NAV

Trodusquemine

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

Identification

Generic Name
Trodusquemine
DrugBank Accession Number
DB06333
Background

Trodusquemine, a spermine metabolite of cholesterol, is a naturally occurring aminosterol that inhibits protein tyrosine phosphatase 1B. It has demonstrated the ability to stimulate regeneration of heart and multiple other tissues in animal models 2.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 685.07
Monoisotopic: 684.522342608
Chemical Formula
C37H72N4O5S
Synonyms
  • Trodusquemine
External IDs
  • MSI-1436
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Pharmacology

Indication

Investigated for use/treatment in obesity and diabetes mellitus type 2.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Trodusquemine is a spermine metabolite of cholesterol which possibly acts on the paraventricular nucleus in the hypothalamus. Trodusquemine suppresses feeding, prevents reduction in energy expenditure, causes hormonal changes, and induces patterns of neuropeptide expression normally associated with weight loss. Trosdusquemine enhances insulin sensitivity through inhibition of protein tyrosine phostphatase 1B centrally and peripherally (PTP-1B), dopamine and norepinephrine reuptake, an ion transport modulator and a downregulator of Agouti-related peptide (AgRP) and neuropeptide Y (NPY) expression.

TargetActionsOrganism
UTyrosine-protein phosphatase non-receptor type 1Not AvailableHumans
USodium-dependent dopamine transporterNot AvailableHumans
USodium-dependent noradrenaline transporterNot AvailableHumans
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.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Trodusquemine hydrochloride7VON0S1S42Not AvailableDJYRGAKPWPDNTA-YPRMBGODSA-N

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
KKC12PIF16
CAS number
186139-09-3
InChI Key
WUJVPODXELZABP-FWJXURDUSA-N
InChI
InChI=1S/C37H72N4O5S/c1-26(2)34(46-47(43,44)45)13-10-27(3)30-11-12-31-35-32(15-17-37(30,31)5)36(4)16-14-29(24-28(36)25-33(35)42)41-23-9-22-40-20-7-6-19-39-21-8-18-38/h26-35,39-42H,6-25,38H2,1-5H3,(H,43,44,45)/t27-,28-,29+,30-,31+,32+,33-,34-,35+,36+,37-/m1/s1
IUPAC Name
{[(3R,6R)-6-[(1R,3aS,3bR,4R,5aR,7S,9aS,9bS,11aR)-7-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]amino}-4-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-3-yl]oxy}sulfonic acid
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)NCCCNCCCCNCCCN)[C@H](C)CC[C@@H](OS(O)(=O)=O)C(C)C

References

General References
  1. Ahima RS, Patel HR, Takahashi N, Qi Y, Hileman SM, Zasloff MA: Appetite suppression and weight reduction by a centrally active aminosterol. Diabetes. 2002 Jul;51(7):2099-104. [Article]
  2. Smith AM, Maguire-Nguyen KK, Rando TA, Zasloff MA, Strange KB, Yin VP: The protein tyrosine phosphatase 1B inhibitor MSI-1436 stimulates regeneration of heart and multiple other tissues. NPJ Regen Med. 2017 Mar 3;2:4. doi: 10.1038/s41536-017-0008-1. eCollection 2017. [Article]
ChemSpider
8093615
BindingDB
50333649
ChEMBL
CHEMBL508583
ZINC
ZINC000049833385
Wikipedia
Trodusquemine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
1CompletedTreatmentDiabetes Mellitus / Obesity2
1CompletedTreatmentObesity1
1TerminatedTreatmentMetastatic Breast Cancer1

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 Solubility0.000255 mg/mLALOGPS
logP2.59ALOGPS
logP2.93Chemaxon
logS-6.4ALOGPS
pKa (Strongest Acidic)-1.3Chemaxon
pKa (Strongest Basic)10.97Chemaxon
Physiological Charge3Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area145.94 Å2Chemaxon
Rotatable Bond Count20Chemaxon
Refractivity192.01 m3·mol-1Chemaxon
Polarizability84.8 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/MSsplash10-000i-0100094000-4e2baaa89cdd3be88af6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001j-6000009000-4d98936034cbebd7c2a5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0c04-3300190000-7dfbcbba4c458eb96377
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-dfa3dfd1a0a4dcef9704
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9100011000-df8a3758a8f500003546
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06sl-9500352000-4ad131cbc603f94ee1c0
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-282.7938643
predicted
DarkChem Lite v0.1.0
[M+H]+273.1228643
predicted
DarkChem Lite v0.1.0
[M+Na]+272.8558643
predicted
DarkChem Lite v0.1.0

Targets

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Details1. Tyrosine-protein phosphatase non-receptor type 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EI...
Gene Name
PTPN1
Uniprot ID
P18031
Uniprot Name
Tyrosine-protein phosphatase non-receptor type 1
Molecular Weight
49966.44 Da
Details2. Sodium-dependent dopamine transporter
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
Details3. Sodium-dependent noradrenaline transporter
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da

Drug created at March 19, 2008 16:24 / Updated at February 21, 2021 18:52