Details of the Drug

General Information of Drug (ID: DMG3F94)

Drug Name
Mestranol
Synonyms
Devocin; Menophase; Mestranolo; Mestranolum; Norquen; Ovastol; Component of Norinyl; Component of Norquen; Component of Ovulen; Ethynylestradiol methyl ether; Mestranol [Steroidal oestrogens]; Mestranolo [DCIT]; EE3ME; Ethinyl Estradiol 3 Methyl Ether; SC 4725; Component of Ortho-Novum; Delta-MVE; EE(sub3)ME; EthinylEstradiol 3-Methyl Ether; Ethinylestradiol 3-methyl ether; Ethinyloestradiol 3-methyl ether; Ethynylestradiol 3-methyl ether; Ethynyloestradiol 3-methyl ether; Inostral (steroid); Mestranolum [INN-Latin]; Mestranol (JP15/USP/INN); Mestranol [USAN:INN:BAN:JAN]; Alpha.-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-meth; (17beta)-17-ethynyl-3-(methyloxy)estra-1,3,5(10)-trien-17-ol; 17-Ethynyl-3-methoxy-1,3,5(10)-oestratien-17-beta-ol; 17-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17-ol; 17-Ethynylestradiol 3-methyl ether; 17-Ethynyloestradiol 3-methyl ether; 17-alpha-Ethinyl estradiol 3-methyl ether; 17-alpha-Ethinyl oestradiol 3-methyl ether; 17-alpha-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17-beta-ol; 17-alpha-Ethynyloestradiol methyl ether; 17-ethynyl-3-methoxyestra-1(10),2,4-trien-17beta-ol; 17-ethynyl-3-methoxyoestra-1(10),2,4-trien-17beta-ol; 17alpha-Ethinyl estradiol 3-methyl ether; 17alpha-Ethinyl oestradiol 3-methyl ether; 17alpha-Ethinylestradiol 3-methyl ether; 17alpha-Ethynylestradiol 3-methyl ether; 17alpha-Ethynylestradiol methyl ether; 17alpha-Ethynyloestradiol 3-methyl ether; 17beta-Estradiol, 17-ethynyl-, 3-(methyl ether); 3-Methoxy-17-alpha-19-norpregna-1,3,5(10)-trien-20-yn-17-ol; 3-Methoxy-17-alpha-ethinylestradiol; 3-Methoxy-17-alpha-ethinyloestradiol; 3-Methoxy-17-alpha-ethynyl-1,3,5(10)-estratrien-17-beta-ol; 3-Methoxy-17-alpha-ethynyl-1,3,5(10)-oestratrien-17-beta-ol; 3-Methoxy-17-alpha-ethynylestradiol; 3-Methoxy-17-alpha-ethynyloestradiol; 3-Methoxy-17-ethynyloestradiol-17-beta; 3-Methoxy-17alpha-ethinylestradiol; 3-Methoxy-17alpha-ethinyloestradiol; 3-Methoxy-17alpha-ethynyl-1,3,5(10)-estratrien-17beta-ol; 3-Methoxy-17alpha-ethynyl-1,3,5(10)-oestratrien-17beta-ol; 3-Methoxy-17alpha-ethynylestradiol; 3-Methoxy-17alpha-ethynyloestradiol; 3-Methoxy-19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol; 3-Methoxy-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17beta-ol; 3-Methoxyethynylestradiol; 3-Methoxyethynyloestradiol; 3-Methylethynylestradiol; 3-Methylethynyloestradiol; 3-O-Methylethynylestradiol
Indication
Disease Entry ICD 11 Status REF
Contraception QA21 Approved [1]
Menorrhagia GA20.50 Approved [2]
Endometriosis GA10 Investigative [2]
Therapeutic Class
Estrogens
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 310.4
Logarithm of the Partition Coefficient (xlogp) 4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C21H26O2
IUPAC Name
(8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC
InChI
InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1
InChIKey
IMSSROKUHAOUJS-MJCUULBUSA-N
Cross-matching ID
PubChem CID
6291
ChEBI ID
CHEBI:6784
CAS Number
72-33-3
DrugBank ID
DB01357
TTD ID
D0J1ML
INTEDE ID
DR1034
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Agonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [5]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Amphiregulin (AREG) OTJFOR67 AREG_HUMAN Gene/Protein Processing [7]
Calmin (CLMN) OT7U5J3T CLMN_HUMAN Gene/Protein Processing [7]
Carbonic anhydrase 12 (CA12) OT6WNFU8 CAH12_HUMAN Gene/Protein Processing [7]
CD44 antigen (CD44) OT9TTJ41 CD44_HUMAN Gene/Protein Processing [7]
Coagulation factor VII (F7) OTGNJ97M FA7_HUMAN Gene/Protein Processing [8]
Cyclin-G2 (CCNG2) OTII38K2 CCNG2_HUMAN Gene/Protein Processing [7]
Delta-aminolevulinic acid dehydratase (ALAD) OTHM9GSH HEM2_HUMAN Gene/Protein Processing [7]
DNA endonuclease RBBP8 (RBBP8) OTRHJ3GI CTIP_HUMAN Gene/Protein Processing [7]
DNA-binding protein inhibitor ID-3 (ID3) OTUULW5Z ID3_HUMAN Gene/Protein Processing [7]
Dual specificity tyrosine-phosphorylation-regulated kinase 2 (DYRK2) OTMDVWPS DYRK2_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Contraception
ICD Disease Classification QA21
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 9.78E-01 -3.38E-03 -5.71E-02
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 9.09E-01 -9.26E-02 -3.68E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 9.85E-01 2.24E-02 7.33E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Mestranol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Sarecycline DMLZNIQ Moderate Decreased absorption of Mestranol due to formation of complexes caused by Sarecycline . Acne vulgaris [ED80] [9]
Emapalumab DMZG5WL Moderate Altered metabolism of Mestranol due to Emapalumab alters the formation of CYP450 enzymes. Adaptive immunity immunodeficiency [4A01] [10]
Siltuximab DMGEATB Moderate Altered metabolism of Mestranol due to Siltuximab alters the formation of CYP450 enzymes. Anemia [3A00-3A9Z] [10]
ABT-492 DMJFD2I Moderate Decreased absorption of Mestranol due to formation of complexes caused by ABT-492. Bacterial infection [1A00-1C4Z] [9]
Omadacycline DMR2J95 Moderate Decreased absorption of Mestranol due to formation of complexes caused by Omadacycline. Bacterial infection [1A00-1C4Z] [9]
Alpelisib DMEXMYK Moderate Increased metabolism of Mestranol caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [11]
Linaclotide DM4EGV0 Moderate Altered absorption of Mestranol caused by Linaclotide. Irritable bowel syndrome [DD91] [12]
R0-93877 DMM4U9G Moderate Altered absorption of Mestranol caused by R0-93877. Irritable bowel syndrome [DD91] [13]
Exjade DMHPRWG Moderate Increased metabolism of Mestranol caused by Exjade mediated induction of CYP450 enzyme. Mineral absorption/transport disorder [5C64] [14]
Carfilzomib DM48K0X Major Additive thrombogenic effects by the combination of Mestranol and Carfilzomib. Multiple myeloma [2A83] [15]
Romidepsin DMT5GNL Moderate Antagonize the effect of Mestranol when combined with Romidepsin. Mycosis fungoides [2B01] [11]
Ustekinumab DMHTYK3 Moderate Altered metabolism of Mestranol due to Ustekinumab alters the formation of CYP450 enzymes. Psoriasis [EA90] [10]
Tocilizumab DM7J6OR Moderate Altered metabolism of Mestranol due to Tocilizumab alters the formation of CYP450 enzymes. Rheumatoid arthritis [FA20] [10]
Rilonacept DMGLUQS Moderate Altered metabolism of Mestranol due to Rilonacept alters the formation of CYP450 enzymes. Rheumatoid arthritis [FA20] [10]
Sarilumab DMOGNXY Moderate Altered metabolism of Mestranol due to Sarilumab alters the formation of CYP450 enzymes. Rheumatoid arthritis [FA20] [10]
⏷ Show the Full List of 15 DDI Information of This Drug

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: 7087).
2 Mestranol FDA Label
3 Short-term effects of environmentally relevant concentrations of EDC mixtures on Mytilus galloprovincialis digestive gland. Aquat Toxicol. 2008 May 30;87(4):272-9.
4 Prescribrt's digital referenve - Ethinyl estradiol/norethindrone; mestranol/norethindrone - Drug Summary
5 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.
6 Loss of orally administered drugs in GI tract. Saudi Pharm J. 2012 Oct;20(4):331-44.
7 Moving toward integrating gene expression profiling into high-throughput testing: a gene expression biomarker accurately predicts estrogen receptor alpha modulation in a microarray compendium. Toxicol Sci. 2016 May;151(1):88-103.
8 Vascular complications of long-term oestrogen therapy. Front Horm Res. 1977;5:174-91. doi: 10.1159/000401993.
9 Friedman CI, Huneke AL, Kim MH, Powell J "The effect of ampicillin on oral contraceptive effectiveness." Obstet Gynecol 55 (1980): 33-7. [PMID: 7188714]
10 Product Information. Cosentyx (secukinumab). Novartis Pharmaceuticals, East Hanover, NJ.
11 Fuhr U, Maier-Bruggemann A, Blume H, et al. "Grapefruit juice increases oral nimodipine bioavailability." Int J Clin Pharmacol Ther 36 (1998): 126-32. [PMID: 9562227]
12 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
13 Cerner Multum, Inc. "Australian Product Information.".
14 Gunston GD, Mehta U "Potentially serious drug interactions with grapefruit juice." S Afr Med J 90 (2000): 41. [PMID: 10721388]
15 Faculty of Sexual & Reproductive Healthcare "FSRH Clinical Guidance: Drug Interactions with Hormonal Contraception.".