DT-Web

DB06713 - Norelgestromin


Identification
Name Norelgestromin
Accession Number DB06713
Type small molecule
Description Norelgestromin is a drug used in contraception. Norelgestromin is the active progestin responsible for the progestational activity that occurs in women after application of ORTHO EVRA patch.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 327.4605
Groups approved
Monoisotopic Weight 327.219829177
Pharmacology
Indication Norelgestromin is used for contraception and menopausal hormonal therapy. Norelgestromin may potentially be used in breast cancer treatment due to its inhibitory effect on estrone sulfatase . They convert sulfated steroid precursors to estrogen during pregnancy.
Mechanism of action Norelgestromin inhibits estrone sulfatase, which converts sulfated steroid precursors to estrogen during pregnancy. Norgelgestromin/ethinylestradiol suppresses follicular development, induces changes to the endometrium, which decreases chances of implantation and thickens the cervical mucus, impeding sperm swimming into the uterus. It also has similar agonisting binding affinities as its parent compound, Norgestimate, for progesterone and estrogen receptors.
Absorption Not Available
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms Not Available
Interactions
Drug Interactions
Drug Mechanism of interaction
Artemether Artemether may decrease the effectiveness of norelgestromin by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Bexarotene Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norelgestromin, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Colesevelam Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness.
Food Interactions Not Available

Targets


Progesterone receptor
Name Progesterone receptor
Gene Name PGR
Pharmacological action yes
Actions agonist
References
  • Pasqualini JR: Breast cancer and steroid metabolizing enzymes: the role of progestogens. Maturitas. 2009 Dec;65 Suppl 1:S17-21. Epub 2009 Dec 3. - Pubmed
  • London RS, Chapdelaine A, Upmalis D, Olson W, Smith J: Comparative contraceptive efficacy and mechanism of action of the norgestimate-containing triphasic oral contraceptive. Acta Obstet Gynecol Scand Suppl. 1992;156:9-14. - Pubmed
  • Graziottin A: A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. - Pubmed
  • Kuhnz W, Fritzemeier KH, Hegele-Hartung C, Krattenmacher R: Comparative progestational activity of norgestimate, levonorgestrel-oxime and levonorgestrel in the rat and binding of these compounds to the progesterone receptor. Contraception. 1995 Feb;51(2):131-9. - Pubmed
  • Juchem M, Pollow K, Elger W, Hoffmann G, Mobus V: Receptor binding of norgestimate--a new orally active synthetic progestational compound. Contraception. 1993 Mar;47(3):283-94. - Pubmed
DTHybrid score 0.7749

Enzymes


Steryl-sulfatase
Name Steryl-sulfatase
Gene Name STS
Actions inhibitor
References
  • Pasqualini JR, Chetrite GS: Recent insight on the control of enzymes involved in estrogen formation and transformation in human breast cancer. J Steroid Biochem Mol Biol. 2005 Feb;93(2-5):221-36. - Pubmed
  • Pasqualini JR, Caubel P, Friedman AJ, Philippe JC, Chetrite GS: Norelgestromin as selective estrogen enzyme modulator in human breast cancer cell lines. Effect on sulfatase activity in comparison to medroxyprogesterone acetate. J Steroid Biochem Mol Biol. 2003 Feb;84(2-3):193-8. - Pubmed
  • Pasqualini JR: The selective estrogen enzyme modulators in breast cancer: a review. Biochim Biophys Acta. 2004 Jun 7;1654(2):123-43. - Pubmed
DTHybrid score 1.5552

Predictions


Id Partner name Gene Name Score
136 Estrogen receptor ESR1 0.1298
146 Androgen receptor AR 0.0486
4512 Cytochrome P450 3A4 CYP3A4 0.0474
871 Glucocorticoid receptor NR3C1 0.0359
737 Mineralocorticoid receptor NR3C2 0.0293
1588 Multidrug resistance protein 1 ABCB1 0.0218
6241 Nuclear receptor coactivator 2 NCOA2 0.0206
756 Sex hormone-binding globulin SHBG 0.0195
6107 Cytochrome P450 3A7 CYP3A7 0.0173
596 3-oxo-5-alpha-steroid 4-dehydrogenase 1 SRD5A1 0.0172
66 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type II HSD3B2 0.0167
4118 Cytochrome P450 3A5 CYP3A5 0.0163
3811 Cytochrome P450 19A1 CYP19A1 0.0159
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0151
1649 Small inducible cytokine A2 CCL2 0.0127
226 Gonadotropin-releasing hormone receptor GNRHR 0.0103
3923 Cholinesterase BCHE 0.0094
290 Prostaglandin G/H synthase 2 PTGS2 0.0091
723 Cytosolic phospholipase A2 PLA2G4A 0.0091
232 Corticosteroid-binding globulin SERPINA6 0.0088
862 Multidrug resistance-associated protein 1 ABCC1 0.0082
4924 Cytochrome P450 2C8 CYP2C8 0.008
4757 Cytochrome P450 2C9 CYP2C9 0.0073
6016 Cytochrome P450 2C19 CYP2C19 0.0062
4119 Cytochrome P450 2D6 CYP2D6 0.0057
587 Serum albumin ALB 0.0051
380 Cytochrome P450 17A1 CYP17A1 0.0036
6141 Sodium/bile acid cotransporter SLC10A1 0.003
6147 Solute carrier family 22 member 3 SLC22A3 0.0025
1898 Cytochrome P450 1B1 CYP1B1 0.0025
776 Bile salt export pump ABCB11 0.0025
6144 Solute carrier family 22 member 2 SLC22A2 0.0021
6145 Solute carrier family 22 member 1 SLC22A1 0.0021
5718 Cytochrome P450 2A6 CYP2A6 0.002
6024 Cytochrome P450 1A1 CYP1A1 0.002
4200 Cytochrome P450 1A2 CYP1A2 0.0016
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