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Identification
NameDienestrol
Accession NumberDB00890  (APRD00917)
TypeSmall Molecule
GroupsApproved
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
Synonyms
alpha-dienestrol diacetate
Cycladiene
Dehydrostilbestrol
Dienestrol
Diènestrol
Dienestrol
Dienestrolum
DV
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ortho Dienestrol Crmcream.01 %vaginalOrtho Pharmaceutical, Division Of Janssen Ortho Inc.1951-12-312002-08-02Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EstraguardNot Available
EstraguardNot Available
EstroralNot Available
Ortho DienestrolOrtho-McNeil Pharmaceutical
RestrolNot Available
RetalonNot Available
SexadienLEO Pharma A/S
SynestrolNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIRRW32X4U1F
CAS number13029-44-2
WeightAverage: 266.3343
Monoisotopic: 266.13067982
Chemical FormulaC18H18O2
InChI KeyInChIKey=NFDFQCUYFHCNBW-SCGPFSFSSA-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/b17-3+,18-4+
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenylpropene
  • Styrene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor use in the treatment of atrophic vaginitis and kraurosis vulvae.
PharmacodynamicsEstrogens 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 actionDienestrol 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.
Related Articles
AbsorptionSystemic 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 distributionNot Available
Protein binding50 to 80%
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier-0.7087
Caco-2 permeable+0.8916
P-glycoprotein substrateNon-substrate0.5491
P-glycoprotein inhibitor INon-inhibitor0.7795
P-glycoprotein inhibitor IINon-inhibitor0.9557
Renal organic cation transporterNon-inhibitor0.8322
CYP450 2C9 substrateNon-substrate0.7849
CYP450 2D6 substrateNon-substrate0.8857
CYP450 3A4 substrateNon-substrate0.544
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8605
CYP450 2D6 inhibitorNon-inhibitor0.8201
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8844
Ames testNon AMES toxic0.9658
CarcinogenicityNon-carcinogens0.7133
BiodegradationNot ready biodegradable0.7876
Rat acute toxicity1.8229 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7994
hERG inhibition (predictor II)Non-inhibitor0.8584
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Ortho mcneil pharmaceutical inc
  • Sanofi aventis us llc
  • Solvay pharmaceuticals
Packagers
Dosage forms
FormRouteStrength
Creamvaginal.01 %
Prices
Unit descriptionCostUnit
Dienestrol powder442.23USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point233-234Short, W.F. and Hobday, G.1; U.S. Patent 2,464,203; March 15,1949; assigned to Boots Pure Drug Company Limited, England.
water solubility3 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP5.9Not Available
logS-4.95ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0123 mg/mLALOGPS
logP5.18ALOGPS
logP4.83ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.1ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.36 m3·mol-1ChemAxon
Polarizability30.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.48 KB)
SpectraNot Available
References
Synthesis Reference

Short, W.F. and Hobday, G.1; U.S. Patent 2,464,203; March 15,1949; assigned to Boots
Pure Drug Company Limited, England.
Adler, E.; U.S. Patent 2,465,505; March 29,1949; assigned to Hoffmann-La Roche Inc.

General ReferencesNot Available
External Links
ATC CodesG03CB01G03CC02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (75.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
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. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
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:3334987 ]
  2. Grove RI, Korach KS: Estrogen stimulation of phosphatidylinositol metabolism in mouse uterine tissue. Endocrinology. 1987 Sep;121(3):1083-8. [PubMed:3622377 ]
  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:9048584 ]
  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:9558716 ]
  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:15276617 ]
  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. doi: 10.1016/j.bone.2008.09.016. Epub 2008 Oct 11. [PubMed:18976723 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on May 04, 2016 20:36