1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene

• ChemBase ID: 154
• Molecular Formular: C23H21ClO3
• Molecular Mass: 380.86404
• Monoisotopic Mass: 380.11792221
• SMILES: Cl/C(=C(/c1ccc(OC)cc1)\c1ccc(OC)cc1)/c1ccc(OC)cc1
• Canonical SMILES: COc1ccc(cc1)/C(=C(\c1ccc(cc1)OC)/Cl)/c1ccc(cc1)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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene; 1-[2-chloro-1,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
• IUPAC Traditional name: chlorotrianisene; 1-[2-chloro-1,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
• Brand Name: Anisene; Chlorotrisin; Clorestrolo; Clorotrisin; Hormonisene; Khlortrianizen; Merbentul; Metace; Rianil; Tace; Tace-Fn; Trianisestrol
• Synonyms: Chlorotrianisenum [INN-Latin]; Chlorotrianisine; Chlorotrianizen; Chlortrianisen; Chlortrianisene; Chlortrianisenum; Chlortrianisestrol; Chlortrianisoestrolum; Clorotrianiseno [INN-Spanish]; CTA; Chloortrianisestrol; Chlorestrolo; Chlortrianizen; Chlorotrianisene; TACE; Chlorotrianisene

Database IDs

• CAS Number: 569-57-3
• EC Number: 209-318-6
• MDL Number: MFCD00048044
• PubChem SID: 46508811; 24892934; 160963617
• PubChem CID: 11289
• CHEBI ID: 3641
• ATC CODE: G03CA06
• CHEMBL: 1200761
• Chemspider ID: 10815
• DrugBank ID: DB00269
• KEGG ID: D00269
• Unique Ingredient Identifier: 6V5034L121
• Wikipedia Title: Chlorotrianisene

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.427335
• LogD (pH = 7.4): 5.427335
• Log P: 5.427335
• Molar Refractivity: 119.1713 cm^3
• Polarizability: 42.46953 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.95
• LOG S: -6.28
• Solubility (Water): 1.99e-04 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 6.4

Safety Information

• RTECS: KV0600000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: Oral
• Protein Bound: 50 to 80%
• Legal Status: Discontinued
• Pregnancy Category: X (US)

Product Information

• Purity: ~95%
• Empirical Formula (Hill Notation): C23H21ClO3

DETAILS

DrugBank - DB00269

• Drug Groups: approved
• Description: A powerful synthetic, non-steroidal estrogen. [PubChem]
• Indication: Used to treat symptoms of menopause, deficiencies in ovary function (including underdevelopment of female sexual characteristics and some types of infertility), and in rare cases, prostate cancer. Chlorotrianisene may also be used to prevent breast engorgement following childbirth.
• Pharmacology: Chlorotrianisene is a nonsteroidal synthetic estrogen. After menopause, when the body no longer produces estrogen, chlorotrianisene is used as a simple replacement of estrogen. The estrogen-stimulated endometrium may bleed within 48-72 hours after discontinuance of estrogen therapy. Paradoxically, prolonged estrogen therapy may cause shrinkage of the endometrium and an increase in size of the myometrium. Estrogens have a weak anabolic effect and may cause sodium retention with associated fluid retention and edema. Estrogens may also decrease elevated blood cholesterol and phospholipid concentrations. Estrogens affect bone by increasing calcium deposition and accelerating epiphyseal closure, following initial growth stimulation. During the preovulatory or nonovulatory phase of the menstrual cycle, estrogen is the principal determinant in the onset of menstruation. A decline of estrogenic activity at the end of the menstrual cycle also may induce menstruation; however, the cessation of progesterone secretion is the most important factor during the mature ovulatory phase of the menstrual cycle. The benefit derived from estrogen therapy in the prevention of postpartum breast engorgement must be carefully weighed against the potential increased risk of puerperal thromboembolism associated with the use of large doses of estrogens.
• Toxicity: Acute overdosage of large doses of oral contraceptives in chidren reportedly produces almost no toxicity except nausea and vomiting. Acute overdosage of estrogens may cause nausea, and withdrawal bleeding may occur in females.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized principally in the liver, although the kidneys, gonads, and muscle tissues may be involved to some extent. The metabolic fate of the synthetic estrogens has not been fully elucidated.
• Absorption: Absorption following oral administration is rapid.
• Protein Binding: 50-80%
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - C7128

Biochem/physiol Actions
Non-steroidal estrogenic compound which is metabolized by liver microsomal enzymes primarily to the mono-O-demethylated derivative.1