Norgestrel
Identification
- Name
- Norgestrel
- Accession Number
- DB09389
- Description
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
Structure for Norgestrel (DB09389)
- 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.
- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism AProgesterone receptor binderHumans A3-oxo-5-alpha-steroid 4-dehydrogenase 1 inhibitorHumans UAndrogen receptor 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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 Unlock Additional DataAbametapir The serum concentration of Norgestrel can be increased when it is combined with Abametapir. Abciximab Norgestrel may decrease the anticoagulant activities of Abciximab. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Norgestrel. Acetaminophen The metabolism of Norgestrel can be increased when combined with Acetaminophen. Acetazolamide The metabolism of Norgestrel can be increased when combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norgestrel. Acetylsalicylic acid Norgestrel may decrease the anticoagulant activities of Acetylsalicylic acid. Acitretin The therapeutic efficacy of Norgestrel can be decreased when used in combination with Acitretin. Alitretinoin The therapeutic efficacy of Norgestrel can be decreased when used in combination with Alitretinoin. Alpelisib The metabolism of Norgestrel can be increased when combined with Alpelisib. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- 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
- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataOvrette Tablets Tablet Oral Pfizer Canada Ulc Not applicable Not applicable Canada 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cryselle Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Oral A-S Medication Solutions 2002-07-24 2019-09-30 US 
Cryselle Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Kit Oral Physicians Total Care, Inc. 2003-10-16 Not applicable US 
Cryselle Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Oral Teva Pharmaceuticals USA, Inc. 2002-07-24 Not applicable US 
Cryselle Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Oral REMEDYREPACK INC. 2018-05-17 2020-03-27 US Elinest Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Kit Oral NorthStar Rx LLC 2012-01-07 Not applicable US Lo-femenal 21 Tablets Norgestrel (300 mcg) + Ethinylestradiol (30 mcg) Tablet Oral Pfizer Canada Ulc 2001-05-14 2014-04-04 Canada Lo-ovral-28 Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Kit Oral Physicians Total Care, Inc. 1976-03-01 2012-06-30 US Lo/Ovral Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Tablet Oral Wyeth Ltd. 1975-04-01 2008-12-31 US Lo/Ovral-28 Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Kit Oral A S Medication Solutions 1976-03-01 Not applicable US Lo/Ovral-28 Norgestrel (0.3 mg/1) + Ethinylestradiol (0.03 mg/1) Kit Oral Akrimax Pharmaceuticals, LLC 1976-03-01 2014-05-01 US
Categories
- ATC Codes
- G03FA10 — Norgestrel and estrogen
- G03FA — Progestogens and estrogens, fixed combinations
- G03F — PROGESTOGENS AND ESTROGENS IN COMBINATION
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G03FB — Progestogens and estrogens, sequential preparations
- G03F — PROGESTOGENS AND ESTROGENS IN COMBINATION
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Adrenal Cortex Hormones
- Combination Contraceptives (with Estrogen and derivatives)
- Contraceptive Agents, Female
- Contraceptives, Oral
- Contraceptives, Oral, Synthetic
- Contraceptives, Postcoital
- 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
- Norpregnanes
- Norpregnenes
- Norsteroids
- Progestin Contraceptives
- Progestins
- Progestogens and Estrogens, Sequential Preparations
- 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 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)
Chemical Identifiers
- UNII
- 3J8Q1747Z2
- 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
- External Links
- KEGG Drug
- D00954
- PubChem Compound
- 4542
- PubChem Substance
- 347827838
- ChemSpider
- 4383
- 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
Phase Status Purpose Conditions Count 3 Not Yet Recruiting Treatment Female Infertility 1 3 Recruiting Other Contraception 1 3 Terminated Other Contraception 1 2 Completed Treatment Contraception 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral Tablet, film coated Oral 0.5 mg Tablet, coated Oral 50 mcg Tablet Oral Tablet Oral Tablet, coated Oral 2 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00583 mg/mL ALOGPS logP 3.25 ALOGPS logP 3.66 ChemAxon logS -4.7 ALOGPS pKa (Strongest Acidic) 17.91 ChemAxon pKa (Strongest Basic) -1.5 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 37.3 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 92.03 m3·mol-1 ChemAxon Polarizability 36.83 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
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 LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-03di-2924000000-eb357f64cb0652555ccb
Targets
- 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
- 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. [PubMed:11521119]
- 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
- 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. [PubMed:11075290]
- 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
- 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. [PubMed:3139361]
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
- 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. [PubMed:23715232]
- 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
- 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. [PubMed:639763]
- 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. [PubMed:8631191]
Drug created on November 30, 2015 12:10 / Updated on October 21, 2020 01:55
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