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Menopause symptom GA30.0 Withdrawn from market [1]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
Logarithm of the Partition Coefficient (xlogp) 6.4
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
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
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]

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) 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 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.