Identification
- Summary
Norelgestromin is a progestin used for the prevention of pregnancy in women who elect to use a transdermal patch as a method of contraception.
- Brand Names
- Evra, Xulane, Zafemy
- Generic Name
- Norelgestromin
- DrugBank Accession Number
- DB06713
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Norelgestromin (DB06713)
- Weight
- Average: 327.468
Monoisotopic: 327.219829178 - Chemical Formula
- C21H29NO2
- Synonyms
- 17-Deacetylnorgestimate
- 17-Deacylnorgestimate
- 18-Methylnorethindrone oxime
- D-Norgestrel 3-oxime
- Deacetylnorgestimate
- Levonorgestrel 3-oxime
- Levonorgestrel oxime
- Norelgestromin
- Norelgestromina
- Norplant 3-oxime
- External IDs
- BRN 4202099
- RWJ 10553
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.
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- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Norelgestromin is used for contraception and menopausal hormonal therapy transdermally or in combination with ethinyl estradiol as a vaginal ring. Norelgestromin, in combination with ethinyl estradiol inhibits ovulation by suppressing gonadotropins.
- 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.
Target Actions Organism AProgesterone receptor agonistHumans USerum albumin Not Available Humans UAndrogen receptor partial agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Norelgestromin can be increased when it is combined with Abametapir. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Norelgestromin. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Norelgestromin. Acetaminophen The metabolism of Norelgestromin can be increased when combined with Acetaminophen. Acetazolamide The metabolism of Norelgestromin can be increased when combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norelgestromin. Alpelisib The metabolism of Norelgestromin can be increased when combined with Alpelisib. Alteplase The therapeutic efficacy of Alteplase can be decreased when used in combination with Norelgestromin. Aminoglutethimide The metabolism of Norelgestromin can be increased when combined with Aminoglutethimide. Amiodarone The metabolism of Norelgestromin can be decreased when combined with Amiodarone. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Evra Norelgestromin (6 mg) + Ethinylestradiol (600 mcg) Patch Transdermal Gedeon Richter Plc. 2020-12-22 Not applicable EU 
Evra Norelgestromin (6 mg) + Ethinylestradiol (600 mcg) Patch Transdermal Gedeon Richter Plc. 2020-12-22 Not applicable EU Evra Norelgestromin (200 mcg / 24 hour) + Ethinylestradiol (35 mcg / 24 hour) Patch, extended release Transdermal Searchlight Pharma Inc 2003-12-24 Not applicable Canada 
Evra Norelgestromin (6 mg) + Ethinylestradiol (600 mcg) Patch Transdermal Gedeon Richter Plc. 2020-12-22 Not applicable EU Evra -(6/0.75) Norelgestromin (6 mg) + Ethinylestradiol (0.75 mg) Patch, extended release Transdermal Janssen Pharmaceuticals 2002-10-24 2006-02-22 Canada EVRA TRANSDERMAL PATCH (6 mg/600 mcg) Norelgestromin (6 mg) + Ethinylestradiol (600 mcg) Patch Transdermal JOHNSON & JOHNSON PTE. LTD. 2003-09-17 Not applicable Singapore Norelgestromin and Ethinly Estradiol Norelgestromin (150 ug/1d) + Ethinylestradiol (35 ug/1d) Patch Transdermal Amneal Pharmaceuticals NY LLC 2021-02-26 Not applicable US 
Ortho Evra Norelgestromin (150 ug/1d) + Ethinylestradiol (35 ug/1d) Patch, extended release Transdermal Janssen Pharmaceutical, Inc. 2001-11-20 2015-08-31 US Ortho Evra Norelgestromin (6 mg/7[USP'U]) + Ethinylestradiol (0.75 mg/7[USP'U]) Patch, extended release Transdermal Physicians Total Care, Inc. 2002-09-13 2011-02-28 US Ortho Evra Norelgestromin (6 mg/7d) + Ethinylestradiol (0.75 mg/7d) Patch, extended release Transdermal Ortho-McNeil-Janssen Pharmaceutical, Inc. 2001-11-20 2012-07-31 US
Categories
- ATC Codes
- G03AA13 — Norelgestromin and ethinylestradiol
- Drug Categories
- Adrenal Cortex Hormones
- Amines
- Combination Contraceptives (with Estrogen and derivatives)
- Contraceptive Agents, Female
- Contraceptive Agents, Hormonal
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Hormonal Contraceptives for Systemic Use
- Hydroxylamines
- Norpregnanes
- Norpregnenes
- Norsteroids
- Pharmaceutical Preparations
- Progestins
- Reproductive Control Agents
- Sex Hormones and Modulators of the Genital System
- Steroids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Estrane steroids
- Direct Parent
- Estrane steroids
- Alternative Parents
- 17-hydroxysteroids / Delta-4-steroids / Ynones / Tertiary alcohols / Ketoximes / Cyclic alcohols and derivatives / Acetylides / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 17-hydroxysteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Delta-4-steroid / Estrane-skeleton / Hydrocarbon derivative / Hydroxysteroid / Ketoxime
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- R0TAY3X631
- CAS number
- 53016-31-2
- InChI Key
- ISHXLNHNDMZNMC-XUDSTZEESA-N
- InChI
- 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/t16-,17+,18+,19-,20-,21-/m0/s1
- IUPAC Name
- (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol
- SMILES
- [H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(C=C3CC[C@@]21[H])=NO
References
- Synthesis Reference
Zoltan Tuba, Sandor Maho, Gyorgy Keseru, Jozsef Kozma, Janos Horvath, Gabor Balogh, "Process of making isomers of norelgestromin and methods using the same." U.S. Patent US20050032764, issued February 10, 2005.
US20050032764- General References
- Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. [Article]
- Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D05205
- PubChem Compound
- 62930
- PubChem Substance
- 99443265
- ChemSpider
- 56648
- 326374
- ChEBI
- 135398
- ChEMBL
- CHEMBL1200807
- ZINC
- ZINC000410428674
- Wikipedia
- Norelgestromin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Bone; Disorder, Development and Growth 1 4 Completed Other Healthy Subjects (HS) 1 4 Completed Treatment Contraception 1 4 Completed Treatment Contraception / Female Contraception 1 4 Completed Treatment Female Contraception 1 3 Completed Prevention Contraception 1 3 Completed Treatment Contraception 1 3 Completed Treatment Contraception / Female Contraception 2 2 Completed Prevention Human Immunodeficiency Virus (HIV) Infections / Pregnancy 1 2 Completed Treatment Metrorrhagia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Patch Transdermal 600 mcg Solution Transdermal Patch, extended release Transdermal Patch Transdermal - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5876746 No 1999-03-02 2015-11-20 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00605 mg/mL ALOGPS logP 3.18 ALOGPS logP 3.67 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 11.47 Chemaxon pKa (Strongest Basic) 3.12 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 52.82 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 95.85 m3·mol-1 Chemaxon Polarizability 38.4 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9958 Blood Brain Barrier + 0.9436 Caco-2 permeable + 0.5219 P-glycoprotein substrate Substrate 0.6364 P-glycoprotein inhibitor I Non-inhibitor 0.5618 P-glycoprotein inhibitor II Non-inhibitor 0.8348 Renal organic cation transporter Non-inhibitor 0.6802 CYP450 2C9 substrate Non-substrate 0.7663 CYP450 2D6 substrate Non-substrate 0.8257 CYP450 3A4 substrate Substrate 0.6965 CYP450 1A2 substrate Non-inhibitor 0.7341 CYP450 2C9 inhibitor Non-inhibitor 0.6798 CYP450 2D6 inhibitor Non-inhibitor 0.8528 CYP450 2C19 inhibitor Non-inhibitor 0.529 CYP450 3A4 inhibitor Non-inhibitor 0.5718 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.846 Ames test Non AMES toxic 0.5162 Carcinogenicity Non-carcinogens 0.8087 Biodegradation Not ready biodegradable 0.9948 Rat acute toxicity 2.4050 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7294 hERG inhibition (predictor II) Non-inhibitor 0.7284
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
- Gene Name
- PGR
- Uniprot ID
- P06401
- Uniprot Name
- Progesterone receptor
- Molecular Weight
- 98979.96 Da
References
- 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. [Article]
- 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. [Article]
- Graziottin A: A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Hammond GL, Abrams LS, Creasy GW, Natarajan J, Allen JG, Siiteri PK: Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. Contraception. 2003 Feb;67(2):93-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 Da
References
- Prifti S, Lelle I, Strowitzki T, Rabe T: Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells. Gynecol Endocrinol. 2004 Jul;19(1):18-21. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sulfuric ester hydrolase activity
- Specific Function
- Conversion of sulfated steroid precursors to estrogens during pregnancy.
- Gene Name
- STS
- Uniprot ID
- P08842
- Uniprot Name
- Steryl-sulfatase
- Molecular Weight
- 65491.72 Da
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. [Article]
- 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. [Article]
- Pasqualini JR: The selective estrogen enzyme modulators in breast cancer: a review. Biochim Biophys Acta. 2004 Jun 7;1654(2):123-43. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
Drug created at May 16, 2010 17:47 / Updated at February 21, 2021 18:52