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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=C6C(O[C@@H]2[C@@]36CCN4CC7CC7)=C(O)C=C5

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

Description

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

Unknown
149124
PubMed

PubMed

TitleDatePubMed
A combined [11C]diprenorphine PET study and fMRI study of acupuncture analgesia.
2008-11-03
The runner's high: opioidergic mechanisms in the human brain.
2008-11
Opioid receptor PET reveals the psychobiologic correlates of reward processing.
2008-08
Post-endocytic fates of delta-opioid receptor are regulated by GRK2-mediated receptor phosphorylation and distinct beta-arrestin isoforms.
2008-07
CXCR2 chemokine receptor antagonism enhances DOP opioid receptor function via allosteric regulation of the CXCR2-DOP receptor heterodimer.
2008-06-01
Membrane partitioning of various delta-opioid receptor forms before and after agonist activations: the effect of cholesterol.
2008-06
Imaging of opioid receptors in the central nervous system.
2008-05
Agonist-promoted Lys63-linked polyubiquitination of the human kappa-opioid receptor is involved in receptor down-regulation.
2008-04
Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as mu opioid receptor antagonists with improved opioid receptor selectivity profiles.
2008-03-15
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.
2007-12-12
Endogenous heptapeptide Met-enkephalin-Gly-Tyr binds differentially to duplicate delta opioid receptors from zebrafish.
2007-12
A select set of opioid ligands induce up-regulation by promoting the maturation and stability of the rat kappa-opioid receptor in human embryonic kidney 293 cells.
2007-11
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.
2007-10-26
Balancing bias, reliability, noise properties and the need for parametric maps in quantitative ligand PET: [(11)C]diprenorphine test-retest data.
2007-10-15
N-Glycosylation of the human kappa opioid receptor enhances its stability but slows its trafficking along the biosynthesis pathway.
2007-09-25
Motor cortex stimulation for pain control induces changes in the endogenous opioid system.
2007-08-28
Low sensitivity of the positron emission tomography ligand [11C]diprenorphine to agonist opiates.
2007-08
Brain opioid receptor binding in early abstinence from opioid dependence: positron emission tomography study.
2007-07
Electron density analyses of opioids: a comparative study.
2007-06-28
Upregulation of opioid receptor binding following spontaneous epileptic seizures.
2007-04
Cholesterol reduction by methyl-beta-cyclodextrin attenuates the delta opioid receptor-mediated signaling in neuronal cells but enhances it in non-neuronal cells.
2007-02-15
Salvinorin A: allosteric interactions at the mu-opioid receptor.
2007-02
The inhibitory effect of opioids on HepG2 cells is mediated via interaction with somatostatin receptors.
2007-01-19
Differential brain opioid receptor availability in central and peripheral neuropathic pain.
2007-01
The opioid ligand binding of human mu-opioid receptor is modulated by novel splice variants of the receptor.
2006-05-19
Delta and mu opioid receptors from the brain of a urodele amphibian, the rough-skinned newt Taricha granulosa: cloning, heterologous expression, and pharmacological characterization.
2006-05-01
Opioidergic activation in the medial pain system after heat pain.
2006-05
High opiate receptor binding potential in the human lateral pain system.
2006-04-15
Opioidergic changes in the pineal gland and hypothalamus in cluster headache: a ligand PET study.
2006-04-11
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.
2006-04
Comparison of the antinociceptive response to morphine and morphine-like compounds in male and female Sprague-Dawley rats.
2006-03
Characterization of opioid-binding sites in zebrafish brain.
2006-02
Matrix metalloproteinase 2 secretion in WEHI 164 fibrosarcoma cells is nitric oxide-related and modified by morphine.
2006-01-13
Gender dependent rate of metabolism of the opioid receptor-PET ligand [18F]fluoroethyldiprenorphine.
2006
Optimal duration of PET studies with 18F-fluoroethyl-diprenorphine.
2005-12
Functional complementation and the analysis of opioid receptor homodimerization.
2005-09
Opioid antagonists differ according to negative intrinsic efficacy in a mouse model of acute dependence.
2005-08
Binding profile of the endogenous novel heptapeptide Met-enkephalin-Gly-tyr in zebrafish and rat brain.
2005-08
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.
2005-07
Functional expression of mammalian opioid receptors in insect cells and high-throughput screening platforms for receptor ligand mimetics.
2005-04
What to learn from in vivo opioidergic brain imaging?
2005-04
The role of opioids in restless legs syndrome: an [11C]diprenorphine PET study.
2005-04
Antagonist efficacy in MORS196L mutant is affected by the interaction between transmembrane domains of the opioid receptor.
2005-04
Autoradiography in opioid triple knockout mice reveals opioid and opioid receptor like binding of naloxone benzoylhydrazone.
2005-02
Overdose during chemical restraint in a black rhinoceros (Diceros bicornis).
2005-01
Using [11C]diprenorphine to image opioid receptor occupancy by methadone in opioid addiction: clinical and preclinical studies.
2005-01
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
Opioid binding in DYT1 primary torsion dystonia: an 11C-diprenorphine PET study.
2004-12
Neuroleptanalgesia in wild Asian elephants (Elephas maximus maximus).
2004-10
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:41:29 GMT 2025
Edited
by admin
on Wed Apr 02 08:41:29 GMT 2025
Record UNII
1F0L5N25ZZ
Record Status Validated (UNII)
Record Version
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Name Type Language
DIPRENORPHINE
INN   MI  
INN  
Official Name English
REVIVON
Preferred Name English
M-5050
Code 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 Wed Apr 02 08:41:29 GMT 2025 , Edited by admin on Wed Apr 02 08:41:29 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C166495
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
MESH
D004174
Created by admin on Wed Apr 02 08:41:29 GMT 2025 , Edited by admin on Wed Apr 02 08:41:29 GMT 2025
PRIMARY
PUBCHEM
443408
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
DRUG BANK
DB01548
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
CAS
14357-78-9
Created by admin on Wed Apr 02 08:41:29 GMT 2025 , Edited by admin on Wed Apr 02 08:41:29 GMT 2025
PRIMARY
MERCK INDEX
m4650
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL281786
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID00903941
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
238-325-7
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
FDA UNII
1F0L5N25ZZ
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
SMS_ID
100000082351
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
WIKIPEDIA
Diprenorphine
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
INN
2639
Created by admin on Wed Apr 02 08:41:30 GMT 2025 , Edited by admin on Wed Apr 02 08:41:30 GMT 2025
PRIMARY
EVMPD
SUB07220MIG
Created by admin on Wed Apr 02 08:41:29 GMT 2025 , Edited by admin on Wed Apr 02 08:41:29 GMT 2025
PRIMARY
Related Record Type Details
MU-TYPE OPIOID RECEPTOR
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
MU-TYPE OPIOID RECEPTOR
TARGET -> INHIBITOR
Ki
Structure of Diprenorphine H-3
LABELED -> NON-LABELED
DELTA-TYPE OPIOID RECEPTOR
TARGET -> INHIBITOR
Assumed Kd similar to all opioid receptors
Kd
Structure of DIPRENORPHINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
KAPPA-TYPE OPIOID RECEPTOR
TARGET -> INHIBITOR
Assumed Kd similar to all opioid receptors
Kd
Related Record Type Details
Structure of DIPRENORPHINE
ACTIVE MOIETY
NIH
NCATS
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