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.
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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
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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
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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 2 1 Completed Treatment Obesity 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 282.7938643 predictedDarkChem Lite v0.1.0 [M+H]+ 273.1228643 predictedDarkChem Lite v0.1.0 [M+Na]+ 272.8558643 predictedDarkChem Lite v0.1.0
Targets
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- 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 at March 19, 2008 16:24 / Updated at February 21, 2021 18:52