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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H35NO4
Molecular Weight 413.5506
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORBUPRENORPHINE

SMILES

CC(C)(C)[C@](C)([C@@]1([H])C[C@]23CC[C@@]1([C@@]4([H])[C@]53CCN[C@]2([H])Cc6ccc(c(c65)O4)O)OC)O

InChI

InChIKey=YOYLLRBMGQRFTN-IOMBULRVSA-N
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

HIDE SMILES / InChI

Molecular Formula C25H35NO4
Molecular Weight 413.5506
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Norbuprenorphine is a major metabolite of buprenorphine and potent agonist of μ, δ, and κ opioid receptors. Norbuprenorphine is the only known active metabolite of buprenorphine. It has been shown to be a respiratory depressant in rats, but only at concentrations at least 50-fold greater than those observed following application to humans of BuTrans 20 mcg/h. Compared with buprenorphine, norbuprenorphine causes minimal antinociception but greater respiratory depression. In rats, nor-buprenorphine had 1/50th the analgesic potency of buprenor-phine but 10-fold greater respiratory depressant potency. Norbuprenorphine is an in vitro substrate of the efflux transporter P-glycoprotein (Mdr1). Norbuprenorphine is an in vitro and in vivo substrate of P-glycoprotein. P-glycoprotein-mediated efflux influences brain access and antinociceptive, but not the respiratory, effects of norbuprenorphine.

CNS Activity

Curator's Comment:: Norbuprenorphine contributes to the central effects seen after chronic BUP administration as this study demonstrated its entry into the sheep brain.

Approval Year

PubMed

PubMed

TitleDatePubMed
Interaction of buprenorphine and its metabolite norbuprenorphine with cytochromes p450 in vitro.
2003 Jun
Buprenorphine: clinical pharmacokinetics in the treatment of opioid dependence.
2005
Patents

Sample Use Guides

Sheep were administered 0.6 mg kg(-1) Norbuprenorphine as 4-min i.v. infusions.
Route of Administration: Intravenous
Compared with buprenorphine, norbuprenorphine demonstrated a lower inhibitory potency with CYP2D6(22.4% inhibition at 20uM norbuprenorphine) and CYP3A4 (13.6%inhibition at 20uM) in microsomes from human cDNA-expressing lymphoblast cells.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:35:00 UTC 2021
Edited
by admin
on Fri Jun 25 20:35:00 UTC 2021
Record UNII
7E53B4O073
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORBUPRENORPHINE
Common Name English
Code System Code Type Description
WIKIPEDIA
Norbuprenorphine
Created by admin on Fri Jun 25 20:35:00 UTC 2021 , Edited by admin on Fri Jun 25 20:35:00 UTC 2021
PRIMARY
CAS
78715-23-8
Created by admin on Fri Jun 25 20:35:00 UTC 2021 , Edited by admin on Fri Jun 25 20:35:00 UTC 2021
PRIMARY
MESH
C043585
Created by admin on Fri Jun 25 20:35:00 UTC 2021 , Edited by admin on Fri Jun 25 20:35:00 UTC 2021
PRIMARY
PUBCHEM
114976
Created by admin on Fri Jun 25 20:35:00 UTC 2021 , Edited by admin on Fri Jun 25 20:35:00 UTC 2021
PRIMARY
FDA UNII
7E53B4O073
Created by admin on Fri Jun 25 20:35:00 UTC 2021 , Edited by admin on Fri Jun 25 20:35:00 UTC 2021
PRIMARY
Related Record Type Details
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