From Wikipedia, the free encyclopedia
Chemical compound
Levonorgestrel butanoate
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
[(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
Formula C 25 H 34 O 3
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 ),
[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]
See also
References
^
a
b
c 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 .
^ Bhasin S (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 .
^
a
b
c
d Runnebaum BC, Rabe T, Kiesel L (6 December 2012).
Female Contraception: Update and Trends . Springer Science & Business Media. pp. 429–.
ISBN
978-3-642-73790-9 .
^
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 .
S2CID
12896179 .
^ Koetsawang S (1991). "The injectable contraceptive: present and future trends". Ann. N. Y. Acad. Sci . 626 (1): 30–42.
Bibcode :
1991NYASA.626...30K .
doi :
10.1111/j.1749-6632.1991.tb37897.x .
PMID
1829341 .
S2CID
27008012 .
^ 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
^
a
b
c
d
e
f Artini PG, Genazzani AR, Petraglia F (11 December 2001).
Advances in Gynecological Endocrinology . CRC Press. pp. 105–.
ISBN
978-1-84214-071-0 .
^ Coutifaris C, Mastroianni L (15 August 1997).
New Horizons in Reproductive Medicine . CRC Press. pp. 101–.
ISBN
978-1-85070-793-6 .
^ Singh SK (4 September 2015).
Mammalian Endocrinology and Male Reproductive Biology . CRC Press. pp. 270–.
ISBN
978-1-4987-2736-5 .
^ Senanayake P, Potts M (14 April 2008).
Atlas of Contraception, Second Edition . CRC Press. pp. 49–.
ISBN
978-0-203-34732-4 .
^ Knörr K, Beller FK, Lauritzen C (17 April 2013).
Lehrbuch der Gynäkologie . Springer-Verlag. pp. 214–.
ISBN
978-3-662-00942-0 .
^ Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C (8 March 2013).
Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion . Springer-Verlag. pp. 583–.
ISBN
978-3-642-95583-9 .
^ Labhart A (6 December 2012).
Clinical Endocrinology: Theory and Practice . Springer Science & Business Media. pp. 554–.
ISBN
978-3-642-96158-8 .
^ Horský J, Presl J (1981).
"Hormonal Treatment of Disorders of the Menstrual Cycle" . In Horsky J, Presl K (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy . Developments in Obstetrics and Gynecology. Springer Science & Business Media. pp. 309–332.
doi :
10.1007/978-94-009-8195-9_11 .
ISBN
978-94-009-8195-9 .
^ Ufer J (1969).
The Principles and Practice of Hormone Therapy in Gynaecology and Obstetrics . de Gruyter. p. 49.
ISBN
9783110006148 . 17α-Hydroxyprogesterone caproate is a depot progestogen which is entirely free of side actions. The dose required to induce secretory changes in primed endometrium is about 250 mg. per menstrual cycle.
^ Pschyrembel W (1968).
Praktische Gynäkologie: für Studierende und Ärzte . Walter de Gruyter. pp. 598, 601.
ISBN
978-3-11-150424-7 .
^ Ferin J (September 1972).
"Effects, Duration of Action and Metabolism in Man" . In Tausk M (ed.). Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents . Vol. II. Pergamon Press. pp. 13–24.
ISBN
978-0080168128 .
OCLC
278011135 .
^ Henzl MR, Edwards JA (10 November 1999). "Pharmacology of Progestins: 17α-Hydroxyprogesterone Derivatives and Progestins of the First and Second Generation". In Sitruk-Ware R, Mishell DR (eds.).
Progestins and Antiprogestins in Clinical Practice . Taylor & Francis. pp. 101–132.
ISBN
978-0-8247-8291-7 .
^ Brotherton J (1976).
Sex Hormone Pharmacology . Academic Press. p. 114.
ISBN
978-0-12-137250-7 .
^ Sang GW (April 1994). "Pharmacodynamic effects of once-a-month combined injectable contraceptives". Contraception . 49 (4): 361–85.
doi :
10.1016/0010-7824(94)90033-7 .
PMID
8013220 .
^ Toppozada MK (April 1994). "Existing once-a-month combined injectable contraceptives". Contraception . 49 (4): 293–301.
doi :
10.1016/0010-7824(94)90029-9 .
PMID
8013216 .
^ Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S (2014).
"Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control" (PDF) . World J Pharm Pharm Sci . 3 (10): 364–392.
ISSN
2278-4357 . Archived from
the original (PDF) on 2017-08-10. Retrieved 2016-08-24 .
^ Goebelsmann U (1986).
"Pharmacokinetics of Contraceptive Steroids in Humans" . In Gregoire AT, Blye RP (eds.). Contraceptive Steroids: Pharmacology and Safety . Reproductive Biology. Springer Science & Business Media. pp. 67–111.
doi :
10.1007/978-1-4613-2241-2_4 .
ISBN
978-1-4613-2241-2 .
^ Becker H, Düsterberg B, Klosterhalfen H (1980). "[Bioavailability of cyproterone acetate after oral and intramuscular application in men (author's transl)]" [Bioavailability of Cyproterone Acetate after Oral and Intramuscular Application in Men]. Urologia Internationalis . 35 (6): 381–5.
doi :
10.1159/000280353 .
PMID
6452729 .
^ Moltz L, Haase F, Schwartz U, Hammerstein J (May 1983). "[Treatment of virilized women with intramuscular administration of cyproterone acetate]" [Efficacy of Intra muscularly Applied Cyproterone Acetate in Hyperandrogenism]. Geburtshilfe und Frauenheilkunde . 43 (5): 281–7.
doi :
10.1055/s-2008-1036893 .
PMID
6223851 .
S2CID
260160042 .
^ Wright JC, Burgess DJ (29 January 2012).
Long Acting Injections and Implants . Springer Science & Business Media. pp. 114–.
ISBN
978-1-4614-0554-2 .
^ Chu YH, Li Q, Zhao ZF (April 1986).
"Pharmacokinetics of megestrol acetate in women receiving IM injection of estradiol-megestrol long-acting injectable contraceptive" . The Chinese Journal of Clinical Pharmacology . Archived from
the original on 2021-05-25. Retrieved 2020-11-25 . The results showed that after injection the concentration of plasma MA increased rapidly. The meantime of peak plasma MA level was 3rd day, there was a linear relationship between log of plasma MA concentration and time (day) after administration in all subjects, elimination phase half-life t1/2β = 14.35 ± 9.1 days.
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g.,
levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g.,
norethisterone acetate ,
norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g.,
nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g.,
trenbolone acetate ,
trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )