Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C31H50O4 |
| Molecular Weight | 486.7263 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCC(O)=O)[C@H](C)CCCC(C)C
InChI
InChIKey=WLNARFZDISHUGS-MIXBDBMTSA-N
InChI=1S/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1
Cholesteryl hemisuccinate (CHEMS) is an acidic cholesterol ester. It self-assembles into bilayers in alkaline and neutral aqueous media. CHEMS exhibits pH sensitive polymorphism. It consists of succinic acid esterified to the beta-hydroxyl group of cholesterol. It was shown; that CHEMS was potent inhibitors of acetylcholinesterase and it alone or in combination with tetrahydroaminoacridine could be used in the treatment of organophosphate poisoning and Alzheimer's disease. It was also revealed, that CHEMS upon incorporation into the cell membrane, which presumably promotes the expression of latent tumor-associated antigens, induced a marked increase in specific immunogenicity of tumor cells.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P22303|||Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) |
0.79 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Inactive ingredient | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cholesteryl hemisuccinate treatment protects rodents from the toxic effects of acetaminophen, adriamycin, carbon tetrachloride, chloroform and galactosamine. | 1997 Feb 7 |
|
| How well does cholesteryl hemisuccinate mimic cholesterol in saturated phospholipid bilayers? | 2014 Feb |
Patents
Sample Use Guides
The anticholinesterase properties of tetrahydroaminoacridine (THA, Tacrine), alpha-tocopheryl hemisuccinate (TS), and cholesteryl hemisuccinate (CS), given alone and in combination, were examined in vitro. TS and CS are weak inhibitors of BChE (IC50 of 100 microM and 168 microM, respectively) but potent inhibitors of ACHE (IC50 of 1.73 microM and 0.79 microM, respectively. The addition of 0.5 microM CS or TS to an ACHE preparation reduced THA's IC50 value from 0.40 microM or 0.18 microM, respectively. Inhibition of AChE by THA, TS and CS are mixed non-competitive while THA inhibition of BChE is mixed non-competitive and TS and CS inhibition of BChE are simple non-competitive. Ihibition of cholinesterases by TS and CS occurs immediately (50 to 75%), during the first 30 min of incubation (25 to 50%) and is dependent on the anionic charged portion of the molecule.
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1510-21-0
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216-148-6
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DTXSID10934145
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T3J4KS4201
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138742
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628321
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65082
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SUBSTANCE RECORD
