Estradiol
Title: Estradiol
CAS Registry Number: 50-28-2
CAS Name: (17b)-Estra-1,3,5(10)-triene-3,17-diol
Additional Names: b-estradiol; cis-estradiol; 3,17-epidihydroxyestratriene; dihydrofollicular hormone; dihydrofolliculin; dihydroxyestrin; dihydrotheelin
Trademarks: Climara (Berlex); Estrace (Warner-Chilcott); Estraderm (Novartis); Estradot (Novartis); Estring (Pharmacia & Upjohn); Estrofem (Novo Nordisk); Estrogel (Solvay); Evorel (Janssen-Cilag); Menostar (Berlex); Systen (Janssen-Cilag); Vivelle (Novartis); Vivelle-Dot (Novartis); Zumenon (Solvay)
Molecular Formula: C18H24O2
Molecular Weight: 272.38
Percent Composition: C 79.37%, H 8.88%, O 11.75%
Literature References: Potent mammalian estrogenic hormone produced by the ovary. Triggers the production of gonadotropins leading to ovulation. Isoln from follicular fluid of sow ovaries: D. W. MacCorquodale et al., J. Biol. Chem. 115, 435 (1936). Has also been isolated from urine of pregnant women and mares. Prepn from estrone: A. Butenandt, C. Georgens, Z. Physiol. Chem. 248, 129 (1937); F. Hildebrandt et al., US 2096744 (1938 to Schering); from cholesterol: H. H. Inhoffen, G. Zühlsdorff, Ber. 74, 1914 (1941). Total syntheses: U. Eder et al., Ber. 109, 2948 (1976); W. Oppolzer, D. A. Roberts, Helv. Chim. Acta 63, 1703 (1980). Pharmacology: R. W. Lievertz, Am. J. Obstet. Gynecol. 156, 1289 (1987). HPLC determn in plasma and urine: W. Slikker et al., J. Chromatogr. 224, 205 (1981). Pharmacokinetics: W. Kuhnz et al., Arzneim.-Forsch. 43, 966 (1993). Clinical evaluation in osteoporosis: J. W. W. Studd et al., Br. J. Obstet. Gynaecol. 101, 787 (1994). Comprehensive description: E. G. Salole, Anal. Profiles Drug Subs. 15, 283-318 (1986). Physiologic review: H. G. Burger, Int. J. Gynaecol. Obstet. 1989, Suppl. 1, 5-9. Review of clinical safety and efficacy in estrogen replacement therapy: A. Cheang et al., Drug Saf. 9, 365-379 (1993); H. L. Judd, J. Reprod. Med. 39, 343-352 (1994).
Properties: White crystalline powder. Prisms from 80% alc, stable in air, mp 173-179°. [a]D25 +76 to +83° (dioxane). uv max: 225, 280 nm. Precipitated by digitonin. Practically insol in water. Freely sol in alcohol; sol in acetone, dioxane, other organic solvents; solns of fixed alkali hydroxides; sparingly sol in vegetable oils. 1 mg = 10,000 international units.
Melting point: mp 173-179°
Optical Rotation: [a]D25 +76 to +83° (dioxane)
Absorption maximum: uv max: 225, 280 nm
 
Derivative Type: Hemihydrate
CAS Registry Number: 35380-71-3
Trademarks: Estroclim (Sigma-Tau); Menorest (Novartis); Vagifem (Novo Nordisk)
Molecular Formula: C18H24O2.½H2O
Molecular Weight: 281.39
Percent Composition: C 76.83%, H 8.96%, O 14.21%
 
Derivative Type: 3-Acetate
CAS Registry Number: 4245-41-4
Trademarks: Femring (Warner-Chilcott); Femtrace (Warner-Chilcott)
Molecular Formula: C20H26O3
Molecular Weight: 314.42
Percent Composition: C 76.40%, H 8.33%, O 15.27%
 
Derivative Type: 3-Benzoate
CAS Registry Number: 50-50-0
Additional Names: Estradiol benzoate
Trademarks: Agofollin (Biotika); Duralease (Merial); Ovahormon (Teikoku Zoki); Progynon B (Schering AG)
Molecular Formula: C25H28O3
Molecular Weight: 376.49
Percent Composition: C 79.75%, H 7.50%, O 12.75%
Properties: Crystals from alc, mp 191-196°. Stable in air. [a]D25 +58 to +63° (c = 2 in dioxane). Sol in alc, acetone, dioxane; slightly sol in ether, vegetable oils.
Melting point: mp 191-196°
Optical Rotation: [a]D25 +58 to +63° (c = 2 in dioxane)
 
Derivative Type: 17b-Cyclopentanepropanoate
CAS Registry Number: 313-06-4
Additional Names: Estradiol cypionate; ECP
Molecular Formula: C26H36O3
Molecular Weight: 396.56
Percent Composition: C 78.75%, H 9.15%, O 12.10%
Literature References: Prepn: Ott, US 2611773 (1952 to Upjohn).
Properties: Crystals from benzene + petr ether, mp 151-152°. [a]D25 +45° (chloroform). Sol in ether, methanol, benzene, chloroform, peanut oil, cottonseed oil, corn oil, sesame oil.
Melting point: mp 151-152°
Optical Rotation: [a]D25 +45° (chloroform)
 
Derivative Type: Dipropionate
CAS Registry Number: 113-38-2
Trademarks: Ovahormon Depot (Teikoku)
Molecular Formula: C24H32O4
Molecular Weight: 384.51
Percent Composition: C 74.97%, H 8.39%, O 16.64%
Literature References: Prepn: K. Miescher, C. Scholz, US 2205627 (1940 to Ciba).
Properties: mp 104-105°.
Melting point: mp 104-105°
 
Derivative Type: 17-Heptanoate
CAS Registry Number: 4956-37-0
Additional Names: Estradiol enanthate
Manufacturers' Codes: SQ-16150
Molecular Formula: C25H36O3
Molecular Weight: 384.55
Percent Composition: C 78.08%, H 9.44%, O 12.48%
Literature References: Prepn: Gauthier et al., Ann. Pharm. Fr. 16, 757 (1958).
Properties: Crystals from diisopropyl ether, mp 94-96°.
Melting point: mp 94-96°
 
Derivative Type: 17-Valerate
CAS Registry Number: 979-32-8
Trademarks: Climaval (Novartis); Delestrogen (Monarch); Pelanin Depot (Mochida); Progynon Depot (Schering AG); Progynova (Schering AG)
Molecular Formula: C23H32O3
Molecular Weight: 356.50
Percent Composition: C 77.49%, H 9.05%, O 13.46%
Literature References: Prepn: K. Miescher, C. Scholz, US 2233025 (1941 to Ciba). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 4, 192-208 (1975).
Properties: Crystals, mp 144-145°.
Melting point: mp 144-145°
 
CAUTION: These substances are listed as known human carcinogens: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-115.
Therap-Cat: Estrogen.
Therap-Cat-Vet: Estrogen.
Keywords: Estrogen; Steroidal.

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