Estradiol anthranilate - Misplaced Pages

Chemical compound Pharmaceutical compound

Estradiol anthranilate
Clinical data

Other names	Estradiol 3-anthranilate
Routes of administration	By mouth
Drug class	Estrogen; Estrogen ester
Identifiers
IUPAC name phenanthren-3-yl] 2-aminobenzoate
CAS Number	111111-97-8
PubChem CID	183167
ChemSpider	159275
UNII	O6PNX53TGK
CompTox Dashboard (EPA)	DTXSID70912000
Chemical and physical data
Formula	C₂₅H₂₉NO₃
Molar mass	391.511 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC3(1CC2O)CCC4=C3C=CC(=C4)OC(=O)C5=CC=CC=C5N
InChI InChI=1S/C25H29NO3/c1-25-13-12-18-17-9-7-16(29-24(28)20-4-2-3-5-22(20)26)14-15(17)6-8-19(18)21(25)10-11-23(25)27/h2-5,7,9,14,18-19,21,23,27H,6,8,10-13,26H2,1H3/t18-,19-,21+,23+,25+/m1/s1 Key:KZDLYRDWDPOBMR-CWWQDXLCSA-N

Estradiol anthranilate, or estradiol 3-anthranilate, is a synthetic estrogen and estrogen ester – specifically, the C3 anthranilic acid ester of estradiol – which was described in the late 1980s and was never marketed. In dogs, the oral bioavailability of estradiol anthranilate was found to be 5-fold higher than that of unmodified estradiol. However, a subsequent study found that the oral bioavailability of estradiol and estradiol anthranilate did not differ considerably in rats (4.3% and 3.2%, respectively), suggestive of a major species difference.

References

^ Hussain MA, Aungst BJ, Shefter E (January 1988). "Prodrugs for improved oral beta-estradiol bioavailability". Pharmaceutical Research. 5 (1): 44–47. doi:10.1023/A:1015863412137. PMID 3244608. S2CID 7308414.
^ Lokind KB, Lorenzen FH, Bundgaard H (1991). "Oral bioavailability of 17β-estradiol and various ester prodrugs in the rat". International Journal of Pharmaceutics. 76 (1–2): 177–182. doi:10.1016/0378-5173(91)90356-S. ISSN 0378-5173.
^ Kuhnz W, Blode, Zimmerman H (6 December 2012). "Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Science & Business Media. pp. 263–. doi:10.1007/978-3-642-60107-1_15. ISBN 978-3-642-60107-1.
^ Aungst BJ, Matz N (26 August 2007). "Prodrugs to Reduce Presystemic Metabolism". In Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J (eds.). Prodrugs: Challenges and Rewards. Biotechnology: Pharmaceutical Aspects. Springer Science & Business Media. pp. 347–. doi:10.1007/978-0-387-49785-3_8. ISBN 978-0-387-49785-3.
Hansen J, Mørk N, Bundgaard H (1992). "Phenyl carbamates of amino acids as prodrug forms for protecting phenols against first-pass metabolism". International Journal of Pharmaceutics. 81 (2–3): 253–261. doi:10.1016/0378-5173(92)90017-V. ISSN 0378-5173.

v t e Estradiol
Topics	Estradiol (as a hormone) Estradiol (as a medication) Pharmacodynamics of estradiol Pharmacokinetics of estradiol Estrogen (as a hormone) Estrogen (as a medication) Menopausal hormone therapy Feminizing hormone therapy Estradiol-containing birth control pill Combined injectable birth control High-dose estrogen Hydroxylation of estradiol
Esters	Estradiol acetate Estradiol acetylsalicylate Estradiol anthranilate Estradiol benzoate butyrate Estradiol benzoate cyclooctenyl ether Estradiol benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol diacetate Estradiol dibutyrate Estradiol dienantate Estradiol dipropionate Estradiol distearate Estradiol disulfate Estradiol diundecylate Estradiol diundecylenate Estradiol enantate Estradiol furoate Estradiol glucuronide Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol phenylpropionate Estradiol phosphate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol salicylate Estradiol stearate Estradiol sulfamate Estradiol sulfate Estradiol undecylate Estradiol undecylenate Estradiol valerate Estramustine phosphate (estradiol normustine phosphate) Estrogen ester Polyestradiol phosphate
Related	Estrone Estriol Estetrol Ethinylestradiol Conjugated estrogens Esterified estrogens Estrone sulfate Estropipate (piperazine estrone sulfate)

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

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, 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
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

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

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See also

References