: unhealthy Condition: myeloid leukemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 18 Sources: |
| Anorexia | 1 pt DLT |
1000 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: myelodysplastic syndrome Sex: M+F Food Status: UNKNOWN Population Size: 35 Sources: |
| emesis | 2 patients DLT |
1000 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: myelodysplastic syndrome Sex: M+F Food Status: UNKNOWN Population Size: 35 Sources: |
| Nausea | 3 patients DLT |
1000 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: |
unhealthy n = 35 Health Status: unhealthy Condition: myelodysplastic syndrome Sex: M+F Food Status: UNKNOWN Population Size: 35 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| MRI monitoring of tumor response to a novel VEGF tyrosine kinase inhibitor in an experimental breast cancer model. | 2002 Aug |
|
| Anthranilic acid amides: a novel class of antiangiogenic VEGF receptor kinase inhibitors. | 2002 Dec 19 |
|
| Inhibitors of the vascular endothelial growth factor receptor. | 2002 Oct |
|
| The vascular endothelial growth factor receptor tyrosine kinase inhibitor PTK787/ZK222584 inhibits growth and migration of multiple myeloma cells in the bone marrow microenvironment. | 2002 Sep 1 |
|
| PTK/ZK (Novartis). | 2003 Aug |
|
| p190RhoGAP can act to inhibit PDGF-induced gliomas in mice: a putative tumor suppressor encoded on human chromosome 19q13.3. | 2003 Feb 15 |
|
| Novel therapies for multiple myeloma. | 2003 Jan |
|
| Hepatocyte growth factor/scatter factor can induce angiogenesis independently of vascular endothelial growth factor. | 2003 Jan 1 |
|
| Identification of a new chemical class of potent angiogenesis inhibitors based on conformational considerations and database searching. | 2003 Sep 15 |
|
| PTK787/ZK222584, an inhibitor of vascular endothelial growth factor receptor tyrosine kinases, decreases glioma growth and vascularization. | 2004 Aug |
|
| Degradation of PKB/Akt protein by inhibition of the VEGF receptor/mTOR pathway in endothelial cells. | 2004 Jun 3 |
|
| Dissecting tumor maintenance requirements using bioluminescence imaging of cell proliferation in a mouse glioma model. | 2004 Nov |
|
| Future directions with angiogenesis inhibitors in colorectal cancer. | 2004 Oct |
|
| [Problems in the current target therapy of malignancies]. | 2005 |
|
| PTK787/ZK222584, a tyrosine kinase inhibitor of vascular endothelial growth factor receptor, reduces uptake of the contrast agent GdDOTA by murine orthotopic B16/BL6 melanoma tumours and inhibits their growth in vivo. | 2005 Aug |
|
| Perspectives in colorectal cancer - Sixth Annual Conference. Metastatic colorectal cancer. | 2005 Dec |
|
| Targeting vascular endothelial growth factor and angiogenesis for the treatment of colorectal cancer. | 2005 Feb |
|
| Combined vascular endothelial growth factor and platelet-derived growth factor inhibition in rat cardiac allografts: beneficial effects on inflammation and smooth muscle cell proliferation. | 2005 Jan 27 |
|
| Phase I clinical and pharmacokinetic study of PTK/ZK, a multiple VEGF receptor inhibitor, in patients with liver metastases from solid tumours. | 2005 Jun |
|
| The realisation of targeted antitumour therapy. | 2005 Jun |
|
| Phase I study of the safety, tolerability, pharmacokinetics, and pharmacodynamics of PTK787/ZK 222584 administered twice daily in patients with advanced cancer. | 2005 Jun 20 |
|
| Phacilitate Cell and Gene Therapy Forum 2005. Cell and gene therapy: a corporate perspective. 24-26 January 2005, Washington, DC, USA. | 2005 Mar |
|
| Arterial spin labeling blood flow magnetic resonance imaging for the characterization of metastatic renal cell carcinoma(1). | 2005 Mar |
|
| Impact of adjuvant inhibition of vascular endothelial growth factor receptor tyrosine kinases on tumor growth delay and local tumor control after fractionated irradiation in human squamous cell carcinomas in nude mice. | 2005 Mar 1 |
|
| Vatalanib (PTK787/ZK 222584) in combination with FOLFOX4 versus FOLFOX4 alone as first-line treatment for colorectal cancer: preliminary results from the CONFIRM-1 trial. | 2005 May |
|
| Angiogenesis and lung cancer: prognostic and therapeutic implications. | 2005 May 10 |
|
| The assessment of antiangiogenic and antivascular therapies in early-stage clinical trials using magnetic resonance imaging: issues and recommendations. | 2005 May 9 |
|
| Update on angiogenesis inhibitors. | 2005 Nov |
|
| Anticancer Drug Discovery and Development - SRI's Seventh Annual Summit. | 2005 Oct |
|
| Targeting multiple signal transduction pathways in lung cancer. | 2005 Sep |
|
| Clinical implications of angiogenesis in cancers. | 2006 |
|
| [Some new findings in the pathogenesis of myeloproliferative disorders and new insight into more effective treatment]. | 2006 |
|
| [Molecular targets in colon cancer]. | 2006 Apr |
|
| Treatment of metastatic colorectal cancer: from cytotoxic agents to molecular agents and multitargeted strategies. | 2006 Dec |
|
| 4-(Azolylphenyl)-phthalazin-1-amines: Novel inhibitors of VEGF receptors I and II. | 2006 Dec |
|
| Lessons from phase III clinical trials on anti-VEGF therapy for cancer. | 2006 Jan |
|
| Antagonism of sphingosine-1-phosphate receptors by FTY720 inhibits angiogenesis and tumor vascularization. | 2006 Jan 1 |
|
| Biological agents versus chemotherapy in the treatment of colorectal cancer. | 2006 Jul |
|
| Phase 1 study of PTK787/ZK 222584, a small molecule tyrosine kinase receptor inhibitor, for the treatment of acute myeloid leukemia and myelodysplastic syndrome. | 2006 Jun |
|
| Biomarkers for assessment of pharmacologic activity for a vascular endothelial growth factor (VEGF) receptor inhibitor, PTK787/ZK 222584 (PTK/ZK): translation of biological activity in a mouse melanoma metastasis model to phase I studies in patients with advanced colorectal cancer with liver metastases. | 2006 Jun |
|
| Hetaryl imidazoles: a novel dual inhibitors of VEGF receptors I and II. | 2006 Mar 1 |
|
| Growth inhibition of orthotopic anaplastic thyroid carcinoma xenografts in nude mice by PTK787/ZK222584 and CPT-11. | 2006 May |
|
| A simple, reproducible method for monitoring the treatment of tumours using dynamic contrast-enhanced MR imaging. | 2006 May 22 |
|
| 1-(Azolyl)-4-(aryl)-phthalazines: novel potent inhibitors of VEGF receptors I and II. | 2006 Nov |
|
| Rational design of RGD-albumin conjugates for targeted delivery of the VEGF-R kinase inhibitor PTK787 to angiogenic endothelium. | 2006 Nov |
|
| Correlation of relative permeability and relative cerebral blood volume in high-grade cerebral neoplasms. | 2006 Oct |
|
| Targeted therapy of breast cancer. | 2007 |
|
| A phase IB, open-label dose-escalating study of the oral angiogenesis inhibitor PTK787/ZK 222584 (PTK/ZK), in combination with FOLFOX4 chemotherapy in patients with advanced colorectal cancer. | 2007 Apr |
|
| Small molecule tyrosine kinase inhibitors in the treatment of solid tumors: an update of recent developments. | 2007 Feb |
|
| Vatalanib: the clinical development of a tyrosine kinase inhibitor of angiogenesis in solid tumours. | 2007 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Vatalanib 1,250 mg orally daily in combination with FOLFOX-4.
https://www.ncbi.nlm.nih.gov/pubmed/21464406
Vatalanib 1250 mg orally was given once daily (cohort 1) or 750-1250 mg once daily in an intra-patient dose escalating schedule (cohort 2) in 28-day cycles.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:10:10 GMT 2023
by
admin
on
Fri Dec 15 16:10:10 GMT 2023
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| Record UNII |
5DX9U76296
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C1967
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NCI_THESAURUS |
C1742
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151194
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5DX9U76296
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DB04879
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212141-54-3
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DTXSID2046919
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m11400
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C404768
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100000091584
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C1868
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CHEMBL101253
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SUB26999
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7994
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Vatalanib
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90620
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QQ-50
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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