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Riligustilide
Names
IUPAC name
(3S ,3′Z ,5′aR ,6′S ,7′aS )-3′-Butylidene-6′-propylspiro[4,5-dihydro-2-benzofuran-3,7′-5,5a,6,7a-tetrahydro-4H -cyclobuta[g ][2]benzofuran]-1,1′-dione
Identifiers
3D model (JSmol )
ChemSpider
InChI=1S/C24H28O4/c1-3-5-11-19-16-13-12-14-17(8-4-2)24(21(14)20(16)23(26)27-19)18-10-7-6-9-15(18)22(25)28-24/h6,9,11,14,17,21H,3-5,7-8,10,12-13H2,1-2H3/b19-11-/t14-,17+,21+,24-/m1/s1
Key: TYSOMZQRYGBSKN-DRQJQJQISA-N
CCC/C=C\1/C2=C([C@@H]3[C@H](CC2)[C@@H]([C@@]34C5=C(C=CCC5)C(=O)O4)CCC)C(=O)O1
Properties
Chemical formula
C 24 H 28 O 4
Molar mass
380.484 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Riligustilide is a nonsteroidal phytoprogestogen that is found in Ligusticum chuanxiong .[1] [2] It is a very weak agonist of the progesterone receptor (EC50 ≈ 81 μM).[1] Another compound in the plant, 3,8-dihydrodiligustilide , is also a phytoprogestogen, but is almost 1,000-fold more potent in comparison (EC50 = 90 nM).[1]
See also [ ]
References [ ]
^ a b c Lim LS, Shen P, Gong YH, Yong EL (2006). "Dimeric progestins from rhizomes of Ligusticum chuanxiong". Phytochemistry . 67 (7): 728–34. doi :10.1016/j.phytochem.2006.01.024 . PMID 16516938 .
^ Ahmed, H.M.M.; Yeh, J.Y.; Lin, W.J.; Forsberg, N.E.; Cheng, W.T.K.; Ou, B.R (2014). "Validation of a luciferase bioassay to detect the progestative activity in gilts whose estrus was induced by an uterotonic herb (Ligusticum chuanxiong)". Livestock Science . 163 : 159–164. doi :10.1016/j.livsci.2014.02.012 . ISSN 1871-1413 .
PR
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (SPRMs ) Antagonists
mPR (PAQR )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
Categories :
Progestogens Cyclobutanes Lactones Alkene derivatives Spiro compounds Genito-urinary system drug stubs Hidden categories:
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