From Wikipedia, the free encyclopedia
Chemical compound
Quadazocine
ATC code
1-cyclopentyl-5-[(1S ,9R )-4-hydroxy-1,10,13-trimethyl-10-azatricyclo[7.3.1.02,7 ]trideca-2,4,6-trien-13-yl]-3-pentanone
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 25 H 37 N O 2
Molar mass 383.576 g·mol−1 3D model (
JSmol )
O=C(CCC1CCCC1)CCC4([C@@H]3N(CC[C@]4(c2c(ccc(O)c2)C3)C)C)C
InChI=1S/C25H37NO2/c1-24-14-15-26(3)23(16-19-9-11-21(28)17-22(19)24)25(24,2)13-12-20(27)10-8-18-6-4-5-7-18/h9,11,17-18,23,28H,4-8,10,12-16H2,1-3H3/t23-,24+,25?/m1/s1
Key:LOYWOYCPSWPKFH-CSIQULDISA-N
Quadazocine (WIN-44,441 ) is an
opioid antagonist of the
benzomorphan family which is used in
scientific research .
[1] It acts as a
silent antagonist at all three of the major
opioid receptors —
μ ,
κ , and
δ ,
[1]
[2] but with a significant preference in
affinity for the μ receptor and the κ2 subtype.
[3]
[4]
[5] As such, it has been touted as a "κ2 -selective" antagonist, though this is not entirely accurate on account of its similar affinity for the μ receptor.
[3]
[5] As would be expected, quadazocine reverses the effects (e.g.,
analgesia ) of
opioid
agonists like
morphine and
fentanyl in animals.
[1]
[6]
See also
References
^
a
b
c Ward SJ, Pierson AK, Michne WF (1983). "Multiple opioid receptor profile in vitro and activity in vivo of the potent opioid antagonist Win 44,441-3". Life Sciences . 33 (Suppl 1): 303–6.
doi :
10.1016/0024-3205(83)90503-9 .
PMID
6319882 .
^ Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J (2006).
"Pharmacological profiles of opioid ligands at kappa opioid receptors" . BMC Pharmacology . 6 : 3.
doi :
10.1186/1471-2210-6-3 .
PMC
1403760 .
PMID
16433932 .
^
a
b Porreca F (1 September 1995).
"Pharmacological characterization of opioid delta and kappa receptors" . In Tseng LF (ed.). Pharmacology of Opioid Peptides . CRC Press. p. 238.
ISBN
978-3-7186-5632-5 . Retrieved 22 April 2012 .
^ Rapaka RS, Sadée W (13 June 2008).
Drug Addiction: From Basic Research to Therapy . Springer. p. 421.
ISBN
978-0-387-76677-5 . Retrieved 22 April 2012 .
^
a
b Zhang WM, Wu S, Yu XC, Wang HX, Bian JS, Wong TM (February 1999). "Effects of U50488 and bremazocine on [Ca2+]i and cAMP in naive and tolerant rat ventricular myocytes: evidence of kappa opioid receptor multiplicity in the heart". Journal of Molecular and Cellular Cardiology . 31 (2): 355–62.
doi :
10.1006/jmcc.1998.9998 .
PMID
10093048 .
^ Negus SS, Zuzga DS, Mello NK (June 2002).
"Sex differences in opioid antinociception in rhesus monkeys: antagonism of fentanyl and U50,488 by quadazocine" . The Journal of Pain . 3 (3): 218–26.
doi :
10.1054/jpai.2002.124734 .
PMID
14622776 .