Norgestrel

Identification

Summary

Norgestrel is a progestin used in combination with ethinyl estradiol for oral contraception and prevention of pregnancy in women.

Brand Names
Cryselle 28, Elinest 28 Day, Lo/ovral 28 Day, Low-ogestrel 28 Day
Generic Name
Norgestrel
DrugBank Accession Number
DB09389
Background

Norgestrel is synthetic steroidal progestin that is used in combination with ethinyl estradiol for oral contraception. Norgestrel is composed of a racemic mixture of two stereoisomers, dextronorgestrel and levonorgestrel. However, only the levorotary enantiomer (levonorgestrel) is biologically active.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 312.453
Monoisotopic: 312.208930142
Chemical Formula
C21H28O2
Synonyms
  • 17-ethynyl-17-hydroxy-18a-homoestr-4-en-3-one
  • LD norgestrel
  • Methylnorethindrone
  • Norgestrel
  • Norgestrelum
External IDs
  • WY 3707
  • WY-3707
  • WY3707

Pharmacology

Indication

Norgestrel in combination with ethinyl estradiol is indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Norgestrel (and more specifically the active stereoisomer levonorgestrel) binds to the progesterone and estrogen receptors within the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like levonorgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. Loss of the LH surge inhibits ovulation and thereby prevents pregnancy.

TargetActionsOrganism
AProgesterone receptor
binder
Humans
A3-oxo-5-alpha-steroid 4-dehydrogenase 1
inhibitor
Humans
UAndrogen receptor
agonist
Humans
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
Medicalerrors
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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.
DrugInteraction
AbametapirThe serum concentration of Norgestrel can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of adverse effects can be increased when Norgestrel is combined with Abciximab.
AcenocoumarolThe risk or severity of adverse effects can be increased when Norgestrel is combined with Acenocoumarol.
AcetaminophenThe metabolism of Norgestrel can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Norgestrel can be increased when combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norgestrel.
AcitretinThe therapeutic efficacy of Norgestrel can be decreased when used in combination with Acitretin.
AlitretinoinThe therapeutic efficacy of Norgestrel can be decreased when used in combination with Alitretinoin.
AlpelisibThe metabolism of Norgestrel can be increased when combined with Alpelisib.
AlteplaseThe risk or severity of adverse effects can be increased when Norgestrel is combined with Alteplase.
Interactions
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Food Interactions
  • Avoid grapefruit products. Grapefruit inhibits CYP3A metabolism, which may increase the serum concentration of norgestrel.
  • Avoid St. John's Wort. This herb induces CYP3A metabolism and may reduce serum levels of norgestrel.
  • Take at the same time every day.

Products

Products
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Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ovrette TabletsTabletOralPfizer Canada UlcNot applicableNot applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CryselleNorgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralREMEDYREPACK INC.2018-05-172020-03-27US flag
CryselleNorgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralRpk Pharmaceuticals, Inc.2002-07-24Not applicableUS flag
CryselleNorgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralPhysicians Total Care, Inc.2003-10-16Not applicableUS flag54868 485120180907 15195 1xobe06
CryselleNorgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralTeva Pharmaceuticals USA, Inc.2002-07-24Not applicableUS flag00555 9049 58 nlmimage10 4236a175
CYCLO-PROGYNOVA 2 MG+2 MG/0.5 MG KAPLI TABLET, 21 ADETNorgestrel (0.5 mg) + Estradiol valerate (2 mg) + Estradiol valerate (2 mg)Tablet, film coatedOralBAYER TÜRK KİMYA SAN. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
ElinestNorgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralNorthStar Rx LLC2012-01-07Not applicableUS flag
Lo-femenal 21 TabletsNorgestrel (300 mcg) + Ethinylestradiol (30 mcg)TabletOralPfizer Canada Ulc2001-05-142014-04-04Canada flag
Lo-ovral-28Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralPhysicians Total Care, Inc.1976-03-012012-06-30US flag
Lo/OvralNorgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1)TabletOralWyeth Ltd.1975-04-012008-12-31US flag
Lo/Ovral-28Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralAkrimax Pharmaceuticals, LLC1976-03-012014-05-01US flag

Categories

ATC Codes
G03FA10 — Norgestrel and estrogenG03FB01 — Norgestrel and estrogenG03AA06 — Norgestrel and ethinylestradiol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, 3-oxo steroid, 17-hydroxy steroid (CHEBI:7630)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
6533-00-2
InChI Key
WWYNJERNGUHSAO-UHFFFAOYSA-N
InChI
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3
IUPAC Name
15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
SMILES
CCC12CCC3C(CCC4=CC(=O)CCC34)C1CCC2(O)C#C

References

General References
Not Available
KEGG Drug
D00954
PubChem Compound
4542
PubChem Substance
347827838
ChemSpider
4383
RxNav
7518
ChEBI
7630
ChEMBL
CHEMBL2107797
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Norgestrel
AHFS Codes
  • 68:12.00 — Contraceptives
FDA label
Download (6.67 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPolycystic Ovaries Syndrome1
4RecruitingTreatmentInfertility1
3Active Not RecruitingOtherContraception1
3TerminatedOtherContraception1
2CompletedTreatmentContraception1
Not AvailableCompletedNot AvailableInfertility / Polycystic Ovarian Syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitOral
Tablet, sugar coatedOral
Tablet, film coatedOral
TabletOral
TabletOral
Kit; tablet, coatedOral
Tablet, coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00583 mg/mLALOGPS
logP3.25ALOGPS
logP3.66ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)17.91ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.03 m3·mol-1ChemAxon
Polarizability36.83 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-2924000000-eb357f64cb0652555ccb

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Binder
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
  1. Hammond GL, Rabe T, Wagner JD: Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. Am J Obstet Gynecol. 2001 Aug;185(2 Suppl):S24-31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Electron carrier activity
Specific Function
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and andro...
Gene Name
SRD5A1
Uniprot ID
P18405
Uniprot Name
3-oxo-5-alpha-steroid 4-dehydrogenase 1
Molecular Weight
29458.18 Da
References
  1. Rabe T, Kowald A, Ortmann J, Rehberger-Schneider S: Inhibition of skin 5 alpha-reductase by oral contraceptive progestins in vitro. Gynecol Endocrinol. 2000 Aug;14(4):223-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
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
  1. Kloosterboer HJ, Vonk-Noordegraaf CA, Turpijn EW: Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 1988 Sep;38(3):325-32. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
References
  1. Moreno I, Quinones L, Catalan J, Miranda C, Roco A, Sasso J, Tamayo E, Caceres D, Tchernitchin AN, Gaete L, Saavedra I: [Influence of CYP3A4/5 polymorphisms in the pharmacokinetics of levonorgestrel: a pilot study]. Biomedica. 2012 Oct-Dec;32(4):570-7. doi: 10.1590/S0120-41572012000400012. [Article]
  2. List of Drugs Interacting with CYP3A4 - The Cancer Therapy Evaluation Program (CTEP) [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Schurenkamper P, Lisse K: [In-vitro studies on the effect of D-norgestrel and norethisterone acetate on the formation of sex steroids in the human ovary]. Endokrinologie. 1978 Feb;71(1):25-34. [Article]
  2. Heikinheimo O, Gordon K, Williams RF, Hodgen GD: Inhibition of ovulation by progestin analogs (agonists vs antagonists): preliminary evidence for different sites and mechanisms of actions. Contraception. 1996 Jan;53(1):55-64. [Article]

Drug created on November 30, 2015 19:10 / Updated on May 07, 2021 21:05