NAV

Squalamine

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

Identification

Generic Name
Squalamine
DrugBank Accession Number
DB06461
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 627.97
Monoisotopic: 627.464493379
Chemical Formula
C34H65N3O5S
Synonyms
  • Squalamine
External IDs
  • MSI-1246
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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

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.
DrugInteraction
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interactions in your software
AcenocoumarolThe risk or severity of bleeding can be increased when Squalamine is combined with Acenocoumarol.
Alendronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Squalamine is combined with Alendronic acid.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Squalamine is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Squalamine is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Squalamine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Squalamine lactate4WE915J1KX320725-47-1ZPYIELFRIYUVQP-BHBJEIPNSA-N
International/Other Brands
Evizon

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Alkaloid or derivatives / Alkyl sulfate / Amine / Azasteroid / Cyclic alcohol / Hydrocarbon derivative / Hydroxysteroid
show 19 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
bile acid (CHEBI:80765) / Marine nature products (C16841)
Affected organisms
Not Available

Chemical Identifiers

UNII
F8PO54Z4V7
CAS number
148717-90-2
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

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. [Article]
KEGG Compound
C16841
ChemSpider
65407
ChEBI
80765
ChEMBL
CHEMBL444929
ZINC
ZINC000030160243
Wikipedia
Squalamine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentNeovascular Age-Related Macular Degeneration (nAMD)1
3Unknown StatusTreatmentAge - Related Macular Degeneration (AMD)1
2CompletedTreatmentNeovascular Age-Related Macular Degeneration (nAMD)1
2CompletedTreatmentRetinal Neovascularization1
2TerminatedNot AvailableMacular Degeneration1

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/MSsplash10-01u0-0200695000-7b1677de4ff729d404ff
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-6000009000-20d8cdb7da3fcf7c2335
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-a4f3951b64da033e2d5b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08g0-5601920000-901a91e142f9c84cdae2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9100011000-093c45a7c8f09bf35f0b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01u0-1400911000-73dd3ad73a8329d62916
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-263.5108474
predicted
DarkChem Lite v0.1.0
[M-H]-254.41911
predicted
DeepCCS 1.0 (2019)
[M+H]+261.6115474
predicted
DarkChem Lite v0.1.0
[M+H]+256.1108
predicted
DeepCCS 1.0 (2019)
[M+Na]+263.2121474
predicted
DarkChem Lite v0.1.0
[M+Na]+262.26764
predicted
DeepCCS 1.0 (2019)

Drug created at March 19, 2008 16:34 / Updated at January 14, 2023 19:03