Semaxanib
Star1
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Semaxanib
- DrugBank Accession Number
- DB06436
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 238.2845
Monoisotopic: 238.11061308 - Chemical Formula
- C15H14N2O
- Synonyms
- Semaxanib
- External IDs
- NSC-696819
- SU-5416
- SU005416
- SU5416
Pharmacology
- Indication
Investigated for use/treatment in colorectal cancer and lung cancer.
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UVascular endothelial growth factor receptor 2 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAlendronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Semaxanib is combined with Alendronic acid. Ambroxol The risk or severity of methemoglobinemia can be increased when Semaxanib is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Semaxanib is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Semaxanib is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Semaxanib is combined with Benzyl alcohol. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as indolines. These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Indolines
- Direct Parent
- Indolines
- Alternative Parents
- Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dihydroindole / Heteroaromatic compound / Hydrocarbon derivative / Lactam show 9 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 71IA9S35AJ
- CAS number
- 194413-58-6
- InChI Key
- WUWDLXZGHZSWQZ-WQLSENKSSA-N
- InChI
- InChI=1S/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8-
- IUPAC Name
- (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one
- SMILES
- CC1=CC(C)=C(N1)\C=C1/C(=O)NC2=CC=CC=C12
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5329098
- PubChem Substance
- 347827770
- ChemSpider
- 4486260
- BindingDB
- 4810
- ChEBI
- 91083
- ChEMBL
- CHEMBL276711
- ZINC
- ZINC000012410091
- PDBe Ligand
- X2M
- Wikipedia
- Semaxanib
- PDB Entries
- 2x2m
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Colorectal Cancer 1 3 Unknown Status Treatment Colorectal Cancer 1 2 Completed Treatment Carcinoma of Unknown Primary / Head And Neck Cancer / Non-Melanoma Skin Cancer 1 2 Completed Treatment Cervical Cancer 1 2 Completed Treatment Gastrointestinal Stromal Tumor (GIST) / Sarcomas 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.104 mg/mL ALOGPS logP 2.64 ALOGPS logP 2.98 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 11.29 Chemaxon pKa (Strongest Basic) -2.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 44.89 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 74.56 m3·mol-1 Chemaxon Polarizability 26.98 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9738 Caco-2 permeable + 0.5838 P-glycoprotein substrate Non-substrate 0.6258 P-glycoprotein inhibitor I Non-inhibitor 0.7324 P-glycoprotein inhibitor II Non-inhibitor 0.9313 Renal organic cation transporter Non-inhibitor 0.8624 CYP450 2C9 substrate Non-substrate 0.849 CYP450 2D6 substrate Non-substrate 0.8516 CYP450 3A4 substrate Substrate 0.5093 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Inhibitor 0.8993 CYP450 3A4 inhibitor Non-inhibitor 0.5121 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8183 Ames test Non AMES toxic 0.5485 Carcinogenicity Non-carcinogens 0.9303 Biodegradation Not ready biodegradable 0.9956 Rat acute toxicity 2.4908 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9818 hERG inhibition (predictor II) Non-inhibitor 0.8521
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03ka-0390000000-9123206ad8ad2312f2ae Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-646df664629687b9c9e2 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-ac85b30f645541f63ccc Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0190000000-b62763ec37227d5097f0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0390000000-4f07a465e92f8ef88f4f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0kte-0920000000-4fdf181f5ebf59997a30 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-6910000000-ebcc833da8be15769392 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 157.78136 predictedDeepCCS 1.0 (2019) [M+H]+ 160.13937 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.23251 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vascular endothelial growth factor-activated receptor activity
- Specific Function
- Tyrosine-protein kinase that acts as a cell-surface receptor for VEGFA, VEGFC and VEGFD. Plays an essential role in the regulation of angiogenesis, vascular development, vascular permeability, and ...
- Gene Name
- KDR
- Uniprot ID
- P35968
- Uniprot Name
- Vascular endothelial growth factor receptor 2
- Molecular Weight
- 151525.555 Da
References
- Fury MG, Zahalsky A, Wong R, Venkatraman E, Lis E, Hann L, Aliff T, Gerald W, Fleisher M, Pfister DG: A Phase II study of SU5416 in patients with advanced or recurrent head and neck cancers. Invest New Drugs. 2007 Apr;25(2):165-72. Epub 2006 Sep 16. [Article]
- Mita MM, Rowinsky EK, Forero L, Eckhart SG, Izbicka E, Weiss GR, Beeram M, Mita AC, de Bono JS, Tolcher AW, Hammond LA, Simmons P, Berg K, Takimoto C, Patnaik A: A phase II, pharmacokinetic, and biologic study of semaxanib and thalidomide in patients with metastatic melanoma. Cancer Chemother Pharmacol. 2007 Feb;59(2):165-74. Epub 2006 May 31. [Article]
- Hoff PM, Wolff RA, Bogaard K, Waldrum S, Abbruzzese JL: A Phase I study of escalating doses of the tyrosine kinase inhibitor semaxanib (SU5416) in combination with irinotecan in patients with advanced colorectal carcinoma. Jpn J Clin Oncol. 2006 Feb;36(2):100-3. Epub 2006 Jan 31. [Article]
Enzymes
1. DetailsProstaglandin G/H synthase 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Sakao S, Taraseviciene-Stewart L, Cool CD, Tada Y, Kasahara Y, Kurosu K, Tanabe N, Takiguchi Y, Tatsumi K, Kuriyama T, Voelkel NF: VEGF-R blockade causes endothelial cell apoptosis, expansion of surviving CD34+ precursor cells and transdifferentiation to smooth muscle-like and neuronal-like cells. FASEB J. 2007 Nov;21(13):3640-52. Epub 2007 Jun 13. [Article]
Drug created at March 19, 2008 16:33 / Updated at January 14, 2023 19:03