Pentarane A

Pentarane A, also known as D'6-pentarane or pregna-D'6-pentarane, as well as 16α,17α-cyclohexanoprogesterone, 16α,17α-tetramethylenepregn-4-ene-3,20-dione, or 17α-acetyl-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 was never marketed.[1][2] The 6α-methylated analogue of pentarane A is known as mecigestone or as pentarane B.[2]

Pentarane A

Clinical data
Other names	D'6-Pentarane; Pregna-D'6-pentarane; 16α,17α-Cyclohexanoprogesterone; 16α,17α-Tetramethylenepregn-4-ene-3,20-dione; 17α-Acetyl-16β,24-cyclo-21-norchol-4-en-3-one
Identifiers
IUPAC name (4aR,4bS,6aS,6bS,10aR,11aS,11bR)-6b-Acetyl-4a,6a-dimethyl-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	38522-51-9
PubChem CID	189105
ChemSpider	164309
CompTox Dashboard (EPA)	DTXSID20959389
Chemical and physical data
Formula	C25H36O2
Molar mass	368.561 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@@]12CCCC[C@@H]1C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CCC5=CC(=O)CC[C@]45C)C
InChI InChI=1S/C25H36O2/c1-16(26)25-11-5-4-6-18(25)15-22-20-8-7-17-14-19(27)9-12-23(17,2)21(20)10-13-24(22,25)3/h14,18,20-22H,4-13,15H2,1-3H3/t18-,20-,21+,22+,23+,24+,25+/m1/s1 Key:QRVBGQLTPQQFJY-IEHCJHDVSA-N

See also

• Acetomepregenol

References

1. 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.
2. 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.