Squalamine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Squalamine
Accession Number
DB06461
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • MSI-1246
International/Other Brands
Evizon
Categories
UNII
F8PO54Z4V7
CAS number
148717-90-2
Weight
Average: 627.97
Monoisotopic: 627.464493379
Chemical Formula
C34H65N3O5S
InChI Key
UIRKNQLZZXALBI-MSVGPLKSSA-N
InChI
InChI=1S/C34H65N3O5S/c1-23(2)31(42-43(39,40)41)12-9-24(3)27-10-11-28-32-29(14-16-34(27,28)5)33(4)15-13-26(21-25(33)22-30(32)38)37-20-8-19-36-18-7-6-17-35/h23-32,36-38H,6-22,35H2,1-5H3,(H,39,40,41)/t24-,25-,26+,27-,28+,29+,30-,31-,32+,33+,34-/m1/s1
IUPAC Name
{[(3R,6R)-6-[(1S,2S,5S,7R,9R,10R,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptan-3-yl]oxy}sulfonic acid
SMILES
CC(C)[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)NCCCNCCCCN)OS(O)(=O)=O

Pharmacology

Indication

Investigated for use/treatment in ovarian cancer, lung cancer, and macular degeneration.

Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Squalamine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Squalamine is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Squalamine is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Squalamine is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Squalamine.
Alendronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Squalamine is combined with Alendronic acid.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Squalamine.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Squalamine.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Squalamine.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Squalamine.
Food Interactions
Not Available

References

General References
  1. Williams JI, Weitman S, Gonzalez CM, Jundt CH, Marty J, Stringer SD, Holroyd KJ, Mclane MP, Chen Q, Zasloff M, Von Hoff DD: Squalamine treatment of human tumors in nu/nu mice enhances platinum-based chemotherapies. Clin Cancer Res. 2001 Mar;7(3):724-33. [PubMed:11297269]
External Links
KEGG Compound
C16841
ChemSpider
65407
ChEBI
80765
ChEMBL
CHEMBL444929
Wikipedia
Squalamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentNeovascular Age Related Macular Degeneration1
2CompletedTreatmentRetinal Neovascularization1
2WithdrawnTreatmentAge-Related Macular Degeneration (ARMD)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
PropertyValueSource
Water Solubility0.000169 mg/mLALOGPS
logP2.48ALOGPS
logP3.24ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)10.89ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area133.91 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity174.42 m3·mol-1ChemAxon
Polarizability77.15 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Bile acids, alcohols and derivatives
Direct Parent
Monohydroxy bile acids, alcohols and derivatives
Alternative Parents
Pregnane-type alkaloids / 7-hydroxysteroids / Azasteroids and derivatives / Sulfated steroids / Alkaloids and derivatives / Sulfuric acid monoesters / Alkyl sulfates / Secondary alcohols / Cyclic alcohols and derivatives / Dialkylamines
show 4 more
Substituents
Monohydroxy bile acid, alcohol, or derivatives / Sulfated steroid skeleton / Steroidal alkaloid / Pregnane-type alkaloid / Hydroxysteroid / 7-hydroxysteroid / Azasteroid / Alkaloid or derivatives / Sulfuric acid ester / Alkyl sulfate
show 19 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
bile acid (CHEBI:80765) / Marine nature products (C16841)

Drug created on March 19, 2008 10:34 / Updated on November 02, 2018 06:16