Estropipate

"Ogen" redirects here. For the character in the Japanese anime, see Ogen (Basilisk). For the melon cultivar, see Galia melon.

Estropipate

Clinical data
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	None
Legal status
Legal status	US: WARNING[1]
Identifiers
IUPAC name [(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	7280-37-7^Y
PubChem CID	5284555
DrugBank	DB04574^Y
ChemSpider	4447610^Y
UNII	SVI38UY019
KEGG	D00948^Y
ChEBI	CHEBI:4873^Y
ChEMBL	ChEMBL1200980^Y
CompTox Dashboard (EPA)	DTXSID3023005
ECHA InfoCard	100.027.906
Chemical and physical data
Formula	C22H32N2O5S
Molar mass	436.57 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=S(=O)(O)Oc1cc4c(cc1)[C@@H]3[C@H]([C@@H]2CCC(=O)[C@@]2(C)CC3)CC4.N1CCNCC1
InChI 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
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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]}

• 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

• v
• t
• e

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/day^b	50 μg/day^b	100 μg/day^b
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
IMTooltip Intramuscular 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 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

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.

• v
• t
• e

Relative oral potencies of estrogens

Estrogen	HFTooltip Hot flashes	VETooltip Vaginal epithelium	UCaTooltip Urinary calcium	FSHTooltip Follicle-stimulating hormone	LHTooltip Luteinizing hormone	HDLTooltip High-density lipoprotein-CTooltip Cholesterol	SHBGTooltip Sex hormone-binding globulin	CBGTooltip Corticosteroid-binding globulin	AGTTooltip 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 UCaTooltip urinary calcium. FSH = Suppression of FSHTooltip follicle-stimulating hormone levels. LH = Suppression of LHTooltip 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

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

See also: Estrogen ester and List of estrogen esters

History

Estropipate was introduced for medical use by Abbott in 1968.^[7] It was approved by the FDATooltip 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 INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, and BANTooltip 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

1. "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
2. "Ogen, estropipate tablets, USP" (PDF). Pharmacia & Upjohn Co. U.S. Food and Drug Administration. December 2004.
3. 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.
4. 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.
5. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1484–. ISBN 978-0-8155-1856-3.
6. 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.
7. Budoff PW (1 August 1983). No more hot flashes, and other good news. Putnam. p. 28. ISBN 978-0-399-12793-9.
8. P & T. CORE Medical Journals. July 1993.
9. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1.
10. "Estropipate". Drugs.com.