Structure via PubChem · Public domain (PubChem)
لوونورژسترول
Sign in to saveAlso 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
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
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 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1982
- Admin. routes
- oral, parenteral, topical
- Indications
- endometriosis, hemorrhage, HIV infection, ovarian carcinoma
via ChEMBL · EBI
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
- Subclass of
- norgestrel
- Mass
- 312.20893
- Has use
- medication
Show 9 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
- subject has role
- essential medicine
- medical condition treated
- adenomyosis
via Wikidata · CC0