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Abandoned drugs
Levonorgestrel butanoate
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    Levonorgestrel butanoate

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    Levonorgestrel butanoate
    Levonorgestrel butanoate.svg
    Clinical data
    Other names LNG-B; HRP-002; Levonorgestrel 17β-butanoate; 17α-Ethynyl-18-methyl-19-nortestosterone 17β-butanoate; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 17β-butanoate
    Routes of
    administration    		 Intramuscular injection
    Drug class Progestogen; Progestogen ester
    ATC code
    • None
    Identifiers
    • [(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] butanoate
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ECHA InfoCard 100.081.125
    Chemical and physical data
    Formula C25H34O3
    Molar mass 382.544 g·mol−1
    3D model (JSmol)
    • CCCC(=O)O[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)CC)C#C
    • InChI=1S/C25H34O3/c1-4-7-23(27)28-25(6-3)15-13-22-21-10-8-17-16-18(26)9-11-19(17)20(21)12-14-24(22,25)5-2/h3,16,19-22H,4-5,7-15H2,1-2H3/t19-,20+,21+,22-,24-,25-/m0/s1
    • Key:GPKLGCALNRZIDS-AYEDEZQKSA-N

    Levonorgestrel butanoate (LNG-B) (developmental code name HRP-002), or levonorgestrel 17β-butanoate, is a steroidal progestin of the 19-nortestosterone group which was developed by the World Health Organization (WHO) in collaboration with the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development as a long-acting injectable contraceptive. It is the C17β butanoate ester of levonorgestrel, and acts as a prodrug of levonorgestrel in the body. The drug is at or beyond the phase III stage of clinical development, but has not been marketed at this time. It was first described in the literature, by the WHO, in 1983, and has been under investigation for potential clinical use since then.

    LNG-B has been under investigation as a long-lasting injectable contraceptive for women. A single intramuscular injection of an aqueous suspension of 5 or 10 mg LNG-B has a duration of 3 months, whereas an injection of 50 mg has a duration of 6 months. The drug was also previously tested successfully as a combined injectable contraceptive with estradiol hexahydrobenzoate, but this formulation was never marketed. LNG-B has been tested successfully in combination with testosterone buciclate as a long-lasting injectable contraceptive for men as well.

    LNG-B may have several advantages over depot medroxyprogesterone acetate, including the use of much lower comparative dosages, reduced progestogenic side effects like hypogonadism and amenorrhea, and a more rapid return in fertility following discontinuation. The drug has a well-established safety record owing to the use of levonorgestrel as an oral contraceptive since the 1960s.

    Parenteral potencies and durations of progestogens
    Compound Form Dose for specific uses (mg) DOA
    TFD POICD CICD
    Algestone acetophenide Oil soln. - – 75–150 14–32 d
    Gestonorone caproate Oil soln. 25–50 – – 8–13 d
    Hydroxyprogest. acetate Aq. susp. 350 – – 9–16 d
    Hydroxyprogest. caproate Oil soln. 250–500 – 250–500 5–21 d
    Medroxyprog. acetate Aq. susp. 50–100 150 25 14–50+ d
    Megestrol acetate Aq. susp. - – 25 >14 d
    Norethisterone enanthate Oil soln. 100–200 200 50 11–52 d
    Progesterone Oil soln. 200 – – 2–6 d
    Aq. soln. ? – – 1–2 d
    Aq. susp. 50–200 – – 7–14 d
    Notes and sources:

    See also



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