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| Clinical data | |
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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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| Chemical and physical data | |
| Formula | C32H46O5 |
| Molar mass | 510.715 g·mol−1 |
| 3D model (JSmol) | |
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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
- ^ a b c d e f g De-Wei Z (1982). "Research activities in the field of oral contraceptives in the People's Republic of China". Acta Obstetricia et Gynecologica Scandinavica Supplement. 105: 51–60. doi:10.3109/00016348209155319. PMID 6952745. S2CID 44858028.
- ^ a b c d e f g Yang YC, Gu XG, Li SX (1982). Proteins and Steroids in Early Pregnancy. pp. 335–342. doi:10.1007/978-3-642-67890-5_22. ISBN 978-3-642-67892-9.
- ^ a b Chi-ming, L. (1983). New Long Acting Contraceptive Progestagen Studies on Synthesis of “Cymegesolate”[J]. Reproduction & Contraception, 4, 011.
- ^ a b Yang YQ, Li SX, Gu XG (August 1985). "[Effect of progestin no. 1 (cymegesolate) on menstrual cycles and plasma levels of progesterone in rhesus monkeys]". Sheng Li Xue Bao (in Chinese). 37 (4): 368–373. PMID 3837333.
- ^ a b Wu JZ, Yun XJ, Wu MZ, Shen HY, Wang AL (February 1983). "[Clinical study of a long-acting progestogen contraceptive 3-cyclopentyl propionate of megestrol acetate (progestin no. 1)]". Sheng Zhi Yu Bi Yun = Reproduction and Contraception (in Chinese). 3 (2): 36–38. PMID 12339176.
- ^ a b 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.
- ^ Sidel'nikova VM, Demidova EM, Borisova I, Dondukova TM, Absava GI, Korkhov VV (September 1990). "[The use of acetomepegrenol in the therapy of threatened abortion]". Akusherstvo I Ginekologiia (in Russian) (9): 37–40. PMID 2278305.
- ^ Grinenko GS, Popova EV, Korkhov VV, Lesik EA, Petrosyan MA, Topil'skaya NI (March 2000). "Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal. 34 (3): 113–114. doi:10.1007/BF02524577. ISSN 1573-9031. S2CID 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].
- ^ Mashkovskii MD (December 2000). "Eightieth Anniversary of the Drug Chemistry Center/All-Russian Pharmaceutical Chemistry Scientific Research Institute". Pharmaceutical Chemistry Journal. 34 (12): 677–680. doi:10.1023/A:1010416205068. ISSN 1573-9031. S2CID 24703856.
- ^ Sergeev PV, Rzheznikov VM, Korkhov VV, Grinenko GS, Semeikin AV, Mayatskaya EE, et al. (July 2005). "Investigation of the Gestagen Activity of 17α-acetoxy-3β-butanoyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal. 39 (7): 358–360. doi:10.1007/s11094-005-0154-4. ISSN 1573-9031. S2CID 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].
This page was last edited on 4 August 2023, at 22:08