Ethandrostate
Chemical compound
Ethandrostate Other names Ethynylandrostenediol 3β-cyclohexanepropionate; 17α-Ethynylandrost-5-ene-3β,17β-diol 3β-cyclohexanepropionate; 17α-Pregn-5-en-20-yne-3β,17β-diol 3β-cyclohexanepropionate; NSC-18216 Routes of administration By mouth , intramuscular injection Drug class Estrogen
[(3S ,8R ,9S ,10R ,13S ,14S ,17R )-17-ethynyl-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a ]phenanthren-3-yl] 3-cyclohexylpropanoate
PubChem CID ChemSpider Formula C 30 H 44 O 3 Molar mass 452.679 g·mol−1 3D model (JSmol )
C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)OC(=O)CCC5CCCCC5
InChI=1S/C30H44O3/c1-4-30(32)19-16-26-24-12-11-22-20-23(33-27(31)13-10-21-8-6-5-7-9-21)14-17-28(22,2)25(24)15-18-29(26,30)3/h1,11,21,23-26,32H,5-10,12-20H2,2-3H3/t23-,24+,25-,26-,28-,29-,30-/m0/s1
Key:VGTIQIQOBZXZAI-IODDZSIWSA-N
Ethandrostate , also known as ethinylandrostenediol 3β-cyclohexanepropionate , is a synthetic steroidal estrogen and ester of ethinylandrostenediol (17α-ethynyl-5-androstenediol) which was developed and studied in people with certain cancers like breast cancer and prostate cancer in the 1950s but was never marketed.[1] [2] [3] [4] Although far less potent by weight than estradiol or estrone , ethandrostate produces estrogenic effects in the vagina , uterus , and mammary glands as well as antigonadotropic and secondary antiandrogenic effects like testicular and prostate atrophy in both animals and humans.[1] [3] [4] Ethandrostate was assessed in humans as an aqueous suspension by intramuscular injection at doses of 100 to 200 mg/day or 100 mg three times per week and by mouth at a dose of 25 mg four times per day.[4] It shows much greater antigonadotropic potency relative to general estrogenic potency in animals when compared with other estrogens.[3] However, this doesn't seem to be the case in humans.[4] In addition to its estrogenic activity, ethandrostate has very weak androgenic activity that manifests only at doses much higher than its estrogenic activity.[3]
Affinities of estrogen receptor ligands for the ERα and ERβ
Ligand
Other names
Relative binding affinities (RBA, %)a
Absolute binding affinities (Ki , nM)a
Action
ERα
ERβ
ERα
ERβ
Estradiol
E2; 17β-Estradiol
100
100
0.115 (0.04–0.24)
0.15 (0.10–2.08)
Estrogen
Estrone
E1; 17-Ketoestradiol
16.39 (0.7–60)
6.5 (1.36–52)
0.445 (0.3–1.01)
1.75 (0.35–9.24)
Estrogen
Estriol
E3; 16α-OH-17β-E2
12.65 (4.03–56)
26 (14.0–44.6)
0.45 (0.35–1.4)
0.7 (0.63–0.7)
Estrogen
Estetrol
E4; 15α,16α-Di-OH-17β-E2
4.0
3.0
4.9
19
Estrogen
Alfatradiol
17α-Estradiol
20.5 (7–80.1)
8.195 (2–42)
0.2–0.52
0.43–1.2
Metabolite
16-Epiestriol
16β-Hydroxy-17β-estradiol
7.795 (4.94–63)
50
?
?
Metabolite
17-Epiestriol
16α-Hydroxy-17α-estradiol
55.45 (29–103)
79–80
?
?
Metabolite
16,17-Epiestriol
16β-Hydroxy-17α-estradiol
1.0
13
?
?
Metabolite
2-Hydroxyestradiol
2-OH-E2
22 (7–81)
11–35
2.5
1.3
Metabolite
2-Methoxyestradiol
2-MeO-E2
0.0027–2.0
1.0
?
?
Metabolite
4-Hydroxyestradiol
4-OH-E2
13 (8–70)
7–56
1.0
1.9
Metabolite
4-Methoxyestradiol
4-MeO-E2
2.0
1.0
?
?
Metabolite
2-Hydroxyestrone
2-OH-E1
2.0–4.0
0.2–0.4
?
?
Metabolite
2-Methoxyestrone
2-MeO-E1
<0.001–<1
<1
?
?
Metabolite
4-Hydroxyestrone
4-OH-E1
1.0–2.0
1.0
?
?
Metabolite
4-Methoxyestrone
4-MeO-E1
<1
<1
?
?
Metabolite
16α-Hydroxyestrone
16α-OH-E1; 17-Ketoestriol
2.0–6.5
35
?
?
Metabolite
2-Hydroxyestriol
2-OH-E3
2.0
1.0
?
?
Metabolite
4-Methoxyestriol
4-MeO-E3
1.0
1.0
?
?
Metabolite
Estradiol sulfate
E2S; Estradiol 3-sulfate
<1
<1
?
?
Metabolite
Estradiol disulfate
Estradiol 3,17β-disulfate
0.0004
?
?
?
Metabolite
Estradiol 3-glucuronide
E2-3G
0.0079
?
?
?
Metabolite
Estradiol 17β-glucuronide
E2-17G
0.0015
?
?
?
Metabolite
Estradiol 3-gluc. 17β-sulfate
E2-3G-17S
0.0001
?
?
?
Metabolite
Estrone sulfate
E1S; Estrone 3-sulfate
<1
<1
>10
>10
Metabolite
Estradiol benzoate
EB; Estradiol 3-benzoate
10
?
?
?
Estrogen
Estradiol 17β-benzoate
E2-17B
11.3
32.6
?
?
Estrogen
Estrone methyl ether
Estrone 3-methyl ether
0.145
?
?
?
Estrogen
ent -Estradiol
1-Estradiol
1.31–12.34
9.44–80.07
?
?
Estrogen
Equilin
7-Dehydroestrone
13 (4.0–28.9)
13.0–49
0.79
0.36
Estrogen
Equilenin
6,8-Didehydroestrone
2.0–15
7.0–20
0.64
0.62
Estrogen
17β-Dihydroequilin
7-Dehydro-17β-estradiol
7.9–113
7.9–108
0.09
0.17
Estrogen
17α-Dihydroequilin
7-Dehydro-17α-estradiol
18.6 (18–41)
14–32
0.24
0.57
Estrogen
17β-Dihydroequilenin
6,8-Didehydro-17β-estradiol
35–68
90–100
0.15
0.20
Estrogen
17α-Dihydroequilenin
6,8-Didehydro-17α-estradiol
20
49
0.50
0.37
Estrogen
Δ8 -Estradiol
8,9-Dehydro-17β-estradiol
68
72
0.15
0.25
Estrogen
Δ8 -Estrone
8,9-Dehydroestrone
19
32
0.52
0.57
Estrogen
Ethinylestradiol
EE; 17α-Ethynyl-17β-E2
120.9 (68.8–480)
44.4 (2.0–144)
0.02–0.05
0.29–0.81
Estrogen
Mestranol
EE 3-methyl ether
?
2.5
?
?
Estrogen
Moxestrol
RU-2858; 11β-Methoxy-EE
35–43
5–20
0.5
2.6
Estrogen
Methylestradiol
17α-Methyl-17β-estradiol
70
44
?
?
Estrogen
Diethylstilbestrol
DES; Stilbestrol
129.5 (89.1–468)
219.63 (61.2–295)
0.04
0.05
Estrogen
Hexestrol
Dihydrodiethylstilbestrol
153.6 (31–302)
60–234
0.06
0.06
Estrogen
Dienestrol
Dehydrostilbestrol
37 (20.4–223)
56–404
0.05
0.03
Estrogen
Benzestrol (B2)
–
114
?
?
?
Estrogen
Chlorotrianisene
TACE
1.74
?
15.30
?
Estrogen
Triphenylethylene
TPE
0.074
?
?
?
Estrogen
Triphenylbromoethylene
TPBE
2.69
?
?
?
Estrogen
Tamoxifen
ICI-46,474
3 (0.1–47)
3.33 (0.28–6)
3.4–9.69
2.5
SERM
Afimoxifene
4-Hydroxytamoxifen; 4-OHT
100.1 (1.7–257)
10 (0.98–339)
2.3 (0.1–3.61)
0.04–4.8
SERM
Toremifene
4-Chlorotamoxifen; 4-CT
?
?
7.14–20.3
15.4
SERM
Clomifene
MRL-41
25 (19.2–37.2)
12
0.9
1.2
SERM
Cyclofenil
F-6066; Sexovid
151–152
243
?
?
SERM
Nafoxidine
U-11,000A
30.9–44
16
0.3
0.8
SERM
Raloxifene
–
41.2 (7.8–69)
5.34 (0.54–16)
0.188–0.52
20.2
SERM
Arzoxifene
LY-353,381
?
?
0.179
?
SERM
Lasofoxifene
CP-336,156
10.2–166
19.0
0.229
?
SERM
Ormeloxifene
Centchroman
?
?
0.313
?
SERM
Levormeloxifene
6720-CDRI; NNC-460,020
1.55
1.88
?
?
SERM
Ospemifene
Deaminohydroxytoremifene
0.82–2.63
0.59–1.22
?
?
SERM
Bazedoxifene
–
?
?
0.053
?
SERM
Etacstil
GW-5638
4.30
11.5
?
?
SERM
ICI-164,384
–
63.5 (3.70–97.7)
166
0.2
0.08
Antiestrogen
Fulvestrant
ICI-182,780
43.5 (9.4–325)
21.65 (2.05–40.5)
0.42
1.3
Antiestrogen
Propylpyrazoletriol
PPT
49 (10.0–89.1)
0.12
0.40
92.8
ERα agonist
16α-LE2
16α-Lactone-17β-estradiol
14.6–57
0.089
0.27
131
ERα agonist
16α-Iodo-E2
16α-Iodo-17β-estradiol
30.2
2.30
?
?
ERα agonist
Methylpiperidinopyrazole
MPP
11
0.05
?
?
ERα antagonist
Diarylpropionitrile
DPN
0.12–0.25
6.6–18
32.4
1.7
ERβ agonist
8β-VE2
8β-Vinyl-17β-estradiol
0.35
22.0–83
12.9
0.50
ERβ agonist
Prinaberel
ERB-041; WAY-202,041
0.27
67–72
?
?
ERβ agonist
ERB-196
WAY-202,196
?
180
?
?
ERβ agonist
Erteberel
SERBA-1; LY-500,307
?
?
2.68
0.19
ERβ agonist
SERBA-2
–
?
?
14.5
1.54
ERβ agonist
Coumestrol
–
9.225 (0.0117–94)
64.125 (0.41–185)
0.14–80.0
0.07–27.0
Xenoestrogen
Genistein
–
0.445 (0.0012–16)
33.42 (0.86–87)
2.6–126
0.3–12.8
Xenoestrogen
Equol
–
0.2–0.287
0.85 (0.10–2.85)
?
?
Xenoestrogen
Daidzein
–
0.07 (0.0018–9.3)
0.7865 (0.04–17.1)
2.0
85.3
Xenoestrogen
Biochanin A
–
0.04 (0.022–0.15)
0.6225 (0.010–1.2)
174
8.9
Xenoestrogen
Kaempferol
–
0.07 (0.029–0.10)
2.2 (0.002–3.00)
?
?
Xenoestrogen
Naringenin
–
0.0054 (<0.001–0.01)
0.15 (0.11–0.33)
?
?
Xenoestrogen
8-Prenylnaringenin
8-PN
4.4
?
?
?
Xenoestrogen
Quercetin
–
<0.001–0.01
0.002–0.040
?
?
Xenoestrogen
Ipriflavone
–
<0.01
<0.01
?
?
Xenoestrogen
Miroestrol
–
0.39
?
?
?
Xenoestrogen
Deoxymiroestrol
–
2.0
?
?
?
Xenoestrogen
β-Sitosterol
–
<0.001–0.0875
<0.001–0.016
?
?
Xenoestrogen
Resveratrol
–
<0.001–0.0032
?
?
?
Xenoestrogen
α-Zearalenol
–
48 (13–52.5)
?
?
?
Xenoestrogen
β-Zearalenol
–
0.6 (0.032–13)
?
?
?
Xenoestrogen
Zeranol
α-Zearalanol
48–111
?
?
?
Xenoestrogen
Taleranol
β-Zearalanol
16 (13–17.8)
14
0.8
0.9
Xenoestrogen
Zearalenone
ZEN
7.68 (2.04–28)
9.45 (2.43–31.5)
?
?
Xenoestrogen
Zearalanone
ZAN
0.51
?
?
?
Xenoestrogen
Bisphenol A
BPA
0.0315 (0.008–1.0)
0.135 (0.002–4.23)
195
35
Xenoestrogen
Endosulfan
EDS
<0.001–<0.01
<0.01
?
?
Xenoestrogen
Kepone
Chlordecone
0.0069–0.2
?
?
?
Xenoestrogen
o,p' -DDT
–
0.0073–0.4
?
?
?
Xenoestrogen
p,p' -DDT
–
0.03
?
?
?
Xenoestrogen
Methoxychlor
p,p' -Dimethoxy-DDT
0.01 (<0.001–0.02)
0.01–0.13
?
?
Xenoestrogen
HPTE
Hydroxychlor; p,p' -OH-DDT
1.2–1.7
?
?
?
Xenoestrogen
Testosterone
T; 4-Androstenolone
<0.0001–<0.01
<0.002–0.040
>5000
>5000
Androgen
Dihydrotestosterone
DHT; 5α-Androstanolone
0.01 (<0.001–0.05)
0.0059–0.17
221–>5000
73–1688
Androgen
Nandrolone
19-Nortestosterone; 19-NT
0.01
0.23
765
53
Androgen
Dehydroepiandrosterone
DHEA; Prasterone
0.038 (<0.001–0.04)
0.019–0.07
245–1053
163–515
Androgen
5-Androstenediol
A5; Androstenediol
6
17
3.6
0.9
Androgen
4-Androstenediol
–
0.5
0.6
23
19
Androgen
4-Androstenedione
A4; Androstenedione
<0.01
<0.01
>10000
>10000
Androgen
3α-Androstanediol
3α-Adiol
0.07
0.3
260
48
Androgen
3β-Androstanediol
3β-Adiol
3
7
6
2
Androgen
Androstanedione
5α-Androstanedione
<0.01
<0.01
>10000
>10000
Androgen
Etiocholanedione
5β-Androstanedione
<0.01
<0.01
>10000
>10000
Androgen
Methyltestosterone
17α-Methyltestosterone
<0.0001
?
?
?
Androgen
Ethinyl-3α-androstanediol
17α-Ethynyl-3α-adiol
4.0
<0.07
?
?
Estrogen
Ethinyl-3β-androstanediol
17α-Ethynyl-3β-adiol
50
5.6
?
?
Estrogen
Progesterone
P4; 4-Pregnenedione
<0.001–0.6
<0.001–0.010
?
?
Progestogen
Norethisterone
NET; 17α-Ethynyl-19-NT
0.085 (0.0015–<0.1)
0.1 (0.01–0.3)
152
1084
Progestogen
Norethynodrel
5(10)-Norethisterone
0.5 (0.3–0.7)
<0.1–0.22
14
53
Progestogen
Tibolone
7α-Methylnorethynodrel
0.5 (0.45–2.0)
0.2–0.076
?
?
Progestogen
Δ4 -Tibolone
7α-Methylnorethisterone
0.069–<0.1
0.027–<0.1
?
?
Progestogen
3α-Hydroxytibolone
–
2.5 (1.06–5.0)
0.6–0.8
?
?
Progestogen
3β-Hydroxytibolone
–
1.6 (0.75–1.9)
0.070–0.1
?
?
Progestogen
Footnotes: a = (1) Binding affinity values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of in-vitro systems with labeled estradiol and human ERα and ERβ proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ). Sources: See template page.
References
^ a b Elva G. Shipley (1962). "Anti-gonadotropic steroids, inhibition of ovulation and mating" . In Dorfman RI (ed.). Bioassay . Elsevier. pp. 179–274. ISBN 978-1-4832-7276-4 .
^ Boccabella A, Bakritges C (January 1956). "Effects of ethandrostate on pituitary and sex organs of rats". Anatomical Record . 124 (2): 260.
^ a b c d Clinton R, Neumann H, Laskowski S, Christiansen R (1957). "Notes - Esters of 17α-Ethinyl-androstane-3β,17β-diol and 17 α-Ethinylandrost-5-ene-3β, 17β-diol". The Journal of Organic Chemistry . 22 (4): 473–475. doi :10.1021/jo01355a627 . ISSN 0022-3263 .
^ a b c d Olson KB, Frawley TF, Stein AA, Shields D (1958). "Ethandrostate: endocrine effects and studies in treatment of cancer". Cancer . 11 (3): 537–45. doi :10.1002/1097-0142(195805/06)11:3<537::aid-cncr2820110313>3.0.co;2-w . PMID 13523561 . S2CID 738607 .
AR Tooltip Androgen receptor
Agonists SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )
Lavender oil
Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g., cadmium )
Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )
Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )
Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )
Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )
Others (e.g., agnuside , rotundifuran )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
PR Tooltip Progesterone receptor
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
Mixed (SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (PAQR Tooltip Progestin and adipoQ receptor )