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Details

Stereochemistry ACHIRAL
Molecular Formula C30H31NO3.CH4O3S
Molecular Weight 549.678
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIOXIFENE MESYLATE

SMILES

CS(O)(=O)=O.COC1=CC=C(C=C1)C2=C(C(=O)C3=CC=C(OCCN4CCCC4)C=C3)C5=C(CC2)C=CC=C5

InChI

InChIKey=RAHJASYQAFJPFD-UHFFFAOYSA-N
InChI=1S/C30H31NO3.CH4O3S/c1-33-25-13-8-23(9-14-25)28-17-12-22-6-2-3-7-27(22)29(28)30(32)24-10-15-26(16-11-24)34-21-20-31-18-4-5-19-31;1-5(2,3)4/h2-3,6-11,13-16H,4-5,12,17-21H2,1H3;1H3,(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C30H31NO3
Molecular Weight 453.572
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Trioxifene (LY133314) is a selective estrogen receptor modulator (SERM) with competitive binding activity against estradiol for estrogen receptor alpha (ERalpha) and antagonistic activity against ERalpha-mediated gene expression. Trioxifene has demonstrated activity in dimethyl-benzanthracene-induced mammary carcinoma in rats and human breast cancer patients. Trioxifene mesylate, an antiestrogen with a high FR affinity, was developed with the hope of improving the response rate of ER-positive patients, especially those with a borderline concentration of ER in their tumors. When used in vitro and in vivo, trioxifene has been shown to bind to the estradiol receptors with a binding affinity exceeding that of estradiol by a factor 1.7, whereas tamoxifen has a relative affinity of only 0.18 compared with trioxifene.

Approval Year

PubMed

PubMed

TitleDatePubMed
Differential interaction of antiestrogens with cytosol estrogen receptors.
1981 Apr
Importance of the alkylaminoethoxy side-chain for the estrogenic and antiestrogenic actions of tamoxifen and trioxifene in the immature rat uterus.
1982 Aug
The selective estrogen receptor modulator trioxifene (LY133314) inhibits metastasis and extends survival in the PAIII rat prostatic carcinoma model.
2003 Sep 15

Sample Use Guides

Fifty-two patients were randomly allocated to dose schedules of 5 mg, 10 mg, and 20 mg orally twice daily.
Route of Administration: Oral
In Vitro Use Guide
Trioxifene competed with [3H]-E2 binding to rhER alpha with an IC50 of 203.49 nM and a Ki of 20.84 nM. The compound was less potent at displacing [3H]-E2 binding to rhER beta, with an IC50 of 1506.04 nM and a Ki of 144.85 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:19:11 UTC 2023
Edited
by admin
on Fri Dec 15 15:19:11 UTC 2023
Record UNII
63ZD22G88L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIOXIFENE MESYLATE
USAN  
USAN  
Official Name English
TRIOXIFENE MESILATE
Common Name English
TRIOXIFENE MESYLATE [USAN]
Common Name English
3,4-DIHYDRO-2-(P-METHOXYPHENYL)-1-NAPHTHYL P-(2-(1-PYRROLIDINYL)ETHOXY)PHENYL KETONE METHANESULFONATE
Common Name English
COMPOUND 133314
Code English
COMPOUND-133314
Code English
METHANONE, (3,4-DIHYDRO-2-(4-METHOXYPHENYL)-1-NAPHTHALENYL)(4-(2-(1-PYRROLIDINYL)ETHOXY)PHENYL)-, METHANESULFONATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Fri Dec 15 15:19:11 UTC 2023 , Edited by admin on Fri Dec 15 15:19:11 UTC 2023
Code System Code Type Description
MESH
C014934
Created by admin on Fri Dec 15 15:19:11 UTC 2023 , Edited by admin on Fri Dec 15 15:19:11 UTC 2023
PRIMARY
FDA UNII
63ZD22G88L
Created by admin on Fri Dec 15 15:19:11 UTC 2023 , Edited by admin on Fri Dec 15 15:19:11 UTC 2023
PRIMARY
CAS
68307-81-3
Created by admin on Fri Dec 15 15:19:11 UTC 2023 , Edited by admin on Fri Dec 15 15:19:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID00218461
Created by admin on Fri Dec 15 15:19:11 UTC 2023 , Edited by admin on Fri Dec 15 15:19:11 UTC 2023
PRIMARY
NCI_THESAURUS
C1414
Created by admin on Fri Dec 15 15:19:11 UTC 2023 , Edited by admin on Fri Dec 15 15:19:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL110057
Created by admin on Fri Dec 15 15:19:11 UTC 2023 , Edited by admin on Fri Dec 15 15:19:11 UTC 2023
PRIMARY
PUBCHEM
50138
Created by admin on Fri Dec 15 15:19:11 UTC 2023 , Edited by admin on Fri Dec 15 15:19:11 UTC 2023
PRIMARY
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