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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

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

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
Receptorphin: a conserved peptide derived from the sequence of the opioid receptor, with opioid displacement activity and potent antiproliferative actions in tumor cells.
2001
Alterations in cortical and basal ganglia levels of opioid receptor binding in a rat model of l-DOPA-induced dyskinesia.
2001 Apr
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.
2001 Feb 2
Comparison of the amino acid residues in the sixth transmembrane domains accessible in the binding-site crevices of mu, delta, and kappa opioid receptors.
2001 Jul 10
Delta9-tetrahydrocannabinol releases and facilitates the effects of endogenous enkephalins: reduction in morphine withdrawal syndrome without change in rewarding effect.
2001 May
Constitutive activation of the mu opioid receptor by mutation of D3.49(164), but not D3.32(147): D3.49(164) is critical for stabilization of the inactive form of the receptor and for its expression.
2001 Oct 9
Molecular basis of differences in (-)(trans)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidiny)-cyclohexyl]benzeneacetamide-induced desensitization and phosphorylation between human and rat kappa-opioid receptors expressed in Chinese hamster ovary cells.
2002 Jan
The local environment at the cytoplasmic end of TM6 of the mu opioid receptor differs from those of rhodopsin and monoamine receptors: introduction of an ionic lock between the cytoplasmic ends of helices 3 and 6 by a L6.30(275)E mutation inactivates the mu opioid receptor and reduces the constitutive activity of its T6.34(279)K mutant.
2002 Oct 8
Effects of intravenous opioids on eye movements in humans: possible mechanisms.
2002 Sep
Dimerization of morphine and orphanin FQ/nociceptin receptors: generation of a novel opioid receptor subtype.
2002 Sep 27
[Binding characteristics of new synthesized opioid receptor ligands to cloned mu opioid receptors stably expressed in CHO cell].
2003 Feb
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
Opioid binding in DYT1 primary torsion dystonia: an 11C-diprenorphine PET study.
2004 Dec
Neuroleptanalgesia in wild Asian elephants (Elephas maximus maximus).
2004 Oct
What to learn from in vivo opioidergic brain imaging?
2005 Apr
Optimal duration of PET studies with 18F-fluoroethyl-diprenorphine.
2005 Dec
Using [11C]diprenorphine to image opioid receptor occupancy by methadone in opioid addiction: clinical and preclinical studies.
2005 Jan
Gender dependent rate of metabolism of the opioid receptor-PET ligand [18F]fluoroethyldiprenorphine.
2006
Characterization of opioid-binding sites in zebrafish brain.
2006 Feb
Comparison of the antinociceptive response to morphine and morphine-like compounds in male and female Sprague-Dawley rats.
2006 Mar
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
Salvinorin A: allosteric interactions at the mu-opioid receptor.
2007 Feb
Differential brain opioid receptor availability in central and peripheral neuropathic pain.
2007 Jan
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
Opioid receptor PET reveals the psychobiologic correlates of reward processing.
2008 Aug
A combined [11C]diprenorphine PET study and fMRI study of acupuncture analgesia.
2008 Nov 3
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:09:25 UTC 2023
Edited
by admin
on Fri Dec 15 15:09:25 UTC 2023
Record UNII
WBS7IEP4SN
Record Status Validated (UNII)
Record Version
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Name Type Language
DIPRENORPHINE HYDROCHLORIDE
GREEN BOOK   MART.  
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
Created by admin on Fri Dec 15 15:09:25 UTC 2023 , Edited by admin on Fri Dec 15 15:09:25 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
240-839-1
Created by admin on Fri Dec 15 15:09:25 UTC 2023 , Edited by admin on Fri Dec 15 15:09:25 UTC 2023
PRIMARY
DRUG BANK
DBSALT001649
Created by admin on Fri Dec 15 15:09:25 UTC 2023 , Edited by admin on Fri Dec 15 15:09:25 UTC 2023
PRIMARY
FDA UNII
WBS7IEP4SN
Created by admin on Fri Dec 15 15:09:25 UTC 2023 , Edited by admin on Fri Dec 15 15:09:25 UTC 2023
PRIMARY
CAS
16808-86-9
Created by admin on Fri Dec 15 15:09:25 UTC 2023 , Edited by admin on Fri Dec 15 15:09:25 UTC 2023
PRIMARY
SMS_ID
300000023738
Created by admin on Fri Dec 15 15:09:25 UTC 2023 , Edited by admin on Fri Dec 15 15:09:25 UTC 2023
PRIMARY
PUBCHEM
21126664
Created by admin on Fri Dec 15 15:09:25 UTC 2023 , Edited by admin on Fri Dec 15 15:09:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID10937434
Created by admin on Fri Dec 15 15:09:25 UTC 2023 , Edited by admin on Fri Dec 15 15:09:25 UTC 2023
PRIMARY
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ACTIVE MOIETY