Mepitiostane

Chemical compound From Wikipedia, the free encyclopedia

Mepitiostane, sold under the brand name Thioderon, is an orally active antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which is marketed in Japan as an antineoplastic agent for the treatment of breast cancer.[1][2][3][4][5] It is a prodrug of epitiostanol.[6][7] The drug was patented and described in 1968.[1]

Trade namesThioderon
Other names10364-S; Epitiostanol 17β-(1-methoxy)cyclopentyl ether; 17β-[(1-Methoxycyclopentyl)oxy]-2α,3α-epithio-5α-androstane
AHFS/Drugs.comInternational Drug Names
Routes of
administrationBy mouth
Quick facts Clinical data, Trade names ...
Mepitiostane
Clinical data
Trade namesThioderon
Other names10364-S; Epitiostanol 17β-(1-methoxy)cyclopentyl ether; 17β-[(1-Methoxycyclopentyl)oxy]-2α,3α-epithio-5α-androstane
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid; Androgen ether; Antiestrogen
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (1S,2S,4R,8S,11R,12S,15S,16S)-15-[(1-methoxycyclopentyl)oxy]-2,16-dimethyl-5-thiapentacyclo[9.7.0.02,8.04,6.012,16]octadecane
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H40O2S
Molar mass404.65 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC4(CCCC4)OC)CC[C@@H]5[C@@]3(C[C@@H]6[C@H](C5)S6)C
  • InChI=1S/C25H40O2S/c1-23-13-10-19-17(7-6-16-14-20-21(28-20)15-24(16,19)2)18(23)8-9-22(23)27-25(26-3)11-4-5-12-25/h16-22H,4-15H2,1-3H3/t16-,17-,18-,19-,20-,21+,22-,23-,24-/m0/s1 â˜’N
  • Key:IVDYZAAPOLNZKG-KWHRADDSSA-N â˜’N
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Medical uses

Mepitiostane is used as an antiestrogen and antineoplastic agent in the treatment of breast cancer.[1][2][3][5] It is also used as an AAS in the treatment of anemia of renal failure.[5] A series of case reports have found it to be effective in the treatment of an estrogen receptor (ER)-dependent meningiomas as well.[8][9][10][11]

Side effects

See also: Anabolic steroid § Adverse effects

Mepitiostane shows a high rate of virilizing side effects such as acne, hirsutism, and voice changes in women.[12]

Pharmacology

Pharmacodynamics

Mepitiostane is described as similar to tamoxifen as an antiestrogen,[8] and through its active form epitiostanol, binds directly to and antagonizes the ER.[13][14][15][16] It is also an AAS.[1][3]

Pharmacokinetics

Mepitiostane is converted into epitiostanol in the body.[6][7]

Chemistry

See also: List of androgens/anabolic steroids

Mepitiostane, also known as epitiostanol 17β-(1-methoxy)cyclopentyl ether,[6] is a synthetic androstane steroid and a derivative of DHT.[1][2][3] It is the C17β (1-methoxy)cyclopentyl ether of epitiostanol, which itself is 2α,3α-epithio-DHT or 2α,3α-epithio-5α-androstan-17β-ol.[6][17] A related AAS is methylepitiostanol (17α-methylepitiostanol), which is an orally active variant of epitiostanol similarly to mepitiostane, though also has a risk of hepatotoxicity.[18]

Society and culture

Generic names

Mepitiostane is the generic name of the drug and its INNTooltip International Nonproprietary Name and JANTooltip Japanese Accepted Name.[1][2][3]

References

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