SCH-57050

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C39H47NO6
Molecular Weight	625.7936
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OEKMGABCSLYWOP-DHUJRADRSA-N

InChI=1S/C39H47NO6/c1-26-32-20-19-31(45-37(42)39(5,6)7)25-33(32)46-35(34(26)27-11-17-30(18-12-27)44-36(41)38(2,3)4)28-13-15-29(16-14-28)43-24-23-40-21-9-8-10-22-40/h11-20,25,35H,8-10,21-24H2,1-7H3/t35-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C39H47NO6
Molecular Weight	625.7936
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11850228
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
UDP-glucuronosyltransferase 1-1 15 Target ID: CHEMBL1287617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11179460	Substrate 661
UDP-glucuronosyltransferase 1-3 6 Target ID: CHEMBL3542435 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11179460	Substrate 661
UDP-glucuronosyltransferase 1-9 11 Target ID: CHEMBL1743319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11179460	Substrate 661
Estrogen receptor 75 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10418981	Antagonist 2778	0.52 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26391916 http://en.pharmacodia.com/web/drug/1_2035.html	Primary		Phase III 656	Unknown Approved Use Unknown
Hot flushes 4 Sources: https://clinicaltrials.gov/ct2/show/NCT01452373	Palliative		Phase III 656	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
SULT2A1 5 AOX1 3	UGT1A3 422 UGT1A7 236 UGT1A10 291 UGT1A8 283 UGT2B4 249 UGT2B7 389 UGT1A9 380 UGT1A1 418 UGT1A4 347 UGT2B15 203 UGT1A6 307 UGT2B17 213

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
AOX1 3	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31289113/	yes [IC50 29.5 uM]
SULT2A1 9	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30918069/	yes [IC50 7 uM]

Drug as victim

Target	Modality	Activity
UGT1A7 236	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	likely
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	major [Km 19 uM]
UGT1A1 418	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	major [Km 63 uM]
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	major [Km 64 uM]
UGT1A8 283	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	major
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	no
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	no
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	no
UGT2B15 203	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	no
UGT2B17 213	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	no
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	no
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11179460/	no

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	155435
Compound Cloud	155436
Hairui	ACJB003	http://www.hairuichem.com/en/product/search.do?q=ACJB003
Lan Pharmatech	LQT-B02702
Lan Pharmatech	LQT-B02703
MolPort	MolPort-046-426-364	https://www.molport.com/shop/molecule-link/MolPort-046-426-364
MuseChem	R045581	https://www.musechem.com/product/R045581.html
eMolecules	260193583	https://orderbb.emolecules.com/search/#?query=260193583
eMolecules	85163536	https://orderbb.emolecules.com/search/#?query=85163536
mcule	MCULE-1919792695	https://mcule.com/MCULE-1919792695/
mcule	MCULE-5402471704	https://mcule.com/MCULE-5402471704/

PubMed

Title	Date	PubMed
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	9270018
EM-652 (SCH 57068), a third generation SERM acting as pure antiestrogen in the mammary gland and endometrium.	1999 Apr-Jun	10418981
Glucuronidation of the nonsteroidal antiestrogen EM-652 (SCH 57068), by human and monkey steroid conjugating UDP-glucuronosyltransferase enzymes.	2001 Mar	11179460

Patents

Sample Use Guides

In Vivo Use Guide

20 mg daily for 6-8 months

Route of Administration: Oral

In Vitro Use Guide

As measured by competition studies in human breast cancer tissue, the anity 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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:47:03 GMT 2023` Edited by `admin` on `Fri Dec 15 15:47:03 GMT 2023`
Record UNII	XCR716LECP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCH-57050

Code

English

SCH57050

Code

English

EM-800

Code

English

PROPANOIC ACID, 2,2-DIMETHYL-, (2S)-3-(4-(2,2-DIMETHYL-1-OXOPROPOXY)PHENYL)-4-METHYL-2-(4-(2-(1-PIPERIDINYL)ETHOXY)PHENYL)-2H-1-BENZOPYRAN-7-YL ESTER

Systematic Name

English

EM800

Code

English

Code System Code Type Description

EPA CompTox

DTXSID60939529

Created by admin on Fri Dec 15 15:47:03 GMT 2023 , Edited by admin on Fri Dec 15 15:47:03 GMT 2023

PRIMARY

PUBCHEM

9873952

Created by admin on Fri Dec 15 15:47:03 GMT 2023 , Edited by admin on Fri Dec 15 15:47:03 GMT 2023

PRIMARY

FDA UNII

XCR716LECP

Created by admin on Fri Dec 15 15:47:03 GMT 2023 , Edited by admin on Fri Dec 15 15:47:03 GMT 2023

PRIMARY

CAS

182167-03-9

Created by admin on Fri Dec 15 15:47:03 GMT 2023 , Edited by admin on Fri Dec 15 15:47:03 GMT 2023

PRIMARY

Related Record Type Details


					815LJ9X0D1

ACOLBIFENE

METABOLITE ACTIVE -> PRODRUG

Amount:

Related Record Type Details


					815LJ9X0D1

ACOLBIFENE

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11850228Curator'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

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11850228
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

Drug as perpetrator