Details of the Drug

General Information of Drug (ID: DM3PS2E)

Drug Name

Squalamine

Synonyms

Squalamine; 148717-90-2; Squalamine [INN]; UNII-F8PO54Z4V7; F8PO54Z4V7; CHEBI:80765; 3beta-N-1-(N-(3-(4-Aminobutyl))-1,3-diaminopropane)-7alpha,24-dihydroxy-5alpha-cholestane 24-sulfate; (3beta,5alpha,7alpha,24R)-3-((3-(4-(Aminobutyl)amino)propyl)amio)cholestane-7,24-diol 24-(hydrogen sulfate); 3-((3-(4-(Aminobutyl)amino)propyl)amio)cholestane-7,24-diol 24-(hydrogen sulfate), (3beta,5alpha,7alpha,24R)-; Cholestane-7,24-diol, 3-((3-(4-(aminobutyl)amino)propyl)amio)-, 24-(hydrogen sulfate), (3beta,5alpha,7alpha,24R)-

Indication

Disease Entry	ICD 11	Status	REF
Solid tumour/cancer	2A00-2F9Z	Phase 3	[1]
Diabetic macular edema	9B71.02	Phase 2	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

628

Logarithm of the Partition Coefficient (xlogp)

4.3

Rotatable Bond Count (rotbonds)

16

Hydrogen Bond Donor Count (hbonddonor)

5

Hydrogen Bond Acceptor Count (hbondacc)

8

Chemical Identifiers

Formula: C34H65N3O5S
IUPAC Name: [(3R,6R)-6-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-[3-(4-aminobutylamino)propylamino]-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl] hydrogen sulfate
Canonical SMILES: C[C@H](CC[C@H](C(C)C)OS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@@H]4[C@@]3(CC[C@@H](C4)NCCCNCCCCN)C)O)C
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
InChIKey: UIRKNQLZZXALBI-MSVGPLKSSA-N

Cross-matching ID

PubChem CID: 72495
ChEBI ID: CHEBI:80765
CAS Number: 148717-90-2
UNII: F8PO54Z4V7
DrugBank ID: DB06461
TTD ID: D07PVB

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Fibroblast growth factor-2 (FGF2)	TTGKIED	FGF2_HUMAN	Modulator	[3]
Platelet-derived growth factor A (PDGFA)	TTSM78N	PDGFA_HUMAN	Inhibitor	[2]
Vascular endothelial growth factor (VEGF)	TT9HKJA	VEGFA_HUMAN ; VEGFB_HUMAN ; VEGFC_HUMAN ; VEGFD_HUMAN	Modulator	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Solid tumour/cancer

ICD Disease Classification

2A00-2F9Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Fibroblast growth factor-2 (FGF2)	DTT	FGF2	6.36E-03	0.05	0.3

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	ClinicalTrials.gov (NCT00139282) A Safety and Efficacy Study of Squalamine Lactate for Injection (MSI-1256F) for "Wet" Age-Related Macular Degeneration. U.S. National Institutes of Health.
2	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3	Clinical pipeline report, company report or official report of Ohr Pharmaceutical.