Estrogen medication
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
Legal status
[(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
(verify)
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 .
[2]
[3]
[4]
[5] It is a
salt of
estrone sulfate and
piperazine , and is
transformed into
estrone and
estradiol in the body.
[3]
[4] It is taken
by mouth .
[2]
Medical uses
Estropipate is used to:
[2] [
additional citation(s) needed ]
Available forms
Estropipate was available in the form of 0.75, 1.5, 3, and 6 mg oral tablets and 1.5 mg/gram vaginal cream. Estropipate is no longer available in the United States.
Pharmacology
Pharmacodynamics
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 Tooltip Hot flashes
VE Tooltip Vaginal epithelium
UCa Tooltip Urinary calcium
FSH Tooltip Follicle-stimulating hormone
LH Tooltip Luteinizing hormone
HDL Tooltip High-density lipoprotein -
C Tooltip Cholesterol
SHBG Tooltip Sex hormone-binding globulin
CBG Tooltip Corticosteroid-binding globulin
AGT Tooltip Angiotensinogen
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 Tooltip urinary calcium .
FSH = Suppression of
FSH Tooltip follicle-stimulating hormone levels.
LH = Suppression of
LH Tooltip luteinizing hormone 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
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 Tooltip Food and Drug Administration in the
United States in 1991.
[8]
Society and culture
Generic names
Estropipate is the
generic name of the drug and its
INN Tooltip International Nonproprietary Name ,
USAN Tooltip United States Adopted Name , and
BAN Tooltip British Approved Name .
[3]
[4]
[9]
[6]
[10]
Brand names
Estropipate was marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.
[10]
[3]
[9]
[6]
Availability
Estropipate has been discontinued in the
United States . 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
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