WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 527409
CAS#: 4952-56-1
Description: Caprospinol, also known as SP-233, is a β-Amyloid (Aβ) protein neurotoxicity inhibitor potentially for the treatment of Alzheimer's disease. Caprospinol crosses the blood-brain barrier, accumulates in the brain, and restores cognitive impairment in a pharmacological rat model of AD. Caprospinol is stable, does not bind to known steroid receptors, is devoid of mutagenic and genotoxic properties, and is devoid of acute toxicity in rodents.
MedKoo Cat#: 527409
Name: Caprospinol
CAS#: 4952-56-1
Chemical Formula: C33H52O4
Exact Mass: 512.3866
Molecular Weight: 512.775
Elemental Analysis: C, 77.30; H, 10.22; O, 12.48
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Synonym: Caprospinol; SP-233; SP 233; SP233
IUPAC/Chemical Name: (4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl hexanoate
InChi Key: VMOZFSWFUBLCNN-AAPULDEBSA-N
InChi Code: 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
SMILES Code: [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C[C@@H](OC(CCCCC)=O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 512.775 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Papadopoulos V, Lecanu L. Caprospinol: discovery of a steroid drug candidate to treat Alzheimer's disease based on 22R-hydroxycholesterol structure and properties. J Neuroendocrinol. 2012 Jan;24(1):93-101. doi: 10.1111/j.1365-2826.2011.02167.x. Review. PubMed PMID: 21623958.
2: Lecanu L, Rammouz G, McCourty A, Sidahmed EK, Greeson J, Papadopoulos V. Caprospinol reduces amyloid deposits and improves cognitive function in a rat model of Alzheimer's disease. Neuroscience. 2010 Jan 20;165(2):427-35. doi: 10.1016/j.neuroscience.2009.10.033. PubMed PMID: 19850110.
3: Lecanu L, Tillement L, Rammouz G, Tillement JP, Greeson J, Papadopoulos V. Caprospinol: moving from a neuroactive steroid to a neurotropic drug. Expert Opin Investig Drugs. 2009 Mar;18(3):265-76. doi: 10.1517/13543780902762827 . Review. PubMed PMID: 19243278.
4: 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. PubMed PMID: 16787656.
5: Chojnacki JE, Liu K, Saathoff JM, Zhang S. Bivalent ligands incorporating curcumin and diosgenin as multifunctional compounds against Alzheimer's disease. Bioorg Med Chem. 2015 Nov 15;23(22):7324-31. doi: 10.1016/j.bmc.2015.10.032. PubMed PMID: 26526742; PubMed Central PMCID: PMC4641451.
6: Tillement L, Lecanu L, Papadopoulos V. Further evidence on mitochondrial targeting of β-amyloid and specificity of β-amyloid-induced mitotoxicity in neurons. Neurodegener Dis. 2011;8(5):331-44. doi: 10.1159/000323264. PubMed PMID: 21311166.
