CELASTROL METHYL ESTER

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 Search

SMILES

[H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]23C)C(=O)OC

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19096011
Curator's Comment: description was created based on several sources, including https://www.nature.com/nature/journal/v173/n4417/abs/1731237b0.html | https://www.ncbi.nlm.nih.gov/pubmed/25308129

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 Target	Pharmacology	Potency
26S proteosome 7 Target ID: CHEMBL2364701 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17541980	Inhibitor 8297	3.0 µM [IC50]
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19096011	Inhibitor 8297
Vascular endothelial growth factor receptor 2 104 Target ID: P35968 Gene ID: 3791.0 Gene Symbol: KDR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22669041	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17541980 https://www.ncbi.nlm.nih.gov/pubmed/16093444 https://www.ncbi.nlm.nih.gov/pubmed/19096011	Primary		Preclinical	Unknown Approved Use Unknown
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25308129	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo.	2009 Apr 23	19096011
Pristimerin, a naturally occurring triterpenoid, protects against autoimmune arthritis by modulating the cellular and soluble immune mediators of inflammation and tissue damage.	2014 Dec	25308129

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.

Name

Type

Language

CELASTROL METHYL ESTER

Common Name

English

24,25,26-TRINOROLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID, 3-HYDROXY-9,13-DIMETHYL-2-OXO-, METHYL ESTER, (9.BETA.,13.ALPHA.,14.BETA.,20.ALPHA.)-

Systematic Name

English

NSC-99281

Code

English

PRISTIMERIN

Brand Name

English

(9.BETA.,13.ALPHA.,14.BETA.,20.ALPHA.)-3-HYDROXY-9,13-DIMETHYL-2-OXO-24,25,26-TRINOROLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID

Systematic Name

English

CELASTROL METHYL ESTER [MI]

Common Name

English

Code System Code Type Description

CAS

1258-84-0