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β-Funaltrexamine

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Chemical compound

Pharmaceutical compound

β-Funaltrexamine
Clinical data

Other names	Funaltrexamine; β-Funaltrexamine; Beta-Funaltrexamine; β-FNA; Beta-FNA
Identifiers
IUPAC name methyl (E)-4-[[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]amino]-4-oxobut-2-enoate or Methyl (2E)-4-{[17-(cyclopropylmethyl)-3,14-dihydroxy-4,5α-epoxymorphinan-6β-yl]amino}-4-oxobut-2-enoate
CAS Number	72782-05-9
PubChemCID	5311018
ChemSpider	4470557
UNII	9YX958J3X9
KEGG	C18127
ChEBI	CHEBI:81527
ChEMBL	ChEMBL473136
CompTox Dashboard(EPA)	DTXSID501316803
Chemical and physical data
Formula	C₂₅H₃₀N₂O₆
Molar mass	454.523 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC(=O)/C=C/C(=O)N[C@@H]1CC[C@]2([C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)O)CCN3CC6CC6)O
InChI InChI=1S/C25H30N2O6/c1-32-20(30)7-6-19(29)26-16-8-9-25(31)18-12-15-4-5-17(28)22-21(15)24(25,23(16)33-22)10-11-27(18)13-14-2-3-14/h4-7,14,16,18,23,28,31H,2-3,8-13H2,1H3,(H,26,29)/b7-6+/t16-,18-,23+,24+,25-/m1/s1 Key:PQKHESYTSKMWFP-WZJCLRDWSA-N

β-Funaltrexamine (β-FNA) is anirreversible (covalently bonding)opioid antagonist that was used to create the firstcrystal structure of theμ-opioid receptor (MOR).^[1] It isselective for antagonism of the MOR over theδ-opioid receptor (DOR) andκ-opioid receptor (KOR).^[2] Chemically, it is analtrexone derivative with a methyl-fumaramide group in the 6-position. In addition to its MOR irreversible antagonism, β-FNA is a reversibleagonist of theκ-opioid receptor (KOR) and produces KOR-mediatedanalgesic effects in animals.^[2]^[3]^[4] This has limited its usefulness and contributed to the development ofmethocinnamox as a more selective functionally irreversible antagonist of the MOR with no significant opioid agonistic actions.^[3]

^Manglik A, Kruse AC, Kobilka TS, Thian FS, Mathiesen JM, Sunahara RK, et al. (March 2012)."Crystal structure of the µ-opioid receptor bound to a morphinan antagonist".Nature.485 (7398):321–6.Bibcode:2012Natur.485..321M.doi:10.1038/nature10954.PMC 3523197.PMID 22437502.
^^a ^bWard SJ, Portoghese PS, Takemori AE (June 1982). "Pharmacological profiles of beta-funaltrexamine (beta-FNA) and beta-chlornaltrexamine (beta-CNA) on the mouse vas deferens preparation".Eur J Pharmacol.80 (4):377–384.doi:10.1016/0014-2999(82)90083-8.PMID 6286325.
^^a ^bBroadbear JH, Sumpter TL, Burke TF, Husbands SM, Lewis JW, Woods JH, Traynor JR (September 2000). "Methocinnamox is a potent, long-lasting, and selective antagonist of morphine-mediated antinociception in the mouse: comparison with clocinnamox, beta-funaltrexamine, and beta-chlornaltrexamine".J Pharmacol Exp Ther.294 (3):933–940.PMID 10945843.
^Qi JA, Heyman JS, Sheldon RJ, Koslo RJ, Porreca F (March 1990). "Mu antagonist and kappa agonist properties of beta-funaltrexamine (beta-FNA) in vivo: long-lasting spinal analgesia in mice".J Pharmacol Exp Ther.252 (3):1006–1011.PMID 2156986.