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Chemical compound
Delmadinone acetate
Trade names Tardak, others Other names DMA; RS-1310; 1-Dehydrochlormadinone acetate; 1,6-Didehydro-6-chloro-17α-acetoxyprogesterone; 6-Chloro-17α-hydroxypregna-1,4,6-triene-3,20-dione
Drug class
Progestogen ;
Progestin ;
Progestogen ester ;
Steroidal antiandrogen
ATCvet code
[(8R ,9S ,10R ,13S ,14S ,17R )-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-9,11,12,14,15,16-hexahydro-8H -cyclopenta[a ]phenanthren-17-yl] acetate
CAS Number
PubChem
CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.033.821
Formula C 23 H 27 Cl O 4
Molar mass 402.92 g·mol−1 3D model (
JSmol )
O=C\1\C=C/[C@]4(C(=C/1)C(\Cl)=C/[C@@H]2[C@@H]4CC[C@@]3([C@@](OC(=O)C)(C(=O)C)CC[C@@H]23)C)C
InChI=1S/C23H27ClO4/c1-13(25)23(28-14(2)26)10-7-18-16-12-20(24)19-11-15(27)5-8-21(19,3)17(16)6-9-22(18,23)4/h5,8,11-12,16-18H,6-7,9-10H2,1-4H3/t16-,17+,18+,21-,22+,23+/m1/s1
Key:CGBCCZZJVKUAMX-DFXBJWIESA-N
Delmadinone acetate (DMA ), sold under the brand name Tardak among others, is a
progestin and
antiandrogen which is used in
veterinary medicine to treat
androgen-dependent conditions such as
benign prostatic hyperplasia .
[1]
[2]
[3]
[4] It must be used with care as it has the potential to cause
adrenal insufficiency via inhibition of
adrenocorticotropic hormone (ACTH) secretion from the
pituitary gland .
[5] DMA is the C17α acetate ester of
delmadinone , which, in contrast to DMA, was never marketed for medical use.
[1]
[2]
Uses
Veterinary
DMA is used to treat
androgen-dependent conditions in animals.
[6] It is most commonly used to treat
benign prostatic hyperplasia .
[6] However, it can also be used to treat
hypersexuality in male dogs and cats,
perianal gland tumors in dogs, and
hormone -driven
aggression in dogs.
[6]
Pharmacology
Pharmacodynamics
DMA is a
progestogen with
antigonadotropic and hence
antiandrogenic and
antiestrogenic effects. In addition, DMA binds to the
androgen receptor , and likely acts as an
antagonist of this receptor similarly to related drugs like
chlormadinone acetate and
osaterone acetate .
[7]
Chemistry
DMA, also known as 1-dehydrochlormadinone acetate, as well as 1,6-didehydro-6-chloro-17α-acetoxyprogesterone or '6-chloro-17α-hydroxypregna-1,4,6-triene-3,20-dione, is a
synthetic
pregnane
steroid and a
derivative of
progesterone .
[1]
[2]
[4] It is specifically a derivative of
17α-hydroxyprogesterone with a
chlorine atom at the C6 position, a
double bond between the C1 and C2 positions, another double bond between the C6 and C7 positions, and an
acetate
ester at the C17α position.
[1]
[2]
Analogues of DMA include other 17α-hydroxyprogesterone derivatives such as
chlormadinone acetate ,
cyproterone acetate ,
hydroxyprogesterone caproate ,
medroxyprogesterone acetate ,
megestrol acetate , and
osaterone acetate .
[1]
[2]
History
DMA was first described in the literature in 1959 and has been marketed since at least 1972.
[1]
[8]
[9] It was marketed by this year in
Europe and the
United Kingdom under the brand names Tardak and Zenadrex.
[9] It was under development for use in the
United States as well but does not seem to have ultimately been marketed in this country.
[9]
Society and culture
Generic names
Delmadinone acetate is the
generic name of the drug and its
USAN Tooltip United States Adopted Name and
BANM Tooltip British Approved Name .
[1]
[2]
[3]
[4] Delmadinone is the
INN Tooltip International Nonproprietary Name and
BAN Tooltip British Approved Name of the unesterified free
alcohol form.
[1]
[2]
[3]
[4]
Brand names
DMA is most commonly sold as Tardak , but has also been marketed under a variety of other brand names including Delmate , Estrex , Tardastren , Tardastrex , Vetadinon , and Zenadrex .
[1]
[2]
[4]
Availability
DMA is available in
Europe and
Oceania .
[2]
[4] It is specifically marketed in the
United Kingdom ,
France ,
Belgium ,
Germany ,
Austria ,
Switzerland , the
Netherlands ,
Finland ,
Australia , and
New Zealand .
[2]
[4]
References
^
a
b
c
d
e
f
g
h
i Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 354–.
ISBN
978-1-4757-2085-3 .
^
a
b
c
d
e
f
g
h
i
j
Index Nominum 2000: International Drug Directory . Taylor & Francis US. 2000. p. 298.
ISBN
978-3-88763-075-1 . Retrieved 30 May 2012 .
^
a
b
c Morton I, Hall JM (1999).
Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer. p. 92.
ISBN
978-0-7514-0499-9 . Retrieved 30 May 2012 .
^
a
b
c
d
e
f
g
"List of Progestins" . Drugs.com .
^ Court EA, Watson AD, Church DB, Emslie DR (August 1998).
"Effects of delmadinone acetate on pituitary-adrenal function, glucose tolerance and growth hormone in male dogs" (PDF) . Australian Veterinary Journal . 76 (8): 555–560.
doi :
10.1111/j.1751-0813.1998.tb10216.x .
PMID
9741725 .
^
a
b
c McLauchlan G, Ramsey I (2008). "Update on medical management of benign prostatic hyperplasia". Companion Animal . 13 (7): 39–41.
doi :
10.1111/j.2044-3862.2008.tb00313.x .
ISSN
1464-4630 .
^ McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (May 2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". The Journal of Steroid Biochemistry and Molecular Biology . 110 (1–2): 39–47.
doi :
10.1016/j.jsbmb.2007.10.008 .
PMID
18395441 .
S2CID
5612000 .
^ Ringold HJ, Batres E, Bowers A, Edwards J, Zderic J (1959). "Steroids. Cxxvii.16-Halo Progestational Agents". Journal of the American Chemical Society . 81 (13): 3485–3486.
doi :
10.1021/ja01522a090 .
ISSN
0002-7863 .
^
a
b
c
Modern Veterinary Practice . Vol. 53. 1972. p. 46. John T. Bryans, University of Kentucky, Lexington. Thoroughbred Record 194(22): 1634-1636, 1971. In the clinical review entitled "Antiandrogen Treatment of Prostate Disorders" (MVP Oct, p 46} the product should have been identified as delta-chlor- madinone acetate (delta-CAP, rather than as CAP). This compound, also known as delmadinone acetate, has unique properties and is marketed in Europe and the UK as Tardak® and Zenadrex®; It is presently subject to clinical investigation in the US for FDA approval.
Androgens (incl.
AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor
antagonists
Steroidogenesis inhibitors
Antigonadotropins
D2 receptor
antagonists (
prolactin releasers ) (e.g.,
domperidone ,
metoclopramide ,
risperidone ,
haloperidol ,
chlorpromazine ,
sulpiride )
Estrogens (e.g.,
bifluranol ,
diethylstilbestrol ,
estradiol ,
estradiol esters ,
ethinylestradiol ,
ethinylestradiol sulfonate ,
paroxypropione )
GnRH agonists (e.g.,
leuprorelin )
GnRH antagonists (e.g.,
cetrorelix )
Progestogens (incl.,
chlormadinone acetate ,
cyproterone acetate ,
hydroxyprogesterone caproate ,
gestonorone caproate ,
medroxyprogesterone acetate ,
megestrol acetate )
Others
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A
GR Tooltip Glucocorticoid receptor
PR Tooltip Progesterone receptor
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Testosterone derivatives: Progestins:
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17α-Allyl-19-nortestosterone
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Levonorgestrel esters (e.g.,
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Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
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Norelgestromin
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Norethisterone esters (e.g.,
norethisterone acetate ,
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Noretynodrel
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Norgestimate
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Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
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Bolandiol
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Bolandione
Dimethisterone
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Dimethandrolone
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Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
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nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g.,
trenbolone acetate ,
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Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )