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    Levonorgestrel
    Levonorgestrel

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1738
    CAS #: 797-63-7 Purity ≥98%

    Description: Levonorgestrel is a potent female hormone that prevents ovulation and therefore used in a number of birth control methods. Levonorgestrel is a synthetic progestin that binds to progesterone and androgen receptors but not the estrogen receptor. It induces apoptosis in ovarian epithelium cells. Levonorgestrel suppresses the stimulation of progesterone secretion induced by oLH, dibutyryl-cAMP and Pregnenolone in rats luteal cells. Levonorgestrel also inhibits constrictions evoked by either a high potassium (K(+)) solution or phorbol myristate acetate (PMA) in the absence and presence of extracellular calcium (Ca(2+)). Levonorgestrel is useful within 120 hours as emergency birth control. It becomes less effective the longer after sex and only works before pregnancy has occurred. It is also combined with an estrogen to make combined oral birth control pill. 

    References: J Steroid Biochem Mol Biol. 1994;50:161-6; Br J Pharmacol. 2000;130:1911-8; Exp Anim. 2011;60:363-71.

    Related CAS#:13635-16-0 (Levonorgestrel hexanoate); 86679-33-6 (Levonorgestrel butyrate); 39366-37-5 (Ethinylestradiol mixture with Levonorgestrel)

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    Molecular Weight (MW)312.45 
    FormulaC21H28O2 
    CAS No.797-63-7 (Levonorgestrel); 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 45 mg/mL (144.0 mM) 
    Water: <1 mg/mL
    Ethanol: 2 mg/mL (6.4 mM)
    Other info
    Chemical Name: (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
    InChi Key: WWYNJERNGUHSAO-XUDSTZEESA-N
    InChi Code: 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/t16-,17+,18+,19-,20-,21-/m0/s1
    SMILES Code: CC[[email protected]]12CC[[email protected]]3[[email protected]@H](CCC4=CC(CC[[email protected]]34)=O)[[email protected]@H]1CC[[email protected]@]2(O)C#C 
    SynonymsLevonorgestrel, Norgestrel, Microval, Postinor, Mirena, Plan B


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    In Vitro

    In vitro activity: Levonorgestrel suppresses the stimulation of progesterone secretion induced by oLH, dibutyryl-cAMP and Pregnenolone in rats luteal cells. Levonorgestrel also inhibits constrictions evoked by either a high potassium (K(+)) solution or phorbol myristate acetate (PMA) in the absence and presence of extracellular calcium (Ca(2+)). Levonorgestrel depresses contractions evoked by Ca(2+) and reduces (45)Ca(2+) influx in depolarized veins. Levonorgestrel increases levels of cyclic AMP and inhibits PMA-induced activation of protein kinase C in veins. Levonorgestrel causes endothelium-independent relaxations of jugular veins via inhibition of Ca(2+) entry and of protein kinase Cactivation. Levonorgestrel inhibition of both estrogen-induced pituitary weight increment and hyperprolactinemia is reduced by mifepristone, whereas Flutamide is unable to block Levonorgestrel effects. 

    In VivoLevonorgestrel down-regulates the mRNA expression of follicle-stimulating hormone receptor (FSHR), luteinizing hormone receptor (LHR), estrogen receptor (ER) β and progesterone receptor (PR) in the ovary, and ERα and PR in the uterus of Mongolian gerbils. Levonorgestrel causes a significant upregulation of the mRNA expression of the gene encoding luteinising hormone β-subunit (lhβ) and the suppression of the mRNA expression of the gene encoding follicle-stimulating hormone β-subunit (fshβ) in the pituitary of both male and female roach. Levonorgestrel disrupts the reproductive system of pubertalroach by affecting the pituitary gonadotropin expression and the sex steroid levels in pubertal roach (Rutilus rutilus).   
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    References J Steroid Biochem Mol Biol. 1994 Aug;50(3-4):161-6; Br J Pharmacol. 2000 Aug;130(8):1911-8; Exp Anim. 2011;60(4):363-71. 


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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