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
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
| 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
| Title | Date | PubMed |
|---|---|---|
| Opioid binding in DYT1 primary torsion dystonia: an 11C-diprenorphine PET study. | 2004 Dec |
|
| Neuroleptanalgesia in wild Asian elephants (Elephas maximus maximus). | 2004 Oct |
|
| 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 |
|
| Gender dependent rate of metabolism of the opioid receptor-PET ligand [18F]fluoroethyldiprenorphine. | 2006 |
|
| 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 |
|
| Opioidergic activation in the medial pain system after heat pain. | 2006 May |
|
| 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 |
|
| Motor cortex stimulation for pain control induces changes in the endogenous opioid system. | 2007 Aug 28 |
|
| 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 |
|
| Salvinorin A: allosteric interactions at the mu-opioid receptor. | 2007 Feb |
|
| Cholesterol reduction by methyl-beta-cyclodextrin attenuates the delta opioid receptor-mediated signaling in neuronal cells but enhances it in non-neuronal cells. | 2007 Feb 15 |
|
| 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 |
|
| Electron density analyses of opioids: a comparative study. | 2007 Jun 28 |
|
| 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 Nov |
|
| 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 |
|
| N-Glycosylation of the human kappa opioid receptor enhances its stability but slows its trafficking along the biosynthesis pathway. | 2007 Sep 25 |
|
| 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 |
|
| Membrane partitioning of various delta-opioid receptor forms before and after agonist activations: the effect of cholesterol. | 2008 Jun |
|
| CXCR2 chemokine receptor antagonism enhances DOP opioid receptor function via allosteric regulation of the CXCR2-DOP receptor heterodimer. | 2008 Jun 1 |
|
| Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as mu opioid receptor antagonists with improved opioid receptor selectivity profiles. | 2008 Mar 15 |
|
| Imaging of opioid receptors in the central nervous system. | 2008 May |
|
| The runner's high: opioidergic mechanisms in the human brain. | 2008 Nov |
|
| A combined [11C]diprenorphine PET study and fMRI study of acupuncture analgesia. | 2008 Nov 3 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:01:15 UTC 2023
by
admin
on
Sat Dec 16 17:01:15 UTC 2023
|
| Record UNII |
1F0L5N25ZZ
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
WHO-VATC |
QV03AB92
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
C166495
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
D004174
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
443408
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
DB01548
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
14357-78-9
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
m4650
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | Merck Index | ||
|
CHEMBL281786
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
DTXSID00903941
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
238-325-7
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
1F0L5N25ZZ
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
100000082351
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
Diprenorphine
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
2639
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 UTC 2023
|
PRIMARY | |||
|
SUB07220MIG
Created by
admin on Sat Dec 16 17:01:16 UTC 2023 , Edited by admin on Sat Dec 16 17:01:16 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 |
|
