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Chemical compound
Mepitiostane
Trade names Thioderon Other names 10364-S; Epitiostanol 17β-(1-methoxy)cyclopentyl ether; 17β-[(1-Methoxycyclopentyl)oxy]-2α,3α-epithio-5α-androstane
AHFS /
Drugs.com
International Drug Names
Routes of administration
By mouth
Drug class
Androgen ;
Anabolic steroid ;
Androgen ether ;
Antiestrogen
ATC code
Legal status
In general: ℞ (Prescription only)
(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 )
Formula C 25 H 40 O 2 S
Molar mass 404.65 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
N Key:IVDYZAAPOLNZKG-KWHRADDSSA-N
N
N Y
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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]
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
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
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
INN Tooltip International Nonproprietary Name and
JAN Tooltip Japanese Accepted Name .
[1]
[2]
[3]
References
^
a
b
c
d
e
f Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. p. 768.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d
Index Nominum 2000: International Drug Directory . Taylor & Francis. January 2000. pp. 648–.
ISBN
978-3-88763-075-1 .
^
a
b
c
d
e Morton IK, Hall JM (6 December 2012).
Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. pp. 175–.
ISBN
978-94-011-4439-1 .
^
"Mepitiostane" .
^
a
b
c Erslev AJ (1991).
Erythropoietin: molecular, cellular, and clinical biology . Johns Hopkins University Press. p. 229.
ISBN
978-0-8018-4221-4 .
^
a
b
c
d Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J, eds. (12 March 2007).
Prodrugs: Challenges and Rewards . Springer Science & Business Media. pp. 660–.
ISBN
978-0-387-49782-2 .
^
a
b Borchardt RT, Smith PL, Wilson G (29 June 2013).
Models for Assessing Drug Absorption and Metabolism . Springer Science & Business Media. pp. 101–.
ISBN
978-1-4899-1863-5 .
^
a
b Newton HB (19 December 2005).
Handbook of Brain Tumor Chemotherapy . Academic Press. pp. 470–.
ISBN
978-0-08-045593-8 .
^ Lee JH (11 December 2008).
Meningiomas: Diagnosis, Treatment, and Outcome . Springer Science & Business Media. pp. 293–5.
ISBN
978-1-84628-784-8 .
^ Oura S, Sakurai T, Yoshimura G, Tamaki T, Umemura T, Kokawa Y, et al. (July 2000). "Regression of a presumed meningioma with the antiestrogen agent mepitiostane. Case report". Journal of Neurosurgery . 93 (1): 132–135.
doi :
10.3171/jns.2000.93.1.0132 .
PMID
10883917 .
^ Miyai M, Takenaka K, Hayashi K, Kato M, Uematsu K, Murai H (August 2014). "[Effect of an oral anti-estrogen agent (mepitiostane) on the regression of intracranial meningiomas in the elderly]". Brain and Nerve = Shinkei Kenkyu No Shinpo (in Japanese). 66 (8): 995–1000.
PMID
25082321 .
^ Inoue K, Okazaki K, Morimoto T, Hayashi M, Uyama S, Sonoo H, et al. (May 1978). "Therapeutic value of mepitiostane in the treatment of advanced breast cancer". Cancer Treatment Reports . 62 (5): 743–745.
PMID
657160 .
^ Matsuzawa A, Yamamoto T (December 1977). "Antitumor effect of two oral steroids, mepitiostane and fluoxymesterone, on a pregnancy-dependent mouse mammary tumor (TPDMT-4)". Cancer Research . 37 (12): 4408–4415.
PMID
922732 .
^ Timmerman H (20 November 1995).
QSAR and Drug Design: New Developments and Applications . Elsevier. pp. 125, 145.
ISBN
978-0-08-054500-4 .
^ Matsuzawa A (1986).
"Hormone dependence and independence of mammary tumors in mice" . International Review of Cytology . 103 : 303–40.
doi :
10.1016/s0074-7696(08)60839-6 .
ISBN
9780123645036 .
PMID
3017886 .
^ Croll RP, Wang C (2007). "Possible roles of sex steroids in the control of reproduction in bivalve molluscs". Aquaculture . 272 (1–4): 76–86.
doi :
10.1016/j.aquaculture.2007.06.031 .
ISSN
0044-8486 .
^ Porter CJ, Charman WN (29 June 2013).
"Model Systems for Intestinal Lympahtic Transport Studies" . In Borchardt RT, Smith PL, Wilson G (eds.). Models for Assessing Drug Absorption and Metabolism . Springer Science & Business Media. pp. 101–.
ISBN
978-1-4899-1863-5 .
^ Rahnema CD, Crosnoe LE, Kim ED (March 2015).
"Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem" . Andrology . 3 (2): 150–155.
doi :
10.1111/andr.307 .
PMID
25684733 .
S2CID
6999218 .
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