NAV

Semaxanib

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
3D
Similar Structures
Weight
Average: 238.2845
Monoisotopic: 238.11061308
Chemical Formula
C15H14N2O
Synonyms
  • Semaxanib
External IDs
  • NSC-696819
  • SU-5416
  • SU005416
  • SU5416
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Pharmacology

Indication

Investigated for use/treatment in colorectal cancer and lung cancer.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UVascular endothelial growth factor receptor 2Not AvailableHumans
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
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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.
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Alendronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Semaxanib is combined with Alendronic acid.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Semaxanib is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Semaxanib is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Semaxanib is combined with Benzocaine.
Benzyl alcoholThe 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
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);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentColorectal Cancer1
3Unknown StatusTreatmentColorectal Cancer1
2CompletedTreatmentCarcinoma of Unknown Primary / Head And Neck Cancer / Non-Melanoma Skin Cancer1
2CompletedTreatmentCervical Cancer1
2CompletedTreatmentGastrointestinal Stromal Tumor (GIST) / Sarcomas1

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
PropertyValueSource
Water Solubility0.104 mg/mLALOGPS
logP2.64ALOGPS
logP2.98Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.29Chemaxon
pKa (Strongest Basic)-2.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area44.89 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity74.56 m3·mol-1Chemaxon
Polarizability26.98 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9738
Caco-2 permeable+0.5838
P-glycoprotein substrateNon-substrate0.6258
P-glycoprotein inhibitor INon-inhibitor0.7324
P-glycoprotein inhibitor IINon-inhibitor0.9313
Renal organic cation transporterNon-inhibitor0.8624
CYP450 2C9 substrateNon-substrate0.849
CYP450 2D6 substrateNon-substrate0.8516
CYP450 3A4 substrateSubstrate0.5093
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorNon-inhibitor0.5121
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8183
Ames testNon AMES toxic0.5485
CarcinogenicityNon-carcinogens0.9303
BiodegradationNot ready biodegradable0.9956
Rat acute toxicity2.4908 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9818
hERG inhibition (predictor II)Non-inhibitor0.8521
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03ka-0390000000-9123206ad8ad2312f2ae
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-646df664629687b9c9e2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-ac85b30f645541f63ccc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0190000000-b62763ec37227d5097f0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0390000000-4f07a465e92f8ef88f4f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kte-0920000000-4fdf181f5ebf59997a30
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6910000000-ebcc833da8be15769392
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.78136
predicted
DeepCCS 1.0 (2019)
[M+H]+160.13937
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.23251
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Vascular endothelial growth factor receptor 2
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
  1. 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]
  2. 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]
  3. 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

Details1. Prostaglandin 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
  1. 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