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Menopause symptom	GA30.0	Withdrawn from market	[1]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

Affected Organisms

Humans and other mammals

ATC Code

G03CA06: Chlorotrianisene

G03CA: Natural and semisynthetic estrogens, plain

G03C: ESTROGENS

G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

G: GENITO URINARY SYSTEM AND SEX HORMONES

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

380.9

Logarithm of the Partition Coefficient (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 []
Metabolism: The drug is metabolized via the liver []

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Deep vein thrombosis	Not Available	F2	OTNFSM49	[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: CHEMBL3641
CAS Number: 569-57-3
UNII: 6V5034L121
DrugBank ID: DB00269
TTD ID: D0X0KJ

Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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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]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Antithrombin-III (SERPINC1)	OTDFATG0	ANT3_HUMAN	Gene/Protein Processing	[4]
Prothrombin (F2)	OTNFSM49	THRB_HUMAN	Drug Response	[2]

Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	FDA Approved Drug Products from FDA Official Website. 2008. Application Number: (ANDA) 017675.
2	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
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	The effect of chlorotrianisene as postpartum lactation suppression on blood coagulation factors. Am J Obstet Gynecol. 1979 Jul 1;134(5):518-22. doi: 10.1016/0002-9378(79)90832-9.