Mecigestone

{{Short description|Chemical compound}}

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| 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

| image = Mecigestone.svg

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| CAS_number = 58212-84-3

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| PubChem = 124372

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| ChemSpiderID = 110790

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| UNII = N3UWJ2K7NF

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| C=26 | H=38 | O=2

| 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

| StdInChI_Ref =

| StdInChI = 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

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| StdInChIKey = OAICPORQJIVREU-SGCXAXHESA-N

| synonyms = Pentarane B; 6α-Methyl-16α,17α-cyclohexanoprogesterone

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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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA8|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=8–}}{{cite journal| vauthors = Fedyushkina IV, Skvortsov VS, Romero Reyes IV, Levina IS |title=Molecular docking and 3D-QSAR of 16α,17α-cycloalkanoprogesterone derivatives as ligands of the progesterone receptor|journal=Biochemistry (Moscow) Supplement Series B|volume=8|issue=2|year=2014|pages=168–176|issn=1990-7508|doi=10.1134/S1990750814020048|s2cid=96191380}}{{cite journal | vauthors = Kamernitzky AV, Levina IS, Kulikova LE, Ignatov VN, Korkhov VV, Nikitina GV, Terekhina AI | title = Pregna-D'-pentaranes - a new class of active gestagenes | journal = Journal of Steroid Biochemistry | volume = 16 | issue = 1 | pages = 61–67 | date = January 1982 | pmid = 7062740 | doi = 10.1016/0022-4731(82)90144-3 }}{{cite journal| vauthors = Nazarov AK, Zavarzin IV, Nazarov GV, Aksenov AV, Levina IS |title=Preparation and Bioavailability Evaluation of Micronized Steroidal Mecigestone Drug Substance|journal=Pharmaceutical Chemistry Journal|volume=49|issue=10|year=2016|pages=706–710|issn=0091-150X|doi=10.1007/s11094-016-1357-6|s2cid=6216213}}{{cite journal | vauthors = Bhakta A, Herman M, Levina IS, Moudgil VK | title = Interaction of cycloalkanoprogesterones with mammalian progesterone receptor: binding of pregna-D'-pentaranes in the calf uterine cytosol | journal = Molecular and Cellular Biochemistry | volume = 125 | issue = 2 | pages = 153–161 | date = August 1993 | pmid = 8283970 | doi = 10.1007/BF00936444 | s2cid = 20319611 }} It is the 6α-methylated analogue of pentarane A, which is also known as D'6-pentarane or pregna-D'6-pentarane.