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Delmadinone acetate

From Wikipedia, the free encyclopedia
Veterinary progestin and antiandrogen
Pharmaceutical compound
Delmadinone acetate
Clinical data
Trade namesTardak, others
Other namesDMA; RS-1310; 1-Dehydrochlormadinone acetate; 1,6-Didehydro-6-chloro-17α-acetoxyprogesterone; 6-Chloro-17α-hydroxypregna-1,4,6-triene-3,20-dione
Routes of
administration
Intramuscular injection
Drug classProgestogen;Progestin;Progestogen ester;Steroidal antiandrogen
ATCvet code
Legal status
Legal status
  • Veterinary use only
Identifiers
  • [(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
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.033.821Edit this at Wikidata
Chemical and physical data
FormulaC23H27ClO4
Molar mass402.92 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 nameTardak among others, is aprogestin andantiandrogen used inveterinary medicine to treatandrogen-dependent conditions such asbenign prostatic hyperplasia in male dogs.[1][2][3][4]

Delmadinone acetate must be used with caution, as it can causeadrenal insufficiency through inhibition ofadrenocorticotropic hormone (ACTH) secretion from thepituitary gland.[5]

DMA is the C17α acetate ester ofdelmadinone, which, in contrast to DMA, was never marketed for medical use.[1][2]

Uses

[edit]

Veterinary

[edit]

Delmadinone acetate (DMA) is used in veterinary medicine to treatandrogen-dependent conditions in animals.[6] Its most common use is for the treatment ofbenign prostatic hyperplasia in male dogs.[6] It may also be prescribed for managinghypersexuality in male dogs and cats,perianal gland tumors in dogs, andhormone-drivenaggression in dogs.[6]

Pharmacology

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Pharmacodynamics

[edit]

Delmadinone acetate (DMA) is aprogestogen withantigonadotropic, and thereforeantiandrogenic andantiestrogenic, effects. In addition, DMA binds to theandrogen receptor and is thought to act as anantagonist of this receptor, similarly to related drugs such aschlormadinone acetate andosaterone acetate.[7]

Chemistry

[edit]
See also:List of progestogens,Progestogen ester,List of progestogen esters,Steroidal antiandrogen, andList of steroidal antiandrogens

Delmadinone acetate (DMA), also known as 1-dehydrochlormadinone acetate, 1,6-didehydro-6-chloro-17α-acetoxyprogesterone, or 6-chloro-17α-hydroxypregna-1,4,6-triene-3,20-dione, is asyntheticpregnanesteroid and aderivative ofprogesterone.[1][2][4] It is specifically a17α-hydroxyprogesterone derivative, characterized by the presence of achlorine atom at the C6 position, adouble bond between the C1 and C2 positions, another double bond between the C6 and C7 positions, and anacetateester at the C17α position.[1][2]Structural analogues of DMA include other 17α-hydroxyprogesterone derivatives such aschlormadinone acetate,cyproterone acetate,hydroxyprogesterone caproate,medroxyprogesterone acetate,megestrol acetate, andosaterone acetate.[1][2]

History

[edit]

Delmadinone acetate (DMA) was first described in the scientific literature in 1959 and has been marketed since at least 1972.[1][8][9] By that time, it was marketed inEurope and theUnited Kingdom under the brand namesTardak andZenadrex.[9] It was also under development for use in theUnited States, but it does not appear to have been marketed there.[9]

Society and culture

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Generic names

[edit]

Delmadinone acetate is thegeneric name of the drug and itsUSANTooltip United States Adopted Name andBANMTooltip British Approved Name.[1][2][3][4]Delmadinone is theINNTooltip International Nonproprietary Name andBANTooltip British Approved Name of the unesterified freealcohol form.[1][2][3][4]

Brand names

[edit]

DMA is most commonly marketed under the brand nameTardak, but has also been sold under several other brand names, includingDelmate,Estrex,Tardastren,Tardastrex,Vetadinon, andZenadrex.[1][2][4]

Availability

[edit]

DMA is available inEurope andOceania.[2][4] It is marketed specifically inthe United Kingdom,France,Belgium,Germany,Austria,Switzerland,the Netherlands,Finland,Australia, andNew Zealand.[2][4]

References

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  1. ^abcdefghiElks J (14 November 2014).The Dictionary of Drugs: Chemical Data, Structures and Bibliographies. Springer. pp. 354–.ISBN 978-1-4757-2085-3.
  2. ^abcdefghijIndex Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 298.ISBN 978-3-88763-075-1. Retrieved30 May 2012.
  3. ^abcMorton I, Hall JM (1999).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer. p. 92.ISBN 978-0-7514-0499-9. Retrieved30 May 2012.
  4. ^abcdefg"List of Progestins".Drugs.com. Retrieved5 October 2025.
  5. ^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".Australian Veterinary Journal.76 (8):555–560.doi:10.1111/j.1751-0813.1998.tb10216.x.PMID 9741725.
  6. ^abcMcLauchlan 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.
  7. ^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.
  8. ^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.
  9. ^abcModern 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.
Progestogens
(andprogestins)
PRTooltip Progesterone receptoragonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptorantagonists
Androgens
(incl.AASTooltip anabolic–androgenic steroid)
ARTooltip Androgen receptoragonists
Progonadotropins
Antiandrogens
ARTooltip Androgen receptorantagonists
Steroidogenesis
inhibitors
5α-Reductase
Others
Antigonadotropins
Others
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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