Chemical compound
Etynodiol diacetate
Trade names Ovulen, Demulen, others Other names Ethynodiol diacetate; Norethindrol diacetate; 3β-Hydroxynorethisterone 3β,17β-diacetate;
[1] 17α-Ethynylestr-4-ene-3β,17β-diyl diacetate; CB-8080; SC-11800
License data
Pregnancy category
Routes of administration
By mouth
Drug class
Progestogen ;
Progestin ;
Progestogen ester
ATC code
Legal status
AU :
S4 (Prescription only)
US :
℞-only
[2]
[3]
In general: ℞ (Prescription only)
[(3S ,8R ,9S ,10R ,13S ,14S ,17R )-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H -cyclopenta[a ]phenanthren-3-yl] acetate
CAS Number
PubChem
CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.005.496
Formula C 24 H 32 O 4
Molar mass 384.516 g·mol−1 3D model (
JSmol )
O=C(O[C@@H]4/C=C3\[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)OC(=O)C)[C@@H]2CC3)C)CC4)C
InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
Key:ONKUMRGIYFNPJW-KIEAKMPYSA-N
Etynodiol diacetate , or ethynodiol diacetate , sold under the brand name Ovulen among others, is a
progestin medication which is used in
birth control pills .
[4]
[5]
[6] The medication is available only in combination with an
estrogen .
[7] It is taken
by mouth .
[8]
Etynodiol diacetate is a progestin, or a
synthetic
progestogen , and hence is an
agonist of the
progesterone receptor , the
biological target of progestogens like
progesterone .
[9]
[10] It has weak
androgenic and
estrogenic activity and no other important
hormonal activity.
[11]
[12]
[13] The medication is a
prodrug of
norethisterone in the body, with
etynodiol occurring as an
intermediate .
[9]
[10]
[14]
Etynodiol, a related compound, was discovered in 1954, and etynodiol diacetate was introduced for medical use in 1965.
[15]
[16] The combination ethynodiol with mestranol (Ovulen) was approved for medical use in the United States in 1966.
[17] The combination ethinylestradiol with ethynodiol (Demulen) was approved for medical use in the United States in 1970.
[18]
In 2021, the combination with
ethinylestradiol was the 276th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.
[19]
[20]
Medical uses
Etynodiol diacetate is used in combination with an
estrogen such as ethinylestradiol or
mestranol in
combined oral contraceptives for women for the prevention of pregnancy.
[8]
Side effects
Pharmacology
Norethisterone (3-ketoetynodiol), the
active metabolite of etynodiol diacetate.
Etynodiol diacetate is virtually inactive in terms of
affinity for the
progesterone and
androgen receptors and acts as a rapidly converted
prodrug of
norethisterone , with
etynodiol occurring as an
intermediate .
[9]
[10]
[14] Upon
oral administration and during
first-pass metabolism in the
liver , etynodiol diacetate is rapidly converted by
esterases into etynodiol,
[14] which is followed by
oxygenation of the C3
hydroxyl group to produce norethisterone.
[10] In addition to its progestogenic activity, etynodiol diacetate has weak
androgenic activity,
[11]
[12] and, unlike most progestins but similarly to norethisterone and
noretynodrel ,
[21] also has some
estrogenic activity.
[12]
[13]
The
pharmacokinetics of etynodiol diacetate have been reviewed.
[22]
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
Etynodiol diacetate, also known as 3β-hydroxy-17α-ethynyl-19-nortestosterone 3β,17β-diaceate, 3β-hydroxynorethisterone 3β,17β-diacetate, or 17α-ethynylestr-4-ene-3β,17β-diol 3β,17β-diacetate, is a
synthetic
estrane
steroid and a
derivative of
testosterone .
[1]
[5]
[6] It is specifically a derivative of
19-nortestosterone and
17α-ethynyltestosterone , or of
norethisterone (17α-ethynyl-19-nortestosterone), in which the C3
ketone
group has been
dehydrogenated into a C3β
hydroxyl group and
acetate
esters have been attached at the C3β and C17β positions.
[5]
[6] Etynodiol diacetate is the 3β,17β-
diacetate
ester of
etynodiol (17α-ethynylestr-4-ene-3β,17β-diol).
[5]
[6]
Synthesis
Ethynodiol diacetate synthesis:
[23] F. B. Colton,
U.S. patent 2,843,609 (1958 to
Searle ). Prepn of the 3-acetate, 17-acetate, and diacetate: P. D. Klimstra,
U.S. patent 3,176,013 (1965 to Searle); see also:
[24]
Chemical syntheses of etynodiol diacetate have been published.
[22]
Reduction of
norethisterone (1 ) affords the 3,17-diol. The 3β-hydroxy compound is the desired product; since reactions at C3 do not show nearly the
stereoselectivity as those at C17 by virtue of the relative lack of stereo-directing proximate substituents, the formation of the desired isomer is engendered by use of a bulky reducing agent, lithium tri-tert-butoxyaluminum hydride. Acetylation of the 3β,17β-diol affords etynodiol diacetate (3 ).
[23]
History
Etynodiol was first
synthesized in 1954, via
reduction of
norethisterone , and etynodiol diacetate was introduced for medical use in 1965.
[15]
[16]
Society and culture
Generic names
Etynodiol diacetate is the
generic name of the drug (the
INN Tooltip International Nonproprietary Name of its free alcohol form is etynodiol), while ethynodiol diacetate is its
USAN Tooltip United States Adopted Name ,
BAN Tooltip British Approved Name , and
JAN Tooltip Japanese Accepted Name .
[5]
[6]
[7] It is also known by its former developmental code names CB-8080 and SC-11800.
[5]
[6]
[7]
Brand names
Etynodiol diacetate is or has been marketed under brand names including Conova, Continuin, Demulen,
[18]
[25] Femulen, Kelnor,
[3]
[25] Lo-Malmorede,
[26] Luteonorm, Luto-Metrodiol, Malmorede,
[27] Metrodiol, Ovulen,
[17]
[25] Soluna, Zovia,
[2] and others.
[5]
[6]
[7]
Availability
Etynodiol diacetate is marketed in only a few countries, including the United States, Canada, Argentina, and Oman.
[7]
References
^
a
b Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, et al. (December 2003). "Classification and pharmacology of progestins". Maturitas . 46 (Suppl 1): S7–S16.
doi :
10.1016/j.maturitas.2003.09.014 .
PMID
14670641 .
^
a
b
"Zovia 1/35- ethynodiol diacetate and ethinyl estradiol tablets kit" .
Archived from the original on 28 September 2022. Retrieved 20 January 2024 .
^
a
b
"Kelnor 1/35- ethynodiol diacetate and ethinyl estradiol kit" .
Archived from the original on 29 March 2023. Retrieved 20 January 2024 .
^ Shoupe D, Haseltine FP (6 December 2012).
Contraception . Springer Science & Business Media. pp. 21–.
ISBN
978-1-4612-2730-4 .
^
a
b
c
d
e
f
g Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 522–.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d
e
f
g
Index Nominum 2000: International Drug Directory . Taylor & Francis US. 2000. p. 422.
ISBN
978-3-88763-075-1 . Retrieved 30 May 2012 .
^
a
b
c
d
e
"Etynodiol" . Drugs.com . Archived from
the original on 5 February 2018. Retrieved 4 February 2018 .
^
a
b Blum RW (22 October 2013).
Adolescent Health Care: Clinical Issues . Elsevier Science. pp. 216–.
ISBN
978-1-4832-7738-7 .
^
a
b
c 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 IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, World Health Organization, International Agency for Research on Cancer (2007).
Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy . World Health Organization. pp. 146–.
ISBN
978-92-832-1291-1 .
^
a
b Tashjian AH, Armstrong EJ (21 July 2011).
Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy . Lippincott Williams & Wilkins. pp. 523–.
ISBN
978-1-4511-1805-6 .
Archived from the original on 11 January 2023. Retrieved 11 October 2016 .
^
a
b
c Becker KL (24 April 2001).
Principles and Practice of Endocrinology and Metabolism . Lippincott Williams & Wilkins. p. 1004.
ISBN
978-0-7817-1750-2 . Retrieved 30 May 2012 .
^
a
b Goroll AH, Mulley AG (27 January 2009).
Primary Care Medicine: Office Evaluation and Management of the Adult Patient . Lippincott Williams & Wilkins. p. 876.
ISBN
978-0-7817-7513-7 . Retrieved 30 May 2012 .
^
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 Petrow V (1971).
"Antifertility agents" . Progress in Medicinal Chemistry . 8 (2): 171–229.
doi :
10.1016/s0079-6468(08)70130-9 .
ISBN
9780408703147 .
PMID
4947236 .
^
a
b William Andrew Publishing (22 October 2013).
Pharmaceutical Manufacturing Encyclopedia, 3rd Edition . Elsevier. pp. 1516–.
ISBN
978-0-8155-1856-3 .
Archived from the original on 20 January 2024. Retrieved 4 February 2018 .
^
a
b
"Ovulen: FDA-Approved Drugs" . U.S.
Food and Drug Administration (FDA) .
Archived from the original on 8 December 2022. Retrieved 20 January 2024 .
^
a
b
"Demulen: FDA-Approved Drugs" . U.S.
Food and Drug Administration (FDA) .
Archived from the original on 10 May 2021. Retrieved 20 January 2024 .
^
"The Top 300 of 2021" . ClinCalc .
Archived from the original on 15 January 2024. Retrieved 14 January 2024 .
^
"Ethinyl Estradiol; Ethynodiol - Drug Usage Statistics" . ClinCalc .
Archived from the original on 18 January 2024. Retrieved 14 January 2024 .
^ Runnebaum BC, Rabe T, Kiesel L (6 December 2012).
Female Contraception: Update and Trends . Springer Science & Business Media. pp. 36–.
ISBN
978-3-642-73790-9 .
^
a
b Konstitution J (27 November 2013).
"Eigenschaften der Gestagene" . Handbuch der Experimentellen Pharmakologie . Cham: Springer-Verlag. pp. 14–15, 286.
ISBN
978-3-642-99941-3 .
^
a
b Klimstra PD, Colton FB (October 1967). "The synthesis of 3beta-hydroxyestr-4-en-17-one and 3beta-hydroxyandrost-4-en-17-one". Steroids . 10 (4): 411–424.
doi :
10.1016/0039-128X(67)90119-5 .
PMID
6064262 .
^ Sondheimer F, Klibansky Y (1959). "Synthesis of 3β-hydroxy analogues of steroidal hormones, a biologically active class of compounds". Tetrahedron . 5 : 15–26.
doi :
10.1016/0040-4020(59)80066-1 .
^
a
b
c
"Estrogen and Progestin (Oral Contraceptives)" .
Archived from the original on 18 January 2024. Retrieved 20 January 2024 .
^
"Lo-Malmorede" .
Archived from the original on 24 March 2021. Retrieved 20 January 2024 .
^
"Malmorede" .
Archived from the original on 1 October 2023. Retrieved 20 January 2024 .
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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 )