Desogestrel

Structural formula
General
Non-proprietary name	Desogestrel
other names	13-Ethyl-11-methylene-18,19-dinor-17 α -pregn-4-en-20-yn-17-ol
Molecular formula	C 22 H 30 O
External identifiers / databases
EC number	258-929-4
ECHA InfoCard	100.053.555
PubChem	40973
ChemSpider	37400
DrugBank	DB00304
Wikidata	Q415304
Drug information
ATC code	G03 AC09 G03 AA09 ; G03 AB05 G03 FB10 ;
Drug class	Progestins
properties
Molar mass	310.47 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 410
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Desogestrel is a third generation synthetic progestin that is used as a hormonal contraceptive for birth control. It is the sole component of pure progestin pills (Cerazette), so-called " estrogen-free mini pills ", which, in addition to changing the consistency of the cervical mucus, also suppress ovulation and thus significantly increase safety.

Progestogens are used in transsexual men to suppress menstrual bleeding unless it disappears by itself through testosterone treatment.

Desogestrel is also contained as a gestagen component in single-phase combination products (Marvelon).

Desogestrel is a prodrug , the gestagenic effect is due to the active metabolite 3-keto-desogestrel.

Desogestrel was first described in 1975. It was first used medicinally in Europe in 1981.

Analytics

For reliable qualitative and quantitative determination, the coupling of HPLC with mass spectrometry is used after appropriate sample preparation .

Adverse drug effects

In the WHO Pharmaceuticals Newsletter 2018 No. 5 it is reported that the use of desogestrel increased the incidence of panic attacks and suicidal behavior. An update of the leaflet is recommended.

Trade names

Monopreparations
Cerazette (D, A, CH), numerous generics (D), Jubrele

Combination
preparations Biviol (D), Desmin (D), Desoren (CH), Gracial (A, CH), Lamuna (D), Liberel (A), Lovelle (D), Marvelon (D, A, CH), Mercilon (A , CH), Novial (D)

Web links

Desogestrel and gestodene increase the risk of thrombosis . (PDF; 40 kB) In: Pharma- Kritik, 8/1995

Individual evidence

↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of desogestrel in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on January 15, 2020, is reproduced from a self-classification by the distributor .
^ G. Cullberg: ORG-2969, a New Progestational Compound . In: Reproduccion , January 1975, Vol. 2, No. 3-4, p. 330
↑ D. Visser, D. Jager, HP De Jongh, J. Van der Vies: Pharmacological profile of a new orally active progestational steroid: Org 2969. ( Memento of January 6, 2018 in the Internet Archive ) In: Acta Endocrinologica , 1975, 80 (Suppl. 199), p. 405.
↑ L. Viinikka, O. Ylikorkala, S. Nummi, P. Virkkunen, T. Ranta, U. Alapiessao, R. Vihk: The inhibition of ovulation by a new and potent progestin: a clinical study. ( Memento of January 7, 2018 in the Internet Archive ) Acta Endocrinologica , 1975, 80 (199), p. 303.
↑ Benno Clemens Runnebaum, Thomas Rabe, Ludwig Kiesel: Female Contraception: Update and Trends . Springer Science & Business Media, December 6, 2012, ISBN 978-3-642-73790-9 , pp. 156-163.
↑ Jeremy A. Holtsclaw: Progress Towards the Total Synthesis of Desogestrel and the Development of a New Chiral Dihydroimidazol-2-ylidene Ligand . University of Michigan, 2007, p. 25: "In 1981, desogestrel was marketed as a new low dose oral contraceptive under the trade names Marvelon® and Desogen®.32"
↑ D Matejícek et al .: High Performance Liquid Chromatography / Ion-Trap Mass Spectrometry for Separation and Simultaneous Determination of Ethynylestradiol, Gestodene, Levonorgestrel, Cyproterone Acetate and Desogestrel . In: Anal Chim Acta , 2007, 588 (2), pp. 304-315. PMID 17386825 .
^ S Yang et al .: Discriminating the Endogenous and Exogenous Urinary Estrogens in Human by Isotopic Ratio Mass Spectrometry and Its Potential Clinical Value . In: Steroids , 78 (2), pp. 297-303. Feb 2013, PMID 23228444
^ Sarah Watson: Desogestrel and severe psychiatric disorders: panic attack, suicidal ideation and self-injurious behavior . In: WHO pharmaceuticals newsletter (= WHO pharmaceuticals newsletter , No. 5). WHO, 2018, pp. 13-16; who.int (PDF)
↑ Watson S, Härmark L: desogestrel and panic attacks - a new Suspected adverse drug reaction reported by patients and healthcare professionals on spontaneous reports. , J Clin Pharmacol. 2018 Aug; 84 (8): 1858-1859, PMID 29797731

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of desogestrel in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on January 15, 2020, is reproduced from a self-classification by the distributor .

[Cullberg1975-2] G. Cullberg: ORG-2969, a New Progestational Compound . In: Reproduccion , January 1975, Vol. 2, No. 3-4, p. 330

[Visser1975-3] D. Visser, D. Jager, HP De Jongh, J. Van der Vies: Pharmacological profile of a new orally active progestational steroid: Org 2969. ( Memento of January 6, 2018 in the Internet Archive ) In: Acta Endocrinologica , 1975, 80 (Suppl. 199), p. 405.

[Viinikka1975-4] L. Viinikka, O. Ylikorkala, S. Nummi, P. Virkkunen, T. Ranta, U. Alapiessao, R. Vihk: The inhibition of ovulation by a new and potent progestin: a clinical study. ( Memento of January 7, 2018 in the Internet Archive ) Acta Endocrinologica , 1975, 80 (199), p. 303.

[RunnebaumRabe2012-5] Benno Clemens Runnebaum, Thomas Rabe, Ludwig Kiesel: Female Contraception: Update and Trends . Springer Science & Business Media, December 6, 2012, ISBN 978-3-642-73790-9 , pp. 156-163.

[Holtsclaw2007-6] Jeremy A. Holtsclaw: Progress Towards the Total Synthesis of Desogestrel and the Development of a New Chiral Dihydroimidazol-2-ylidene Ligand . University of Michigan, 2007, p. 25: "In 1981, desogestrel was marketed as a new low dose oral contraceptive under the trade names Marvelon® and Desogen®.32"

[7] D Matejícek et al .: High Performance Liquid Chromatography / Ion-Trap Mass Spectrometry for Separation and Simultaneous Determination of Ethynylestradiol, Gestodene, Levonorgestrel, Cyproterone Acetate and Desogestrel . In: Anal Chim Acta , 2007, 588 (2), pp. 304-315. PMID 17386825 .

[8] S Yang et al .: Discriminating the Endogenous and Exogenous Urinary Estrogens in Human by Isotopic Ratio Mass Spectrometry and Its Potential Clinical Value . In: Steroids , 78 (2), pp. 297-303. Feb 2013, PMID 23228444

[9] Sarah Watson: Desogestrel and severe psychiatric disorders: panic attack, suicidal ideation and self-injurious behavior . In: WHO pharmaceuticals newsletter (= WHO pharmaceuticals newsletter , No. 5). WHO, 2018, pp. 13-16; who.int (PDF)

[10] Watson S, Härmark L: desogestrel and panic attacks - a new Suspected adverse drug reaction reported by patients and healthcare professionals on spontaneous reports. , J Clin Pharmacol. 2018 Aug; 84 (8): 1858-1859, PMID 29797731