Proscillaridin
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
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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- 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
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Acebutolol may increase the bradycardic activities of Proscillaridin. Acetylsalicylic acid The serum concentration of Proscillaridin can be decreased when it is combined with Acetylsalicylic acid. Alfacalcidol The risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Alfacalcidol is combined with Proscillaridin. Amikacin The risk or severity of adverse effects can be increased when Amikacin is combined with Proscillaridin. Amiloride Amiloride 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
- 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]
- 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]
- External Links
- PubChem Compound
- 5284613
- PubChem Substance
- 347829292
- ChemSpider
- 4447658
- 8795
- ChEBI
- 32065
- ChEMBL
- CHEMBL600325
- ZINC
- ZINC000008214665
- Wikipedia
- Proscillaridin
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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
Property Value Source Water Solubility 0.0427 mg/mL ALOGPS logP 2.37 ALOGPS logP 2.3 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 12.22 Chemaxon pKa (Strongest Basic) 0.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 125.68 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 140.05 m3·mol-1 Chemaxon Polarizability 58.26 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No 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]- 247.3284283 predictedDarkChem Lite v0.1.0 [M-H]- 234.1783283 predictedDarkChem Lite v0.1.0 [M-H]- 207.6823 predictedDeepCCS 1.0 (2019) [M+H]+ 246.0354283 predictedDarkChem Lite v0.1.0 [M+H]+ 235.4105283 predictedDarkChem Lite v0.1.0 [M+H]+ 209.40602 predictedDeepCCS 1.0 (2019) [M+Na]+ 246.2904283 predictedDarkChem Lite v0.1.0 [M+Na]+ 232.4627283 predictedDarkChem Lite v0.1.0 [M+Na]+ 216.35268 predictedDeepCCS 1.0 (2019)
Drug created at June 23, 2017 20:39 / Updated at February 21, 2021 18:54