Estrogenic substances Estrone, a major ingredient in estrogenic substances
Estrone Estrogen 17β-Estradiol Estrogen Equilin Estrogen Trade names Amniotin, Estrogenic Hormones, Estrogenic Substances, Estrolin, Estromone, Folestrin, Follacro, Menformon, Oestroform, Ova-Estrin, Theelestrin, others Other names Natural estrogens; Estrone-like preparations Routes of administration By mouth (tablets , capsules ), topical (ointment ), vaginal (suppository ), intramuscular injection (oil solution )Drug class Estrogen Legal status
Estrogenic substances , also referred to as natural estrogens and sold under the brand name Amniotin among others, is an estrogen medication which was marketed in the 1930s and 1940s and is no longer available.[1] [2] [3] [4] [5] [6] It was a purified extract of animal material such as horse urine , placenta , and/or amniotic fluid , and contained a non-crystalline mixture of estrogens, including estrone , 17β-estradiol , 17α-estradiol , and/or equilin .[3] [1] [7] [8] [5] [9] The medication was thought to contain estrone as its major active ingredient[7] and was described as an estrone-like preparation, or as "essentially estrone".[1] [3] [5] Estrogenic substances was originally produced from the urine of pregnant women, placenta, and/or amniotic fluid, but by the early 1940s, it was manufactured exclusively from the urine of stallions or pregnant mares , similarly to almost all other estrogen preparations on the market.[8] [9] [7] [1]
Estrogenic substances was marketed under a variety of different brand names including Amniotin (Squibb ), Equine Estrogenic Substances (Ayerst), Estrogenic Hormones (Upjohn , others), Estrogenic Substances (Reed & Carnrick, Sharp & Dohme, others), Estrolin (Lakeside), Estromone , Estronat (National Drug), Folestrin (Armour ), Follacro (Schieffelin), Menformon (Roche -Organon ), Neo-Amniotin (Squibb), Oestroform , Ova-Estrin , Theelestrin , and Urestrin (Upjohn), among others.[1] [2] [3] [4] [6] It was provided in various forms and routes of administration including oil solution and aqueous suspension for intramuscular injection , oral tablets and capsules , vaginal suppositories , and topical ointments .[2] [3] [4] [1] [6]
Estrogen medications similar to but distinct from estrogenic substances included conjugated estriol (Emmenin ) and conjugated estrogens (Premarin ).[1] They are also non-crystalline mixtures of estrogens.[1] Estrogenic substances were also distinct from pure crystalline preparations such as estrone , estradiol , estriol , estradiol benzoate , and estradiol dipropionate .[1] The medication should additionally be distinguished from estrogen ovarian extracts, which had little activity and were considered to be essentially inactive.[10] [2]
Progynon and Amniotin were both marketed by 1929.[11] Amniotin was originally prepared from the amniotic fluid of cattle , but was later prepared using other sources such as the urine of pregnant mares.[12] [9]
References
^ a b c d e f g h i "Nomenclature of Endocrine Preparations". Journal of the American Medical Association . 123 (6): 351. 1943. doi :10.1001/jama.1943.02840410033009 . ISSN 0002-9955 .
^ a b c d Fluhmann CF (November 1938). "Estrogenic Hormones: Their Clinical Usage" . Cal West Med . 49 (5): 362–6. PMC 1659459 . PMID 18744783 .
^ a b c d e Greene, R.R. (1941). "Endocrine Therapy for Gynecologic Disorders". Medical Clinics of North America . 25 (1): 155–168. doi :10.1016/S0025-7125(16)36624-X . ISSN 0025-7125 .
^ a b c Fluhmann, C. F. (1944). "Clinical use of extracts from the ovaries". Journal of the American Medical Association . 125 (1): 1. doi :10.1001/jama.1944.02850190003001 . ISSN 0002-9955 .
^ a b c Reifenstein, Edward C. (1944). "Endocrinology: A Synopsis of Normal and Pathologic Physiology, Diagnostic Procedures, and Therapy". Medical Clinics of North America . 28 (5): 1232–1276. doi :10.1016/S0025-7125(16)36180-6 . ISSN 0025-7125 .
^ a b c Maximilian Alexander Goldzieher; Joseph William Goldzieher (1953). Endocrine Treatment in General Practice . Springer Publishing Company. pp. 436–.
^ a b c David Preswick Barr (1940). Modern Medical Therapy in General Practice . William & Wilkins Company. Complex Estrogenic Preparations. 1. Amniotin (Squibb). This is a highly purified but not crystalline preparation derived from pregnant mares' urine. The chief active ingredient is apparently ketohydroxyestrin (estrone).
^ a b Glandular Physiology and Therapy . American Medical Association. 1935. p. 480. Amniotin, E. R. Squibb & Sons: This is an estrogenic preparation originally derived from amniotic fluid; it is not reduced to the crystalline state during manufacture. More recently, according to the firm, the urine of pregnant mares has served as an added source of active material.
^ a b c McCullagh EP (1935). "The Management of Functional Menstrual Disorders" . Cleveland Clinic Quarterly . 2 (4): 52–64.
^ Novak, Emil (1935). "The Therapeutic Use of Estrogenic Substances". JAMA: The Journal of the American Medical Association . 104 (20): 1815. doi :10.1001/jama.1935.92760200002012 . ISSN 0098-7484 .
^ The Female Sex Hormone . C.C. Thomas. 1929. p. 276.
^ Biskind, Morton S. (1935). "Commercial glandular products". Journal of the American Medical Association . 105 (9): 667. doi :10.1001/jama.1935.92760350007009a . ISSN 0002-9955 .
Estrogens
ER Tooltip 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
Ethinylestradiol #
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
Promestriene
Quinestradol
Quinestrol
Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonists (incl. SERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors 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
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
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 (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown