DIPRENORPHINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H35NO4.ClH
Molecular Weight	462.021
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DIPRENORPHINE HYDROCHLORIDE

Structure Search

SMILES

Cl.[H][C@@]12OC3=C4C(C[C@H]5N(CC6CC6)CC[C@@]14[C@@]57CC[C@@]2(OC)[C@H](C7)C(C)(C)O)=CC=C3O

InChI

InChIKey=UNPUINKKJUSSDZ-UVGWPQHUSA-N

InChI=1S/C26H35NO4.ClH/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;1H/t18-,19-,22-,24-,25+,26-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: https://www.drugbank.ca/drugs/DB01548 | https://www.ncbi.nlm.nih.gov/pubmed/10413036 | https://www.ncbi.nlm.nih.gov/pubmed/11526449 | https://pubchem.ncbi.nlm.nih.gov/compound/443408

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
Tramadol reduces the 5-HTP-induced head-twitch response in mice via the activation of mu and kappa opioid receptors.	2003 Jan 31	12570923
Discrimination of a single dose of morphine followed by naltrexone: substitution of other agonists for morphine and other antagonists for naltrexone in a rat model of acute dependence.	2003 Mar	12604679
Altered pain sensitivity and morphine-induced anti-nociception in mice lacking CCK2 receptors.	2003 Mar	12545332
Expression of EGFP-amino-tagged human mu opioid receptor in Drosophila Schneider 2 cells: a potential expression system for large-scale production of G-protein coupled receptors.	2003 Sep	12963349
Distinct changes in the behavioural effects of morphine and naloxone in CCK2 receptor-deficient mice.	2003 Sep 15	12946603
The orvinols and related opioids--high affinity ligands with diverse efficacy profiles.	2004	15032698
Central poststroke pain and reduced opioid receptor binding within pain processing circuitries: a [11C]diprenorphine PET study.	2004 Apr	15030940
Quantification of [18F]diprenorphine kinetics in the human brain with compartmental and non-compartmental modeling approaches.	2004 Aug	15275909
Opioid binding in DYT1 primary torsion dystonia: an 11C-diprenorphine PET study.	2004 Dec	15390064
Na+ modulation, inverse agonism, and anorectic potency of 4-phenylpiperidine opioid antagonists.	2004 Jun 28	15212965
Neuroleptanalgesia in wild Asian elephants (Elephas maximus maximus).	2004 Oct	15509293
Cerebral decreases in opioid receptor binding in patients with central neuropathic pain measured by [11C]diprenorphine binding and PET.	2004 Oct	15324779
Modulation of extracellular signal-regulated kinase (ERK) activity by acute and chronic opioid treatment in neuronal and glial cell lines.	2004 Sep	15341521
Inhibition of ligand binding to G protein-coupled receptors by arachidonic acid.	2005	16186629
Pharmacological characterization of human kappa/mu opioid receptor chimeras that retain high affinity for dynorphin A.	2005	15857313
Functional expression of mammalian opioid receptors in insect cells and high-throughput screening platforms for receptor ligand mimetics.	2005 Apr	15868413
What to learn from in vivo opioidergic brain imaging?	2005 Apr	15737798
The role of opioids in restless legs syndrome: an [11C]diprenorphine PET study.	2005 Apr	15728657
Antagonist efficacy in MORS196L mutant is affected by the interaction between transmembrane domains of the opioid receptor.	2005 Apr	15579496
Opioid antagonists differ according to negative intrinsic efficacy in a mouse model of acute dependence.	2005 Aug	15912139
Binding profile of the endogenous novel heptapeptide Met-enkephalin-Gly-tyr in zebrafish and rat brain.	2005 Aug	15901806
Optimal duration of PET studies with 18F-fluoroethyl-diprenorphine.	2005 Dec	16330575
Autoradiography in opioid triple knockout mice reveals opioid and opioid receptor like binding of naloxone benzoylhydrazone.	2005 Feb	15695161
Overdose during chemical restraint in a black rhinoceros (Diceros bicornis).	2005 Jan	15663740
Using [11C]diprenorphine to image opioid receptor occupancy by methadone in opioid addiction: clinical and preclinical studies.	2005 Jan	15347732
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.	2005 Jul	15843500
Functional complementation and the analysis of opioid receptor homodimerization.	2005 Sep	15967873
Gender dependent rate of metabolism of the opioid receptor-PET ligand [18F]fluoroethyldiprenorphine.	2006	17043729
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	16415176
Opioidergic changes in the pineal gland and hypothalamus in cluster headache: a ligand PET study.	2006 Apr 11	16606930
High opiate receptor binding potential in the human lateral pain system.	2006 Apr 15	16337817
Characterization of opioid-binding sites in zebrafish brain.	2006 Feb	16207834
Matrix metalloproteinase 2 secretion in WEHI 164 fibrosarcoma cells is nitric oxide-related and modified by morphine.	2006 Jan 13	16386243
Comparison of the antinociceptive response to morphine and morphine-like compounds in male and female Sprague-Dawley rats.	2006 Mar	16291875
Opioidergic activation in the medial pain system after heat pain.	2006 May	16527398
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	16375901
The opioid ligand binding of human mu-opioid receptor is modulated by novel splice variants of the receptor.	2006 May 19	16580639
Low sensitivity of the positron emission tomography ligand [11C]diprenorphine to agonist opiates.	2007 Aug	17488881
Salvinorin A: allosteric interactions at the mu-opioid receptor.	2007 Feb	17060492
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	17141202
Differential brain opioid receptor availability in central and peripheral neuropathic pain.	2007 Jan	17137714
Brain opioid receptor binding in early abstinence from opioid dependence: positron emission tomography study.	2007 Jul	17602127
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	17720886
N-Glycosylation of the human kappa opioid receptor enhances its stability but slows its trafficking along the biosynthesis pathway.	2007 Sep 25	17711303
Agonist-promoted Lys63-linked polyubiquitination of the human kappa-opioid receptor is involved in receptor down-regulation.	2008 Apr	18212250
Opioid receptor PET reveals the psychobiologic correlates of reward processing.	2008 Aug	18632824
Post-endocytic fates of delta-opioid receptor are regulated by GRK2-mediated receptor phosphorylation and distinct beta-arrestin isoforms.	2008 Jul	18419762
Membrane partitioning of various delta-opioid receptor forms before and after agonist activations: the effect of cholesterol.	2008 Jun	18423369
Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as mu opioid receptor antagonists with improved opioid receptor selectivity profiles.	2008 Mar 15	18313920
A combined [11C]diprenorphine PET study and fMRI study of acupuncture analgesia.	2008 Nov 3	18562019

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:25 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:25 GMT 2023`
Record UNII	WBS7IEP4SN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIPRENORPHINE HYDROCHLORIDE

Common Name

English

2-((-)-(5R,6R,7R,14S)-9A-CYCLOPROPYLMETHYL-4,5-EPOXY-3-HYDROXY-6-METHOXY-6,14-ETHANOMORPHINAN-7-YL)PROPAN-2-OL HYDROCHLORIDE

Common Name

English

DIPRENORPHINE HYDROCHLORIDE [MART.]

Common Name

English

DIPRENORPHINE HYDROCHLORIDE [GREEN BOOK]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.723