Mecigestone

Mecigestone, also known as pentarane B, as well as 6α-methyl-16α,17α-cyclohexanoprogesterone, 6α-methylcyclohexano[1',2';16,17]pregn-4-ene-3,20-dione, or 17α-acetyl-6α-methyl-16β,24-cyclo-21-norchol-4-en-3-one, is a steroidal progestin that was developed by the Zelinskii Institute of Organic Chemistry of the Russian Academy of Sciences and has been proposed for clinical use as a progestogen but has not been marketed.[1][2][3][4][5] It is the 6α-methylated analogue of pentarane A, which is also known as D'6-pentarane or pregna-D'6-pentarane.[5]

Mecigestone
Clinical data
Other namesPentarane B; 6α-Methyl-16α,17α-cyclohexanoprogesterone
Identifiers
IUPAC name
  • (4aR,4bS,6aS,6bS,10aR,11aS,11bR,13S)-6b-Acetyl-4a,6a,13-trimethyl-4,4b,5,6,7,8,9,10,10a,11,11a,11b,12,13-tetradecahydro-3H-indeno[2,1-a]phenanthren-2-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H38O2
Molar mass382.588 g·mol−1
3D model (JSmol)
SMILES
  • C[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2C[C@@H]4[C@]3(CCCC4)C(=O)C)C)[C@@]5(C1=CC(=O)CC5)C
InChI
  • InChI=1S/C26H38O2/c1-16-13-20-21(24(3)11-8-19(28)15-22(16)24)9-12-25(4)23(20)14-18-7-5-6-10-26(18,25)17(2)27/h15-16,18,20-21,23H,5-14H2,1-4H3/t16-,18+,20+,21-,23-,24+,25-,26-/m0/s1
  • Key:OAICPORQJIVREU-SGCXAXHESA-N

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 8–. ISBN 978-1-4757-2085-3.
  2. Fedyushkina, I. V.; Skvortsov, V. S.; Romero Reyes, I. V.; Levina, I. S. (2014). "Molecular docking and 3D-QSAR of 16α,17α-cycloalkanoprogesterone derivatives as ligands of the progesterone receptor". Biochemistry (Moscow) Supplement Series B. 8 (2): 168–176. doi:10.1134/S1990750814020048. ISSN 1990-7508. S2CID 96191380.
  3. Kamernitzky AV, Levina IS, Kulikova LE, Ignatov VN, Korkhov VV, Nikitina GV, Terekhina AI (1982). "Pregna-D'-pentaranes - a new class of active gestagenes". J. Steroid Biochem. 16 (1): 61–7. doi:10.1016/0022-4731(82)90144-3. PMID 7062740.
  4. Nazarov, A. K.; Zavarzin, I. V.; Nazarov, G. V.; Aksenov, A. V.; Levina, I. S. (2016). "Preparation and Bioavailability Evaluation of Micronized Steroidal Mecigestone Drug Substance". Pharmaceutical Chemistry Journal. 49 (10): 706–710. doi:10.1007/s11094-016-1357-6. ISSN 0091-150X. S2CID 6216213.
  5. Bhakta, Amrita; Herman, Michelle; Levina, Inna S.; Moudgil, V. K. (1993). "Interaction of cycloalkanoprogesterones with mammalian progesterone receptor: binding of pregna-D'-pentaranes in the calf uterine cytosol". Molecular and Cellular Biochemistry. 125 (2): 153–161. doi:10.1007/BF00936444. ISSN 0300-8177. PMID 8283970. S2CID 20319611.



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