DT-Web

DB00890 - Dienestrol


Identification
Name Dienestrol
Accession Number DB00890 (APRD00917)
Type small molecule
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
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 266.3343
Groups approved
Monoisotopic Weight 266.13067982
Pharmacology
Indication For use in the treatment of atrophic vaginitis and kraurosis vulvae.
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).
Protein binding 50 to 80%
Biotransformation Hepatic.
Route of elimination Not Available
Toxicity Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Estrogen receptor
Name Estrogen receptor
Gene Name ESR1
Pharmacological action yes
Actions agonist
References
  • 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
  • Grove RI, Korach KS: Estrogen stimulation of phosphatidylinositol metabolism in mouse uterine tissue. Endocrinology. 1987 Sep;121(3):1083-8. - Pubmed
  • 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
  • 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.
  • 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
  • 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
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 0.6836

Predictions


Id Partner name Gene Name Score
6241 Nuclear receptor coactivator 2 NCOA2 0.2306
869 Estrogen receptor beta ESR2 0.0805
614 Progesterone receptor PGR 0.063
4512 Cytochrome P450 3A4 CYP3A4 0.038
3811 Cytochrome P450 19A1 CYP19A1 0.0258
1588 Multidrug resistance protein 1 ABCB1 0.0187
4757 Cytochrome P450 2C9 CYP2C9 0.0181
66 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type II HSD3B2 0.0149
756 Sex hormone-binding globulin SHBG 0.0139
6228 Nuclear receptor coactivator 1 NCOA1 0.0122
687 Tyrosine-protein phosphatase non-receptor type 1 PTPN1 0.0118
146 Androgen receptor AR 0.0115
4200 Cytochrome P450 1A2 CYP1A2 0.0115
4924 Cytochrome P450 2C8 CYP2C8 0.0109
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0097
6024 Cytochrome P450 1A1 CYP1A1 0.0094
381 Prolactin receptor PRLR 0.0093
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0092
57 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type I HSD3B1 0.0083
2107 Microtubule-associated protein 1A MAP1A 0.0075
6030 Cytochrome P450 2B6 CYP2B6 0.0074
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0062
596 3-oxo-5-alpha-steroid 4-dehydrogenase 1 SRD5A1 0.0057
1852 Microtubule-associated protein 2 MAP2 0.0056
6141 Sodium/bile acid cotransporter SLC10A1 0.0055
6016 Cytochrome P450 2C19 CYP2C19 0.0054
587 Serum albumin ALB 0.0052
1898 Cytochrome P450 1B1 CYP1B1 0.005
5718 Cytochrome P450 2A6 CYP2A6 0.005
6013 Cytochrome P450 2E1 CYP2E1 0.0047
1649 Small inducible cytokine A2 CCL2 0.0046
1284 Nuclear receptor subfamily 1 group I member 2 NR1I2 0.0045
776 Bile salt export pump ABCB11 0.0045
871 Glucocorticoid receptor NR3C1 0.0041
373 Transthyretin TTR 0.004
226 Gonadotropin-releasing hormone receptor GNRHR 0.004
6145 Solute carrier family 22 member 1 SLC22A1 0.0037
4210 Toll-like receptor 4 TLR4 0.0036
6020 Aldehyde oxidase AOX1 0.0035
862 Multidrug resistance-associated protein 1 ABCC1 0.0034
992 Protein tyrosine kinase 2 beta PTK2B 0.0033
1291 cAMP response element-binding protein CREB1 0.0033
3810 Catechol O-methyltransferase COMT 0.0031
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.0031
4118 Cytochrome P450 3A5 CYP3A5 0.0028
6017 Cholesterol side-chain cleavage enzyme, mitochondrial CYP11A1 0.0027
3809 Estrogen-related receptor gamma ESRRG 0.0027
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0026
3830 Calreticulin CALR 0.0025
6035 Nuclear receptor ROR-beta RORB 0.0024
6034 Hydroxyindole O-methyltransferase ASMT 0.0024
6036 Eosinophil peroxidase EPX 0.0024
6142 Solute carrier family 22 member 8 SLC22A8 0.0023
571 Melatonin receptor type 1A MTNR1A 0.0021
362 Melatonin receptor type 1B MTNR1B 0.0021
765 Indoleamine 2,3-dioxygenase IDO1 0.002
817 DNA topoisomerase 2-alpha TOP2A 0.002
6153 Solute carrier organic anion transporter family member 4A1 SLCO4A1 0.002
696 Kappa-type opioid receptor OPRK1 0.002
467 Delta-type opioid receptor OPRD1 0.002
6107 Cytochrome P450 3A7 CYP3A7 0.0019
847 Mu-type opioid receptor OPRM1 0.0019
6158 Solute carrier organic anion transporter family member 1C1 SLCO1C1 0.0018
6147 Solute carrier family 22 member 3 SLC22A3 0.0017
6157 Solute carrier organic anion transporter family member 1B3 SLCO1B3 0.0017
243 Ribosyldihydronicotinamide dehydrogenase [quinone] NQO2 0.0016
468 Cytochrome P450 4A11 CYP4A11 0.0016
1024 Solute carrier family 22 member 11 SLC22A11 0.0015
6144 Solute carrier family 22 member 2 SLC22A2 0.0015
1192 Sulfotransferase 1A1 SULT1A1 0.0015
380 Cytochrome P450 17A1 CYP17A1 0.0014
6149 Solute carrier family 22 member 10 SLC22A10 0.0014
6167 Organic solute transporter subunit beta OSTB 0.0014
6166 Organic solute transporter subunit alpha OSTA 0.0014
465 Calmodulin CALM1 0.0013
1757 Myeloperoxidase MPO 0.0013
6104 Dimethylaniline monooxygenase [N-oxide-forming] 1 FMO1 0.0013
737 Mineralocorticoid receptor NR3C2 0.0012
6155 ATP-binding cassette transporter sub-family C member 11 ABCC11 0.0012
4119 Cytochrome P450 2D6 CYP2D6 0.0012
6085 Fatty acid-binding protein, intestinal FABP2 0.0011
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.0011
6160 Solute carrier organic anion transporter family member 3A1 SLCO3A1 0.0011
6101 Dimethylaniline monooxygenase [N-oxide-forming] 3 FMO3 0.0011
4604 Liver carboxylesterase 1 CES1 0.001
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0009
6148 Multidrug resistance-associated protein 7 ABCC10 0.0008
2164 Multidrug resistance-associated protein 4 ABCC4 0.0008
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0007
1729 Solute carrier family 22 member 6 SLC22A6 0.0007
↑