CAS 53-16-7|estrone|Estrone|Oestrone|(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one|Estronum [INN-Latin]|Estrogenic Substance|Folisan|Oestrin|Fol...

General Information

Structure

Molecular Formula

C₁₈H₂₂O₂

Molecular Mass

270.36608

Exact Mass

270.16197994

Charge

InChI

InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

InChIKey

DNXHEGUUPJUMQT-CBZIJGRNSA-N

Canonic Smiles

Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C

Isomeric Smiles

O=C1[C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(O)cc2)CC1)C

Calculated Properties

JChem

LogD (pH = 7.4)

4.31

LogD (pH = 5.5)

4.31

Log P

4.31

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

10.33

Polar Surface Area

37.30

Polarizability

31.28

Molar Refractivity

79.08

LOG S

-4.18

Data Source

Names and Identifiers

Synonyms

EstroneOestroneESTRONE, U.S.P.3-羟基雌甾-1,3,5(10)-三烯-17-酮雌(三烯酚)酮3-Hydroxy-1,3,5(10)-estratrien-17-one雌酚酮Folliculin雌酮Estrone1,3,5(10)-Estratrien-3-ol-17-oneCristallovar3-Hydroxy-17-keto-estra-1,3,5-trieneCrystogenCrinovaryl(+)-EstroneWynestronAquacrine3-Hydroxyestra-1,3,5(10)-trien-17-oneWAY 164397OestrinOxohydroxyoestrinMenformonFollicular hormone(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-oneProgynonestronefollicular hormoneestroneoestrone3-Hydroxy-1,3,5(10)-estratrien-17-onefolliculinEstrone

IUPAC name

(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-14-one (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one (3aS,3bR,9bS,11aS)-7-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one

IUPAC Traditional name

estrone (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one

Brand Name

FollidrinPenncap MTokokinFemestrone Inj.Estrona [Spanish]SolliculinTheelinEstronUndenFollestrolFolliculinPerlatanEstrone [Usan:Inn]ThelestrinOestrone [Steroidal Oestrogens]MenagenOestroperosFollicunodisEndofolliculinaEstrugenoneEstrogenic SubstanceKetohydroxyestrinDisynformonKetohydroxy-EstratrieneFolipexCrystogenWynestronFolisanFollestrineFollicular HormoneAquacrineEsteroneEstrone-AFolliculine BenzoateEstrolSinafid M-48HormovarineMenformonCrinovarylOestrinOestroneOestronumEstrinDestroneThynestronFemestrone InjectionKetophydroxyestrinWynestronpencap MFolliculineGlandubolinHormestrinEstronaKolponMestronaqOvifollinKetohydroxyoestrinEstrona [INN-Spanish]GSS 33HormofollinOestroformKestroneMenformon ACristallovarFemidynThelykininOVEXHiestroneEstrusolFermidynEstronum [INN-Latin]EstrovarinKetodestrinFolikrin

API Name

Estrone

International Nonproprietary Name (INN)

estrone

Names and Identifiers

Registration numbers

Properties

Pharmacology Properties

Half Life

19 hours

Protein Bound

>95%

Gene Information

human ... ESR1(2099), ESR2(2100), ESRRA(2101), ESRRB(2103), HSD17B1(3292), SERPINA6(866)mouse ... Esr1(13982)rat ... Esr1(24890)

Mechanism of Action

Estrogen

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00655

Drug Groups

approved

Description

Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase.

Indication

For management of perimenopausal and postmenopausal symptoms.

Pharmacology

Estrone, a synthetically prepared or naturally occurring steroidal estrogen obtained from pregnant equine urine, is the primary circulating estrogen after menopause. Estrone is naturally derived from the peripheral conversion of androstenedione by an aromatase enzyme found in adipose tissues and is converted to estradiol in peripheral tissues. The estrogenic potency of estrone is one third that of estradiol. Estropipate is piperazine-stabilized estrone sulfate. Estrone, and estropipate are used to treat abnormalities related to gonadotropin hormone dysfunction, vasomotor symptoms, atrophic vaginitis, and vulvar atrophy associated with menopause, and for the prevention of osteoporosis due to estrogen deficiency.

Toxicity

Symptoms of overdose include nausea and vomiting. Estrogen related side effects include nausea, breast tenderness, fluid retention and edema, headaches and/or migraines, chloasma and poor contact lens fit. Estrogen hormone deficiency is associated with breakthrough bleeding, hypomenorrhea, irritability, depression and menopausal symptoms. Withdrawal bleeds may occur in females.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

43%

Half Life

19 hours

Protein Binding

> 95%

References

• Miyoshi Y, Tanji Y, Taguchi T, Tamaki Y, Noguchi S: Association of serum estrone levels with estrogen receptor-positive breast cancer risk in postmenopausal Japanese women. Clin Cancer Res. 2003 Jun;9(6):2229-33. [Pubmed]

• Kajta M, Lason W, Bien E, Marszal M: Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors. Pol J Pharmacol. 2002 Nov-Dec;54(6):727-9. [Pubmed]

External Links

• [Wikipedia]

Selleck Chemicals

S1665

Research Area: Endocrinology
Biological Activity:
Estrone is an estrogenic hormone secreted by the ovary as well as adipose tissue. Estrone is one of the three estrogens, which also include estriol and estradiol. Estrone is the least abundant of the three hormones, estradiol is always in the reproductive female body, and estriol is abundant primarily during pregnancy. Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol. [1]

MP Biomedicals

05214691

MP Biomedicals Rare Chemical collection

Wikipedia

Estrone

Sigma Aldrich

E9750

Biochem/physiol Actions
Estrone is a luteolytic estrogen produced by the corpus luteum.
Packaging
1, 5, 25 g in glass bottle
500 mg in glass bottle

46573

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

TRC

E889050

A metabolite of 17β-Estradiol.

ChEBI

CHEBI:17263

A 17-oxo steroid that is estra-1,3,5(10)-triene substituted by an hydroxy group at position 3 and an oxo group at position 17.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Estrone

• Goodman-Gruen, D., et al.: J. Clin. Endocrinol. Metab., 81, 2999 (1983)

• Both, D., et al.: Anal. Profiles Drug Subs., 12, 135 (1983)

• Busetta, B. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1972, 274, 153, (cryst struct)

• Posner, G.H. et al., Tetrahedron, 1981, 37, 3921, (synth)

• Both, D., Anal. Profiles Drug Subst., 1983, 12, 135, (rev)

• Barlaam, B. et al., Tet. Lett., 1991, 32, 623, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 589C, (nmr)

• Kuo, C.H. et al., Chem. Ind. (London), 1966, 1340, (synth)

• Crabb, P. et al., Can. J. Chem., 1968, 46, 349, (14 synth, uv, ir)

• IARC Monog., 1979, 21, 343, (tox, rev)

• Quinkert, G. et al., Annalen, 1981, 2335, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4875; 4883

• Caspi, E. et al., Chem. Comm., 1989, 1302, (biosynth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1183; 1192

• Hiraga, K. et al., Chem. Comm., 1969, 1013, (synth)

• Wittstruck, T.A. et al., J.O.C., 1973, 38, 1542, (cmr)

• Birch, A.J. et al., Aust. J. Chem., 1970, 23, 547, (synth)

• Crispin, D.J. et al., J.C.S.(C), 1970, 10, (synth)

• Sergeev, P.V. et al., Zh. Fiz. Khim., 1973, 47, 1643, (ms)

• Cohen, N. et al., J.O.C., 1975, 40, 681, (synth)

• Kametani, T. et al., J.A.C.S., 1976, 98, 3378; 1977, 99, 3461, (synth)

• Danishefsky, S. et al., J.A.C.S., 1976, 98, 4975, (synth)

• Duax, W.L. et al., Acta Cryst. B, 1979, 35, 2656, (cryst struct)

• Hutchinson, J.H. et al., Can. J. Chem., 1987, 65, 1, (synth)

• Taber, D.F. et al., J.O.C., 1987, 52, 28, (synth)

• Takano, S. et al., Tet. Lett., 1992, 33, 1909, (synth)

• Tanaka, K. et al., Org. Lett., 2000, 1915-1917, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1055D, (ir)

• Heftmann, E. et al., Phytochemistry, 1966, 5, 231; 1337, (isol)

• Ziegler, F.E. et al., Tet. Lett., 1981, 1179, (synth)

• Zepter, R., J. Prakt. Chem., 1971, 313, 1139, (synth, uv, pmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EDV000; EDV600

• Rufer, C. et al., Annalen, 1967, 705, 211, (synth)

• Sugahara, T. et al., Tet. Lett., 1996, 37, 7403, (synth)

• Smales, C.M. et al., Acta Cryst. C, 1997, 53, 1082-1084, (cryst struct)

• Douglas, G.H. et al., J.C.S., 1963, 5072, (synth, ir)

• Nicolaou, K.C. et al., J.O.C., 1980, 45, 1403, (synth)

• Grieco, P.A. et al., J.O.C., 1980, 45, 2247, (synth)

• Sunder, N.M. et al., J.C.S. Perkin 1, 1990, 1331, (synth)

• Subba Rao, G.S.R. et al., Aust. J. Chem., 1992, 45, 187, (synth)

• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 153, (bibl, synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

IUPAC Traditional name

estrone (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one

Brand Name

API Name

Estrone

International Nonproprietary Name (INN)

estrone

Molecule Details

DrugBank

DB00655

Drug Groups

approved

Description

Indication

For management of perimenopausal and postmenopausal symptoms.

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

43%

Half Life

19 hours

Protein Binding

> 95%

References

External Links

• [Wikipedia]

Selleck Chemicals

S1665

MP Biomedicals

05214691

MP Biomedicals Rare Chemical collection

Wikipedia

Estrone

Sigma Aldrich

E9750

Biochem/physiol Actions
Estrone is a luteolytic estrogen produced by the corpus luteum.
Packaging
1, 5, 25 g in glass bottle
500 mg in glass bottle

46573

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

TRC

E889050

A metabolite of 17β-Estradiol.

ChEBI

CHEBI:17263

A 17-oxo steroid that is estra-1,3,5(10)-triene substituted by an hydroxy group at position 3 and an oxo group at position 17.

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Estrone

• Goodman-Gruen, D., et al.: J. Clin. Endocrinol. Metab., 81, 2999 (1983)

• Both, D., et al.: Anal. Profiles Drug Subs., 12, 135 (1983)

• Busetta, B. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1972, 274, 153, (cryst struct)

• Posner, G.H. et al., Tetrahedron, 1981, 37, 3921, (synth)

• Both, D., Anal. Profiles Drug Subst., 1983, 12, 135, (rev)

• Barlaam, B. et al., Tet. Lett., 1991, 32, 623, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 589C, (nmr)

• Kuo, C.H. et al., Chem. Ind. (London), 1966, 1340, (synth)

• Crabb, P. et al., Can. J. Chem., 1968, 46, 349, (14 synth, uv, ir)

• IARC Monog., 1979, 21, 343, (tox, rev)

• Quinkert, G. et al., Annalen, 1981, 2335, (synth)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4875; 4883

• Caspi, E. et al., Chem. Comm., 1989, 1302, (biosynth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1183; 1192

• Hiraga, K. et al., Chem. Comm., 1969, 1013, (synth)

• Wittstruck, T.A. et al., J.O.C., 1973, 38, 1542, (cmr)

• Birch, A.J. et al., Aust. J. Chem., 1970, 23, 547, (synth)

• Crispin, D.J. et al., J.C.S.(C), 1970, 10, (synth)

• Sergeev, P.V. et al., Zh. Fiz. Khim., 1973, 47, 1643, (ms)

• Cohen, N. et al., J.O.C., 1975, 40, 681, (synth)

• Kametani, T. et al., J.A.C.S., 1976, 98, 3378; 1977, 99, 3461, (synth)

• Danishefsky, S. et al., J.A.C.S., 1976, 98, 4975, (synth)

• Duax, W.L. et al., Acta Cryst. B, 1979, 35, 2656, (cryst struct)

• Hutchinson, J.H. et al., Can. J. Chem., 1987, 65, 1, (synth)

• Taber, D.F. et al., J.O.C., 1987, 52, 28, (synth)

• Takano, S. et al., Tet. Lett., 1992, 33, 1909, (synth)

• Tanaka, K. et al., Org. Lett., 2000, 1915-1917, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1055D, (ir)

• Heftmann, E. et al., Phytochemistry, 1966, 5, 231; 1337, (isol)

• Ziegler, F.E. et al., Tet. Lett., 1981, 1179, (synth)

• Zepter, R., J. Prakt. Chem., 1971, 313, 1139, (synth, uv, pmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EDV000; EDV600

• Rufer, C. et al., Annalen, 1967, 705, 211, (synth)

• Sugahara, T. et al., Tet. Lett., 1996, 37, 7403, (synth)

• Smales, C.M. et al., Acta Cryst. C, 1997, 53, 1082-1084, (cryst struct)

• Douglas, G.H. et al., J.C.S., 1963, 5072, (synth, ir)

• Nicolaou, K.C. et al., J.O.C., 1980, 45, 1403, (synth)

• Grieco, P.A. et al., J.O.C., 1980, 45, 2247, (synth)

• Sunder, N.M. et al., J.C.S. Perkin 1, 1990, 1331, (synth)

• Subba Rao, G.S.R. et al., Aust. J. Chem., 1992, 45, 187, (synth)

• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 153, (bibl, synth)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Half Life

19 hours

Protein Bound

>95%

Gene Information

human ... ESR1(2099), ESR2(2100), ESRRA(2101), ESRRB(2103), HSD17B1(3292), SERPINA6(866)mouse ... Esr1(13982)rat ... Esr1(24890)

Mechanism of Action

Estrogen

Molecule

ID:537