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Menopause symptom GA30.0 Withdrawn from market [1]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) 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
UNII
6V5034L121
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.