Mecigestone

Mecigestone
Clinical data
Other names	Pentarane 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	58212-84-3;
PubChem CID	124372;
ChemSpider	110790;
CompTox Dashboard (EPA)	DTXSID30973778 ;
Chemical and physical data
Formula	C26H38O2
Molar mass	382.588 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

^ 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.
^ 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.
^ 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.
^ 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.
^ ^a ^b Bhakta 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.

[Elks2014-1] 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.

[FedyushkinaSkvortsov2014-2] 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.

[pmid7062740-3] 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.

[NazarovZavarzin2016-4] 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.

[BhaktaHerman1993-5] Bhakta 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.

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