Estrogen medication
"Ogen" redirects here. For the character in the Japanese anime, see Ogen (Basilisk) . For the melon cultivar, see Galia melon .
Estropipate Trade names Harmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others Other names Piperazine estrone sulfate; Estrone sulfate piperazine salt; Pipestrone AHFS /Drugs.com Monograph Routes of administration By mouth Drug class Estrogen ; Estrogen ester ATC code
[(8R ,9S ,13S ,14S )-13-Methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H -cyclopenta[a ]phenanthren-3-yl] hydrogen sulfate; piperazine
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.027.906 Formula C 22 H 32 N 2 O 5 S Molar mass 436.57 g·mol−1 3D model (JSmol )
O=S(=O)(O)Oc1cc4c(cc1)[C@@H]3[C@H]([C@@H]2CCC(=O)[C@@]2(C)CC3)CC4.N1CCNCC1
InChI=1S/C18H22O5S.C4H10N2/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1
Y Key:HZEQBCVBILBTEP-ZFINNJDLSA-N
Y
Estropipate , also known as piperazine estrone sulfate and sold under the brand names Harmogen , Improvera , Ogen , Ortho-Est , and Sulestrex among others, is an estrogen medication which is used mainly in menopausal hormone therapy in the treatment of menopausal symptoms .[1] [2] [3] [4] It is a salt of estrone sulfate and piperazine , and is transformed into estrone and estradiol in the body.[2] [3] It is taken by mouth .[1]
Medical uses [ ]
Estropipate is used to:[1] [additional citation(s) needed ]
Alleviate symptoms of menopause as menopausal hormone therapy
Treat some types of infertility
Treat some conditions leading to underdevelopment of female sexual characteristics
Treat vaginal atrophy
Treat some types of breast cancer (particularly in men and postmenopausal women)
Treat prostate cancer
Prevent osteoporosis
Estrogen dosages for menopausal hormone therapy
Route/form
Estrogen
Low
Standard
High
Oral
Estradiol
0.5–1 mg/day
1–2 mg/day
2–4 mg/day
Estradiol valerate
0.5–1 mg/day
1–2 mg/day
2–4 mg/day
Estradiol acetate
0.45–0.9 mg/day
0.9–1.8 mg/day
1.8–3.6 mg/day
Conjugated estrogens
0.3–0.45 mg/day
0.625 mg/day
0.9–1.25 mg/day
Esterified estrogens
0.3–0.45 mg/day
0.625 mg/day
0.9–1.25 mg/day
Estropipate
0.75 mg/day
1.5 mg/day
3 mg/day
Estriol
1–2 mg/day
2–4 mg/day
4–8 mg/day
Ethinylestradiol a
2.5–10 μg/day
5–20 μg/day
–
Nasal spray
Estradiol
150 μg/day
300 μg/day
600 μg/day
Transdermal patch
Estradiol
25 μg/dayb
50 μg/dayb
100 μg/dayb
Transdermal gel
Estradiol
0.5 mg/day
1–1.5 mg/day
2–3 mg/day
Vaginal
Estradiol
25 μg/day
–
–
Estriol
30 μg/day
0.5 mg 2x/week
0.5 mg/day
IM or SC injection
Estradiol valerate
–
–
4 mg 1x/4 weeks
Estradiol cypionate
1 mg 1x/3–4 weeks
3 mg 1x/3–4 weeks
5 mg 1x/3–4 weeks
Estradiol benzoate
0.5 mg 1x/week
1 mg 1x/week
1.5 mg 1x/week
SC implant
Estradiol
25 mg 1x/6 months
50 mg 1x/6 months
100 mg 1x/6 months
Footnotes: a = No longer used or recommended, due to health concerns. b = As a single patch applied once or twice per week (worn for 3–4 days or 7 days), depending on the formulation. Note: Dosages are not necessarily equivalent. Sources: See template.
Available forms [ ]
Estropipate is available in the form of 0.75, 1.5, 3, and 6 mg oral tablets .[5]
Pharmacology [ ]
Pharmacodynamics [ ]
See also: Pharmacodynamics of estradiol
Estropipate is a prodrug of estrone and estradiol . Hence, it is an estrogen , or an agonist of the estrogen receptors .
Relative oral potencies of estrogens
Estrogen
HF
VE
UCa
FSH
LH
HDL -C
SHBG
CBG
AGT
Liver
Estradiol
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
Estrone
?
?
?
0.3
0.3
?
?
?
?
?
Estriol
0.3
0.3
0.1
0.3
0.3
0.2
?
?
?
0.67
Estrone sulfate
?
0.9
0.9
0.8–0.9
0.9
0.5
0.9
0.5–0.7
1.4–1.5
0.56–1.7
Conjugated estrogens
1.2
1.5
2.0
1.1–1.3
1.0
1.5
3.0–3.2
1.3–1.5
5.0
1.3–4.5
Equilin sulfate
?
?
1.0
?
?
6.0
7.5
6.0
7.5
?
Ethinylestradiol
120
150
400
60–150
100
400
500–600
500–600
350
2.9–5.0
Diethylstilbestrol
?
?
?
2.9–3.4
?
?
26–28
25–37
20
5.7–7.5
Sources and footnotes
Notes: Values are ratios, with estradiol as standard (i.e., 1.0).
Abbreviations: HF = Clinical relief of
hot flashes .
VE = Increased
proliferation of
vaginal epithelium .
UCa = Decrease in
UCa .
FSH = Suppression of
FSH levels.
LH = Suppression of
LH levels.
HDL -
C ,
SHBG ,
CBG , and
AGT = Increase in the serum levels of these
liver proteins . Liver = Ratio of liver estrogenic effects to general/systemic estrogenic effects (hot flashes/
gonadotropins ).
Sources: See template.
Pharmacokinetics [ ]
See also: Pharmacokinetics of estradiol
Estropipate is hydrolyzed into estrone in the body.[6] Estrone can then be transformed into estradiol by 17β-hydroxysteroid dehydrogenase .
Chemistry [ ]
History [ ]
Estropipate was introduced for medical use by Abbott in 1968.[7] It was approved by the FDA in the United States in 1991.[8]
Society and culture [ ]
Generic names [ ]
Estropipate is the generic name of the drug and its INN , USAN , and BAN .[2] [3] [9] [6] [10]
Brand names [ ]
Estropipate is or has been marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.[10] [2] [9] [6]
Availability [ ]
Estropipate appears to remain available only in the United States .[10] In the past, estropipate has also been marketed in Canada , the United Kingdom , Ireland , Switzerland , Australia , South Africa , Mexico , and Indonesia .[10] [9] [6]
References [ ]
^ a b c "Ogen, estropipate tablets, USP" (PDF) . Pharmacia & Upjohn Co . U.S. Food and Drug Administration. December 2004.
^ a b c d Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 900–. ISBN 978-1-4757-2085-3 .
^ a b c Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. pp. 114–. ISBN 978-94-011-4439-1 .
^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1484–. ISBN 978-0-8155-1856-3 .
^ DiPiro JT, Talbert RL, Yee GC, Matzke GR, Wells BG, Posey ML (23 January 2017). Pharmacotherapy: A Pathophysiologic Approach, Tenth Edition . McGraw-Hill Education. p. 1295. ISBN 978-1-259-58749-8 .
^ a b c d Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2101. ISBN 978-0-85369-840-1 .
^ Budoff PW (1 August 1983). No more hot flashes, and other good news . Putnam. p. 28 . ISBN 978-0-399-12793-9 .
^ P & T. CORE Medical Journals. July 1993.
^ a b c Index Nominum 2000: International Drug Directory . Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1 .
^ a b c d "Estropipate" . Drugs.com .
Estradiol
Topics
Estradiol (as a hormone)
Estradiol (as a medication)
Pharmacodynamics of estradiol
Pharmacokinetics of estradiol
Estrogen (as a hormone)
Estrogen (as a medication)
Menopausal hormone therapy
Feminizing hormone therapy
Estradiol-containing birth control pill
Combined injectable birth control
High-dose estrogen
Hydroxylation of estradiol
Esters Related
Estrogens
ER 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 #
Ethinylestradiol sulfonate
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
Promestriene
Quinestradol
Quinestrol
Progonadotropins
Antiandrogens (e.g., bicalutamide )
GnRH agonists (e.g., GnRH (gonadorelin) , leuprorelin )
Gonadotropins (e.g., FSH , LH )
Antiestrogens
ER antagonists (incl. SERMs /SERDs )
Exclusively antagonistic: Fulvestrant
Noncompetitive inhibitors: Trilostane
Aromatase inhibitors
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
# 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
ER
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
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
Estriol esters
Polyestriol phosphate
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestradiol 3-benzoate
Ethinylestradiol sulfonate
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 , , 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 , )
Mixed (SERMs ) Antagonists
Coregulator-binding modulators: ERX-11
Noncompetitive inhibitors: Trilostane
GPER
Agonists Antagonists Unknown
Diethylstilbestrol
Zearalenone
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens