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Identification
Name Dienestrol
Accession Number DB00890 (APRD00917)
Type small molecule
Groups approved
Description

Dienestrol is a synthetic, non-steroidal estrogen. It is an estrogen receptor agonist. Estrogens work partly by increasing a normal clear discharge from the vagina and making the vulva and urethra healthy. Using or applying an estrogen relieves or lessens: dryness and soreness in the vagina, itching, redness, or soreness of the vulva. Conditions that are treated with vaginal estrogens include a genital skin condition (vulvar atrophy), inflammation of the vagina (atrophic vaginitis), and inflammation of the urethra (atrophic urethritis).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Dehydrostilbestrol
  • Dehydrostilboestrol
  • Dienesterol
  • Dienoestrol
Brand names
  • Agaldog
  • Cycladiene
  • Dienoestrol BP
  • Dienol
  • Dinestrol
  • Dinovex
  • DV
  • Estragard
  • Estraguard
  • Estrodienol
  • Estroral
  • Follormon
  • Gynefollin
  • Hormofemin
  • Isodienestrol
  • Oestrasid
  • Oestrodiene
  • Oestrodienol
  • Oestroral
  • Oestrovis
  • para-Dien
  • Restrol
  • Retalon
  • Sexadien
  • Synestrol
  • Teserene
  • Willnestrol
Brand name mixtures Not Available
Categories
  • Estrogens, Non-Steroidal
CAS number 84-17-3
Weight Average: 266.3343
Monoisotopic: 266.130679820
Chemical Formula C18H18O2
InChI Key InChIKey=NFDFQCUYFHCNBW-UHFFFAOYSA-N
InChI
InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3
Plain Text
IUPAC Name
4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
SMILES
CC=C(C(=CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
Plain Text
Mass Spec show (9.5 KB)
Taxonomy
Kingdom Organic
Classes
  • Stilbenes
Substructures
  • Stilbenes
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Phenols and Derivatives
  • Phenylpropenes
  • Benzene and Derivatives
  • Isoprenes
  • Aromatic compounds
  • Styrene Derivatives
  • Phenyl Esters
Pharmacology
Indication For use in the treatment of atrophic vaginitis and kraurosis vulvae.
Pharmacodynamics Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include 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. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
Mechanism of action Dienestrol is a synthetic, non-steroidal estrogen. Estrogens passively diffuse into target cells of responsive tissues, complex with the estrogen receptors, and enter the cell's nucleus to initiate or enhance gene transcription of protein synthesis after binding to DNA.
Absorption Systemic absorption and mode of action of dienestrol are undetermined.Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include 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. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
Volume of distribution Not Available
Protein binding 50 to 80%
Metabolism

Hepatic.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Ortho mcneil pharmaceutical inc
  • Sanofi aventis us llc
  • Solvay pharmaceuticals
Packagers
Dosage forms
Form Route Strength
Cream Intravaginal
Prices
Unit description Cost Unit
Dienestrol powder 442.23 USD g
Patents Not Available
Properties
State solid
Melting point 227.5 oC
Experimental Properties
Property Value Source
water solubility 3 mg/L PhysProp
logP 5.9 PhysProp
logS -4.95 [ADME Research, USCD] PhysProp
Predicted Properties
Property Value Source
water solubility 1.23e-02 g/l ALOGPS
logP 5.18 ALOGPS
logP 4.83 ChemAxon Molconvert
logS -4.33 ALOGPS
pKa 9.70 ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 40.46 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 84.36 ChemAxon Molconvert
polarizability 30.29 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00898 Link_out
KEGG Compound C08090 Link_out
PubChem Compound 667476 Link_out
PubChem Substance 46504661 Link_out
ChemSpider 2941 Link_out
ChEBI 4518 Link_out
ChEMBL 4518 Link_out
Therapeutic Targets Database DAP001015 Link_out
PharmGKB PA449302 Link_out
Drug Product Database 441295 Link_out
RxList http://www.rxlist.com/cgi/generic2/diene.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Dienestrol Link_out
ATC Codes
  • G03CB01
  • G03CC02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (75.7 KB)
Interactions
Drug Interactions
Drug Interaction
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. Juriansz RL, Huseby RA, Wilcox RB: Interactions of putative estrogens with the intracellular receptor complex in mouse Leydig cells: relationship to preneoplastic hyperplasia. Cancer Res. 1988 Jan 1;48(1):14-8. Pubmed
  2. Grove RI, Korach KS: Estrogen stimulation of phosphatidylinositol metabolism in mouse uterine tissue. Endocrinology. 1987 Sep;121(3):1083-8. Pubmed
  3. Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70. Pubmed
  4. Chae K, Lindzey J, McLachlan JA, Korach KS: Estrogen-dependent gene regulation by an oxidative metabolite of diethylstilbestrol, diethylstilbestrol-4’,4"-quinone. Steroids. 1998 Mar;63(3):149-57. Pubmed
  5. Bovee TF, Helsdingen RJ, Rietjens IM, Keijer J, Hoogenboom RL: Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. J Steroid Biochem Mol Biol. 2004 Jul;91(3):99-109. Pubmed
  6. Maru BS, Tobias JH, Rivers C, Caunt CJ, Norman MR, McArdle CA: Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. Bone. 2009 Jan;44(1):102-12. Epub 2008 Oct 11. Pubmed
  7. 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 15:07

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.