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Mecigestone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Mecigestone
Clinical data
Other namesPentarane B; 6α-Methyl-16α,17α-cyclohexanoprogesterone
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC26H38O2
Molar mass382.588 g·mol−1
3D model (JSmol)
  • 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=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

Mecigestone, also known aspentarane B, as well as6α-methyl-16α,17α-cyclohexanoprogesterone,6α-methylcyclohexano[1',2';16,17]pregn-4-ene-3,20-dione, or17α-acetyl-6α-methyl-16β,24-cyclo-21-norchol-4-en-3-one, is asteroidalprogestin that was developed by the Zelinskii Institute of Organic Chemistry of theRussian Academy of Sciences and has been proposed for clinical use as aprogestogen but has not been marketed.[1][2][3][4][5] It is the 6α-methylatedanalogue ofpentarane A, which is also known as D'6-pentarane or pregna-D'6-pentarane.[5]

See also

[edit]

References

[edit]
  1. ^Elks J (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 IV, Skvortsov VS, Romero Reyes IV, Levina IS (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 (January 1982). "Pregna-D'-pentaranes - a new class of active gestagenes".Journal of Steroid Biochemistry.16 (1):61–67.doi:10.1016/0022-4731(82)90144-3.PMID 7062740.
  4. ^Nazarov AK, Zavarzin IV, Nazarov GV, Aksenov AV, Levina IS (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. ^abBhakta A, Herman M, Levina IS, Moudgil VK (August 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.PMID 8283970.S2CID 20319611.
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists

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