Delmadinone acetate

Last updated
Delmadinone acetate
Delmadinone acetate.svg
Clinical data
Trade names Tardak, 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 class Progestogen; 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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.033.821 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H27ClO4
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 used in veterinary medicine to treat androgen-dependent conditions such as benign prostatic hyperplasia in male dogs. [1] [2] [3] [4]

Contents

Delmadinone acetate must be used with caution, as it can cause adrenal insufficiency through 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

Delmadinone acetate (DMA) is used in veterinary medicine to treat androgen-dependent conditions in animals. [6] Its most common use is for the treatment of benign prostatic hyperplasia in male dogs. [6] It may also be prescribed for managing hypersexuality in male dogs and cats, perianal gland tumors in dogs, and hormone-driven aggression in dogs. [6]

Pharmacology

Pharmacodynamics

Delmadinone acetate (DMA) is a progestogen with antigonadotropic, and therefore antiandrogenic and antiestrogenic, effects. In addition, DMA binds to the androgen receptor and is thought to act as an antagonist of this receptor, similarly to related drugs such as chlormadinone acetate and osaterone acetate. [7]

Chemistry

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 a synthetic pregnane steroid and a derivative of progesterone. [1] [2] [4] It is specifically a 17α-hydroxyprogesterone derivative, characterized by the presence of 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] Structural 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

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 in Europe and the United Kingdom under the brand names Tardak and Zenadrex. [9] It was also under development for use in the United States, but it does not appear to have been marketed there. [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 marketed under the brand name Tardak, but has also been sold under several 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 marketed specifically in the United Kingdom, France, Belgium, Germany, Austria, Switzerland, the Netherlands, Finland, Australia, and New Zealand. [2] [4]

References

  1. 1 2 3 4 5 6 7 8 9 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data, Structures and Bibliographies. Springer. pp. 354–. ISBN   978-1-4757-2085-3.
  2. 1 2 3 4 5 6 7 8 9 10 Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 298. ISBN   978-3-88763-075-1 . Retrieved 30 May 2012.
  3. 1 2 3 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.
  4. 1 2 3 4 5 6 7 "List of Progestins". Drugs.com. Retrieved 5 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. 1 2 3 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.
  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. 1 2 3 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.
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