Proscillaridin

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

Identification

Generic Name
Proscillaridin
DrugBank Accession Number
DB13307
Background

Proscillaridin is a cardiac glycoside that is derived from plants of the genus Scilla and in Drimia maritima (Scilla maritima). Studies suggest the potential cytotoxic and anticancer property of proscillaridin, based on evidence of the drug potently disrupting topoisomerase I and II activity at nanomolar drug concentrations 1 and triggering cell death and blocking cell proliferation of glioblastoma cell lines 2.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 530.658
Monoisotopic: 530.287968312
Chemical Formula
C30H42O8
Synonyms
  • Proscillaridin
External IDs
  • A-32686

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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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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.
DrugInteraction
AcebutololAcebutolol may increase the bradycardic activities of Proscillaridin.
Acetylsalicylic acidThe serum concentration of Proscillaridin can be decreased when it is combined with Acetylsalicylic acid.
AlfacalcidolThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Alfacalcidol is combined with Proscillaridin.
AmikacinThe risk or severity of adverse effects can be increased when Amikacin is combined with Proscillaridin.
AmilorideAmiloride may decrease the excretion rate of Proscillaridin which could result in a higher serum level.
Food Interactions
Not Available

Categories

ATC Codes
C01AB51 — Proscillaridin, combinationsC01AB01 — Proscillaridin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid lactones
Direct Parent
Bufanolides and derivatives
Alternative Parents
Steroidal glycosides / 14-hydroxysteroids / Delta-4-steroids / Hexoses / O-glycosyl compounds / Pyranones and derivatives / Oxanes / Tertiary alcohols / Heteroaromatic compounds / Lactones
show 7 more
Substituents
14-hydroxysteroid / Acetal / Alcohol / Aromatic heteropolycyclic compound / Bufanolide-skeleton / Cyclic alcohol / Delta-4-steroid / Glycosyl compound / Heteroaromatic compound / Hexose monosaccharide
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
KC6BL281EN
CAS number
466-06-8
InChI Key
MYEJFUXQJGHEQK-ALRJYLEOSA-N
InChI
InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1
IUPAC Name
5-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2H-pyran-2-one
SMILES
[H][C@@]1(CC[C@]2(O)[C@]3([H])CCC4=C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)C1=COC(=O)C=C1

References

General References
  1. Bielawski K, Winnicka K, Bielawska A: Inhibition of DNA topoisomerases I and II, and growth inhibition of breast cancer MCF-7 cells by ouabain, digoxin and proscillaridin A. Biol Pharm Bull. 2006 Jul;29(7):1493-7. [Article]
  2. Denicolai E, Baeza-Kallee N, Tchoghandjian A, Carre M, Colin C, Jiglaire CJ, Mercurio S, Beclin C, Figarella-Branger D: Proscillaridin A is cytotoxic for glioblastoma cell lines and controls tumor xenograft growth in vivo. Oncotarget. 2014 Nov 15;5(21):10934-48. [Article]
PubChem Compound
5284613
PubChem Substance
347829292
ChemSpider
4447658
RxNav
8795
ChEBI
32065
ChEMBL
CHEMBL600325
ZINC
ZINC000008214665
Wikipedia
Proscillaridin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0427 mg/mLALOGPS
logP2.37ALOGPS
logP2.3Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.22Chemaxon
pKa (Strongest Basic)0.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area125.68 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity140.05 m3·mol-1Chemaxon
Polarizability58.26 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0102190000-782730d7711a23bc1f5a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0203390000-5eeee9a738ffa02f183b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-1196320000-3d36a604cbe3df315f35
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ktb-6309780000-d82e221f3c2ee19d262a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00e9-7796310000-ab2971d046fca06585bd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-10a7763d7b755378277f
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-247.3284283
predicted
DarkChem Lite v0.1.0
[M-H]-234.1783283
predicted
DarkChem Lite v0.1.0
[M-H]-207.6823
predicted
DeepCCS 1.0 (2019)
[M+H]+246.0354283
predicted
DarkChem Lite v0.1.0
[M+H]+235.4105283
predicted
DarkChem Lite v0.1.0
[M+H]+209.40602
predicted
DeepCCS 1.0 (2019)
[M+Na]+246.2904283
predicted
DarkChem Lite v0.1.0
[M+Na]+232.4627283
predicted
DarkChem Lite v0.1.0
[M+Na]+216.35268
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:39 / Updated at February 21, 2021 18:54