β-Funaltrexamine - Misplaced Pages

(Redirected from Beta-funaltrexamine) 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-isoquinolin-7-yl]amino]-4-oxobut-2-enoate or Methyl (2E)-4-{amino}-4-oxobut-2-enoate
CAS Number	72782-05-9
PubChem CID	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
3D model (JSmol)	Interactive image
SMILES COC(=O)/C=C/C(=O)N1CC2(3CC4=C52(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 an irreversible (covalently bonding) opioid antagonist that was used to create the first crystal structure of the μ-opioid receptor (MOR). It is selective for antagonism of the MOR over the δ-opioid receptor (DOR) and κ-opioid receptor (KOR). Chemically, it is a naltrexone derivative with a methyl-fumaramide group in the 6-position. In addition to its MOR irreversible antagonism, β-FNA is a reversible agonist of the κ-opioid receptor (KOR) and produces KOR-mediated analgesic effects in animals. This has limited its usefulness and contributed to the development of methocinnamox as a more selective functionally irreversible antagonist of the MOR with no significant opioid agonistic actions.

References

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.
^ Ward 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.
^ Broadbear 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.