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 and BANM .[1] [2] [3] [4] Delmadinone is the INN and BAN 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 J. Elks (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 Ian Morton; Judith M. Hall (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" .
^ 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): 555–60. doi :10.1111/j.1751-0813.1998.tb10216.x . PMID 9741725 .
^ a b c McLauchlan, Gerard; Ramsey, Ian (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 (2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol . 110 (1–2): 39–47. doi :10.1016/j.jsbmb.2007.10.008 . PMID 18395441 . S2CID 5612000 .
^ Ringold, H. J.; 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, Volume 53 . 1972. p. 46. John T. Bryans, PhD. el at, 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.
Medical uses
Progestogens and antiprogestogens
Progestogens (and progestins )
PR agonists
Retroprogesterone derivatives: Dydrogesterone
Trengestone
Testosterone derivatives: Estranes: Danazol
Dimethisterone
Ethisterone
19-Nortestosterone derivatives: Estranes: Allylestrenol
Altrenogest
Dienogest
Etynodiol diacetate
Lynestrenol
Norethisterone (norethindrone) #
Norethisterone acetate
Norethisterone enanthate
Noretynodrel
Norgesterone
Norgestrienone
Normethandrone (methylestrenolone)
Norvinisterone
Oxendolone
Quingestanol acetate
Tibolone ; Gonanes: Desogestrel
Etonogestrel
Gestodene
Gestrinone
Levonorgestrel #
Norelgestromin
Norgestimate
Norgestrel
Spirolactone derivatives: Drospirenone
Antiprogestogens
SPRMs PR antagonists
Aglepristone
Mifepristone
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
See also
Progesterone receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
List of progestogens
Androgens and antiandrogens
Androgens (incl. AAS )
AR agonists
Testosterone derivatives: Androstenediol dipropionate
Boldenone undecylenate
Clostebol
Clostebol acetate
Clostebol caproate
Clostebol propionate
Cloxotestosterone acetate
Prasterone (dehydroepiandrosterone, DHEA)
Prasterone enanthate (DHEA enanthate)
Prasterone sulfate (DHEA sulfate)
Quinbolone
Testosterone #
Testosterone esters (e.g., testosterone cypionate , testosterone enanthate , testosterone propionate , testosterone undecanoate , testosterone ester mixtures (Deposterona , Omnadren , Sustanon , Testoviron Depot ))
Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT)
Androstanolone esters
Bolazine capronate
Drostanolone propionate (dromostanolone propionate)
Epitiostanol
Mepitiostane
Mesterolone
Metenolone acetate (methenolone acetate)
Metenolone enanthate (methenolone enanthate)
Stenbolone acetate
19-Nortestosterone derivatives: Bolandiol dipropionate
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norclostebol
Norclostebol acetate
Oxabolone cipionate (oxabolone cypionate)
Trenbolone acetate
Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)
17α-Alkylated testosterone derivatives: Bolasterone
Calusterone
Chlorodehydromethyltestosterone (CDMT)
Fluoxymesterone
Formebolone
Metandienone (methandienone, methandrostenolone)
Methandriol (methylandrostenediol)
Methandriol bisenanthoyl acetate
Methandriol dipropionate
Methandriol propionate
Methyltestosterone
Methyltestosterone 3-hexyl ether
Oxymesterone
Penmesterol
Tiomesterone (thiomesterone)
17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
Furazabol
Mebolazine (dimethazine)
Mestanolone
Oxandrolone
Oxymetholone
Stanozolol
17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
Mibolerone
Norethandrolone
Normethandrone (methylestrenolone, normethisterone)
Propetandrol (propethandrol)
17α-Ethynyltestosterone derivatives: Danazol
Gestrinone
Progestins (e.g., ethisterone (ethynyltestosterone) , levonorgestrel , norgestrel , norethisterone (norethindrone) , lynestrenol , norgestrienone )
Tibolone
Progesterone derivatives: Medroxyprogesterone acetate
Progonadotropins
Antiestrogens (e.g., tamoxifen , clomifene )
GnRH agonists (e.g., GnRH (gonadorelin) , leuprorelin )
Gonadotropins (e.g., LH , hCG )
Antiandrogens
AR antagonists
Nonsteroidal: Apalutamide
Bicalutamide
Cimetidine
Darolutamide
Enzalutamide
Flutamide
Ketoconazole
Nilutamide
Seviteronel †
Topilutamide (fluridil)
Steroidogenesis inhibitors
5α-Reductase
Alfatradiol
Dutasteride
Epristeride
Finasteride
Saw palmetto extract
Others
Abiraterone acetate
Aminoglutethimide
Bifluranol
Cyproterone acetate
Flutamide
Ketoconazole
Nilutamide
Seviteronel †
Spironolactone
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
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
See also
Androgen receptor modulators
Estrogens and antiestrogens
Progestogens and antiprogestogens
List of androgens/anabolic steroids
Drugs used in benign prostatic hyperplasia (G04C )
5α-Reductase inhibitors Alpha-1 blockers
Alfuzosin
Doxazosin
Silodosin
Tamsulosin
Terazosin
Steroidal antiandrogens Herbal products
Pygeum africanum
Saw palmetto extract
Others
Pharmacodynamics
AR
Agonists
Testosterone derivatives: 4-Androstenediol
4-Dehydroepiandrosterone (4-DHEA)
4-Hydroxytestosterone
5-Androstenedione
11-Ketotestosterone
11β-Hydroxyandrostenedione
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
Androstenediol (5-androstenediol)
Androstenedione (4-androstenedione)
Atamestane
Boldenone
Boldione (1,4-androstadienedione)
Clostebol
Clostebol acetate
Clostebol caproate
Clostebol propionate
Cloxotestosterone
Cloxotestosterone acetate
Dehydroandrosterone
DHEA (androstenolone, prasterone; 5-DHEA)
DHEA enanthate (prasterone enanthate)
DHEA sulfate
Exemestane
Formestane
Plomestane
Quinbolone
Silandrone
Testosterone # (+dutasteride )
Testosterone esters
Polytestosterone phloretin phosphate
5α-Dihydrotestosterone derivatives: 1-Androstenediol
1-Androstenedione
1-Androsterone (1-andro, 1-DHEA)
1-Testosterone
3α-Androstanediol
5α-Androst-2-en-17-one
7β-Hydroxyepiandrosterone
11-Ketodihydrotestosterone
Androsterone
Bolazine
Dihydrofluoxymesterone
Dihydrotestosterone (DHT) (androstanolone, stanolone )
Dihydrotestosterone esters
Drostanolone
Epiandrosterone
Epitiostanol
Mepitiostane
Mesabolone
Mesterolone
Methyldiazinol
Nisterime
Prostanozol
Stenbolone
Testifenon (testiphenon, testiphenone)
19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione)
11β-Methyl-19-nortestosterone
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandione (19-nor-4-androstenedione)
Bolmantalate (nandrolone adamantoate)
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
LS-1727 (nandrolone 17β-N -(2-chloroethyl)-N -nitrosocarbamate)
Methoxydienone (methoxygonadiene)
Nandrolone
Norclostebol
Normethandrone (methylestrenolone, normethisterone)
Oxabolone
Oxabolone cipionate (oxabolone cypionate)
Trenbolone
Trenbolone acetate
Trenbolone enanthate
Trenbolone hexahydrobenzylcarbonate
Trenbolone undecanoate
Trendione
Trestolone (MENT)
Trestolone acetate
Trestolone enanthate
17α-Alkylated testosterone derivatives: Bolasterone
Calusterone
Chlorodehydromethylandrostenediol (CDMA)
Chlorodehydromethyltestosterone (CDMT)
Chloromethylandrostenediol (CMA)
Enestebol
Ethyltestosterone
Fluoxymesterone
Formebolone
Hydroxystenozole
Metandienone (methandrostenolone)
Methandriol (methylandrostenediol)
Methandriol bisenanthoyl acetate
Methandriol diacetate
Methandriol dipropionate
Methandriol propionate
Methylclostebol (chloromethyltestosterone)
Methyltestosterone (+esterified estrogens )
Methyltestosterone 3-hexyl ether
Oxymesterone
Penmesterol
Tiomesterone
17α-Alkylated 5α-dihydrotestosterone derivatives: Androisoxazole
Desoxymethyltestosterone
Furazabol
Mebolazine (dimethazine)
Mestanolone
Metenolone
Metenolone acetate
Metenolone enanthate
Methasterone
Methyl-1-testosterone
Methylepitiostanol
Methylstenbolone
Oxandrolone
Oxymetholone
Stanozolol
17α-Alkylated 19-nortestosterone derivatives: Bolenol
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol
Methyldienolone
Methylhydroxynandrolone (MOHN, MHN)
Metribolone
Mibolerone
Norboletone
Norethandrolone
Propetandrol
RU-2309
Tetrahydrogestrinone
17α-Vinyl-19-nortestosterone derivatives: Vinyltestosterone
17α-Ethynyltestosterone derivatives: Danazol
Ethinylandrostenediol
Ethisterone (ethynyltestosterone)
17α-Ethynyl-19-nortestosterone derivatives: Δ4 -Tibolone
Desogestrel
Etonogestrel
Etynodiol
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Norethisterone
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Norgestrel
Norgestrienone
Quingestanol
Tibolone
Mixed (SARMs )
Nonsteroidal:
ACP-105
AC-262536
Acetothiolutamide
Acetoxolutamide
Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
BMS-564929
Enobosarm (ostarine, MK-2866, GTx-024, S-22)
GLPG-0492
GSK2881078
GSK-4336A
LG-121071 (LGD-121071)
LGD-2226
LGD-3303
LGD-4033
LY-2452473
JNJ-28330835
PF-06260414
RAD140
RU-59063
S-23
S-40503
Triclosan
Steroidal:
MK-0773
TFM-4AS-1
YK-11
Antagonists
Nonsteroidal: 5N -Bicalutamide
AA560
Apalutamide
Atraric acid
Bakuchiol
Bicalutamide
Bisphenols (e.g., BADGE , , bisphenol A , bisphenol F , bisphenol S )
BMS-641988
Cimetidine
Cioteronel
Cyanonilutamide
Darolutamide
DDT (via metabolite p,p’-DDE )
Dieldrin
DIMP
Endosulfan
Enzalutamide
EPI-001
EPI-7386
Fenarimol
Flutamide
Hydroxyflutamide
Inocoterone
Inocoterone acetate
Ketoconazole
Ketodarolutamide
Lavender oil
LG-120907
Linuron
Methiocarb
N -Desmethylapalutamide
N -Desmethylenzalutamide
Nilutamide
Pentomone
Phenothrin
Prochloraz
Procymidone
Proxalutamide
Ralaniten (EPI-002)
Ralaniten acetate (EPI-506)
RD-162
Rezvilutamide
RU-22930
RU-56187
RU-57073
RU-58642
RU-58841
Seviteronel
Thalidomide
Topilutamide (fluridil)
Valproic acid
Vinclozolin
GPRC6A
Agonists
Cations (incl. aluminum , calcium , gadolinium , magnesium , strontium , zinc )
Dehydroandrosterone
Dihydrotestosterone
Estradiol
L -α-Amino acids (incl. L -arginine , L -lysine , L -ornithine )
Osteocalcin
SHBG
Testosterone
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids
GR
Agonists Mixed (SEGRMs )
Dagrocorat
Fosdagrocorat
Mapracorat
Antagonists Others
See also
Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
Mineralocorticoid receptor modulators
List of corticosteroids
PR
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Spirolactone derivatives: Canrenoic acid
Canrenone
Drospirenone
Mespirenone
Potassium canrenoate
Prorenone
SC-5233 (spirolactone)
SC-8109
Spironolactone
Spirorenone
Mixed (SPRMs )
Nonsteroidal: Apigenin
Kaempferol
Naringenin
Syringic acid
Antagonists
Nonsteroidal: Darolutamide
Valproic acid
mPR (PAQR )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens