Mytatrienediol

Mytatrienediol
Identifiers

IUPAC name (8R,9S,13S,14S,16S,17R)-3-methoxy-13,16-dimethyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol
Synonyms	SC-6924; Manvene; Anvene; 3-Methoxy-16α-methylestra-1,3,5(10)-triene-16β,17β-diol; 16α-Methylestriol 3-methyl ether; 16β-Hydroxy-16α-methylestradiol 3-methyl ether
CAS Number	5108-94-1
PubChem (CID)	5282364
ChemSpider	4445527
UNII	1G3TKH1O14
KEGG	C14242
ChEBI	CHEBI:34859
Chemical and physical data
Formula	C₂₀H₂₈O₃
Molar mass	316.43452 g/mol
3D model (Jmol)	Interactive image
SMILES CC12CCC3C(C1CC(C2O)(C)O)CCC4=C3C=CC(=C4)OC
InChI InChI=1S/C20H28O3/c1-19-9-8-15-14-7-5-13(23-3)10-12(14)4-6-16(15)17(19)11-20(2,22)18(19)21/h5,7,10,15-18,21-22H,4,6,8-9,11H2,1-3H3/t15-,16-,17+,18-,19+,20+/m1/s1 Key:OOVXZFCPCSVSEM-NADOGSGZSA-N

Mytatrienediol (developmental code name SC-6924; former tentative trade names Manvene, Anvene), also known as 16α-methyl-16β-epiestriol 3-methyl ether or 16β-hydroxy-16α-methylestradiol 3-methyl ether, is a semisynthetic, steroidal, weak estrogen and estrogen ether derived from estriol that was developed in the late 1950s but was never marketed.^[1] It was investigated as a mildly estrogenic drug for men to treat atherosclerosis and improve serum lipid profiles and reduce the risk of myocardial infarction.^[2]^[3]^[4]^[5]^[6]^[7] However, like other estrogens, mytatriendiol was found in clinical trials to produce estrogenic side effects such as breast pain and gynecomastia in men, and its side effects ultimately precluded its use.^[8] The drug was also studied to treat bone pain in patients with multiple myeloma, metastatic bone disease, and osteoporosis, with effectiveness seen.^[9]

References

↑ Gregory Pincus (22 October 2013). Hormones and Atherosclerosis: Proceedings of the Conference Held in Brighton, Utah, March 11-14, 1958. Elsevier Science. pp. 249, 254, 263, 371–374, 411–412, 443–447, 460–461. ISBN 978-1-4832-7064-7.
↑ Marmorston, J.; Moore, F. J.; Kuzma, O. T.; Magidson, O.; Weiner, J. M. (1963). "Effect of Estrogens on Interlipid Relations in Men with Myocardial Infarction.". Experimental Biology and Medicine. 113 (2): 357–361. doi:10.3181/00379727-113-28365. ISSN 1535-3702.
↑ Marmorston, J.; Moore, F. J.; Hopkins, C. E.; Kuzma, O. T.; Weiner, J. (1962). "Clinical Studies of Long-Term Estrogen Therapy in Men with Myocardial Infarction". Experimental Biology and Medicine. 110 (2): 400–408. doi:10.3181/00379727-110-27531. ISSN 1535-3702.
↑ DAVIS FW, SCARBOROUGH WR, MASON RE, SINGEWALD ML, BAKER BM (1958). "Experimental hormonal therapy of atherosclerosis: preliminary observations on the effects of two new compounds". The American Journal of the Medical Sciences. 235 (1): 50–9. PMID 13487586.
↑ Cohen, W. D.; Higano, N.; Robinson, R. W. (1958). "Serum Lipid and Estrogenic Effects of Manvene, a New Estrogen Analog: Comparison with Premarin in Men with Coronary Heart Disease". Circulation. 17 (6): 1035–1040. doi:10.1161/01.CIR.17.6.1035. ISSN 0009-7322.
↑ Spencer, Herta; Kabakow, Bernard; Samachson, Joseph; Laszlo, Daniel (1959). "METABOLIC EFFECTS OF MYTATRIENEDIOL IN MAN*". The Journal of Clinical Endocrinology & Metabolism. 19 (12): 1581–1596. doi:10.1210/jcem-19-12-1581. ISSN 0021-972X.
↑ Marmorston, Jessie (1960). "Estrogen Therapy in Men with Myocardial Infarction". JAMA. 174 (3): 241. doi:10.1001/jama.1960.03030030021004. ISSN 0098-7484.
↑ Bedford, P. D.; Lodge, Brian (1959). "TOXIC EFFECTS OF A NEW ANTILIPAEMIC OESTROGENIC STEROID (MANVENE)". Journal of the American Geriatrics Society. 7 (12): 911–915. doi:10.1111/j.1532-5415.1959.tb00364.x. ISSN 0002-8614.
↑ Kabakow, Bernard (1960). "Effects of Mytatrienediol in Multiple Myeloma, Metastatic Bone Disease, and Osteoporosis". Archives of Internal Medicine. 105 (6): 905. doi:10.1001/archinte.1960.00270180083011. ISSN 0003-9926.

Estrogen receptor modulators

Agonists	Steroidal: 1-Keto-1,2,3,4-tetrahydrophenanthrene 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8,9-Dehydroestrone 8β-VE2 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone acetate 17α-Estradiol (alfatradiol) 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 Cloxestradiol acetate DHEA DHEA-S Digitoxin (digitalis) Diosgenin Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin Estetrol Estradiol Estradiol 3-propionate Estradiol benzoate Estradiol butyrate benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate (estradiol succinate) Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol pivalate (trimethyl estradiol acetate) Estradiol propoxyphenylpropionate Estradiol stearate Estradiol sulfate Estradiol undecylate Estradiol valerate Lipoidal estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol acetate benzoate Estriol glucuronide Estriol sodium succinate Estriol succinate Estriol triacetate Estriol tripropionate Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol (eptamestrol) Ethinyl estradiol Ethinyl estradiol sulfonate Ethinyl estriol Etynodiol diacetate Guggulsterone Hexolame Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Noretynodrel Orestrate Pentolame Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prodiame Prolame Promestriene Quinestradol Quinestrol Non-steroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC Allenoic acid Alternariol Anethole Anol Benzestrol Bifluranol Biochanin A Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol diacetate Diethylstilbestrol dilaurate Diethylstilbestrol dipalmitate Diethylstilbestrol dipropionate Diethylstilbestrol disulfate Diethylstilbestrol monobenzyl ether Dimestrol (dianisylhexene) Dimethylallenolic acid Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Endosulfan ERB-196 (WAY-202196) Estrobin (DBE) Fenarimol Fenestrel FERb 033 Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate ICI-85966 (Stilbostat) Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestilbol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methoxychlor Miroestrol Nyasol (cis-hinokiresinol) Paroxypropione Pentafluranol Phenestrol Photoanethole Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Quadrosilan SC-4289 SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Terfluranol WAY-166818 WAY-200070 Triphenylchlorethylene Triphenylmethylethylene WAY-214156

Mixed (SERMs)	2-Hydroxyestradiol 2-Hydroxyestrone 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epitiostanol Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LY-117018 Menerba Mepitiostane Methylepitiostanol Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Tamoxifen TAS-108 (SR-16234) Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Cytestrol acetate Fulvestrant (ICI-182780) ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) XCT-790 ZK-164015 ZK-191703

GPER

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Ethinyl estradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalanone Zearalenol Zearalenone Zeranol (zearalanol))

Antagonists	CCL18 Estriol G-15 G-36 MIBE

See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators

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