Pentolame

Pentolame
Clinical data

Synonyms	17β-((5-Hydroxypentyl)amino)estradiol; 17β-[(5-Hydroxypentyl)amino]estra-1,3,5(10)-trien-3-ol
Identifiers
IUPAC name (8R,9S,13S,14S,17S)-17-(5-Hydroxypentylamino)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
CAS Number	150748-24-6
PubChem CID	10473548
ChemSpider	8648959
Chemical and physical data
Formula	C₂₃H₃₅NO₂
Molar mass	357.54 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2NCCCCCO)CCC4=C3C=CC(=C4)O
InChI InChI=1S/C23H35NO2/c1-23-12-11-19-18-8-6-17(26)15-16(18)5-7-20(19)21(23)9-10-22(23)24-13-3-2-4-14-25/h6,8,15,19-22,24-26H,2-5,7,9-14H2,1H3/t19-,20-,21+,22+,23+/m1/s1 Key:CYIRNKIFROUCMA-VROINQGHSA-N

Pentolame, also known as 17β-((5-hydroxypentyl)amino)estradiol is a synthetic, steroidal estrogen and a 17β-aminoestrogen with anticoagulant effects that was first described in 1993 and was never marketed.^[1]^[2]^[3]

References

↑ Lemini C, Rubio-Póo C, Silva G, García-Mondragón J, Zavala E, Mendoza-Patiño N, Castro D, Cruz-Almanza R, Mandoki JJ (1993). "Anticoagulant and estrogenic effects of two new 17 beta-aminoestrogens, butolame [17 beta-(4-hydroxy-1-butylamino)-1,3,5(10)-estratrien-3-ol] and pentolame [17 beta-(5-hydroxy-1-pentylamino)-1,3,5(10)-estratrien-3-ol]". Steroids. 58 (10): 457–61. PMID 8256254.
↑ Lemus AE, Jaimez R, Lemini C, Menjivar M, Silva G, Rubio-Poo C, Valenzuela F, Larrea F (1998). "Estrogenic effects of the synthetic aminoestrogen 17 beta-(5-hydroxy-1-pentylamino)-1,3,5(10)-estratrien-3-ol (pentolame)". Steroids. 63 (7–8): 433–8. PMID 9654651.
↑ Jaimez R, Cooney A, Jackson K, Lemus AE, Lemini C, Cárdenas M, García R, Silva G, Larrea F (2000). "In vivo estrogen bioactivities and in vitro estrogen receptor binding and transcriptional activities of anticoagulant synthetic 17beta-aminoestrogens". J. Steroid Biochem. Mol. Biol. 73 (1–2): 59–66. PMID 10822025.

Estrogen receptor modulators

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-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) 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin 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 Cloxestradiol acetate Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Estrofurate Estromustine Estrone Estrone esters Estrone methyl ether Estropipate Etamestrol (eptamestrol) Ethinylestradiol Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate 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 Nonsteroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC β-LGND1 β-LGND2 (GTx-878) AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Doisynoestrol (fenocycline) Doisynolic acid Efavirenz ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-169916 WAY-200070 WAY-204688 (SIM-688) WAY-214156 Unknown/unsorted: ERB-26 ERA-45 ERB-79 ZK-283197 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, 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)	2-Phenylbenzofuran 2-Phenylbenzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Chlorotrianisene Clomifene Clomifenoxide Cyclofenil D-15413 Droloxifene Elacestrant Enclomifene Endoxifen Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene phosphate Nafoxidine Nitromifene NNC 45-0095 NNC 45-0320 NNC 45-0781 NNC 45-1506 Ormeloxifene Ospemifene Panomifene Pipendoxifene Promensil Raloxifene Rimostil (P-081) Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Toremifene Trioxifene TZE-5323 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703 Coregulator-binding modulators: ERX-11

GPER

Agonists

Antagonists

CCL18
Estriol
G-15
G-36
MIBE

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.