| 词条 | Levonorgestrel butanoate |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(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 | image = Levonorgestrel butanoate.svg | width = 250px | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = Intramuscular injection | class = Progestogen; Progestogen ester | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 86679-33-6 | CAS_supplemental = | ATC_prefix = None | ATC_suffix = | ATC_supplemental = | PubChem = 3086228 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 2342903 | UNII = L929CBB126 | KEGG = | ChEBI = | ChEMBL = | synonyms = 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 | C=25 | H=34 | O=3 | molecular_weight = 382.544 g/mol | SMILES = 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 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = GPKLGCALNRZIDS-AYEDEZQKSA-N }}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.[10] 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] See also
References1. ^1 {{cite book|vauthors = King TL, Brucker MC, Kriebs JM, Fahey JO|title=Varney's Midwifery|url=https://books.google.com/books?id=dbaNAQAAQBAJ&pg=PA495|date=21 October 2013|publisher=Jones & Bartlett Publishers|isbn=978-1-284-02542-2|pages=495–}} {{Androgen receptor modulators}}{{Progesterone receptor modulators}}2. ^{{cite book|author=Shalender Bhasin|title=Pharmacology, Biology, and Clinical Applications of Androgens: Current Status and Future Prospects|url=https://books.google.com/books?id=hurRyWje4DMC&pg=PA401|date=13 February 1996|publisher=John Wiley & Sons|isbn=978-0-471-13320-9|pages=401–}} 3. ^1 2 {{cite book|author1=Benno Clemens Runnebaum|author2=Thomas Rabe|author3=Ludwig Kiesel|title=Female Contraception: Update and Trends|url=https://books.google.com/books?id=LtT6CAAAQBAJ&pg=PA429|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-73790-9|pages=429–}} 4. ^1 2 {{cite journal | vauthors = Crabbé P, Archer S, Benagiano G, Diczfalusy E, Djerassi C, Fried J, Higuchi T | title = Long-acting contraceptive agents: design of the WHO Chemical Synthesis Programme | journal = Steroids | volume = 41 | issue = 3 | pages = 243–53 | year = 1983 | pmid = 6658872 | doi = 10.1016/0039-128X(83)90095-8 | url = }} 5. ^{{cite journal | vauthors = Koetsawang S | title = The injectable contraceptive: present and future trends | journal = Ann. N. Y. Acad. Sci. | volume = 626 | issue = | pages = 30–42 | date = 1991 | pmid = 1829341 | doi = 10.1111/j.1749-6632.1991.tb37897.x | url = }} 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. ^1 2 3 4 {{cite book|author1=Paolo Giovanni Artini|author2=Andrea R. Genazzani|author3=Felice Petraglia|title=Advances in Gynecological Endocrinology|url=https://books.google.com/books?id=dknDdAonzlUC&pg=PA105|date=11 December 2001|publisher=CRC Press|isbn=978-1-84214-071-0|pages=105–}} 8. ^{{cite book|author1=C. Coutifaris|author2=L. Mastroianni|title=New Horizons in Reproductive Medicine|url=https://books.google.com/books?id=dmokq_M-gm8C&pg=PA101|date=15 August 1997|publisher=CRC Press|isbn=978-1-85070-793-6|pages=101–}} 9. ^{{cite book|author=Shio Kumar Singh|title=Mammalian Endocrinology and Male Reproductive Biology|url=https://books.google.com/books?id=Y-KYCgAAQBAJ&pg=PA270|date=4 September 2015|publisher=CRC Press|isbn=978-1-4987-2736-5|pages=270–}} 10. ^{{cite book|author1=Pramilla Senanayake|author2=Malcolm Potts|title=Atlas of Contraception, Second Edition|url=https://books.google.com/books?id=7dDKBQAAQBAJ&pg=PA49|date=14 April 2008|publisher=CRC Press|isbn=978-0-203-34732-4|pages=49–}} 10 : Abandoned drugs|Androgens and anabolic steroids|Butyrate esters|Contraception for males|Estranes|Hormonal contraception|Prodrugs|Progestogen esters|Progestogens|World Health Organization |
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