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Identification
Name Chlorotrianisene
Accession Number DB00269 (APRD00715)
Type small molecule
Groups approved
Description

A powerful synthetic, non-steroidal estrogen. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Chloortrianisestrol
  • Chlorestrolo
  • Chlorotrianisenum [INN-Latin]
  • Chlorotrianisine
  • Chlorotrianizen
  • Chlortrianisen
  • Chlortrianisene
  • Chlortrianisenum
  • Chlortrianisestrol
  • Chlortrianisoestrolum
  • Chlortrianizen
  • Clorotrianiseno [INN-Spanish]
  • CTA
Brand names
  • Anisene
  • Chlorotrisin
  • Clorestrolo
  • Clorotrisin
  • Hormonisene
  • Khlortrianizen
  • Merbentul
  • Metace
  • Rianil
  • Tace
  • Tace-Fn
  • Trianisestrol
Brand name mixtures Not Available
Categories
  • Antineoplastic Agents
  • Antineoplastic Agents, Hormonal
  • Estrogens, Non-Steroidal
CAS number 569-57-3
Weight Average: 380.864
Monoisotopic: 380.117922245
Chemical Formula C23H21ClO3
InChI Key InChIKey=BFPSDSIWYFKGBC-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
1-[2-chloro-1,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
SMILES
COC1=CC=C(C=C1)C(Cl)=C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Stilbenes
Substructures
  • Stilbenes
  • Alkanes and Alkenes
  • Phenols and Derivatives
  • Phenylpropenes
  • Ethers
  • Halogen Derivatives
  • Benzene and Derivatives
  • Isoprenes
  • Aromatic compounds
  • Anisoles
  • Styrene Derivatives
  • Phenyl Esters
Pharmacology
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.
Pharmacodynamics 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.
Mechanism of action Chlorotrianisene binds to the estrogen receptor on various estrogen receptor bearing cells. Target cells include cells in the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.
Absorption Absorption following oral administration is rapid.
Volume of distribution Not Available
Protein binding 50-80%
Metabolism

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.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Banner pharmacaps inc
  • Sanofi aventis us llc
Packagers Not Available
Dosage forms
Form Route Strength
Capsule Oral
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 115 oC
Experimental Properties
Property Value Source
logP 6.4 PhysProp
Predicted Properties
Property Value Source
water solubility 1.99e-04 g/l ALOGPS
logP 5.95 ALOGPS
logP 5.43 ChemAxon Molconvert
logS -6.28 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 27.69 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 119.17 ChemAxon Molconvert
polarizability 41.60 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00269 Link_out
PubChem Compound 11289 Link_out
PubChem Substance 46508811 Link_out
ChemSpider 10815 Link_out
ChEBI 3641 Link_out
ChEMBL 3641 Link_out
Therapeutic Targets Database DAP001012 Link_out
PharmGKB PA448955 Link_out
Drug Product Database 0 Link_out
Drugs.com http://www.drugs.com/mtm/chlorotrianisene.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Chlorotrianisene Link_out
ATC Codes
  • G03CA06
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Estrogen receptor

Pharmacological action: yes
Actions: agonist

Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues

Organism class: human
UniProt ID: P03372 Link_out
Gene: ESR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kupfer D, Bulger WH: 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. Pubmed
  2. Jordan VC, Gosden B: Inhibition of the uterotropic activity of estrogens and antiestrogens by the short acting antiestrogen LY117018. Endocrinology. 1983 Aug;113(2):463-8. Pubmed
  3. Wang JY, Xu BH, Tian LJ, Wang Y: [Clinical characteristics and potential prognostic factors of breast cancer patients with liver metastases] Zhonghua Zhong Liu Za Zhi. 2006 Aug;28(8):612-6. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:02

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.