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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H36O11
Molecular Weight 548.5788
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BRUCEANTIN

SMILES

[H][C@]12[C@@H](OC(=O)\C=C(/C)C(C)C)C(=O)O[C@]3([H])C[C@@]4([H])C(C)=C(O)C(=O)C[C@]4(C)[C@@]5([H])[C@@H](O)[C@H](O)[C@]1(OC[C@@]235)C(=O)OC

InChI

InChIKey=IRQXZTBHNKVIRL-GOTQHHPNSA-N
InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1

HIDE SMILES / InChI

Molecular Formula C28H36O11
Molecular Weight 548.5788
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 10
E/Z Centers 1
Optical Activity UNSPECIFIED

Bruceantin is a compound isolated from Brucea antidysenteriea, a plant used in Ethiopia as an anticancer treatment. The primary action of Bruceantin appears to be an inhibition of protein synthesis which takes place at the ribosomal level. Bruceantin induced marked decreases of c-myc mRNA and protein expression in all cell lines. Bruceantin-induced c-myc downregulation might trigger cell death mechanisms preferentially in those cell lines with wild-type p53 protein expression. Bruceantin was evaluated in three separate phase I clinical trials in patients with various types of solid tumors. Hypotension, nausea, and vomiting were common side effects at higher doses, but hematologic toxicity was moderate to insignificant and manifested mainly as thrombocytopenia. Bruceantin was then tested in two separate phase II trials including adult patients with metastatic breast cancer and malignant melanoma. No objective tumor regressions were observed, and clinical trials were terminated.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Translational and posttranslational regulation of c-Myc
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 514 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Altering chemosensitivity by modulating translation elongation.
2009
NF-kappaB inhibitors from Brucea javanica exhibiting intracellular effects on reactive oxygen species.
2010 Sep
Bruceantin inhibits multiple myeloma cancer stem cell proliferation.
2016 Sep
Patents

Sample Use Guides

5 mg/m2/week X 4, every 6 weeks, with a reduction to 3 mg/m2 for patients with hepatic metastases.
Route of Administration: Intravenous
Treatment of HL-60 and RPMI 8226 cells with bruceantin resulted in the formation of apoptotic bodies, as observed by DAPI staining. After a 24 h treatment, the IC50 for apoptosis was 6.7 ng/mL (12.2 nM) and 7.0 ng/mL (12.8 nM), respectively, for these two cell lines.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:42:47 GMT 2023
Edited
by admin
on Sat Dec 16 10:42:47 GMT 2023
Record UNII
S3NW88DI4T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BRUCEANTIN
MI  
Common Name English
PICRAS-3-EN-21-OIC ACID, 15-(((2E)-3,4-DIMETHYL-1-OXO-2-PENTEN-1-YL)OXY)-13,20-EPOXY-3,11,12-TRIHYDROXY-2,16-DIOXO-, METHYL ESTER, (11.BETA.,12.ALPHA.,15.BETA.)-
Systematic Name English
NSC-165563
Code English
NCI-165563
Code English
(-)-BRUCEANTIN
Common Name English
BRUCEANTIN [MI]
Common Name English
Code System Code Type Description
NCI_THESAURUS
C1025
Created by admin on Sat Dec 16 10:42:47 GMT 2023 , Edited by admin on Sat Dec 16 10:42:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID701024969
Created by admin on Sat Dec 16 10:42:47 GMT 2023 , Edited by admin on Sat Dec 16 10:42:47 GMT 2023
PRIMARY
CAS
41451-75-6
Created by admin on Sat Dec 16 10:42:47 GMT 2023 , Edited by admin on Sat Dec 16 10:42:47 GMT 2023
PRIMARY
MERCK INDEX
m2733
Created by admin on Sat Dec 16 10:42:47 GMT 2023 , Edited by admin on Sat Dec 16 10:42:47 GMT 2023
PRIMARY Merck Index
PUBCHEM
5281304
Created by admin on Sat Dec 16 10:42:47 GMT 2023 , Edited by admin on Sat Dec 16 10:42:47 GMT 2023
PRIMARY
FDA UNII
S3NW88DI4T
Created by admin on Sat Dec 16 10:42:47 GMT 2023 , Edited by admin on Sat Dec 16 10:42:47 GMT 2023
PRIMARY
NSC
165563
Created by admin on Sat Dec 16 10:42:47 GMT 2023 , Edited by admin on Sat Dec 16 10:42:47 GMT 2023
PRIMARY