Estradiol benzoate

Structural formula
General
Surname	Estradiol benzoate
other names	Estran-17 β -ol-3-benzoate; [(8 R , 9 S , 13 S , 14 S , 17 S ) -17-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta [ a ] phenanthren-3-yl] benzoate;
Molecular formula	C 25 H 28 O 3
External identifiers / databases
EC number	200-043-7
ECHA InfoCard	100,000,040
PubChem	222757
DrugBank	DB13953
Wikidata	Q11450699
properties
Molar mass	376.49 g mol −1
Physical state	firmly
Melting point	191-198 ° C
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 351-360
	P: 201-281-308 + 313
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Estradiol benzoate is a synthetic compound from the class of steroid hormones . It is the ester of the naturally occurring female sex hormone estradiol with benzoic acid .

history

Estradiol benzoate is one of the first artificial estrogens to hit the market as a drug. It was developed by the Schering company and sold under the brand name Progynon-B from 1933.

Extraction and presentation

The synthesis takes place through the reduction of estrone to estradiol and the reaction with benzoyl chloride in potassium hydroxide.

properties

Physical Properties

It is a white, crystalline, odorless powder.
Melting point: 191-196 ° C
Rotation value: [α] _{D ²⁵} = +57 to +63 in 1,4-dioxane
UV: 230 nm

Chemical properties

Estradiol benzoate is a chiral compound and has five stereocenters.

Pharmacological properties

The C-18 steroid structure with the aromatic A-ring and the hydroxy functions at C-17 and C-3 are responsible for the estrogenic effect of natural and synthetic estrogens. The esterification of one or both hydroxyl groups increases the effectiveness. After oral administration, estradiol benzoate has a high first-pass effect of over 80% , which is comparable to that of estradiol . However, estradiol esters are suitable for intramuscular or subcutaneous administration. They are slowly absorbed from oily solutions and broken down with a delay.

use

Estradiol esters are used for hormone replacement therapy during menopause. It is also used as a hair spirit for the local treatment of the scalp in the case of androgenic hair loss.

In addition, estradiol benzoate was used in veterinary medicine (veterinary medicine) to interrupt pregnancy in undesirably mated bitches and to treat prostatic hyperplasia in males.

There are no approved drugs in the United States.

proof

Estradiol benzoate can be identified by gas chromatography with mass spectrometry coupling , the m / z peaks at 105, 77 and 376.

literature

H. Lüllmann, K. Mohr, M. Wehling, L. Hein: Pharmakologie und Toxikologie , Thieme Verlag 2016, 18th edition, 476–478. ISBN 978-3-13-368518-4 .

Individual evidence

↑ ^a ^b ^c ^d data sheet Estradiol benzoate from Sigma-Aldrich , accessed on June 19, 2017 ( PDF ).
↑ Helga Satzinger, Adolf Butenandt, Hormone and Gender, in: Wolfgang Schieder, Achim Trunk, Adolf Butenandt and the Kaiser Wilhelm Society, Wallsteinverlag 2004 p. 102, cf. Schering (2) in the Sybodo Museum, Innsbruck.
↑ Medicine. Commun. Schering Heft 8, Nov. 1933, p. 209, cf. Schering (4) in the Sybodo Museum, Innsbruck.
↑ ^a ^b ^c ^d ^e F. von Bruchhausen (Ed.): Hager's Handbook of Pharmaceutical Practice Materials EO, Springer Verlag, 1993, p. 82, ISBN 978-3-642-63428-4 , doi: 10.1007 / 978-3 -642-57994-3 .
↑ Harald Schmidt (Ed.): Pharmacology and Toxicology for Study and Practice , 2007, ISBN 978-3-7945-2295-8 .
↑ Manuchair Ebadi (October 31, 2007). Desk Reference of Clinical Pharmacology, Second Edition. CRC Press. P. 249-. ISBN 978-1-4200-4744-8 .
↑ C. Berg: Minoxidil now also approved for women . Pharmaceutical newspaper, issue 12/2004.
↑ estradiol benzoate ad us. vet., injection solution (archive entry ) at www.vetpharm.uzh.ch; accessed on November 17, 2019.

^ Richard Witherspoon (June 1, 1994). Presidents List of Articles Which May Be Designated Or Modified As Eligible Articles for Purposes of the US Generalized System of Preferences. DIANE Publishing. 64 f. ISBN 978-0-7881-1433-5 .

↑ Entry on Estradiol Benzoate (mass spectrum, electron ionization). In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed November 17, 2019.

[Sigma-1] ta sheet Estradiol benzoate from Sigma-Aldrich , accessed on June 19, 2017 ( PDF ).

[2] Helga Satzinger, Adolf Butenandt, Hormone and Gender, in: Wolfgang Schieder, Achim Trunk, Adolf Butenandt and the Kaiser Wilhelm Society, Wallsteinverlag 2004 p. 102, cf. Schering (2) in the Sybodo Museum, Innsbruck.

[3] Medicine. Commun. Schering Heft 8, Nov. 1933, p. 209, cf. Schering (4) in the Sybodo Museum, Innsbruck.

[Hager-4] F. von Bruchhausen (Ed.): Hager's Handbook of Pharmaceutical Practice Materials EO, Springer Verlag, 1993, p. 82, ISBN 978-3-642-63428-4 , doi: 10.1007 / 978-3 -642-57994-3 .

[5] Harald Schmidt (Ed.): Pharmacology and Toxicology for Study and Practice , 2007, ISBN 978-3-7945-2295-8 .

[6] Manuchair Ebadi (October 31, 2007). Desk Reference of Clinical Pharmacology, Second Edition. CRC Press. P. 249-. ISBN 978-1-4200-4744-8 .

[7] C. Berg: Minoxidil now also approved for women . Pharmaceutical newspaper, issue 12/2004.

[8] estradiol benzoate ad us. vet., injection solution (archive entry ) at www.vetpharm.uzh.ch; accessed on November 17, 2019.

[9] Richard Witherspoon (June 1, 1994). Presidents List of Articles Which May Be Designated Or Modified As Eligible Articles for Purposes of the US Generalized System of Preferences. DIANE Publishing. 64 f. ISBN 978-0-7881-1433-5 .

[NIST-10] Entry on Estradiol Benzoate (mass spectrum, electron ionization). In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed November 17, 2019.