Cymegesolate Explained

Cymegesolate (developmental code name Progestin No. 1), also known as cypionyl megestrol acetate or as megestrol acetate 3β-cypionate, is a progestin medication which was never marketed.[1] [2] [3] [4] [5] [6] It was developed in China in the late 1970s and early to mid 1980s for use as a hormonal contraceptive. The medication was formulated at a dose of 50–100 mg in combination with a "trace" dose of 0.25–0.5 mg quinestrol as a long-lasting, once-a-month combined oral contraceptive pill. This combination has been studied in 1,213 women across a total of 9,651 menstrual cycles, with contraceptive effectiveness of over 99.13% and "very few side effects." At the high dose (100 mg / 0.5 mg), it showed an anovulation rate of only about 60%, and instead mediated its contraceptive effects via a marked anti-implantation effect.

Chemistry

See also: Progestogen ester and List of progestogen esters.

Cymegesolate, also known as megestrol acetate 3β-cypionate, as well as 17α-acetoxy-6-dehydro-6-methylprogesterone 3β-cyclopentylpropionate or 17α-acetoxy-6-methylpregna-4,6-diene-3,20-dione 3β-cyclopentylpropionate, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone. It is the C3β cypionate (cyclopentylpropionate) ester of megestrol acetate. A closely related medication is acetomepregenol (mepregenol diacetate; also known as megestrol 3β,17α-diacetate), which, in contrast, has been marketed.[7] [8] [9] [10]

Notes and References

  1. De-Wei Z . Research activities in the field of oral contraceptives in the People's Republic of China . Acta Obstetricia et Gynecologica Scandinavica Supplement . 105 . 51–60 . 1982 . 6952745 . 10.3109/00016348209155319 . 44858028 .
  2. Book: Yang YC, Gu XG, Li SX . Proteins and Steroids in Early Pregnancy. 1982. 335–342. 10.1007/978-3-642-67890-5_22. 978-3-642-67892-9.
  3. Chi-ming, L. (1983). New Long Acting Contraceptive Progestagen Studies on Synthesis of “Cymegesolate”[J]. Reproduction & Contraception, 4, 011.
  4. Yang YQ, Li SX, Gu XG . [Effect of progestin no. 1 (cymegesolate) on menstrual cycles and plasma levels of progesterone in rhesus monkeys] . zh . Sheng Li Xue Bao . 37 . 4 . 368–373 . August 1985 . 3837333 .
  5. Wu JZ, Yun XJ, Wu MZ, Shen HY, Wang AL . [Clinical study of a long-acting progestogen contraceptive 3-cyclopentyl propionate of megestrol acetate (progestin no. 1)] . Chinese . Sheng Zhi Yu Bi Yun = Reproduction and Contraception . 3 . 2 . 36–38 . February 1983 . 12339176 .
  6. Xue-jing, W. J. Z. Y., & Mo-zhen, W. (1983). Clinical Study of a Long-Acting Progestogen Contraceptive 3-Cyclopentyl Propionate of Megestrol Acetate (Progestin No. 1)[J]. Reproduction & Contraception, 2, 009.
  7. Sidel'nikova VM, Demidova EM, Borisova I, Dondukova TM, Absava GI, Korkhov VV . [The use of acetomepegrenol in the therapy of threatened abortion] . ru . Akusherstvo I Ginekologiia . 9 . 37–40 . September 1990 . 2278305 .
  8. Grinenko GS, Popova EV, Korkhov VV, Lesik EA, Petrosyan MA, Topil'skaya NI . Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one. Pharmaceutical Chemistry Journal. 1573-9031. 113–114. 34. 3. March 2000. 10.1007/BF02524577 . 44235508. Note that 3,17-diacetoxy-6-methylpregna-4,6-dien-20-one (1b), a structural analog of compound 1a, is certified in Russia under the trade name acetomepregnol and recommended for therapeutic purposes in gynecological practice and as a contraceptive preparation in combination with estrogens [4]..
  9. Mashkovskii MD . Eightieth Anniversary of the Drug Chemistry Center/All-Russian Pharmaceutical Chemistry Scientific Research Institute. Pharmaceutical Chemistry Journal. 1573-9031. 677–680. 34. 12. 10.1023/A:1010416205068. December 2000. 24703856.
  10. Sergeev PV, Rzheznikov VM, Korkhov VV, Grinenko GS, Semeikin AV, Mayatskaya EE, Samoilikov RV . 6 . Investigation of the Gestagen Activity of 17α-acetoxy-3β-butanoyloxy-6-methylpregna-4,6-dien-20-one. Pharmaceutical Chemistry Journal. 1573-9031. 358–360. 39. 7. 10.1007/s11094-005-0154-4 . July 2005. 35450212. Gestagens are widely used in medicine as drugs for the treatment of breast and uterine tumors, endometriosis, uterine bleeding, and premenstrual syndrome, as a means of hormonal therapy and maintenance of pregnancy, and as contraceptives [1, 2]. In clinics, drugs of this group are represented by acetomepregenol (AMP), medroxyprogesterone acetate (MPA), levonorgestrel, progesterone, didrogesterone, etc. [1]..

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