CHEBI:6784 - mestranol

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ChEBI Name mestranol
ChEBI ID CHEBI:6784
Definition A terminal acetylenic compound that is (17α)-17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB9258118, ZINC000003875484
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Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth. Side effects of fluoxymesterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage and cardiovascular side effects like high blood pressure. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization. Fluoxymesterone was first described in 1956 and was introduced for medical use in 1957. In addition to its medical use, fluoxymesterone is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.
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Formula C21H26O2
Net Charge 0
Average Mass 310.42994
Monoisotopic Mass 310.19328
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
SMILES [H][C@]12CC[C@@]3(C)[C@@]([H])(CC[C@@]3(O)C#C)[C@]1([H])CCc1cc(OC)ccc21
Roles Classification
Biological Role(s): xenoestrogen
A synthetic or semi-synthetic compound that has oestrogenic activity.
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
xenoestrogen
A synthetic or semi-synthetic compound that has oestrogenic activity.
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ChEBI Ontology
Outgoing mestranol (CHEBI:6784) has functional parent 17β-estradiol (CHEBI:16469)
mestranol (CHEBI:6784) has role prodrug (CHEBI:50266)
mestranol (CHEBI:6784) has role xenoestrogen (CHEBI:76988)
mestranol (CHEBI:6784) is a 17β-hydroxy steroid (CHEBI:35343)
mestranol (CHEBI:6784) is a aromatic ether (CHEBI:35618)
mestranol (CHEBI:6784) is a terminal acetylenic compound (CHEBI:73477)
IUPAC Name
17-ethynyl-3-methoxyestra-1(10),2,4-trien-17β-ol
INNs Sources
mestranol KEGG DRUG
mestranolum ChemIDplus
Synonyms Sources
(+)-17α-Ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene NIST Chemistry WebBook
(+)-17α-Ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-oestratriene NIST Chemistry WebBook
17-ethynyl-3-methoxyoestra-1(10),2,4-trien-17β-ol ChEBI
3-Methoxy-17α-ethynylestradiol NIST Chemistry WebBook
3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol NIST Chemistry WebBook
Ethynylestradiol 3-methyl ether NIST Chemistry WebBook
Mestranol KEGG COMPOUND
Manual Xrefs Databases
1714 DrugCentral
C07618 KEGG COMPOUND
D00575 KEGG DRUG
DB01357 DrugBank
HMDB0015446 HMDB
LSM-2693 LINCS
Mestranol Wikipedia
US2666769 Patent
View more database links
Registry Numbers Types Sources
2625905 Reaxys Registry Number Reaxys
72-33-3 CAS Registry Number KEGG COMPOUND
72-33-3 CAS Registry Number ChemIDplus
Citations
Temes TA, Andersen H, Gilberg D, Bonerz M (2002)
Determination of estrogens in sludge and sediments by liquid extraction and GC/MS/MS.
Analytical chemistry 74, 3498-3504 [PubMed:12139060]
[show Abstract]
Ahmad T, Akhtar S, Haider S (1991)
A study on stability of mestranol.
Pakistan journal of pharmaceutical sciences 4, 63-70 [PubMed:16414683]
[show Abstract]
Last Modified
22 February 2017