levonorgestrel

Also known as (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy- 1,2,6,7,8,9,10,11,12,13,14,15,16, 17- tetradecahydrocyclopenta[a] phenanthren-3-one, Jadelle, 17alpha-Ethynyl-18-homo-19-nortestosterone, 13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one, Postinor, (-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one, 18-Methylnorethisterone, 18-Methyl-17-alpha-ethynyl-19-nortestosterone

Key facts

Drug.synonyms: LNG; LNG-EC; d-Norgestrel; d(–)-Norgestrel; D-Norgestrel; WY-5104; SH-90999; NSC-744007; 18-Methylnorethisterone; 17α-Ethynyl-18-methyl-19-nortestosterone; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one; 13β-Ethyl-17α-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
Drug.IUPAC_name: (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Drug.C: 21
Drug.H: 28
Drug.O: 2 <!--
Drug.LogP: 3.8 unk param -->
Drug.SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
Drug.StdInChI: 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/t16-,17+,18+,19-,20-,21-/m0/s1
Drug.StdInChIKey: WWYNJERNGUHSAO-XUDSTZEESA-N
Drug.melting_point: 235
Drug.melting_high: 237
Drug.Watchedfields: changed
Drug.verifiedrevid: 462091161
Drug.image: Levonorgestrel.svg
Drug.image_class: skin-invert-image
Drug.width: 225
Drug.image2: Levonorgestrel molecule ball.png
Drug.image_class2: bg-transparent

via Wikipedia infobox

Chemical data

Formula: C21H28O2
Molecular weight: 312.4 g/mol
IUPAC name: (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
InChIKey: WWYNJERNGUHSAO-XUDSTZEESA-N
XLogP: 3.3
Polar surface area: 37.3 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

7,560 papers

Effect of levonorgestrel emergency contraception on implantation and fertility: A review.Contraception · 2022
Levonorgestrel. Clinical pharmacokinetics.Clinical pharmacokinetics · 1995
Low-dose ethinylestradiol/levonorgestrel.Drugs · 2005
Levonorgestrel-releasing intra-uterine systems as female contraceptives.Expert opinion on pharmacotherapy · 2018
Levonorgestrel-Releasing Intrauterine System for Regression of Endometrial Hyperplasia.American family physician · 2021

via PubMed

Wikidata facts

Mass: 312.20893

Show 7 more facts

Commons category: Levonorgestrel
chemical formula: C₂₁H₂₈O₂
World Health Organisation international non-proprietary name: levonorgestrel
canonical SMILES: CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
defined daily dose: 1.5
isomeric SMILES: CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C
NCI Thesaurus ID: C47585

Sources (5)

via Wikidata · CC0

~24 min read

Article

31 sections

Contents

Medical uses
Birth control
Emergency birth control
Hormone therapy
Available forms
By mouth
Skin patch
Intrauterine device
Implant
Contraindications
Side effects
Overdose
Interactions
Pharmacology
Pharmacodynamics
Progestogenic activity
Antigonadotropic effects
Androgenic activity
Other activity
Pharmacokinetics
Chemistry
Synthesis
History
Society and culture
Generic names
Brand names
Availability
Accessibility
Research
References
External links

Levonorgestrel is a hormonal medication used in a number of birth control methods. It is combined with an estrogen to make combination birth control pills. As an emergency birth control, sold under the brand names Plan B One-Step and Julie, among others, it is useful within 72 hours of unprotected sex. The more time that has passed since sex, the less effective the medication becomes. Levonorgestrel works by preventing or delaying ovulation so an egg cannot be released. The dosage used for emergency contraception is ineffective when ovulation has already occurred, and has been found to have no effect on implantation. It decreases the chances of pregnancy by 57–93%. In an intrauterine device (IUD), such as Mirena among others, it is effective for the long-term prevention of pregnancy. A levonorgestrel-releasing implant is also available in some countries.

Common side effects include nausea, breast tenderness, headaches, and increased, decreased, or irregular menstrual bleeding. When used as an emergency contraceptive, if pregnancy occurs, there is no evidence that its use harms the fetus. It is safe to use during breastfeeding. Birth control that contains levonorgestrel will not change the risk of sexually transmitted infections. It is a progestin and has effects similar to those of the hormone progesterone. It works primarily by preventing ovulation and closing off the cervix to prevent the passage of sperm.