Androgen and anabolic steroid
Lynestrenol
Trade names Exluton, Ministat, others Other names Linestrenol; Lynenol;
[1] NSC-37725; 17α-Ethynylestr-4-en-17β-ol; 19-Nor-17α-pregn-4-en-20-yn-17-ol
[1]
AHFS /
Drugs.com
International Drug Names
Routes of administration
By mouth
Drug class
Progestogen ;
Progestin
ATC code
(8R ,9S ,10R ,13S ,14S ,17R )-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H -cyclopenta[a ]phenanthren-17-ol
CAS Number
PubChem
CID
ChemSpider
UNII
KEGG
CompTox Dashboard (
EPA )
ECHA InfoCard
100.000.139
Formula C 20 H 28 O
Molar mass 284.443 g·mol−1 3D model (
JSmol )
C#C[C@]2(O)CC[C@H]1[C@H]4[C@H](CC[C@@]12C)[C@@H]3\C(=C/CCC3)CC4
InChI=1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,6,15-18,21H,4-5,7-13H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
Y Key:YNVGQYHLRCDXFQ-XGXHKTLJSA-N
Y
(verify)
Lynestrenol , sold under the brand names Exluton and Ministat among others, is a
progestin medication which is used in
birth control pills and in the treatment of
gynecological disorders .
[2]
[3]
[4] The medication is available both alone and in combination with an
estrogen .
[3]
[5]
[6] It is taken
by mouth .
[7]
[8]
Lynestrenol is a progestin, or a
synthetic
progestogen , and hence is an
agonist of the
progesterone receptor , the
biological target of progestogens like
progesterone .
[9] It has weak
androgenic and
estrogenic activity and no other important
hormonal activity.
[9]
[10] The medication is a
prodrug of
norethisterone in the body, with
etynodiol occurring as an
intermediate .
[10]
[11]
[12]
Lynestrenol was discovered in the late 1950s and was introduced for medical use in 1961.
[13]
[14] It has mostly been used in
Europe and elsewhere in the world and was never marketed in the
United States .
[6]
[15]
[16]
[17]
Medical uses
Lynestrenol is used as a component of
oral contraceptives in combination with an
estrogen and is used in the treatment of
gynecological disorders such as
menstrual disorders .
[4]
Side effects
Pharmacology
Norethisterone (3-ketolynestrenol), the
active metabolite of lynestrenol.
Lynestrenol itself does not bind to the
progesterone receptor and is inactive as a
progestogen .
[7]
[8] It is a
prodrug , and upon
oral administration , is rapidly and almost completely
converted into
norethisterone , a potent progestogen, in the
liver during
first-pass metabolism .
[7]
[8] No other
metabolites besides norethisterone are formed from lynestrenol.
[8] As such, its
pharmacological activity is essentially identical to that of norethisterone.
[9] The conversion of lynestrenol into norethisterone is catalyzed by
CYP2C9 (28.0%),
CYP2C19 (49.8%), and
CYP3A4 (20.4%), while other
cytochrome P450
enzymes are each responsible for no more than 1.0% of the total conversion.
[8] It appears that lynestrenol first undergoes
hydroxylation of the C3 position, forming
etynodiol as an
intermediate ,
[12] followed by
oxygenation of the
hydroxyl group to form norethisterone.
[11]
The
peak blood levels are reached within 2 to 4 hours after oral administration, 97% of the administered dose being
bound to plasma proteins .[
citation needed ] Lynestrenol and its metabolites are predominantly
excreted in
urine , less in
feces ,
active metabolite norethisterone
elimination half-life being 16 or 17 hours.[
citation needed ]
The
pharmacokinetics of lynestrenol have been reviewed.
[18]
Relative affinities (%) of
norethisterone , metabolites, and prodrugs
Compound
Typea
PR Tooltip Progesterone receptor
AR Tooltip Androgen receptor
ER Tooltip Estrogen receptor
GR Tooltip Glucocorticoid receptor
MR Tooltip Mineralocorticoid receptor
SHBG Tooltip Sex hormone-binding globulin
CBG Tooltip Corticosteroid binding globulin
Norethisterone
–
67–75
15
0
0–1
0–3
16
0
5α-Dihydronorethisterone
Metabolite
25
27
0
0
?
?
?
3α,5α-Tetrahydronorethisterone
Metabolite
1
0
0–1
0
?
?
?
3α,5β-Tetrahydronorethisterone
Metabolite
?
0
0
?
?
?
?
3β,5α-Tetrahydronorethisterone
Metabolite
1
0
0–8
0
?
?
?
Ethinylestradiol
Metabolite
15–25
1–3
112
1–3
0
0.18
0
Norethisterone acetate
Prodrug
20
5
1
0
0
?
?
Norethisterone enanthate
Prodrug
?
?
?
?
?
?
?
Noretynodrel
Prodrug
6
0
2
0
0
0
0
Etynodiol
Prodrug
1
0
11–18
0
?
?
?
Etynodiol diacetate
Prodrug
1
0
0
0
0
?
?
Lynestrenol
Prodrug
1
1
3
0
0
?
?
Notes: Values are percentages (%). Reference
ligands (100%) were
promegestone for the
PR Tooltip progesterone receptor ,
metribolone for the
AR Tooltip androgen receptor ,
estradiol for the
ER Tooltip estrogen receptor ,
dexamethasone for the
GR Tooltip glucocorticoid receptor ,
aldosterone for the
MR Tooltip mineralocorticoid receptor ,
dihydrotestosterone for
SHBG Tooltip sex hormone-binding globulin , and
cortisol for
CBG Tooltip Corticosteroid-binding globulin . Footnotes: a =
Active or inactive
metabolite ,
prodrug , or neither of norethisterone. Sources: See template.
Chemistry
Lynestrenol, also known as 17α-ethynyl-3-desoxy-19-nortestosterone or as 17α-ethynylestr-4-en-17β-ol, is a
synthetic
estrane
steroid and a
derivative of
19-nortestosterone .
[2]
[3]
[9]
[19] It differs from
norethisterone (17α-ethynyl-19-nortestosterone) and
etynodiol (17α-ethynyl-3-deketo-3β-hydroxy-19-nortestosterone) only by the lack of a
ketone
group and
hydroxyl group at the C3 position, respectively.
[11]
Synthesis
Chemical syntheses of lynestrenol have been published.
[2]
[18]
In another approach to analogues,
nortestosterone (1 ) is first converted to the di
thioketal (2 ) by treatment with
dithioglycol in the presence of
boron trifluoride . (The mild conditions of this reaction compared to those usually employed in preparing the oxygen ketals probably accounts for the double bond remaining at 4,5). Treatment of this derivative with sodium in liquid ammonia affords the 3-desoxy analog (3 ). Oxidation by means of
Jones reagent followed by
ethynylation of the
17-ketone leads to the orally active progestin (6 ).
Lynestrenol synthesis:
[20]
[21]
History
Lynestrenol was developed by the
Dutch
pharmaceutical company
Organon in the late 1950s and was introduced for medical use in 1961.
[13]
[14] It received a Dutch
patent for lynestrenol in 1957,
[13] and lynestrenol subsequently became a component of Lyndiol , the first Dutch contraceptive pill, in 1962.
[1]
[13]
[14] Around this time, pre- and post-marketing
clinical trials of lynestrenol were conducted, and in 1965, a study consisting of 200 Dutch women was published.
[13] Lynestrenol was approved, in the
United Kingdom , in combination with
mestranol in 1963 and in combination with
ethinylestradiol in 1969.
[16]
Society and culture
Generic names
Lynestrenol is the
generic name of the drug and its
INN Tooltip International Nonproprietary Name ,
USAN Tooltip United States Adopted Name ,
BAN Tooltip British Approved Name , and
JAN Tooltip Japanese Accepted Name , while lynestrénol is its
DCF Tooltip Dénomination Commune Française and linestrenolo is its
DCIT Tooltip Denominazione Comune Italiana .
[2]
[3]
[4]
[6] Lynoestrenol was formerly the
BAN Tooltip British Approved Name of the drug, but it was eventually changed to lynestrenol .
[2]
[3]
[4]
[6]
Brand names
Lynestrenol has been marketed alone as Exluton, Exlutona, and Orgametril, in combination with mestranol as Anacyclin, Lyndiol, Lyndiol 1, Lyndiol 2.5, Nonovul, and Noracycline, and in combination with ethinylestradiol as Anacyclin, Fysioquens, Minilyn, and Ministat, among other formulations and brand names.
[5]
[22]
Availability
Lynestrenol has been used mainly in
Europe
[15] and is also marketed elsewhere throughout the world.
[6] The drug was never marketed in the
United States .
[16]
[17]
References
^
a
b
c
Consolidated List of Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments . United Nations Publications. 1983. pp. 134–.
ISBN
978-92-1-130230-1 .
^
a
b
c
d
e Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 747–.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d
e
Index Nominum 2000: International Drug Directory . Taylor & Francis. 2000. pp. 624–.
ISBN
978-3-88763-075-1 .
^
a
b
c
d Morton IK, Hall JM (6 December 2012).
Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. pp. 170–.
ISBN
978-94-011-4439-1 .
^
a
b Muller (19 June 1998).
European Drug Index: European Drug Registrations, Fourth Edition . CRC Press. pp. 74, 467, 525.
ISBN
978-3-7692-2114-5 .
^
a
b
c
d
e
"Lynestreno" . Drugs.com l .
^
a
b
c Odlind V, Weiner E, Victor A, Johansson ED (January 1979). "Plasma levels of norethindrone after single oral dose administration of norethindrone and lynestrenol". Clinical Endocrinology . 10 (1): 29–38.
doi :
10.1111/j.1365-2265.1979.tb03030.x .
PMID
436304 .
S2CID
10774483 .
^
a
b
c
d
e Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O (May 2008). "Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone". The Journal of Steroid Biochemistry and Molecular Biology . 110 (1–2): 56–66.
doi :
10.1016/j.jsbmb.2007.09.025 .
PMID
18356043 .
S2CID
10809537 .
^
a
b
c
d Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (2008). "Classification and pharmacology of progestins". Maturitas . 61 (1–2): 171–180.
doi :
10.1016/j.maturitas.2008.11.013 .
PMID
19434889 .
^
a
b Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric . 8 (Suppl 1): 3–63.
doi :
10.1080/13697130500148875 .
PMID
16112947 .
S2CID
24616324 .
^
a
b
c Stanczyk FZ (September 2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Reviews in Endocrine & Metabolic Disorders . 3 (3): 211–224.
doi :
10.1023/A:1020072325818 .
PMID
12215716 .
S2CID
27018468 .
^
a
b Hammerstein J (December 1990). "Prodrugs: advantage or disadvantage?". American Journal of Obstetrics and Gynecology . 163 (6 Pt 2): 2198–2203.
doi :
10.1016/0002-9378(90)90561-K .
PMID
2256526 .
^
a
b
c
d
e Oudtshoorn N (2002).
"Drugs for People: The culture of testing hormonal contraceptives for women and menGijswijt-Hofstra M, van Heteren GM, Tansey EM" . Biographies of Remedies: Drugs, Medicines and Contraceptives in Dutch and Anglo-American Healing Cultures . Rodopi. pp. 128–129.
ISBN
90-420-1577-2 .
^
a
b
c
Drugs Available Abroad . Gale Research. 1991.
ISBN
978-0-8103-7177-4 . LYNESTRENOL Countries Where Available and Release Dates: Austria; Belgium (1961); Finland (1972); France (1970); Federal Republic of Germany (1962); Mexico (1973); Netherlands (1962); Republic of South Africa (1974); Spain (1971); Sweden (1964); Switzerland.
^
a
b Magnusson C, Baron JA (22 May 2000).
"Hormone Replacement Therapy and Breast Cancer" . In Lobo RA, Kelsey J, Marcus R (eds.). Menopause: Biology and Pathobiology . Academic Press. pp. 585–.
ISBN
978-0-08-053620-0 .
^
a
b
c Gelijns A (1991).
Innovation in Clinical Practice: The Dynamics of Medical Technology Development . National Academies. pp. 167–. NAP:13513.
^
a
b
"Drugs@FDA: FDA-Approved Drugs" .
^
a
b
Die Gestagene . Springer-Verlag. 27 November 2013. pp. 15–16, 283.
ISBN
978-3-642-99941-3 .
^ Stanczyk FZ (November 2003). "All progestins are not created equal". Steroids . 68 (10–13): 879–890.
doi :
10.1016/j.steroids.2003.08.003 .
PMID
14667980 .
S2CID
44601264 .
^ de Winter MS, Siegmann CM, Szpilfogel SA (1959). 17-Alkylated 3-deoxo-19-nortestosterones. Chem. Ind (Report). p. 905.
^
"Cingestol | C20H28O" . ChemSpider .
^ Kolbe HK, Bergman RF (April 1976). Population/fertility control thesaurus. Population Information Program, Science Communication Division (Report). Department of Medical and Public Affairs, George Washington University.
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Agonists
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ER Tooltip Estrogen receptor
Agonists
Steroidal:
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3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
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17α-Dihydroequilenin
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17α-Ethynyl-3α-androstanediol
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Abiraterone
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RU-16117
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Testosterone derivatives: Progestins:
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RU-2309
Tetrahydrogestrinone
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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 )