Delmadinone acetate

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]

Delmadinone acetate
Clinical data
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
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 InfoCard 100.033.821
Chemical and physical data
Formula C23H27ClO4
Molar mass 402.92 g·mol−1
3D model (JSmol)
  • O=C1C=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 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]

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]

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 syntheticpregnanesteroid 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 acetateester 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]

. . . Delmadinone acetate . . .

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. . . Delmadinone acetate . . .