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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H35NO4
Molecular Weight 425.5604
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPRENORPHINE

SMILES

CO[C@]12CC[C@@]3(C[C@@H]1C(C)(C)O)[C@H]4CC5=CC=C(O)C6=C5[C@@]3(CCN4CC7CC7)[C@H]2O6

InChI

InChIKey=OIJXLIIMXHRJJH-KNLIIKEYSA-N
InChI=1S/C26H35NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-7,15,18-19,22,28-29H,4-5,8-14H2,1-3H3/t18-,19-,22-,24-,25+,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H35NO4
Molecular Weight 425.5604
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

As a narcotic antagonist similar in action to naloxone, DIPRENORPHINE is used to remobilize animals after analgesia by super-potent opioid analgesics such as etorphine and carfentanil. It is not used in humans. Diprenorphine binds approximately equally to the three subtypes of opioid receptors (mu, delta, and kappa) and antagonizes them. This compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. The therapeutic efficacy of many other compounds can be decreased when used in combination with Diprenorphine (54 compounds mentioned on www.drugbank.ca).

Approval Year

PubMed

PubMed

TitleDatePubMed
Enhanced spontaneous activity of the mu opioid receptor by cysteine mutations: characterization of a tool for inverse agonist screening.
2003 Dec 1
trans-3,4-dimethyl-4-(3-carboxamidophenyl)piperidines: a novel class of micro-selective opioid antagonists.
2003 Dec 15
Comparison of etorphine-detomidine and medetomidine-ketamine anesthesia in captive addax (Addax nasomaculatus).
2003 Sep
The orvinols and related opioids--high affinity ligands with diverse efficacy profiles.
2004
Central poststroke pain and reduced opioid receptor binding within pain processing circuitries: a [11C]diprenorphine PET study.
2004 Apr
Quantification of [18F]diprenorphine kinetics in the human brain with compartmental and non-compartmental modeling approaches.
2004 Aug
Opioid binding in DYT1 primary torsion dystonia: an 11C-diprenorphine PET study.
2004 Dec
Na+ modulation, inverse agonism, and anorectic potency of 4-phenylpiperidine opioid antagonists.
2004 Jun 28
Bootstrapped DEPICT for error estimation in PET functional imaging.
2004 Mar
Neuroleptanalgesia in wild Asian elephants (Elephas maximus maximus).
2004 Oct
Cerebral decreases in opioid receptor binding in patients with central neuropathic pain measured by [11C]diprenorphine binding and PET.
2004 Oct
Modulation of extracellular signal-regulated kinase (ERK) activity by acute and chronic opioid treatment in neuronal and glial cell lines.
2004 Sep
In rats, acute morphine dependence results in antagonist-induced response suppression of intracranial self-stimulation.
2004 Sep
Inhibition of ligand binding to G protein-coupled receptors by arachidonic acid.
2005
Pharmacological characterization of human kappa/mu opioid receptor chimeras that retain high affinity for dynorphin A.
2005
Functional expression of mammalian opioid receptors in insect cells and high-throughput screening platforms for receptor ligand mimetics.
2005 Apr
What to learn from in vivo opioidergic brain imaging?
2005 Apr
The role of opioids in restless legs syndrome: an [11C]diprenorphine PET study.
2005 Apr
Antagonist efficacy in MORS196L mutant is affected by the interaction between transmembrane domains of the opioid receptor.
2005 Apr
Opioid antagonists differ according to negative intrinsic efficacy in a mouse model of acute dependence.
2005 Aug
Binding profile of the endogenous novel heptapeptide Met-enkephalin-Gly-tyr in zebrafish and rat brain.
2005 Aug
Optimal duration of PET studies with 18F-fluoroethyl-diprenorphine.
2005 Dec
Autoradiography in opioid triple knockout mice reveals opioid and opioid receptor like binding of naloxone benzoylhydrazone.
2005 Feb
Overdose during chemical restraint in a black rhinoceros (Diceros bicornis).
2005 Jan
Using [11C]diprenorphine to image opioid receptor occupancy by methadone in opioid addiction: clinical and preclinical studies.
2005 Jan
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.
2005 Jul
Functional complementation and the analysis of opioid receptor homodimerization.
2005 Sep
Adenylyl cyclase superactivation induced by long-term treatment with opioid agonist is dependent on receptor localized within lipid rafts and is independent of receptor internalization.
2006 Apr
Opioidergic changes in the pineal gland and hypothalamus in cluster headache: a ligand PET study.
2006 Apr 11
High opiate receptor binding potential in the human lateral pain system.
2006 Apr 15
Characterization of opioid-binding sites in zebrafish brain.
2006 Feb
Matrix metalloproteinase 2 secretion in WEHI 164 fibrosarcoma cells is nitric oxide-related and modified by morphine.
2006 Jan 13
Comparison of the antinociceptive response to morphine and morphine-like compounds in male and female Sprague-Dawley rats.
2006 Mar
Delta and mu opioid receptors from the brain of a urodele amphibian, the rough-skinned newt Taricha granulosa: cloning, heterologous expression, and pharmacological characterization.
2006 May 1
The opioid ligand binding of human mu-opioid receptor is modulated by novel splice variants of the receptor.
2006 May 19
Upregulation of opioid receptor binding following spontaneous epileptic seizures.
2007 Apr
Low sensitivity of the positron emission tomography ligand [11C]diprenorphine to agonist opiates.
2007 Aug
Endogenous heptapeptide Met-enkephalin-Gly-Tyr binds differentially to duplicate delta opioid receptors from zebrafish.
2007 Dec
Agonist treatment did not affect association of mu opioid receptors with lipid rafts and cholesterol reduction had opposite effects on the receptor-mediated signaling in rat brain and CHO cells.
2007 Dec 12
Differential brain opioid receptor availability in central and peripheral neuropathic pain.
2007 Jan
The inhibitory effect of opioids on HepG2 cells is mediated via interaction with somatostatin receptors.
2007 Jan 19
Brain opioid receptor binding in early abstinence from opioid dependence: positron emission tomography study.
2007 Jul
Balancing bias, reliability, noise properties and the need for parametric maps in quantitative ligand PET: [(11)C]diprenorphine test-retest data.
2007 Oct 15
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.
2007 Oct 26
Agonist-promoted Lys63-linked polyubiquitination of the human kappa-opioid receptor is involved in receptor down-regulation.
2008 Apr
Opioid receptor PET reveals the psychobiologic correlates of reward processing.
2008 Aug
Post-endocytic fates of delta-opioid receptor are regulated by GRK2-mediated receptor phosphorylation and distinct beta-arrestin isoforms.
2008 Jul
CXCR2 chemokine receptor antagonism enhances DOP opioid receptor function via allosteric regulation of the CXCR2-DOP receptor heterodimer.
2008 Jun 1
Imaging of opioid receptors in the central nervous system.
2008 May
The runner's high: opioidergic mechanisms in the human brain.
2008 Nov
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:27:07 UTC 2023
Edited
by admin
on Thu Jul 06 22:27:07 UTC 2023
Record UNII
1F0L5N25ZZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPRENORPHINE
INN   MI  
INN  
Official Name English
M-5050
Code English
REVIVON
Brand Name English
diprenorphine [INN]
Common Name English
M5050
Code English
DIPRENORPHINE [MI]
Common Name English
M. 5050
Code English
6,14-ETHENOMORPHINAN-7-METHANOL, 17-(CYCLOPROPYLMETHYL)-4,5-EPOXY-18,19-DIHYDRO-3-HYDROXY-6-METHOXY-.ALPHA.,.ALPHA.-DIMETHYL-, (5.ALPHA.,7.ALPHA.)-
Common Name English
DIPRENORFIN
Common Name English
Classification Tree Code System Code
WHO-VATC QV03AB92
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C166495
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
MESH
D004174
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
PUBCHEM
443408
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
DRUG BANK
DB01548
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
CAS
14357-78-9
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
MERCK INDEX
M4650
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL281786
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID00903941
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
ECHA (EC/EINECS)
238-325-7
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
FDA UNII
1F0L5N25ZZ
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
SMS_ID
100000082351
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
WIKIPEDIA
Diprenorphine
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
INN
2639
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
EVMPD
SUB07220MIG
Created by admin on Thu Jul 06 22:27:08 UTC 2023 , Edited by admin on Thu Jul 06 22:27:08 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
In contrast to naloxone, diprenorphine (0.03 mgkg−1i.p.)reversed equipotent doses of morphine and fentanyl to the same degree. Assay done on SH-SY5Y cells displacing [3H]DIPRENORPHINE.
Ki
TARGET -> INHIBITOR
Ki
LABELED -> NON-LABELED
TARGET -> INHIBITOR
Assumed Kd similar to all opioid receptors
Kd
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Assumed Kd similar to all opioid receptors
Kd
Related Record Type Details
ACTIVE MOIETY