Trodusquemine

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

Identification

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Name
Trodusquemine
Accession Number
DB06333
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
  • Trodusquemine
External IDs
MSI-1436
Product Ingredients
IngredientUNIICASInChI Key
Trodusquemine hydrochloride7VON0S1S42Not AvailableDJYRGAKPWPDNTA-YPRMBGODSA-N
Categories
UNII
KKC12PIF16
CAS number
186139-09-3
Weight
Average: 685.07
Monoisotopic: 684.522342608
Chemical Formula
C37H72N4O5S
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

Pharmacology

Indication

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

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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:12086938]
  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. [PubMed:29302341]
External Links
ChemSpider
8093615
BindingDB
50333649
ChEMBL
CHEMBL508583
Wikipedia
Trodusquemine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentBMI >30 kg/m21
1CompletedTreatmentBMI >30 kg/m2 / Diabetes Mellitus (DM)2
1TerminatedTreatmentMetastatic Breast Cancer (MBC)1

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
Not Available

Taxonomy

Classification
Not classified

Targets

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
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
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 on March 19, 2008 10:24 / Updated on May 01, 2019 13:20