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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H35NO4
Molecular Weight 413.5497
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORBUPRENORPHINE

SMILES

[H][C@@]12OC3=C4C(C[C@H]5NCC[C@@]14[C@@]56CC[C@@]2(OC)[C@]([H])(C6)[C@](C)(O)C(C)(C)C)=CC=C3O

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 413.5497
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Sheep were administered 0.6 mg kg(-1) Norbuprenorphine as 4-min i.v. infusions.
Route of Administration: Intravenous
In Vitro Use Guide
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
Record UNII
7E53B4O073
Record Status Validated (UNII)
Record Version