Desogestrel

• CAT Number: A000060
• CAS Number: 54024-22-5
• Molecular Formula: C22H30O
• Molecular Weight: 310.47
• Purity: ≥95%
• Storage: Store at -20°C
• IUPAC Name: (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
• InChI: InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
• InChIKey: RPLCPCMSCLEKRS-BPIQYHPVSA-N
• SMILES: CCC12CC(=C)C3C(C1CCC2(C#C)O)CCC4=CCCCC34

Desogestrel (INN, USAN, BAN, CAS 54024-22-5) is a progestin used in hormonal contraceptives. Most combined oral contraceptive pills (COCPs, or simply OCs) on the market today contain both an estrogen (ethinyl estradiol is common) plus a progestin (a synthetic progesterone-like agent) such as desogestrel. Desogestrel-containing birth control pills are sometimes referred to as /third generation/ oral contraceptives. In contrast, birth control pills that are considered /second generation/ (Tri-Levlen, for example) contain an estrogen and a progestin, but the progestin is different, such as levonorgestrel. Desogestrel behaves as a prodrug to etonogestrel (3-ketodesogestrel). It has low androgenic activity. (last updated: 3/3/2016). Desogestrel is a synthetic progestogen structurally related to levonorgestrel, with progesterone hormone receptor agonistic activity, used as a contraceptive and hormone replacement agent. Upon administration, desogestrel binds intracellular progesterone receptors in progesterone responsive tissue and the resultant complex interacts with DNA causing either gene transcription or gene repression. This eventually leads to an inhibition of gonadotropin releasing hormone (GnRH) secretion from the hypothalamus and a subsequent inhibition of luteinizing hormone (LH) and follicle-stimulating hormone (FSH) release. This prevents ovulation and alters the cervical mucus. 

Overview of Clinical Research

Desogestrel is a progesterone receptor agonist.

Reference

1: Park MJ, Jeon GH. Pulmonary embolism in a healthy woman using the oral contraceptives containing desogestrel. Obstet Gynecol Sci. 2017 Mar;60(2):232-235. doi: 10.5468/ogs.2017.60.2.232. Epub 2017 Mar 16. PubMed PMID: 28344968; PubMed Central PMCID: PMC5364109.
2: Tanmahasamut P, Saejong R, Rattanachaiyanont M, Angsuwathana S, Techatraisak K, Sanga-Areekul N. Postoperative desogestrel for pelvic endometriosis-related pain: a randomized controlled trial. Gynecol Endocrinol. 2017 Jul;33(7):534-539. doi: 10.1080/09513590.2017.1296124. Epub 2017 Mar 7. PubMed PMID: 28266234.
3: Merki-Feld GS, Imthurn B, Dubey R, Sándor PS, Gantenbein AR. Improvement of migraine with change from combined hormonal contraceptives to progestin-only contraception with desogestrel: How strong is the effect of taking women off combined contraceptives? J Obstet Gynaecol. 2017 Apr;37(3):338-341. doi: 10.1080/01443615.2016.1234438. Epub 2017 Jan 27. PubMed PMID: 28129717.
4: Peters K, Gordon N, Ricciotti N, Hsieh J, Howard B, Weiss H. Hemostatic effects of two desogestrel-containing combined oral contraceptive regimens: a multinational, multicenter, randomized, open-label study. Clin Exp Obstet Gynecol. 2016;43(3):334-40. PubMed PMID: 27328486.
5: Joubert F, Perrin-Terrin AS, Verkaeren E, Cardot P, Fiamma MN, Frugière A, Rivals I, Similowski T, Straus C, Bodineau L. Desogestrel enhances ventilation in ondine patients: Animal data involving serotoninergic systems. Neuropharmacology. 2016 Aug;107:339-350. doi: 10.1016/j.neuropharm.2016.03.041. Epub 2016 Apr 1. PubMed PMID: 27040794.
6: Regidor PA, Colli E, Schindler AE. Drospirenone as estrogen-free pill and hemostasis: coagulatory study results comparing a novel 4 mg formulation in a 24 + 4 cycle with desogestrel 75 μg per day. Gynecol Endocrinol. 2016 Sep;32(9):749-751. Epub 2016 Mar 30. PubMed PMID: 27028425.
7: Kancheva Landolt N, Bunupuradah T, Kosalaraksa P, Ubolyam S, Thammajaruk N, Cremers S, Zott R, Kerr S, Ananworanich J; HIV-NAT 176 study. High Variability of Hormonal Levels and No Clinically Relevant Interaction Between Ethinyl Estradiol, Desogestrel and Lopinavir/Ritonavir in a Small Sample of HIV-positive Adolescents. J Acquir Immune Defic Syndr. 2016 Aug 15;72(5):507-12. doi: 10.1097/QAI.0000000000000997. PubMed PMID: 26990825.
8: Brache V, Cochon L, Duijkers IJ, Levy DP, Kapp N, Monteil C, Abitbol JL, Klipping C. A prospective, randomized, pharmacodynamic study of quick-starting a desogestrel progestin-only pill following ulipristal acetate for emergency contraception. Hum Reprod. 2015 Dec;30(12):2785-93. doi: 10.1093/humrep/dev241. Epub 2015 Sep 23. PubMed PMID: 26405263.
9: Duijkers IJ, Heger-Mahn D, Drouin D, Skouby S. A randomised study comparing the effect on ovarian activity of a progestogen-only pill (POP) containing desogestrel and a new POP containing drospirenone in a 24/4 regimen. Eur J Contracept Reprod Health Care. 2015;20(6):419-27. doi: 10.3109/13625187.2015.1044082. Epub 2015 Jun 15. PubMed PMID: 26073333.
10: Bitzer J, Banal-Silao MJ, Ahrendt HJ, Restrepo J, Hardtke M, Wissinger-Graefenhahn U, Trummer D. Hormone withdrawal-associated symptoms with ethinylestradiol 20 μg/drospirenone 3 mg (24/4 regimen) versus ethinylestradiol 20 μg/desogestrel 150 μg (21/7 regimen). Int J Womens Health. 2015 May 18;7:501-9. doi: 10.2147/IJWH.S77942. eCollection 2015. PubMed PMID: 26056491; PubMed Central PMCID: PMC4445871.