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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H78O3
Molecular Weight 667.099
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of 7.BETA.-HYDROXYCHOLESTERYL 3-OLEATE

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H](C)CCCC(C)C

InChI

InChIKey=MEOFSGIGKMJGOJ-FTKDFQSGSA-N
InChI=1S/C45H78O3/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-42(47)48-37-28-30-44(5)36(32-37)33-41(46)43-39-27-26-38(35(4)24-22-23-34(2)3)45(39,6)31-29-40(43)44/h14-15,33-35,37-41,43,46H,7-13,16-32H2,1-6H3/b15-14-/t35-,37+,38-,39+,40+,41+,43+,44+,45-/m1/s1

HIDE SMILES / InChI
7β-hydroxycholesteryl-3-oleate has been shown to inhibit astrogliosis and intracranial glioblastoma growth. Local administration of 7β-hydroxycholesteryl-3-oleate inhibits growth of experimental rat C6 glioblastoma. These data suggest that 7β-hydroxycholesteryl-3-oleate might be useful for local glioblastoma chemotherapy. 7β-hydroxycholesteryl-3-oleate is a potent inhibitor of the endogenous cholesterol biosynthesis in brain showing a correlation between cholesterogenesis and reactive astrocyte proliferation. 7β-hydroxycholesteryl-3-oleate can reduce the astrocytic reaction following spinal cord injury, promoting the serotonergic reinnervation of a denervated territory. On 17 December 2010, orphan designation (EU/3/10/816) was granted by the European Commission to Intsel Chimos SA, France, for 7-beta-hydroxy cholesteryl-3-beta-oleate for the treatment of glioma. The substance is going to be injected directly into the brain tumour contained within liposomes, which are expected to carry the medicine into the glioma cells.

Approval Year

PubMed

PubMed

TitleDatePubMed
Local administration of 7 beta-hydroxycholesteryl-3-oleate inhibits growth of experimental rat C6 glioblastoma.
1994 Feb 15
Effect of oxysterol treatment on cholesterol biosynthesis and reactive astrocyte proliferation in injured rat brain cortex.
1995 Nov

Sample Use Guides

Wistar rats: Α midline skin incision was made, and the skull was perforated using α dental drill 2 mm right of the midline and 4.5 mm anterior to the lambda. Lesions were performed by lowering an epoxylite-coated (except at the tip) stainless steel electrode 2.0 mm under the skull surface and applying α 2-mA DC for 10 s. Treatment consisted of injection, in the lesion site, of 2 uΙ of α liposome suspension (containing 12 nmol of 7 beta-hydroxycholesteryl-3-oleate ) within 4 min using α Hamilton syringe
Route of Administration: Other
Name Type Language
7.BETA.-HYDROXYCHOLESTERYL 3-OLEATE
Common Name English
7-BETA-HYDROXYCHOLESTERYL-3-BETA-OLEATE
Systematic Name English
7.BETA.-HYDROXYCHOLESTEROL 3-OLEATE
Common Name English
CHOLEST-5-ENE-3,7-DIOL, 3-(9Z)-9-OCTADECENOATE, (3.BETA.,7.BETA.)-
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 343511
Created by admin on Sat Dec 16 04:55:37 GMT 2023 , Edited by admin on Sat Dec 16 04:55:37 GMT 2023
Code System Code Type Description
SMS_ID
100000183814
Created by admin on Sat Dec 16 04:55:37 GMT 2023 , Edited by admin on Sat Dec 16 04:55:37 GMT 2023
PRIMARY
EU-Orphan Drug
EU/3/10/816(POSITIVE)
Created by admin on Sat Dec 16 04:55:37 GMT 2023 , Edited by admin on Sat Dec 16 04:55:37 GMT 2023
PRIMARY Treatment of glioma 17/12/2010 Positive
CAS
141099-60-7
Created by admin on Sat Dec 16 04:55:37 GMT 2023 , Edited by admin on Sat Dec 16 04:55:37 GMT 2023
PRIMARY
FDA UNII
A59FMD985O
Created by admin on Sat Dec 16 04:55:37 GMT 2023 , Edited by admin on Sat Dec 16 04:55:37 GMT 2023
PRIMARY
PUBCHEM
70179250
Created by admin on Sat Dec 16 04:55:37 GMT 2023 , Edited by admin on Sat Dec 16 04:55:37 GMT 2023
PRIMARY