Delmadinone acetate

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]

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
Routes of administration	Intramuscular injection
Drug class	Progestogen; Progestin; Progestogen ester; Steroidal antiandrogen
ATCvet code	QG03DX91 (WHO)
Legal status
Legal status	Veterinary use only
Identifiers
IUPAC name [(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	13698-49-2
PubChem CID	10135765
ChemSpider	8311278
UNII	92833M0LD9
ChEMBL	ChEMBL2104598
CompTox Dashboard (EPA)	DTXSID60160018
ECHA InfoCard	100.033.821
Chemical and physical data
Formula	C23H27ClO4
Molar mass	402.92 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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 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

See also: List of progestogens, Progestogen ester, List of progestogen esters, Steroidal antiandrogen, and List 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 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 USANTooltip United States Adopted Name and BANMTooltip British Approved Name.^[1][2][3][4] Delmadinone is the INNTooltip International Nonproprietary Name and BANTooltip 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]