Identification
- Generic Name
- Caprospinol
- DrugBank Accession Number
- DB05263
- Background
Caprospinol (SP-233) is the first drug ever to demonstrate the correlation of clearing beta-amyloid from the brain. It also improves the brain histopathology and recovers memory function.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Caprospinol (DB05263)
- Weight
- Average: 512.775
Monoisotopic: 512.386560154 - Chemical Formula
- C33H52O4
- Synonyms
- Diosgenin caproate
- External IDs
- J2.343.184J
- SP 233
- SP-233
Pharmacology
- Indication
Alzheimer's Disease
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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
Caprospinol cleared beta-amyloid plaque formation and restored memory capacity in-vivo; confirming in-vitro studies showing Caprospinol binds ß-amyloid directly and inhibits the formation of neurotoxic amyloid-derived diffusible ligands (ADDLs) by forming stable heavy complexes with the peptide. In addition, the studies demonstrated Caprospinol protects mitochondria function, thus protecting cell viability and decreased cell death.
- 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
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Triterpenoids
- Direct Parent
- Triterpenoids
- Alternative Parents
- Spirostanes and derivatives / Steroid esters / Delta-5-steroids / Ketals / Fatty acid esters / Oxanes / Tetrahydrofurans / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives show 3 more
- Substituents
- Acetal / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Delta-5-steroid / Fatty acid ester / Fatty acyl / Hydrocarbon derivative / Ketal show 12 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9BU4T267E4
- CAS number
- 4952-56-1
- InChI Key
- VMOZFSWFUBLCNN-AAPULDEBSA-N
- InChI
- InChI=1S/C33H52O4/c1-6-7-8-9-29(34)36-24-13-15-31(4)23(18-24)10-11-25-26(31)14-16-32(5)27(25)19-28-30(32)22(3)33(37-28)17-12-21(2)20-35-33/h10,21-22,24-28,30H,6-9,11-20H2,1-5H3/t21-,22+,24+,25-,26+,27+,28+,30+,31+,32+,33-/m1/s1
- IUPAC Name
- (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-yl hexanoate
- SMILES
- [H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CO1)O2)OC(=O)CCCCC
References
- General References
- Tillement L, Lecanu L, Yao W, Greeson J, Papadopoulos V: The spirostenol (22R, 25R)-20alpha-spirost-5-en-3beta-yl hexanoate blocks mitochondrial uptake of Abeta in neuronal cells and prevents Abeta-induced impairment of mitochondrial function. Steroids. 2006 Aug;71(8):725-35. Epub 2006 Jun 19. [Article]
- External Links
- PubChem Compound
- 16394575
- PubChem Substance
- 347827721
- ChemSpider
- 17460070
- ZINC
- ZINC000097971833
Clinical Trials
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 1.55e-05 mg/mL ALOGPS logP 6.34 ALOGPS logP 7.4 Chemaxon logS -7.5 ALOGPS pKa (Strongest Basic) -4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 44.76 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 147.85 m3·mol-1 Chemaxon Polarizability 64.08 Å3 Chemaxon Number of Rings 6 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]- 216.0077 predictedDeepCCS 1.0 (2019) [M+H]+ 217.70628 predictedDeepCCS 1.0 (2019) [M+Na]+ 223.86313 predictedDeepCCS 1.0 (2019)
Drug created at November 18, 2007 18:22 / Updated at June 12, 2020 16:52