Details of the Drug

General Information of Drug (ID: DMSV2WZ)

Drug Name

Chlorotrianisene

Synonyms

Anisene; Chloortrianisestrol; Chlorestrolo; Chlorotrianisenum; Chlorotrianisestrol; Chlorotrianisine; Chlorotrianizen; Chlorotrisin; Chlortrianisen; Chlortrianisene; Chlortrianisenum; Chlortrianisestrol; Chlortrianisoestrolum; Chlortrianizen; Clorestrolo; Clorotrianisene; Clorotrianiseno; Clorotrisin; Hormonisene; Khlortrianizen; Merbentul; Metace; Rianil; TACE; Triagen; Trianisestrol; Chlorotrianisene [Nonsteroidal oestrogens]; Clorotrianisene [DCIT]; Chlorotrianisene (INN); Chlorotrianisene [BAN:INN]; Chlorotrianisene [INN:BAN]; Chlorotrianisenum [INN-Latin]; Clorotrianiseno [INN-Spanish]; TACE (TN); Tace (pharmaceutical); Tace-fn; Chlorotris(p-methoxyphenyl)ethylene; Tri-p-anisylchloroethylene; Tris(p-methoxyphenyl)chloroethylene; 1,1',1''-(1-Chloro-1-ethenyl-2-ylidene)-tris(4-methoxybenzene); 1,1',1''-(2-chloroethene-1,1,2-triyl)tris(4-methoxybenzene); 1,1',1''-(2-chloroethene-1,1,2-triyl)tris[4-(methyloxy)benzene]; 1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene

Indication

Disease Entry	ICD 11	Status	REF
Menopause symptom	GA30.0	Withdrawn from market	[1]

Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

380.9

Topological Polar Surface Area (xlogp)

6.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is rapidly absorbed following oral administration [2]
Metabolism: The drug is metabolized via the liver [2]

Chemical Identifiers

Formula: C23H21ClO3
IUPAC Name: 1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
Canonical SMILES: COC1=CC=C(C=C1)C(=C(C2=CC=C(C=C2)OC)Cl)C3=CC=C(C=C3)OC
InChI: InChI=1S/C23H21ClO3/c1-25-19-10-4-16(5-11-19)22(17-6-12-20(26-2)13-7-17)23(24)18-8-14-21(27-3)15-9-18/h4-15H,1-3H3
InChIKey: BFPSDSIWYFKGBC-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 11289
ChEBI ID: CHEBI:3641
CAS Number: 569-57-3
DrugBank ID: DB00269
TTD ID: D0X0KJ

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Estrogen receptor (ESR)	TTZAYWL	ESR1_HUMAN	Binder	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2008. Application Number: (ANDA) 017675.
2	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
3	Inactivation of the uterine estrogen receptor binding of estradiol during P-450 catalyzed metabolism of chlorotrianisene (TACE). Speculation that TACE antiestrogenic activity involves covalent binding to the estrogen receptor. FEBS Lett. 1990 Feb 12;261(1):59-62.
4	Modulators of vascular sex hormone receptors and their effects in estrogen-deficiency states associated with menopause. Recent Pat Cardiovasc Drug Discov. 2008 Nov;3(3):165-86.
5	Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201.
6	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
7	17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8.
8	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 620).
9	Clinical pipeline report, company report or official report of Shionogi (2011).
10	Effect of selective estrogen receptor modulators on cell proliferation and estrogen receptor activities in normal human prostate stromal and epithe... Prostate Cancer Prostatic Dis. 2009;12(4):375-81.