Butagest

Butagest
Clinical data
Other namesButerol; 17α-Acetoxy-3β-butanoyloxy-6-methyl-pregna-4,6-dien-20-one; 17α-Acetoxy-6-methyl-20-oxopregna-4,6-dien-3β-yl butyrate; 6-Methyl-17α-hydroxy-δ6-progesterone 3β-butanoate 17α-acetate
Drug classProgestogen; Progestogen ester
Identifiers
  • [(3S,8R,9S,10R,13S,14S,17R)-17-Acetyl-17-acetyloxy-6,10,13-trimethyl-1,2,3,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-yl] butanoate
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H40O5
Molar mass456.623 g·mol−1
3D model (JSmol)
  • CCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3C=C(C2=C1)C)CC[C@@]4(C(=O)C)OC(=O)C)C)C
  • InChI=1S/C28H40O5/c1-7-8-25(31)32-20-9-12-26(5)22-10-13-27(6)23(21(22)15-17(2)24(26)16-20)11-14-28(27,18(3)29)33-19(4)30/h15-16,20-23H,7-14H2,1-6H3/t20-,21+,22-,23-,26+,27-,28-/m0/s1
  • Key:VWKIFEBMJRFARL-NAEKRLSBSA-N

Butagest, also known as buterol, is a modification of megestrol acetate in which the C-3 ketone has been replaced by a C3β butanoyloxy moeity. It is chemically known as 3β-hydroxy-6-methyl-17α-hydroxypregna-4,6-dien-20-one 3β-butanoate 17α-acetate or 6-methyl-17α-hydroxy-δ6-progesterone 3β-butanoate 17α-acetate and is a steroidal progestin which was developed in Russia for potential clinical use as a progesterone supplement primarily for hormone replacement therapy but it was never marketed for reasons which are still unclear.

Pharmacology

Butagest is a synthetic progestin that mimics the physiological actions of natural progesterone. It is used in various therapeutic contexts, including hormone replacement therapy, fertility treatments, and menstrual irregularities.

Mechanism of action

Butagest acts as an agonist at progesterone receptors in various tissues. Its primary actions include:

By stabilizing the endometrium, it prevents abnormal uterine bleeding and aids in maintaining hormonal balance during assisted reproductive therapies.

Pharmacokinetics

Adverse effects

The use of butagest, which contains progesterone, is associated with several adverse effects. These vary depending on the dose, route of administration, and individual susceptibility.

Common adverse effects

Gastrointestinal

Neurological

Breasts

Mood and behavioral

Skin

Reproductive

Serious adverse effects

These effects require immediate medical attention:

Cardiovascular

Hepatic

Endocrine and metabolic

Neurological

Allergic reactions

Cancer risks

Precautions

Butagest should be used cautiously in patients with a history of:

Regular monitoring is recommended for those with:

Toxicology

The toxicology of progesterone, the active ingredient in butagest, has been studied extensively. Below are key findings:

Acute toxicity

Progesterone exhibits low acute toxicity. Overdose typically results in mild symptoms such as nausea and dizziness, without life-threatening effects.

Chronic toxicity

Long-term high-dose use may increase the risk of thromboembolic disorders, cardiovascular diseases, and hormone-sensitive cancers such as breast cancer.

Carcinogenicity

Progesterone is classified by the International Agency for Research on Cancer (IARC) as possibly carcinogenic to humans (Group 2B).

Environmental toxicity

Improper disposal of progesterone can disrupt aquatic ecosystems, as it is an endocrine-disrupting compound.

See also

References

  1. ↑ Fedotcheva TA, Kruglov AG, Teplova VV, Fedotcheva NI, Rzheznikov VM, Shimanovskiĭ NL (2012). "[Effect of steroid hormones on production of reactive oxygen species in mitochondria]". Biofizika. 57 (6): 1014–9. PMID 23272582.
  2. ↑ Sergeev PV, Semeĭkin AV, Smirnova ZS, et al. (2004). "[Antitumor activity of the new gestagen 17alpha-acetoxy-3beta-butanoyloxy-6-methyl-pregna-4,6-dien-20-one]". Eksp Klin Farmakol. 67 (4): 54–6. PMID 15500049.
  3. ↑ Tapil'skaia NI, Petrosian MA, Lesik EA (2002). "[Therapeutic efficacy of novel 17alpha-hydroxyprogesterone derivatives in experimental preterm labor]". Eksp Klin Farmakol. 65 (1): 44–5. PMID 12025785.
  4. ↑ Fedotcheva, T. A., Semeykin, A. V., Schimanowsky, N. L., & Rzheznikov, V. M. (2004, July). New progestin butagest is a perspective antiproliferative agent and chemosensitizer. In FUNDAMENTAL & CLINICAL PHARMACOLOGY (Vol. 18, pp. 84-84). 111 RIVER ST, HOBOKEN 07030-5774, NJ USA: WILEY-BLACKWELL.
  5. ↑ Korkhov VV, Lesik EA, Petrosian MA (2005). "[Gestagenic and contraceptive activity of new synthetic progesterone analogs in experimental animals]". Eksp Klin Farmakol. 68 (1): 39–41. PMID 15786963.
  6. ↑ Kareva EN, Grinenko GS, Gasparian ND, Ovchinnikova EV, Gorenkova OS (2006). "[Influence of the structure of synthetic gestagens on their binding to progesteron receptors in the endometrium]". Eksp Klin Farmakol. 69 (4): 36–8. PMID 16995436.
  7. 1 2 "Progesterone and Cancer Risk". IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. 72: 563–590. 1999. Retrieved 2024-11-30.
  8. ↑ "Progesterone: Hazardous Substances Data Bank (HSDB)". National Center for Biotechnology Information (NCBI). Retrieved 2024-11-30.
  9. ↑ IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Volume 72. Lyon, France: International Agency for Research on Cancer. 1999. ISBN 978-92-832-1272-0.
  10. ↑ "Environmental Impact of Hormonal Pharmaceuticals". Journal of Environmental Toxicology. 45 (3): 275–282. 2020. doi:10.1016/j.envtox.2020.01.015 (inactive 16 July 2026).{{cite journal}}: CS1 maint: DOI inactive as of July 2026 (link)

Further reading