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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H65N3O5S
Molecular Weight 627.962
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SQUALAMINE

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)NCCCNCCCCN)[C@H](C)CC[C@@H](OS(O)(=O)=O)C(C)C

InChI

InChIKey=UIRKNQLZZXALBI-MSVGPLKSSA-N
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

HIDE SMILES / InChI

Molecular Formula C34H65N3O5S
Molecular Weight 627.962
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Squalamine is a steroid-polyamine conjugate compound with broad-spectrum antimicrobial activity and anti-angiogenic activity. Squalamine selectively inhibits new blood vessel formation; this activity is thought to be mediated through inhibition of the sodium-hydrogen antiporter sodium-proton exchangers (specifically the NHE3 isoform) causing inhibition of hydrogen ion efflux from endothelial cells, with subsequent reduction of cellular proliferation. Studies in tumor-bearing mice have shown that squalamine inhibits angiogenesis and tumor growth in xenograft models of lung, breast, ovarian, and prostate cancer and in brain and breast allograft tumor models in rats. Squalamine also has been shown to prevent lung metastases in the murine Lewis lung carcinoma model, both as a single agent and in combination with various other chemotherapeutics. Squalamine does not appear to have substantial direct effects on primary tumor growth in animal models when administered as a single agent. However, enhanced antitumor responses are observed when squalamine is administered in combination with cytotoxic chemotherapeutic agents when compared with cytotoxic agents used alone. Squalamine 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.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

PubMed

Sample Use Guides

In Vivo Use Guide
100 mg/m(2)/day and escalated to 400 mg/m(2)/day
Route of Administration: Intravenous
Substance Class Chemical
Record UNII
F8PO54Z4V7
Record Status Validated (UNII)
Record Version