Chemistry:Cymegesolate
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| Other names | Cypionyl megestrol acetate; Megestrol acetate 3β-cypionate; Megestrol acetate 3β-cyclopentylpropionate; Progestin No. 1; Progestin I; Progestagen I; 17α-Acetoxy-6-dehydro-6-methylprogesterone 3β-cypionate; 17α-Acetoxy-6-methylpregna-4,6-diene-3,20-dione 3β-cypionate |
| Routes of administration | By mouth[1][2] |
| Drug class | Progestin; Progestogen; Progestogen ester |
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| Formula | C32H46O5 |
| Molar mass | 510.715 g·mol−1 |
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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.[1][2][3][4][5][6] 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.[1][2] 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."[1] 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.[2]
Chemistry
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.[1][2] It is the C3β cypionate (cyclopentylpropionate) ester of megestrol acetate.[1][2] 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]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "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. doi:10.3109/00016348209155319. PMID 6952745.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 Proteins and Steroids in Early Pregnancy. 1982. pp. 335–342. doi:10.1007/978-3-642-67890-5_22. ISBN 978-3-642-67892-9.
- ↑ 3.0 3.1 Chi-ming, L. (1983). New Long Acting Contraceptive Progestagen Studies on Synthesis of “Cymegesolate”[J]. Reproduction & Contraception, 4, 011.
- ↑ 4.0 4.1 "[Effect of progestin no. 1 (cymegesolate) on menstrual cycles and plasma levels of progesterone in rhesus monkeys]" (in zh). Sheng Li Xue Bao 37 (4): 368–373. August 1985. PMID 3837333.
- ↑ 5.0 5.1 "[Clinical study of a long-acting progestogen contraceptive 3-cyclopentyl propionate of megestrol acetate (progestin no. 1)]" (in Chinese). Sheng Zhi Yu Bi Yun = Reproduction and Contraception 3 (2): 36–38. February 1983. PMID 12339176.
- ↑ 6.0 6.1 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.
- ↑ "[The use of acetomepegrenol in the therapy of threatened abortion]" (in ru). Akusherstvo I Ginekologiia (9): 37–40. September 1990. PMID 2278305.
- ↑ "Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal 34 (3): 113–114. March 2000. doi:10.1007/BF02524577. ISSN 1573-9031. "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].".
- ↑ "Eightieth Anniversary of the Drug Chemistry Center/All-Russian Pharmaceutical Chemistry Scientific Research Institute". Pharmaceutical Chemistry Journal 34 (12): 677–680. December 2000. doi:10.1023/A:1010416205068. ISSN 1573-9031.
- ↑ "Investigation of the Gestagen Activity of 17α-acetoxy-3β-butanoyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal 39 (7): 358–360. July 2005. doi:10.1007/s11094-005-0154-4. ISSN 1573-9031. "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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