Muparfostat
Identification
- Generic Name
- Muparfostat
- DrugBank Accession Number
- DB05808
- Background
Muparfostat (PI-88) is a mixture of highly sulfated, monophosphorylated mannose oligosaccharides, derived from the extracellular phosphomannan of the yeast Pichia (Hansenula) holstii, with potential antiangiogenic activity.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 1384.99
Monoisotopic: 1383.703516181 - Chemical Formula
- C18H33O49PS10
- Synonyms
- .ALPHA.-D-MANNAN, (1->3)-, 6-(DIHYDROGEN PHOSPHATE) TRIS(HYDROGEN SULFATE)
- Heparanase inhibitor PI-88
- Mannopentaose phosphate sulfate
- Phosphomannopentaose sulfate
- Sulfated mannopentaose phosphate
Pharmacology
- Indication
Investigated for use/treatment in hepatocellular carcinoma, liver cancer, melanoma, and multiple myeloma.
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
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
PI-88 retards the growth of primary tumours by inhibiting new blood vessel growth (angiogenesis) in two ways: Heparan sulfate mimicry causes inhibition of heparanase, which prevents the release of angiogenic growth factors from the extracellular matrix (ECM). Interaction with angiogenic growth factors VEGF (Vascular Endothelial Growth Factor), FGF-1 (Fibroblast Growth Factor -1) and FGF-2, reduces their functional activity. PI-88 binds with high (nanomolar) affinity to these growth factors.
- 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. View sample adverse effects data in our new Data Library!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 Muparfostat sodium 4ROB1M2DHD 1020105-88-7 Not applicable
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- P2BKS6T40H
- CAS number
- 1020105-89-8
- InChI Key
- RIYITPRTNFEGIA-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H33O49PS10/c19-68(20,21)52-1-4-8(61-72(31,32)33)12(64-75(40,41)42)15(66-77(46,47)48)17(55-4)58-10-7(60-71(28,29)30)5(2-53-69(22,23)24)56-16(14(10)65-76(43,44)45)59-13-11(63-74(37,38)39)9(62-73(34,35)36)6(3-54-70(25,26)27)57-18(13)67-78(49,50)51/h4-18H,1-3H2,(H2,19,20,21)(H,22,23,24)(H,25,26,27)(H,28,29,30)(H,31,32,33)(H,34,35,36)(H,37,38,39)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)
- IUPAC Name
- (2-{[3,5-bis(sulfooxy)-2-[(sulfooxy)methyl]-6-{[2,4,5-tris(sulfooxy)-6-[(sulfooxy)methyl]oxan-3-yl]oxy}oxan-4-yl]oxy}-6-[(phosphonooxy)methyl]-4,5-bis(sulfooxy)oxan-3-yl)oxidanesulfonic acid
- SMILES
- OP(O)(=O)OCC1OC(OC2C(OS(O)(=O)=O)C(COS(O)(=O)=O)OC(OC3C(OS(O)(=O)=O)OC(COS(O)(=O)=O)C(OS(O)(=O)=O)C3OS(O)(=O)=O)C2OS(O)(=O)=O)C(OS(O)(=O)=O)C(OS(O)(=O)=O)C1OS(O)(=O)=O
References
- General References
- Fairweather JK, Hammond E, Johnstone KD, Ferro V: Synthesis and heparanase inhibitory activity of sulfated mannooligosaccharides related to the antiangiogenic agent PI-88. Bioorg Med Chem. 2008 Jan 15;16(2):699-709. Epub 2007 Oct 18. [Article]
- Basche M, Gustafson DL, Holden SN, O'Bryant CL, Gore L, Witta S, Schultz MK, Morrow M, Levin A, Creese BR, Kangas M, Roberts K, Nguyen T, Davis K, Addison RS, Moore JC, Eckhardt SG: A phase I biological and pharmacologic study of the heparanase inhibitor PI-88 in patients with advanced solid tumors. Clin Cancer Res. 2006 Sep 15;12(18):5471-80. [Article]
- External Links
- Human Metabolome Database
- HMDB0254947
- PubChem Substance
- 347910242
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Cancer / Hepatocellular Carcinoma / Hepatoma / Liver Cancer / Primary Liver Cancer 1 3 Terminated Treatment Cancer / Hepatocellular Carcinoma / Liver Cancer 1 2 Completed Treatment Hepatocellular Carcinoma 1 2 Completed Treatment Lung Cancer 1 2 Completed Treatment Melanoma 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 1.24 mg/mL ALOGPS logP -1.2 ALOGPS logP -6 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) -3.4 Chemaxon Physiological Charge -12 Chemaxon Hydrogen Acceptor Count 38 Chemaxon Hydrogen Donor Count 12 Chemaxon Polar Surface Area 748.91 Å2 Chemaxon Rotatable Bond Count 29 Chemaxon Refractivity 211.54 m3·mol-1 Chemaxon Polarizability 103.9 Å3 Chemaxon Number of Rings 3 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Drug created at November 18, 2007 18:27 / Updated at September 28, 2023 05:47