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Levonorgestrel

From Wikipedia, the free encyclopedia

Levonorgestrel chemical structure
Levonorgestrel
Systematic (IUPAC) name
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
Identifiers
CAS number 17489-40-6
ATC code G03AC03
PubChem 13109
DrugBank APRD00754
Chemical data
Formula C21H28O2
Mol. weight 312.446 g/mol
Pharmacokinetic data
Bioavailability ~100%
Protein binding 55%
Metabolism Hepatic
Half life  ?
Excretion Renal: 45%; Fecal:32%
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes Implant; Insert (extended-release); Tablet

Levonorgestrel (or L-Norgestrel) is a molecule used in hormonal contraceptives. It is a 19-nortestosterone progestin derived from testosterone. It has mostly progestogenic effects, but also has androgenic and estrogenic effects.

Contents

[edit] Oral contraceptives

At a relatively low dose, levonorgestrel can be formulated as a monophasic, biphasic, or triphasic tablet. In the United States, the available dosages for the monophasic formulation range from 0.1 to 0.15 mg. This range is slightly modified in biphasic and triphasic forms.

[edit] Emergency contraception

Levonorgestrel is used in emergency contraception pills, both in a combined regimen which includes estrogen, and as a levonorgestrel-only method. There are many names for levonorgestrel-only emergency contraception products, including Plan B, Levonelle One Step, and Postinor-2.

[edit] IUD

Levonorgestrel is the active ingredient in Mirena.

[edit] Contraceptive implants

Levonorgestrel is the active ingredient in Norplant and Jadelle.


Sex hormones and related medications (primarily G03, also L02, H01C) edit
Progestogens:
(receptor)

Desogestrel, Drospirenone, Dydrogesterone, Ethisterone, Etonogestrel, Ethynodiol diacetate, Gestodene, Gestonorone, Levonorgestrel, Lynestrenol, Medroxyprogesterone, Megestrol, Norelgestromin, Norethisterone, Norethynodrel, Norgestimate, Norgestrel, Norgestrienone, Tibolone
Antiprogestogen: Mifepristone

Androgens:
(receptor)

Androstanolone, Fluoxymesterone, Mesterolone, Methyltestosterone, Testosterone, (see also anabolic steroids)
Antiandrogens: Bicalutamide, Cyproterone, Flutamide, Nilutamide, Spironolactone

Estrogens:
(receptor)

Chlorotrianisene, Dienestrol, Diethylstilbestrol, Estradiol, Estriol, Estrone, Ethinylestradiol, Fosfestrol, Mestranol, Polyestradiol phosphate
Selective estrogen receptor modulator: Bazedoxifene, Clomifene, Fulvestrant, Raloxifene, Tamoxifen, Toremifene
Aromatase inhibitor: Aminogluthetimide, Anastrozole, Exemestane, Formestane, Letrozole, Vorozole

Gonadotropins:
(FSHR/LHCGR)

ovulation stim.: Clomifene, Urofollitropin
Antigonadotropins: Danazol, Gestrinone

GnRH:
(receptor)

Gonadotropin-releasing hormone agonist: Buserelin, Goserelin, Leuprorelin, Nafarelin, Triptorelin
Gonadotropin-releasing hormone antagonist: Abarelix

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