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
Structure for Trodusquemine (DB06333)
- Weight
- Average: 685.07
Monoisotopic: 684.522342608 - Chemical Formula
- C37H72N4O5S
- Synonyms
- Trodusquemine
- External IDs
- MSI-1436
Pharmacology
- Indication
Investigated for use/treatment in obesity and diabetes mellitus type 2.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism UTyrosine-protein phosphatase non-receptor type 1 Not Available Humans USodium-dependent dopamine transporter Not Available Humans USodium-dependent noradrenaline transporter Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Trodusquemine hydrochloride 7VON0S1S42 Not Available DJYRGAKPWPDNTA-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
- 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]
- 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]
- External Links
- ChemSpider
- 8093615
- BindingDB
- 50333649
- ChEMBL
- CHEMBL508583
- ZINC
- ZINC000049833385
- Wikipedia
- Trodusquemine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Treatment Diabetes Mellitus / Obesity (Disorder) 2 1 Completed Treatment Obesity (Disorder) 1 1 Terminated Treatment Metastatic Breast Cancer 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
Property Value Source Water Solubility 0.000255 mg/mL ALOGPS logP 2.59 ALOGPS logP 2.93 ChemAxon logS -6.4 ALOGPS pKa (Strongest Acidic) -1.3 ChemAxon pKa (Strongest Basic) 10.97 ChemAxon Physiological Charge 3 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 145.94 Å2 ChemAxon Rotatable Bond Count 20 ChemAxon Refractivity 192.01 m3·mol-1 ChemAxon Polarizability 84.8 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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 16:24 / Updated on February 21, 2021 18:52