Norelgestromin
Norelgestromin is only found in individuals that have used or taken this drug. It 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. Norelgestromin inhibits estrone slifatase, which converts slifated steroid precursors to estrogen during pregnancy. Norgelgestromin/ethinylestradiol suppresses follicliar 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.
MOLSDFPDBSMILESInChI
Structure for HMDB15658 (Norelgestromin)
C21H29NO2
327.4605
327.219829177
15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol
orthra evra
53016-31-2
CCC12CCC3C(CCC4=CC(CCC34)=NO)C1CCC2(O)C#C
InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3
ISHXLNHNDMZNMC-UHFFFAOYSA-N
This compound belongs to the class of chemical entities known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
Chemical entities
Organic compounds
Lipids and lipid-like moleclies
Steroids and steroid derivatives
Estrane steroids
Aliphatic homopolycyclic compounds
Not Available
Expected but not Quantified
Solid
Not Available
Not Available
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Not Available
None
None
DB06713
Not Available
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11498267
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Not Available
Norelgestromin
HMDB15658
HMDB15658
Not Available
13752005
Not Available
Not Available
- Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. [PubMed:11499185 ]
- Abrams LS, Skee DM, Wong FA, Anderson NJ, Leese PT: Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. J Clin Pharmacol. 2001 Nov;41(11):1232-7. [PubMed:11697756 ]
- Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. [PubMed:15966567 ]
Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- Conversion of sulfated steroid precursors to estrogens during pregnancy.
- Gene Name:
- STS
- Uniprot ID:
- P08842
- Molecular weight:
- 65491.72
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:15860265 ]
- 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:12711003 ]
- Pasqualini JR: The selective estrogen enzyme modulators in breast cancer: a review. Biochim Biophys Acta. 2004 Jun 7;1654(2):123-43. [PubMed:15172700 ]
- General function:
- Involved in sequence-specific DNA binding transcription factor activity
- Specific function:
- Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
- Gene Name:
- PGR
- Uniprot ID:
- P06401
- Molecular weight:
- 98980.0
References
- Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. [PubMed:11499185 ]
- Pasqualini JR: Breast cancer and steroid metabolizing enzymes: the role of progestogens. Maturitas. 2009 Dec;65 Suppl 1:S17-21. doi: 10.1016/j.maturitas.2009.11.006. Epub 2009 Dec 3. [PubMed:19962254 ]
- 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:1324557 ]
- Graziottin A: A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. [PubMed:17107221 ]
- 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:7750291 ]
- 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:8384965 ]
- General function:
- Involved in sequence-specific DNA binding transcription factor activity
- 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. Can activate the transcriptional activity of TFF1
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular weight:
- 66215.4
References
- Pasqualini JR: Differential effects of progestins on breast tissue enzymes. Maturitas. 2003 Dec 10;46 Suppl 1:S45-54. [PubMed:14670645 ]
- Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. [PubMed:2175153 ]
- Shields-Botella J, Duc I, Duranti E, Puccio F, Bonnet P, Delansorne R, Paris J: An overview of nomegestrol acetate selective receptor binding and lack of estrogenic action on hormone-dependent cancer cells. J Steroid Biochem Mol Biol. 2003 Nov;87(2-3):111-22. [PubMed:14672731 ]