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569-57-3 molecular structure
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1-[2-chloro-1,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene

ChemBase ID: 154
Molecular Formular: C23H21ClO3
Molecular Mass: 380.86404
Monoisotopic Mass: 380.11792221
SMILES and InChIs

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

Cite this record

CBID:154 http://www.chembase.cn/molecule-154.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-[2-chloro-1,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
IUPAC Traditional name
1-[2-chloro-1,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
chlorotrianisene
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
CAS Number
569-57-3
EC Number
209-318-6
MDL Number
MFCD00048044
PubChem SID
24892934
160963617
46508811
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
C7128 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 5.427335  LogD (pH = 7.4) 5.427335 
Log P 5.427335  Molar Refractivity 119.1713 cm3
Polarizability 42.46953 Å3 Polar Surface Area 27.69 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 5.95  LOG S -6.28 
Solubility (Water) 1.99e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Hydrophobicity(logP)
6.4 expand Show data source
RTECS
KV0600000 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Admin Routes
Oral expand Show data source
Protein Bound
50 to 80% expand Show data source
Legal Status
Discontinued expand Show data source
Pregnancy Category
X (US) expand Show data source
Purity
~95% expand Show data source
Empirical Formula (Hill Notation)
C23H21ClO3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank - DB00269 external link
Item Information
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 external link
Biochem/physiol Actions
Non-steroidal estrogenic compound which is metabolized by liver microsomal enzymes primarily to the mono-O-demethylated derivative.1

REFERENCES

REFERENCES

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PATENTS

PATENTS

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