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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H52O4
Molecular Weight 512.7636
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAPROSPINOL

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@@]6(CC[C@@H](C)CO6)O2)OC(=O)CCCCC

InChI

InChIKey=VMOZFSWFUBLCNN-AAPULDEBSA-N
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

HIDE SMILES / InChI

Molecular Formula C33H52O4
Molecular Weight 512.7636
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Caprospinol, also known as SP-233, a spirostenol derivative, protects neuronal cells against β-Amyloid (Abeta(1-42)) protein toxicity by binding to and inactivating this peptide. It was shown, that caprospinol crossed the blood-brain barrier, accumulated in the brain, and restored cognitive impairment in a pharmacological rat model of Alzheimer's disease. It was suggested, that the drug could be considered as a promising drug for Alzheimer's disease treatment.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P05067|||Q13764|||Q8WZ99
Gene ID: 351.0
Gene Symbol: APP
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Caprospinol: moving from a neuroactive steroid to a neurotropic drug.
2009 Mar
Caprospinol reduces amyloid deposits and improves cognitive function in a rat model of Alzheimer's disease.
2010 Jan 20
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:38:55 GMT 2023
Edited
by admin
on Sat Dec 16 09:38:55 GMT 2023
Record UNII
9BU4T267E4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAPROSPINOL
Common Name English
((20S,22R,25R)-SPIROSTA-5-ENE-3.BETA.-OL)HEXANOATE
Systematic Name English
SP-233
Code English
(22R,25R)-20.ALPHA.-SPIROST-5-EN-3.BETA.-YL HEXANOATE
Systematic Name English
J2.343.184J
Code English
DIOSGENIN, HEXANOATE
Common Name English
DIOSGENIN CAPROATE
Common Name English
SPIROST-5-EN-3-OL, 3-HEXANOATE, (3.BETA.,25R)-
Systematic Name English
Code System Code Type Description
PUBCHEM
16394575
Created by admin on Sat Dec 16 09:38:55 GMT 2023 , Edited by admin on Sat Dec 16 09:38:55 GMT 2023
PRIMARY
DRUG BANK
DB05263
Created by admin on Sat Dec 16 09:38:55 GMT 2023 , Edited by admin on Sat Dec 16 09:38:55 GMT 2023
PRIMARY
FDA UNII
9BU4T267E4
Created by admin on Sat Dec 16 09:38:55 GMT 2023 , Edited by admin on Sat Dec 16 09:38:55 GMT 2023
PRIMARY
CAS
4952-56-1
Created by admin on Sat Dec 16 09:38:55 GMT 2023 , Edited by admin on Sat Dec 16 09:38:55 GMT 2023
PRIMARY