DU-41165 Other names 6-Fluoro-16-methylene-17α-acetoxy-δ6 -retroprogesterone; 6-Fluoro-16-methylene-17α-hydroxy-9β,10α-pregna-4,6-diene-3,20-dione 17α-acetate; 6-Fluoro-16-methylene-3,20-dioxo-9β,10α-pregna-4,6-dien-17α-yl acetate Routes of administration By mouth Drug class Progestin ; Progestogen
[(8R ,9R ,10S ,13S ,14S ,17R )-17-Acetyl-6-fluoro-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a ]phenanthren-17-yl] acetate
CAS Number PubChem CID ChemSpider CompTox Dashboard (EPA ) Formula C 24 H 29 F O 4 Molar mass 400.490 g·mol−1 3D model (JSmol )
CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@@H]3[C@H]2C=C(C4=CC(=O)CC[C@@]34C)F)C)OC(=O)C
InChI=1S/C24H29FO4/c1-13-10-19-17-12-21(25)20-11-16(28)6-8-22(20,4)18(17)7-9-23(19,5)24(13,14(2)26)29-15(3)27/h11-12,17-19H,1,6-10H2,2-5H3/t17-,18-,19+,22+,23+,24+/m1/s1
Key:XSSIGSNQDKHHLD-JBARXXBASA-N
DU-41165 , also known as 6-fluoro-16-methylene-17α-acetoxy-δ6 -retroprogesterone , is a progestin which was developed by Philips-Duphar in the 1970s and was never marketed.[1] [2] It is a combined derivative of 17α-hydroxyprogesterone and retroprogesterone .[1] [2] The drug shows extremely high potency as a progestogen in animals.[1] It has been found to possess 158% of the relative binding affinity of promegestone for the progesterone receptor expressed in rat uterus (relative to 74% for the closely related progestin DU-41164 ).[1] DU-41165 also showed 28% of the affinity of RU-28362 for the glucocorticoid receptor expressed in rat liver , but no affinity for the mineralocorticoid receptor expressed in rat kidney (<0.003% of that of ).[1] The drug showed no androgenic , anabolic , or estrogenic activity in animals, but did show some antiandrogenic and glucocorticoid activity at high doses.[1] Although highly potent in animals, DU-41165 produced little or no progestogenic effect at dosages of 50 and 200 µg/day in women, suggesting major species differences.[1] DU-41165 has been studied as a potential photoaffinity label for the progesterone receptor.[1]
References [ ]
^ a b c d e f g h Morsink L, de Wachter AM, Brenner P, Cekan SZ, Guerrero R, Hagenfeldt K, Diczfalusy E (May 1976). "Endocrine effects of two new retro-steroids in animal models and in women". Acta Endocrinol . 82 (1): 193–212. doi :10.1530/acta.0.0820193 . PMID 57688 .
^ a b Pinney KG, Carlson KE, Katzenellenbogen JA (February 1990). "[3H]DU41165: a high affinity ligand and novel photoaffinity labeling reagent for the progesterone receptor". J. Steroid Biochem . 35 (2): 179–89. doi :10.1016/0022-4731(90)90272-T . PMID 2308335 .
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 )
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 )
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