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]
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 |
|
Legal status | |
Legal status | |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.027.906 |
Chemical and physical data | |
Formula | C22H32N2O5S |
Molar mass | 436.57 g·mol−1 |
3D model (JSmol) | |
| |
| |
(verify) |
Medical uses edit
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
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 | ||||
Ethinylestradiola | 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 edit
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 edit
Pharmacodynamics edit
Estropipate is a prodrug of estrone and estradiol. Hence, it is an estrogen, or an agonist of the estrogen receptors.
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 edit
Estropipate is hydrolyzed into estrone in the body.[6] Estrone can then be transformed into estradiol by 17β-hydroxysteroid dehydrogenase.
Chemistry edit
History edit
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 edit
Generic names edit
Estropipate is the generic name of the drug and its INN , USAN , and BAN .[3][4][9][6][10]
Brand names edit
Estropipate was marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.[10][3][9][6]
Availability edit
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 edit
- ^ "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.
- ^ 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.
- ^ 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 "Estropipate". Drugs.com.