Drug Information

Drug (ID: DG00850) and It's Reported Resistant Information

• Name: Mestranol
• Synonyms: Mestranol; 72-33-3; Norquen; Menophase; Devocin; Ovastol; Ethynylestradiol 3-methyl ether; EE3ME; Mestranolum; 3-Methoxyethynylestradiol; EE(sub3)ME; Ethynylestradiol methyl ether; 3-Methylethynylestradiol; 3-O-Methylethynylestradiol; Compound 33355; Inostral; 3-Methylethynyloestradiol; 3-Methoxyethynyloestradiol; 3-Methoxy-17alpha-ethynylestradiol; SC 4725; 17-Ethynyloestradiol 3-methyl ether; UNII-B2V233XGE7; component of Norinyl; component of Ortho-Novum; (8R,9S,13S,14S,17R)-17-Ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol; EE3-ME; Ethinylestradiol 3-methyl ether; Ethinyloestradiol 3-methyl ether; Ethynyloestradiol 3-methyl ether; MLS000028595; B2V233XGE7; CHEBI:6784; 17-Ethynylestradiol 3-methyl ether; component of Ovulen; component of Norquen; delta-MVE; 17alpha-Ethynylestradiol 3-methyl ether; (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; Inostral (steroid); Mestranolo [DCIT]; NCGC00093347-02; Mestranolo; SMR000059128; (17beta)-17-ethynyl-3-(methyloxy)estra-1,3,5(10)-trien-17-ol; DSSTox_CID_814; DSSTox_RID_75804; DSSTox_GSID_20814; Mestranolum [INN-Latin]; Caswell No. 547A; .delta.-MVE; 17alpha-Ethinyl estradiol 3-methyl ether; 17-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17-ol; 3-Methoxy-17alpha-ethinylestradiol; 3-Methoxy-17alpha-ethinyloestradiol; 3-Methoxy-17alpha-ethynyloestradiol; 3-Methoxy-17-alpha-ethinylestradiol; 3-Methoxy-17-alpha-ethynylestradiol; 17alpha-Ethynylestradiol methyl ether; 3-Methoxy-17-alpha-ethinyloestradiol; 3-Methoxy-17-alpha-ethynyloestradiol; CCRIS 377; 17-alpha-Ethynyloestradiol methyl ether; 17alpha-Ethinylestradiol 3-methyl ether; 8027 C. B.; 17alpha-Ethynyloestradiol 3-methyl ether; 3-Methoxy-17-ethynyloestradiol-17-beta; Mestranol [Steroidal oestrogens]; 17alpha-Ethinyl oestradiol 3-methyl ether; HSDB 3588; 17-alpha-Ethinyl estradiol 3-methyl ether; 17-alpha-Ethinyl oestradiol 3-methyl ether; EINECS 200-777-8; NSC 84032; EPA Pesticide Chemical Code 115401; 17beta-Estradiol, 17-ethynyl-, 3-(methyl ether); BRN 2625905; NSC84032; 17-Ethynyl-3-methoxy-1,3,5(10)-oestratien-17-beta-ol; AI3-51798; NSC-84032; 3-Methoxy-17alpha-ethynyl-1,3,5(10)-estratrien-17beta-ol; 3-Methoxy-17alpha-ethynyl-1,3,5(10)-oestratrien-17beta-ol; 17-alpha-Ethynyl-3-methoxy-1,3,5(10)-estratrien-17-beta-ol; 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; CAS-72-33-3; 3-Methoxy-17-alpha-19-norpregna-1,3,5(10)-trien-20-yn-17-ol; 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; 19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-, (17alpha)-; Prestwick_966; Mestranol, 99%; Mestranol [USAN:USP:INN:BAN:JAN]; EEI3ME; Estra-1,3,5(10)-trien-17beta-ol, 17-ethynyl-3-methoxy-; Opera_ID_872; 17alpha-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-methoxy-; Estra-1,3,5(10)-trien-17-beta-ol, 17-alpha-ethynyl-3-methoxy-; Prestwick0_000846; Prestwick1_000846; Prestwick2_000846; Prestwick3_000846; (+)-17-alpha-Ethynyl-17-beta-hydroxy-3-methoxy-1,3,5(10)-estratriene; (17-alpha)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol; 17-ethynyl-3-methoxyestra-1(10),2,4-trien-17-ol; EE-3ME; EE3 ME; (+)-17-alpha-Ethynyl-17-beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene; 17-alpha-Ethynyl-3-methoxy-17-beta-hydroxy-delta-1,3,5(10)-estratriene; 17-alpha-Ethynyl-3-methoxy-17-beta-hydroxy-delta-1,3,5(10)-oestratriene; 3,17-beta-Dihydroxy-17-alpha-ethynyl-1,3,5(10)-estratriene-3-methyl ether; SCHEMBL41391; BSPBio_000831; MLS001077321; MLS001424224; BIDD:ER0199; SPBio_002752; Mestranol (JP17/USP/INN); BPBio1_000915; ethynylestradiol-3-methyl ether; GTPL7087; 17-ethynyl-3-methoxyestra-1(10),2,4-trien-17beta-ol; CHEMBL1201151; DTXSID0020814; 17-ethynyl-3-methoxyoestra-1(10),2,4-trien-17beta-ol; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17beta-ol; HMS1570J13; HMS2051J22; HMS2097J13; HMS2230L20; HMS3714J13; HY-B0390; ZINC3815424; Tox21_111200; Tox21_301837; 17-alpha-19-Norpregna-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-; 4-Cyano-3-fluorophenyl4-butylbenzoate; AKOS005267152; Tox21_111200_1; CCG-101067; DB01357; MCULE-6161762887; NC00317; NCGC00093347-03; NCGC00093347-05; NCGC00093347-07; NCGC00179410-01; NCGC00255342-01; AC-13293; AS-56063; H072; S2125; Mestranol, VETRANAL(TM), analytical standard; C07618; C76306; D00575; 003M689; Q904308; SR-01000695429; SR-01000695429-4; BRD-K31920458-001-03-8; BRD-K31920458-001-23-6; Mestranol, European Pharmacopoeia (EP) Reference Standard; (17beta)-17-ethynyl-3-methoxyestra-1(10),2,4-trien-17-ol; Mestranol, United States Pharmacopeia (USP) Reference Standard; 17.Alpha.-19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-meth; (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-estratriene; (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene; (+ )-17.alpha.-Ethynyl-17.beta.-hydroxy-3-methoxy-1,3, 5(10)-oestratriene; (+)-17.alpha.-Ethynyl-17.beta.-hydroxy-3-methoxy-1,3, 5(10)-estratriene; (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol; (8R,13S,17R)-17-Ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
• Indication:
  In total 1 Indication(s)
  Contraception [ICD-11: QA21]; Approved; [1]
• Drug Resistance Disease(s):
  Disease(s) with Resistance Information Discovered by Cell Line Test for This Drug (2 diseases)
  Brain cancer [ICD-11: 2A00]; [1]
  Ovarian cancer [ICD-11: 2C73]; [1]
• Target: Estrogen receptor (ESR); ESR1_HUMAN; [1]
• Formula: C21H26O2
• IsoSMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC
• 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
• PubChem CID: 6291
• ChEBI ID: CHEBI:6784
• TTD Drug ID: D0J1ML
• INTEDE ID: DR1034
• DrugBank ID: DB01357

Type(s) of Resistant Mechanism of This Drug

  RTDM: Regulation by the Disease Microenvironment

Drug Resistance Data Categorized by Their Corresponding Diseases

ICD-02: Benign/in-situ/malignant neoplasm

Brain cancer [ICD-11: 2A00]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Regulation by the Disease Microenvironment (RTDM)

Key Molecule: L1 cell adhesion molecule (L1CAM) [1]

• Molecule Alteration: Expression; Down-regulation
• Resistant Disease: Glioblastoma [ICD-11: 2A00.02]
• Experimental Note: Revealed Based on the Cell Line Data
• Cell Pathway Regulation: Cell migration; Activation; hsa04670
• In Vitro Model: MDCK cells; Kidney; Canis lupus familiaris (Dog) (Canis familiaris); CVCL_0422
• Experiment for Molecule Alteration: Puromycin selection and monitored regularly for the maintenance of L1 silencing assay
• Experiment for Drug Resistance: Migration assay
• Mechanism Description: With OVCAR3 cells treated with anagrelide, 2-hydroxy-5-fluoropyrimidine and mestranol , the gap width closure was seen from 48 h onward at all concentrations tested. Similar results were obtained with U251 cells, and L1's metastatic potential is further evidenced by its promotion of epithelial-mesenchymal transition, endothelial cell transcytosis and resistance to chemo- and radiotherapy.

Ovarian cancer [ICD-11: 2C73]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Regulation by the Disease Microenvironment (RTDM)

Key Molecule: L1 cell adhesion molecule (L1CAM) [1]

• Molecule Alteration: Expression; Down-regulation
• Resistant Disease: Ovarian cancer [ICD-11: 2C73.0]
• Experimental Note: Revealed Based on the Cell Line Data
• Cell Pathway Regulation: Cell migration; Activation; hsa04670
• In Vitro Model: 22RV1 cells; Prostate; Homo sapiens (Human); CVCL_1045
• Experiment for Molecule Alteration: Puromycin selection and monitored regularly for the maintenance of L1 silencing assay
• Experiment for Drug Resistance: Migration assay
• Mechanism Description: With OVCAR3 cells treated with anagrelide, 2-hydroxy-5-fluoropyrimidine and mestranol , the gap width closure was seen from 48 h onward at all concentrations tested. Similar results were obtained with U251 cells, and L1's metastatic potential is further evidenced by its promotion of epithelial-mesenchymal transition, endothelial cell transcytosis and resistance to chemo- and radiotherapy.

References

• Ref 1: Antagonistic L1 Adhesion Molecule Mimetic Compounds Inhibit Glioblastoma Cell Migration In Vitro .Biomolecules. 2022 Mar 12;12(3):439. doi: 10.3390/biom12030439. 10.3390/biom12030439