General Information of Drug (ID: DM27U4Y)

Drug Name
Desogestrel Drug Info
Synonyms
Cerazette; Desogen; Desogestrelum; Organon Brand of Desogestrel; ORG 2969; Desogestrelum [INN-Latin]; Desogestrel (USAN/INN); Desogestrel [USAN:BAN:INN]; Alpha-pregn-4-en-20-yn-17-ol, 13-Ethyl-11-methylene-18,19-dinor-17; (17alpha)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol; (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; 13 Ethyl 11 methylene 18,19 dinor 17 alpha pregn 4 en 20 yn 17 ol; 13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-ol; 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol; 17alpha-ethynyl-11-methylidene-18a-homo-estr-4-en-17beta-ol
Indication
Disease Entry ICD 11 Status REF
Contraception QA21 Approved [1]
Therapeutic Class
Contraceptive Agents
Cross-matching ID
PubChem CID
40973
ChEBI ID
CHEMBL1533
CAS Number
CAS 54024-22-5
TTD Drug ID
DM27U4Y
INTEDE Drug ID
DR0438

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Drug(s) Targeting Progesterone receptor (PGR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [7]
Ulipristal DMBNI20 Contraception QA21 Approved [8]
Etonogestrel DMKA8J4 Contraception QA21 Approved [9]
Megestrol DMDH9KX Breast cancer 2C60-2C65 Approved [10]
Segesterone acetate; ethinyl estradiol DMFEGB0 Contraception QA21 Approved [11]
Norgestimate DMYP4XC Acne vulgaris ED80 Approved [9]
Dydrogesterone DMAKIDV Menstrual disorder GA20.3 Approved [12]
Medroxyprogesterone DMBGWPH Solid tumour/cancer 2A00-2F9Z Approved [12]
Ethynodiol Diacetate DMZM84R Contraception QA21 Approved [13]
Levonorgestrel DM1DP7T Atypical endometrial hyperplasia Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [15]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [16]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [17]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [18]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [19]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [20]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [21]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [22]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [16]
Verapamil DMA7PEW Angina pectoris BA40 Approved [23]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2C9 (CYP2C9)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [24]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [25]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [26]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [27]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [28]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [27]
Verapamil DMA7PEW Angina pectoris BA40 Approved [29]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [30]
Estrone DM5T6US Acne vulgaris ED80 Approved [31]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [32]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Mephenytoin 4-hydroxylase (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Acute otitis media AB00 Approved [33]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [24]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [34]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [35]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [27]
Verapamil DMA7PEW Angina pectoris BA40 Approved [36]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [37]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [32]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [38]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [39]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [40]
Meclofenamic acid DM05FXR Ankylosing spondylitis FA92.0 Approved [41]
Diazepam DM08E9O Alcohol withdrawal Approved [42]
Levonorgestrel DM1DP7T Atypical endometrial hyperplasia Approved [5]
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [41]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [41]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [43]
Quercetin DM3NC4M Obesity 5B81 Approved [44]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [45]
Glimepiride DM5FSJA Diabetic complication 5A2Y Approved [46]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Methotrexate DM2TEOL Anterior urethra cancer Approved [47]
Quercetin DM3NC4M Obesity 5B81 Approved [48]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [49]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [50]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [51]
Testosterone enanthate DMB6871 N. A. N. A. Approved [52]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [53]
Folic Acid DMEMBJC Colorectal carcinoma Approved [54]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [55]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [56]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Progesterone receptor (PGR) TTUV8G9 PRGR_HUMAN Modulator [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [5]
Vitamin K-dependent protein S (PROS1) OTXQWNOI PROS_HUMAN Gene/Protein Processing [6]

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7065).
2 Preclinical experience with two selective progesterone receptor modulators on breast and endometrium. Steroids. 2000 Oct-Nov;65(10-11):733-40.
3 The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. Br J Clin Pharmacol. 2005 Jul;60(1):69-75.
4 The role of CYP2C in the in vitro bioactivation of the contraceptive steroid desogestrel. J Pharmacol Exp Ther. 1998 Dec;287(3):975-82.
5 Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3. Chem Biol Interact. 2011 May 30;191(1-3):227-33.
6 Protein S levels are lower in women receiving desogestrel-containing combined oral contraceptives (COCs) than in women receiving levonorgestrel-containing COCs at steady state and on cross-over. Br J Haematol. 2001 Jun;113(4):898-904. doi: 10.1046/j.1365-2141.2001.02853.x.
7 Clinical pipeline report, company report or official report of lipocine.
8 Mullard A: 2010 FDA drug approvals. Nat Rev Drug Discov. 2011 Feb;10(2):82-5.
9 Pharmacological profile of progestins. Maturitas. 2008 Sep-Oct;61(1-2):151-7.
10 Focus on anastrozole and breast cancer. Curr Med Res Opin. 2003;19(8):683-8.
11 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
12 Dienogest is a selective progesterone receptor agonist in transactivation analysis with potent oral endometrial activity due to its efficient pharm... Steroids. 2008 Feb;73(2):222-31.
13 Contribution of functional groups of 19-nor-progestogens to binding to progesterone and estradiol-17beta receptors in rabbit uterus. Endocrinology. 1977 Jun;100(6):1579-84.
14 Met909 plays a key role in the activation of the progesterone receptor and also in the high potency of 13-ethyl progestins. Mol Pharmacol. 2009 Jun;75(6):1317-24.
15 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
16 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
17 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
18 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
19 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
20 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
21 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
22 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
23 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
24 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
25 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
26 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
27 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
28 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
29 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
30 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
31 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
32 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
33 High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8.
34 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
35 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
36 Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21.
37 Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry. 1999 Oct 26;38(43):14264-70.
38 Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
39 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
40 Bringing in vitro analysis closer to in vivo: studying doxorubicin toxicity and associated mechanisms in 3D human microtissues with PBPK-based dose modelling. Toxicol Lett. 2018 Sep 15;294:184-192.
41 Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs. Chem Biol Interact. 2009 Mar 16;178(1-3):221-7.
42 Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5.
43 In-vivo effects of simvastatin and rosuvastatin on global gene expression in peripheral blood leucocytes in a human inflammation model. Pharmacogenet Genomics. 2008 Feb;18(2):109-20.
44 AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids. Chem Biol Interact. 2009 Mar 16;178(1-3):138-44.
45 Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
46 Initro inhibition of AKR1Cs by sulphonylureas and the structural basis. Chem Biol Interact. 2015 Oct 5;240:310-5.
47 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
48 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
49 Development of a neural teratogenicity test based on human embryonic stem cells: response to retinoic acid exposure. Toxicol Sci. 2011 Dec;124(2):370-7.
50 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
51 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
52 Haemostatic effects of supraphysiological levels of testosterone in normal men. Thromb Haemost. 1995 Aug;74(2):693-7.
53 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
54 Folic acid supplementation dysregulates gene expression in lymphoblastoid cells--implications in nutrition. Biochem Biophys Res Commun. 2011 Sep 9;412(4):688-92. doi: 10.1016/j.bbrc.2011.08.027. Epub 2011 Aug 16.
55 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
56 Effects of oral and transvaginal ethinyl estradiol on hemostatic factors and hepatic proteins in a randomized, crossover study. J Clin Endocrinol Metab. 2007 Jun;92(6):2074-9. doi: 10.1210/jc.2007-0026. Epub 2007 Mar 20.