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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H40O4
Molecular Weight 464.6362
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CELASTROL METHYL ESTER

SMILES

COC(=O)[C@]1(C)CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]3(C)[C@@H]2C1

InChI

InChIKey=JFACETXYABVHFD-WXPPGMDDSA-N
InChI=1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1

HIDE SMILES / InChI

Description

Pristimerin, the methyl ester of celasterol, is a triterpenoid quinone methide isolated from Pristimerae indica. Pristimerin shows anticancer activity in vitro towards myeloma, prostate, breast, ovarian cancer cell lines and inhibits xenografted plasmacytoma tumors in mice. In a rat model of adjuvant arthritis, pristimerin effectively inhibited both arthritic inflammation and cartilage and bone damage in the joints. Pristimerin acts by inhibiting NF-kB signaling pathway and the 26S proteasome.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
In a study of human myeloma xenograft tumors in nude mice, a liposomal formulation of the pristimerin was developed, successfully incorporating 98.7% of the drug and given by intravenous tail vein injection. Statistically significant tumor growth inhibition occurred at pristimerin doses of 2 to 3 mg/kg intravenously twice weekly.
Route of Administration: Intravenous
In Vitro Use Guide
Cytotoxicity of pristimerin towards human myeloma cell lines U266, H929, KMS18, OPM1 was assessed by MTT assay at 72 hours. The median IC50 of pristimerin against myeloma cell lines is approximately 200 nM.