Chemistry:Squalamine

Squalamine

Names
IUPAC name (24R)-3β-({3-[(3-Aminopropyl)amino]propyl}amino)-7α-hydroxycholestan-24-yl hydrogen sulfate
Systematic IUPAC name (3R,6R)-6-[(1R,3aS,3bR,4R,5aR,7S,9aS,9bS,11aR)-7-({3-[(3-Aminopropyl)amino]propyl}amino)-4-hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-3-yl hydrogen sulfate
Identifiers
CAS Number	148717-90-2
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL444929 ChEMBL507931
ChemSpider	65407
KEGG	C16841
PubChem CID	72495
UNII	F8PO54Z4V7 Y
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 Key: UIRKNQLZZXALBI-MSVGPLKSSA-N InChI=1/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 Key: UIRKNQLZZXALBI-MSVGPLKSBB
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
Properties
Chemical formula	C34H65N3O5S
Molar mass	628 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tracking categories (test):

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Squalamine is a steroid-polyamine conjugate compound with broad spectrum antimicrobial activity and anti-angiogenic activity. It was studied as a potential cancer drug and as a potential treatment for wet macular degeneration but as of 2018 had not succeeded in Phase III trials for any use.

Pharmacology

Squalamine disrupts microbial membranes; the exact mechanism is not known.

Squalamine appears to have an anti-angiogenic effect in mammalian cells by binding to calmodulin once it is taken up by the cell; this prevents signal transduction downstream of pro-angiogenic factors like VEGF.

Chemistry

Squalamine is a steroid-polyamine conjugate.

It was first isolated from the liver of sharks of the genus Squalus but methods to make it synthetically have been subsequently developed.

Research

Squalamine was studied as a potential drug to treat several forms of cancer and wet macular degeneration by scientists at Magainin Pharmaceuticals (subsequently called Genaera), but the company ran out of money and closed in 2009. Squalamine and some other drug assets were sold to Ohr Pharmaceutical for $200,000 by Genaera's liquidator.

It was studied in an eye drop formulation as a potential way to treat wet macular degeneration in combination with ranibizumab by Ohr Pharmaceuticals. A Phase II trial failed in 2015, but Ohr said a subpopulation with choroidal neovascularization responded well enough to justify a Phase III trial. Ohr announced that the Phase III trial had failed in January 2018.