Estriol glucuronide - Misplaced Pages

(Redirected from Estriol 16α-glucuronide) Chemical compound Pharmaceutical compound

Estriol glucuronide
Clinical data

Other names	Estriol glucuronidate; (16α,17β)-16,17-Dihydroxyestra-1,3,5(10)-trien-3-yl D-glucopyranosiduronic acid; β-D-Glucopyranuronic acid, monoglycoside with (16α,17β)-estra-1,3,5(10)-triene-3,16,17-triol
Routes of administration	By mouth
Identifiers
IUPAC name (2S,3S,4S,5R,6R)-6-phenanthren-16-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Number	28808-07-3
PubChem CID	122281
ChemSpider	134818
CompTox Dashboard (EPA)	DTXSID30939935
ECHA InfoCard	100.161.795
Chemical and physical data
Formula	C₂₄H₃₂O₉
Molar mass	464.511 g·mol
3D model (JSmol)	Interactive image
SMILES C12CC3(1C(2O)O4((((O4)C(=O)O)O)O)O)CCC5=C3C=CC(=C5)O
InChI InChI=InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(21(24)29)32-23-19(28)17(26)18(27)20(33-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23-,24+/m1/s1 Key:FQYGGFDZJFIDPU-JRSYHJKYSA-N

Estriol glucuronide (E3G), or oestriol glucuronide, also known as estriol monoglucuronide, as well as estriol 16α-β-D-glucosiduronic acid, is a natural, steroidal estrogen and the glucuronic acid (β-D-glucopyranuronic acid) conjugate of estriol. It occurs in high concentrations in the urine of pregnant women as a reversibly formed metabolite of estriol. Estriol glucuronide is a prodrug of estriol, and was the major component of Progynon and Emmenin, estrogenic products manufactured from the urine of pregnant women that were introduced in the 1920s and 1930s and were the first orally active estrogens. Emmenin was succeeded by Premarin (conjugated equine estrogens), which is sourced from the urine of pregnant mares and was introduced in 1941. Premarin replaced Emmenin due to the fact that it was easier and less expensive to produce.

Estrogen glucuronides can be deglucuronidated into the corresponding free estrogens by β-glucuronidase in tissues that express this enzyme, such as the mammary gland. As a result, estrogen glucuronides have estrogenic activity via conversion into estrogens.

The positional isomer of estriol 16α-glucuronide, estriol 3-glucuronide, also occurs as an endogenous metabolite of estriol, although to a much lower extent in comparison.

References

Hill RA, Makin HL, Kirk DN, Murphy GM (23 May 1991). Dictionary of Steroids. CRC Press. pp. 274–. ISBN 978-0-412-27060-4.
^ Hashimoto Y, Neeman M (April 1963). "Isolation and characterization of estriol 16 alpha-glucosiduronic acid from human pregnancy urine". The Journal of Biological Chemistry. 238 (4): 1273–1282. doi:10.1016/S0021-9258(18)81175-9. PMID 14010351.
Smith RL, Williams RT (2 December 2012). "Implication of the Conjugation of Drug and Other Exogenous Substances". In Dutton G (ed.). Glucuronic Acid Free and Combined: Chemistry, Biochemistry, Pharmacology, and Medicine. Elsevier. pp. 457–492 (466). ISBN 978-0-323-14398-1.
^ Rooke T (1 January 2012). "Chapter 3: Life after the Thyroid". The Quest for Cortisone. MSU Press. pp. 54–. ISBN 978-1-60917-326-5.
^ Li A (2003). "Marketing Menopause: Science and the Public Relations of Premarin". In Feldberg GD (ed.). Women, Health and Nation: Canada and the United States Since 1945. McGill-Queen's Press - MQUP. pp. 103–. ISBN 978-0-7735-2501-6. JSTOR j.ctt7zxvb.10.
Crook D (20 August 2015). "Estrogens used in current menopause therapies". In Panay N, Briggs P, Kovacs G (eds.). Managing the Menopause. Cambridge University Press. pp. 118–123. ISBN 978-1-107-45182-7.
^ Zhu BT, Conney AH (January 1998). "Functional role of estrogen metabolism in target cells: review and perspectives". Carcinogenesis. 19 (1): 1–27. doi:10.1093/carcin/19.1.1. PMID 9472688.
Wishart DS, Guo A, Oler E, Wang F, Anjum A, Peters H, et al. "Metabocard for Estriol-3-glucuronide". Human Metabolome Database. HMDB0010335.
Oettel M, Schillinger E, Kuhnz W, Blode H, Zimmermann 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. 261-322 (265). doi:10.1007/978-3-642-60107-1_15. ISBN 978-3-642-60107-1.
Musey PI, Kirdani RY, Bhanalaph T, Sandberg AA (December 1973). "Estriol metabolism in the baboon: analysis of urinary and biliary metabolites". Steroids. 22 (6): 795–817. doi:10.1016/0039-128X(73)90054-8. PMID 4203562.

External links

Metabocard for Estradiol 17-Glucuronide - Human Metabolome Database

Metabolites: 5α-Dihydrocortisol
3α,5α-Tetrahydrocortisol

Cholestanes: 24S-Hydroxycholesterol
Cholesterol

Others

Estrogens and antiestrogens

Estrogens

ERTooltip Estrogen receptor agonists

Steroidal: Alfatradiol
Certain androgens/anabolic steroids (e.g., testosterone, testosterone esters, methyltestosterone, metandienone, nandrolone esters) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone)
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol
Estradiol
Estradiol esters (e.g., estradiol acetate, estradiol benzoate, estradiol cypionate, estradiol enanthate, estradiol undecylate, estradiol valerate, polyestradiol phosphate, estradiol ester mixtures (Climacteron))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate, polyestriol phosphate)
Estrogenic substances
Estrone
Estrone esters
- Estrone sulfate
- Estropipate (piperazine estrone sulfate)
Ethinylestradiol
- Ethinylestradiol sulfonate
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
- Prasterone enanthate
- Prasterone sulfate
Promestriene
Quinestradol
Quinestrol

Progonadotropins

Antiandrogens (e.g., bicalutamide)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., FSHTooltip follicle-stimulating hormone, LHTooltip luteinizing hormone)

Antiestrogens

ERTooltip Estrogen receptor antagonists (incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)	Acolbifene Anordrin Bazedoxifene Broparestrol Clomifene Cyclofenil Enclomifene Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen Toremifene Exclusively antagonistic: Elacestrant Fulvestrant Noncompetitive inhibitors: Trilostane
Aromatase inhibitors	First-generation: Aminoglutethimide Testolactone Second-generation: Fadrozole Formestane Third-generation: Anastrozole Exemestane Letrozole
Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone esters, oxandrolone, fluoxymesterone) D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) GnRH agonists (e.g., leuprorelin, goserelin) GnRH antagonists (e.g., cetrorelix, elagolix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)
Others	Mixed mechanism of action: Danazol Gestrinone Androstenedione immunogens: Androvax (androstenedione albumin) Ovandrotone albumin (Fecundin)

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

See also: Estrogen receptor modulators; Androgens and antiandrogens; Progestogens and antiprogestogens; List of estrogens

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 Niacin Niacinamide 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

External links