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Active metabolite of buprenorphine
Norbuprenorphine
ATC code
(5α,6β,14β,18R )-18-[(1S )-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
ECHA InfoCard
100.208.387
Formula C 25 H 35 N O 4
Molar mass 413.558 g·mol−1 3D model (
JSmol )
C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN[C@@H]3Cc6c5c(c(cc6)O)O4)OC)(C(C)(C)C)O
InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1
Key:YOYLLRBMGQRFTN-IOMBULRVSA-N
Norbuprenorphine is a major
active metabolite of the
opioid modulator
buprenorphine . It is a
μ-opioid ,
δ-opioid , and
nociceptin receptor
full agonist ,
[1]
[2] and a
κ-opioid receptor
partial agonist .
[2] In rats, unlike buprenorphine, norbuprenorphine produces marked
respiratory depression but with very little
antinociceptive effect.
[3] In explanation of these properties, norbuprenorphine has been found to be a high affinity
P-glycoprotein
substrate , and in accordance, shows very limited
blood-brain-barrier penetration.
[3]
Norbuprenorphine
See also
References
^ Yassen A, Kan J, Olofsen E, Suidgeest E, Dahan A, Danhof M (May 2007). "Pharmacokinetic-pharmacodynamic modeling of the respiratory depressant effect of norbuprenorphine in rats". The Journal of Pharmacology and Experimental Therapeutics . 321 (2): 598–607.
doi :
10.1124/jpet.106.115972 .
PMID
17283225 .
S2CID
11921738 .
^
a
b Huang P, Kehner GB, Cowan A, Liu-Chen LY (May 2001).
"Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist" . The Journal of Pharmacology and Experimental Therapeutics . 297 (2): 688–95.
PMID
11303059 .
^
a
b Brown SM, Campbell SD, Crafford A, Regina KJ, Holtzman MJ, Kharasch ED (October 2012).
"P-glycoprotein is a major determinant of norbuprenorphine brain exposure and antinociception" . J. Pharmacol. Exp. Ther . 343 (1): 53–61.
doi :
10.1124/jpet.112.193433 .
PMC
3464040 .
PMID
22739506 .