Gestonorone caproate

Gestonorone caproate
Clinical data
Trade names Depostat, Primostat
Synonyms SH-582; SH-80582; NSC-84054; Gestonorone hexanoate; Gestronol hexanoate; Gestronol caproate; Norhydroxy-progesterone caproate; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione hexanoate; 17α-Hydroxy-19-norprogesterone hexanoate
Routes of
Intramuscular injection[1][2][3]
Drug class Progestin; Progestogen; Progestogen ester; Antigonadotropin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
CAS Number
PubChem CID
ECHA InfoCard 100.013.646
Chemical and physical data
Formula C26H38O4
Molar mass 414.578 g/mol
3D model (JSmol)

Gestonorone caproate, also known as gestronol hexanoate or norhydroxyprogesterone caproate and sold under the brand names Depostat and Primostat, is a progestin medication which is used in the treatment of enlarged prostate and endometrial cancer.[3][4][1][5] It is not effective by mouth and must be given by injection into muscle, typically once a week.[6]

Side effects of gestonorone caproate are similar to those of other progestins. Gestonorone caproate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[7][8] It has no other important hormonal activity.[9][10]

Gestonorone caproate was discovered in 1960 and was introduced for medical use by 1973.[11][12] It has been used widely throughout Europe, including in the United Kingdom, and has also been marketed in certain other countries such as Japan, China, and Mexico.[1][13][14][15] However, it has since mostly been discontinued, and it remains available today only in a handful of countries, including the Czech Republic, Japan, Mexico, and Russia.[15][16]

Medical uses

Gestonorone caproate is used in the treatment of benign prostatic hypertrophy and endometrial cancer.[3][17]

Side effects

Side effects of gestonorone caproate are similar to those of other progestins.



Gestonorone caproate is a strong, long-acting, and pure progestogen,[7][8] possessing no androgenic, anabolic, antiandrogenic, estrogenic, antiestrogenic, corticosteroid, or teratogenic effects.[9][10] In animals, it is approximately 25 times more potent than progesterone or hydroxyprogesterone caproate.[10] In humans, 100 or 200 mg intramuscular gestonorone caproate has been said to be equivalent to 1,000 mg intramuscular hydroxyprogesterone caproate.[18][19]

Like other potent progestins, gestonorone caproate possesses potent antigonadotropic activity and is capable of markedly suppressing the gonadal production and circulating levels of sex hormones such as testosterone and estradiol.[10][20][21] A clinical study found that 400 mg/week intramuscular gestonorone caproate suppressed testosterone levels by 75% in men, while orchiectomy as a comparator reduced testosterone levels by 91%.[22][23] Levels of luteinizing hormone, conversely, remained unchanged.[22]


Like the closely related progestins hydroxyprogesterone caproate and 19-norprogesterone, gestonorone caproate shows poor activity orally and must be administered parenterally; specifically, via intramuscular injection.[6] Gestonorone caproate is administered once weekly by intramuscular injection, via which it acts as a depot.[24][25][26]


Gestonorone caproate, also known as norhydroxyprogesterone caproate, 17α-hydroxy-19-norprogesterone 17α-hexanoate, or 17α-hydroxy-19-norpregn-4-ene-3,20-dione 17α-hexanoate, is a synthetic norpregnane steroid and a derivative of progesterone.[27][13] It is specifically a combined derivative of 17α-hydroxyprogesterone and 19-norprogesterone, or of gestronol (17α-hydroxy-19-norprogesterone), with a hexanoate (caproate) ester at the C17α position.[27][13] Analogues and derivatives of gestonorone caproate include algestone acetophenide (dihydroxyprogesterone acetophenide), demegestone, hydroxyprogesterone caproate, nomegestrol acetate, norgestomet, and segesterone acetate (nestorone, elcometrine), as well as 18-methylsegesterone acetate.[27][13]


Gestonorone caproate was first described in 1960.[11] It was developed by Schering and has been marketed since at least 1973.[12]

Society and culture

Generic names

Gestonorone caproate is the generic name of the drug and its INN, USAN, and JAN, while gestronol hexanoate is its BANM.[27][13] It has also been referred to as norhydroxyprogesterone caproate.[14]

Brand names

Gestonorone caproate has been marketed exclusively under the brand names Depostat and Primostat.[27][13][14][15][16]


Gestonorone caproate has been available widely in Europe, including in the United Kingdom, and has also been marketed in Japan, China, Mexico, and certain other countries.[1][13][14][15] However, it has been discontinued in most countries and its availability is more limited today; it appears to remain marketed only in the Czech Republic, Japan, Mexico, and Russia.[15][16][28] It has not been marketed in the United States, Canada, and many other countries.[13][14][15][16]


SH-834 was a combination of 90 mg estradiol valerate and 300 mg gestonorone caproate for weekly intramuscular injection that was developed by Schering in the 1970s.[29][30] It was investigated clinically as a treatment for breast cancer and was found to be effective, but does not seem to have been marketed.[29][31][32]


  1. 1 2 3 4 Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 338–. ISBN 978-3-7692-2114-5.
  2. Jeffrey K. Aronson (21 February 2009). Meyler's Side Effects of Endocrine and Metabolic Drugs. Elsevier. pp. 289–. ISBN 978-0-08-093292-7.
  3. 1 2 3 I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 132–. ISBN 978-94-011-4439-1.
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  6. 1 2 Breuer H, Lisboa BP (1966). "[Studies on the metabolism of 17-alpha-hydroxy-19-norprogesterone caproate by humans in vivo and of 17-alpha-hydroxy-19-norprogesterone by rats in vitro]". Acta Endocrinologica (in German). 51 (1): 114–30. PMID 4285463.
  7. 1 2 G. Raspé (22 October 2013). Hormones and Embryonic Development: Advances in The Biosciences. Elsevier Science. p. 79. ISBN 978-1-4831-5171-7.
  8. 1 2 Schoonees, R.; De Klerk, J. N.; Murphy, G. P. (1969). "The effect of depostat (SH 582) on the baboon prostate". Journal of Surgical Oncology. 1 (4): 317–324. doi:10.1002/jso.2930010404. ISSN 0022-4790.
  9. 1 2 Schering A.G., Berlin (1968). Depostat (SH 582) a new treatment for prostatic hypertrophy.
  10. 1 2 3 4 Aubrey, D. A.; Khosla, T. (1971). "The effect of 17-alpha-hydroxy-19-norprogesterone caproate (SH 582) on benign prostatic hypertrophy". British Journal of Surgery. 58 (9): 648–652. doi:10.1002/bjs.1800580904. ISSN 0007-1323.
  11. 1 2 Kaiser, R. (1960). Klinische Erfahrungen mit Norprogesteronderivaten. Zbl. Gynäk, 82, 2009.
  12. 1 2 Subbiah, N.; Mortensen, James (1973). "The Treatment of Benign Enlargement of the Prostate with Nor Progesterone Caproate (Primostat)". ANZ Journal of Surgery. 42 (3): 304–307. doi:10.1111/j.1445-2197.1973.tb06805.x. ISSN 1445-1433.
  13. 1 2 3 4 5 6 7 8 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 488. ISBN 978-3-88763-075-1.
  14. 1 2 3 4 5
  15. 1 2 3 4 5 6
  16. 1 2 3 4 Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2105. ISBN 978-0-85369-840-1.
  17. H. John Smith; Hywel Williams (10 October 2005). Smith and Williams' Introduction to the Principles of Drug Design and Action, Fourth Edition. CRC Press. pp. 493–. ISBN 978-0-203-30415-0.
  18. Karlstedt K (1971). "Progesterone treatment for local recurrence and metastases in carcinoma corporis uteri". Acta Radiologica: Therapy, Physics, Biology. 10 (2): 187–92. doi:10.3109/02841867109129755. PMID 5556820. The preparations used were Proluton Depot (17a-hydroxy-progesterone caproate) and in 3 patients SH 5132 (17a-hydroxy-19-norprogesterone caproate); 100 mg of the latter corresponds to 1000 mg of Proluton Depot.
  19. Moe N (1972). "Short-term progestogen treatment of endometrial carcinoma. Histological, histochemical and hormonal studies". Acta Obstet Gynecol Scand. 51 (1): 55–62. doi:10.3109/00016347209154968. PMID 4261828. Thirteen patients with primary adenocarcinoma of the uterine corpus were treated for 21 days with l7alphahydroxy-progesterone-caproate (Primolut Depot@, Schering), 1000 mg daily, or 17alpha-hydroxy-19-nor-progesterone-caproate (DepostatB, Schering), 200 mg daily. These doses can be considered as equivalent.
  20. G. Raspé; W. Brosig (22 October 2013). International Symposium on the Treatment of Carcinoma of the Prostate, Berlin, November 13 to 15, 1969: Life Science Monographs. Elsevier. p. 169. ISBN 978-1-4831-8711-2.
  21. Makrigiannis, D.; Gaca, A. (1971). "Evaluation of Depostat R in prostatic adenoma on the ground of clinical and sphincterotonometric studies". International Urology and Nephrology. 3 (1): 21–29. doi:10.1007/BF02081794. ISSN 0301-1623.
  22. 1 2 Sander S, Nissen-Meyer R, Aakvaag A (1978). "On gestagen treatment of advanced prostatic carcinoma". Scand. J. Urol. Nephrol. 12 (2): 119–21. doi:10.3109/00365597809179977. PMID 694436.
  23. Kjeld JM, Puah CM, Kaufman B, Loizou S, Vlotides J, Gwee HM, Kahn F, Sood R, Joplin GF (1979). "Effects of norgestrel and ethinyloestradiol ingestion on serum levels of sex hormones and gonadotrophins in men". Clinical Endocrinology. 11 (5): 497–504. doi:10.1111/j.1365-2265.1979.tb03102.x. PMID 519881. Another synthetic gestogen, 17-hydroxy-19-norprogesterone caproate (Depostat-Schering), 400 mg by i.m. weekly injections suppressed T levels to 25% of pretreatment values (Sander er al., 1978).
  24. Louis Denis (6 December 2012). The Medical Management of Prostate Cancer. Springer Science & Business Media. pp. 112–. ISBN 978-3-642-73238-6. Gestonorone caproate, another progestational agent, was investigated at our institution. Eighteen patients with painful metastatic [prostate cancer] with objective relapse after orchiectomy were treated with 400 mg/week i.m.
  25. Benno Clemens Runnebaum; T. Rabe; L. Kiesel (6 December 2012). Future Aspects in Contraception: Proceeding of an International Symposium held in Heidelberg, 5–8 September 1984 Part 1 Male Contraception. Springer Science & Business Media. pp. 133–. ISBN 978-94-009-4910-2. Gestonorone [caproate] 100 or 200 mg/week i.m.
  26. Palanca, Ernesto; Juco, Wilfrido (2008). "Conservative treatment of benign prostatic hyperplasia". Current Medical Research and Opinion. 4 (7): 513–520. doi:10.1185/03007997709109342. ISSN 0300-7995. A study was carried out in 30 male patients with benign prostate hyperplasia to assess the effectiveness of treatment with a progestational agent, gestonorone caproate (200 mg), given intramuscularly every 7 days over a period of 2 to 3 months.
  27. 1 2 3 4 5 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 595–. ISBN 978-1-4757-2085-3.
  29. 1 2 Notter, G.; Berndt, G. (2009). "Hormonal Treatment of Mammary Carcinoma with Progynon-Depot and Depostat". Acta Radiologica: Therapy, Physics, Biology. 14 (5): 433–442. doi:10.3109/02841867509132684. ISSN 0567-8064.
  30. Ward, H. W. C. (1972). "PROGESTOGEN THERAPY FOR OVARIAN CARCINOMA". BJOG: An International Journal of Obstetrics and Gynaecology. 79 (6): 555–559. doi:10.1111/j.1471-0528.1972.tb14200.x. ISSN 1470-0328.
  31. Berndt, G.; Stender, H.-St. (2009). "[The combined estrogen-gestagen treatment of metastasizing mammary carcinoma using with SH 834]". 95 (48): 2399–2404. doi:10.1055/s-0028-1108843. ISSN 0012-0472.

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