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Additional information about the drug Desogestrel

Desogestrel, sold under the brand names Cerazette and Mircette among many others, is a progestin medication which is used in birth control pills for women.
Side effects of desogestrel include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, acne, increased hair growth, and others.
Desogestrel was discovered in 1972 and was introduced for medical use in Europe in 1981.
Contents
1 Medical uses
1.1 Available forms
2 Contraindications
3 Side effects
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.1.1 Progestogenic activity
6.1.2 Antigonadotropic effects
6.1.3 Androgenic activity
6.1.4 Glucocorticoid activity
6.1.5 Other activities
6.2 Pharmacokinetics
7 Chemistry
7.1 Synthesis
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Availability
9.4 Controversy
10 Research
11 References
12 Further reading
Medical uses
Desogestrel is used in hormonal contraception in women, specifically in birth control pills.
Available forms
Desogestrel is available alone in the form of 75 µg oral tablets and at a dose of 150 µg in combination with 20 or 30 µg ethinylestradiol in oral tablets.
Contraindications
Contraindications of desogestrel include:
Allergy to desogestrel or any other ingredients
Active thrombosis ( deep vein thrombosis or pulmonary embolism )
Jaundice or severe liver disease
Hormone-sensitive cancers (e.g., breast cancer )
Unexplained vaginal bleeding
Desogestrel is not indicated for use in pregnancy.
Side effects
See also: Etonogestrel § Side effects, and Progestin § Side effects
Common side effects of desogestrel may include menstrual irregularities, amenorrhea, headaches, nausea, breast tenderness, and mood changes (e.g., depression ), as well as weight gain, acne, and hirsutism.
Overdose
No serious harmful effects have been reported with overdose of desogestrel.
Interactions
Inducers of liver enzymes can increase the metabolism of desogestrel and etonogestrel and reduce their circulating levels.
Pharmacology
Pharmacodynamics
Etonogestrel (3-ketodesogestrel), the active form of desogestrel.
Desogestrel is a prodrug of etonogestrel (3-ketodesogestrel), and, via this active metabolite, it has progestogenic activity, antigonadotropic effects, very weak androgenic activity, very weak glucocorticoid activity, and no other hormonal activity.
Relative affinities (%) of desogestrel and metabolites
Compound
PR
AR
ER
GR
MR
SHBG
CBG
Desogestrel
1
0
0
0
0
0
0
Etonogestrel ( 3-keto-DSG )
150
20
0
14
0
15
0
3α-Hydroxydesogestrel
5
0
0
?
?
?
?
3β-Hydroxydesogestrel
13
3
2
?
?
?
?
5α-Dihydroetonogestrel
9
17
0
?
?
?
?
3α-Hydroxy-5α-dihydroetonogestrel
0
0
0
?
?
?
?
3β-Hydroxy-5α-dihydroetonogestrel
1
0
1
?
?
?
?
Values are percentages (%). Reference ligands (100%) were promegestone for the PR, metribolone for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, DHT for SHBG, and cortisol for CBG.
Progestogenic activity
Desogestrel is a progestogen, or an agonist of the progesterone receptor (PR).
Due to its progestogenic activity, desogestrel has potent functional antiestrogenic effects in certain tissues.
Aside from its progestogenic activity, desogestrel also has some off-target hormonal activity at other steroid hormone receptors (see below).
Antigonadotropic effects
Desogestrel has antigonadotropic effects via its progestogenic activity, similarly to other progestogens.
Androgenic activity
Etonogestrel has about 20% of the affinity of metribolone and 50% of the affinity of levonorgestrel for the androgen receptor (AR) while desogestrel has no affinity for this receptor.
In accordance with its very weak androgenic activity, desogestrel has minimal effects on lipid metabolism and the blood lipid profile, although there may still be some significant changes.
Glucocorticoid activity
Desogestrel has no affinity for the glucocorticoid receptor, but etonogestrel has about 14% of the affinity of dexamethasone for this receptor.
v t e Glucocorticoid activity of selected steroids in vitro
Steroid
Type
TR ( ↑ ) a
GR (%) b
Dexamethasone
Corticosteroid
++
100
Ethinylestradiol
Estrogen

0
Etonogestrel
Progestin
+
14
Gestodene
Progestin
+
27
Levonorgestrel
Progestin

1
Medroxyprogesterone acetate
Progestin
+
29
Norethisterone
Progestin

0
Norgestimate
Progestin

1
Progesterone
Progestogen
+
10
Footnotes: a = Thrombin receptor (TR) upregulation (↑) in vascular smooth muscle cells (VSMCs). b = RBA (%) for the glucocorticoid receptor (GR). Strength: – = No effect. + = Pronounced effect. ++ = Strong effect. Source:
Other activities
Desogestrel and etonogestrel have no affinity for the estrogen receptor, and hence have no estrogenic activity.
Pharmacokinetics
The bioavailability of desogestrel has been found to range from 40 to 100%, with an average of 76%.
Desogestrel is a prodrug of etonogestrel (3-ketodesogestrel) and upon ingestion is rapidly and completely transformed into this metabolite in the intestines and liver.
Chemistry
See also: List of progestogens
Desogestrel, also known as 3-deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone or as 11-methylene-17α-ethynyl-18-methylestr-4-en-17β-ol, is a synthetic estrane steroid and a derivative of testosterone.
Synthesis
A chemical synthesis of desogestrel has been published.
History
Desogestrel was synthesized in 1972 by Organon International in the Netherlands and was first described in the literature in 1975.
Society and culture
Generic names
Desogestrel is the generic name of the drug and its INN, USAN, BAN, DCF, DCIT, and JAN.
Brand names
Desogestrel is marketed under a variety of brand names throughout the world including Alenvona, Apri, Azalia, Azurette, Caziant, Cerazette, Cerelle, Cesia, Cyclessa, Denise, Desogen, Desirett, Diamilla, Emoquette, Feanolla, Gedarel, Gracial, Kariva, Laurina, Linessa, Marvelon, Mercilon, Mircette, Mirvala, Novynette, Ortho-Cept, Reclipsen, Regulon, Solia, Velivet, and Viorele among others.
Availability
See also: List of progestogens available in the United States
Desogestrel is available widely throughout the world, including in the United States, Canada, the United Kingdom, Ireland, many other European countries, Australia, New Zealand, South Africa, Latin America, South, East, and Southeast Asia, and elsewhere in the world.
Controversy
In February 2007, the consumer advocacy group Public Citizen released a petition requesting that the Food and Drug Administration ban oral contraceptives containing desogestrel in the United States, citing studies going as far back as 1995 that suggest the risk of dangerous blood clots is doubled for women on such pills in comparison to other oral contraceptives.
Research
Desogestrel has been studied extensively as an antigonadotropin for use in combination with testosterone as a hormonal contraceptive in men.

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