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 rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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 outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Muparfostat sodium4ROB1M2DHD1020105-88-7Not 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
  1. 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]
  2. 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]
Human Metabolome Database
HMDB0254947
PubChem Substance
347910242

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentCancer / Hepatocellular Carcinoma / Hepatoma / Liver Cancer / Primary Liver Cancer1
3TerminatedTreatmentCancer / Hepatocellular Carcinoma / Liver Cancer1
2CompletedTreatmentHepatocellular Carcinoma1
2CompletedTreatmentLung Cancer1
2CompletedTreatmentMelanoma1

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 Solubility1.24 mg/mLALOGPS
logP-1.2ALOGPS
logP-6Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)-3.4Chemaxon
Physiological Charge-12Chemaxon
Hydrogen Acceptor Count38Chemaxon
Hydrogen Donor Count12Chemaxon
Polar Surface Area748.91 Å2Chemaxon
Rotatable Bond Count29Chemaxon
Refractivity211.54 m3·mol-1Chemaxon
Polarizability103.9 Å3Chemaxon
Number of Rings3Chemaxon
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
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at November 18, 2007 18:27 / Updated at September 28, 2023 05:47