Levonorgestrel butanoate

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Levonorgestrel butanoate
Levonorgestrel butanoate.svg
Clinical data
SynonymsLNG-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 classProgestogen; Progestogen ester
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.081.125 Edit this at Wikidata
Chemical and physical data
FormulaC25H34O3
Molar mass382.544 g/mol g·mol−1
3D model (JSmol)

Levonorgestrel butanoate (LNG-B) (developmental code name HRP-002),[1][2] 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.[3][4][5] It is the C17β butanoate ester of levonorgestrel, and acts as a prodrug of levonorgestrel in the body.[4] The drug is at or beyond the phase III stage of clinical development, but has not been marketed at this time.[3] It was first described in the literature, by the WHO, in 1983, and has been under investigation for potential clinical use since then.[4][6]

LNG-B has been under investigation as a long-lasting injectable contraceptive for women.[7] A single intramuscular injection of an aqueous suspension of 5 or 10 mg LNG-B has a duration of 3 months,[3][7] whereas an injection of 50 mg has a duration of 6 months.[1] The drug was also previously tested successfully as a combined injectable contraceptive with estradiol hexahydrobenzoate, but this formulation was never marketed.[7] LNG-B has been tested successfully in combination with testosterone buciclate as a long-lasting injectable contraceptive for men as well.[8][9]

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.[7][10] The drug has a well-established safety record owing to the use of levonorgestrel as an oral contraceptive since the 1960s.[7]

Parenteral potencies and durations of progestogens

Progestogen Type Class TFD
(14 days)
POIC-D
(2–3 months)
CIC-D
(month)
Duration
Algestone acetophenide Synthetic Pregnane ? 75–150 mg 100 mg ≈ 14–32 days
Cyproterone acetate Synthetic Pregnane ? 300 mg ≈ 20 days
Dydrogesterone (aq. susp.)a Synthetic Retropregnane ? 100 mg ≈ 16–38 days
Gestonorone caproate Synthetic Norpregnane 50 mg 25–50 mg ≈ 8–13 days
Hydroxyprogesterone acetate (aq. susp.)a Synthetic Pregnane 350 mg 150–350 mg ≈ 9–16 days
Hydroxyprogesterone caproate Synthetic Pregnane 250–500 mgb 250–500 mg 65–500 mg ≈ 5–21 days
Levonorgestrel butanoate (aq. susp.)a Synthetic Estrane ? 5–50 mg ≈ 3–6 months
Lynestrenol phenylpropionatea Synthetic Estrane ? 50–100 mg ≈ 14–30 days
Medroxyprogesterone acetate (aq. susp.) Synthetic Pregnane 50–100 mg 150 mg 25 mg 50–150 mg ≈ 14–50+ days
Megestrol acetate (aq. susp.) Synthetic Pregnane ? 25 mg 25 mg ≈ >14 daysc
Norethisterone enanthate Synthetic Estrane 100–200 mg 200 mg 50 mg 50–200 mg ≈ 11–52 days
Oxogestone phenylpropionatea Synthetic Pregnane ? 100 mg ≈ 19–20 days
Progesterone Bioidentical Pregnane 200 mgb 25–350 mg ≈ 2–6 days
Progesterone (aq. susp.) Bioidentical Pregnane 50–200 mg 50–300 mg ≈ 7–14 days
Note: All are via i.m. or s.c. injection of oil solution unless noted otherwise. P4 production during the luteal phase is ~25 (15–50) mg/day. The OID of OHPC is 250 to 500 mg/month. Footnotes: a = Studied but never marketed (either as a medication or by this route). b = In divided doses (2 × 125 or 250 mg for OHPC, 10 × 20 mg for P4). c = Half-life is ~14 days. Sources: Main: See template.

See also[edit]

References[edit]

  1. ^ a b King TL, Brucker MC, Kriebs JM, Fahey JO (21 October 2013). Varney's Midwifery. Jones & Bartlett Publishers. pp. 495–. ISBN 978-1-284-02542-2.
  2. ^ Shalender Bhasin (13 February 1996). Pharmacology, Biology, and Clinical Applications of Androgens: Current Status and Future Prospects. John Wiley & Sons. pp. 401–. ISBN 978-0-471-13320-9.
  3. ^ a b c Benno Clemens Runnebaum; Thomas Rabe; Ludwig Kiesel (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 429–. ISBN 978-3-642-73790-9.
  4. ^ a b c Crabbé P, Archer S, Benagiano G, Diczfalusy E, Djerassi C, Fried J, Higuchi T (1983). "Long-acting contraceptive agents: design of the WHO Chemical Synthesis Programme". Steroids. 41 (3): 243–53. doi:10.1016/0039-128X(83)90095-8. PMID 6658872.
  5. ^ Koetsawang S (1991). "The injectable contraceptive: present and future trends". Ann. N. Y. Acad. Sci. 626: 30–42. doi:10.1111/j.1749-6632.1991.tb37897.x. PMID 1829341.
  6. ^ Benagiano, G., & Merialdi, M. (2011). Carl Djerassi and the World Health Organisation special programme of research in human reproduction. Journal für Reproduktionsmedizin und Endokrinologie-Journal of Reproductive Medicine and Endocrinology, 8(1), 10-13. http://www.kup.at/kup/pdf/10163.pdf
  7. ^ a b c d e Paolo Giovanni Artini; Andrea R. Genazzani; Felice Petraglia (11 December 2001). Advances in Gynecological Endocrinology. CRC Press. pp. 105–. ISBN 978-1-84214-071-0.
  8. ^ C. Coutifaris; L. Mastroianni (15 August 1997). New Horizons in Reproductive Medicine. CRC Press. pp. 101–. ISBN 978-1-85070-793-6.
  9. ^ Shio Kumar Singh (4 September 2015). Mammalian Endocrinology and Male Reproductive Biology. CRC Press. pp. 270–. ISBN 978-1-4987-2736-5.
  10. ^ Pramilla Senanayake; Malcolm Potts (14 April 2008). Atlas of Contraception, Second Edition. CRC Press. pp. 49–. ISBN 978-0-203-34732-4.