U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H31NO4.ClH
Molecular Weight 494.022
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACOLBIFENE HYDROCHLORIDE

SMILES

Cl.CC1=C([C@@H](OC2=C1C=CC(O)=C2)C3=CC=C(OCCN4CCCCC4)C=C3)C5=CC=C(O)C=C5

InChI

InChIKey=BYQDPIXWTVEVEA-JMAPEOGHSA-N
InChI=1S/C29H31NO4.ClH/c1-20-26-14-11-24(32)19-27(26)34-29(28(20)21-5-9-23(31)10-6-21)22-7-12-25(13-8-22)33-18-17-30-15-3-2-4-16-30;/h5-14,19,29,31-32H,2-4,15-18H2,1H3;1H/t29-;/m0./s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/10418981 | http://en.pharmacodia.com/web/drug/1_2035.html | http://adisinsight.springer.com/drugs/800013630

Acolbifene, the active metabolite of EM-800, was identified as a pure antagonist that acts on both activation domains of the ERs. It is in Phase III clinical trials for the prevention of breast cancer and vasomotor symptoms (Hot flush) in postmenopausal women. Most commonly reported adverse events included irregular menses, leg/muscle cramps, diarrhea, and hot flashes. No serious adverse events were reported.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 29.5 uM]
yes [IC50 7 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Blockade of the stimulatory effect of estrogens, OH-tamoxifen, OH-toremifene, droloxifene, and raloxifene on alkaline phosphatase activity by the antiestrogen EM-800 in human endometrial adenocarcinoma Ishikawa cells.
1997 Aug 15
EM-652 (SCH 57068), a third generation SERM acting as pure antiestrogen in the mammary gland and endometrium.
1999 Apr-Jun
Glucuronidation of the nonsteroidal antiestrogen EM-652 (SCH 57068), by human and monkey steroid conjugating UDP-glucuronosyltransferase enzymes.
2001 Mar
Patents

Sample Use Guides

20 mg daily for 6-8 months
Route of Administration: Oral
As measured by competition studies in human breast cancer tissue, the anity of EM-652 (Ki=0.047 nM, RBA=291, relative to 17b-estradiol set at 100) studied in the presence of ethanol was 2.9 higher than that of estradiol itself (RBA=6.62).
Name Type Language
ACOLBIFENE HYDROCHLORIDE
USAN  
USAN  
Official Name English
(2S)-3-(4-HYDROXYPHENYL)-4-METHYL-2-(4-(2-PIPERIDIN-1-YLETHOXY)PHENYL)-2H-CHROMEN-7-OL, HYDROCHLORIDE
Systematic Name English
SCH57068 HCL
Code English
ACOLBIFENE HYDROCHLORIDE [USAN]
Common Name English
2H-1-BENZOPYRAN-7-OL, 3-(4-HYDROXYPHENYL)-4-METHYL-2-(4-(2-(1-PIPERIDINYL)ETHOXY)PHENYL)-, HYDROCHLORIDE, (2S)-
Systematic Name English
ACOLBIFENE HCL
Common Name English
SCH-57068 HYDROCHLORIDE
Code English
Classification Tree Code System Code
NCI_THESAURUS C1821
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
Code System Code Type Description
FDA UNII
KXC7811DBY
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
PRIMARY
USAN
LL-83
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
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CAS
252555-01-4
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
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ChEMBL
CHEMBL68055
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
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NCI_THESAURUS
C65213
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
PRIMARY
SMS_ID
300000044626
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
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PUBCHEM
155436
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID30948108
Created by admin on Fri Dec 15 16:14:16 GMT 2023 , Edited by admin on Fri Dec 15 16:14:16 GMT 2023
PRIMARY