DrugBank: Diprenorphine (DB01548)

targets (4)

Identification

Name

Diprenorphine

Accession Number

DB01548

Type

small molecule

Groups

illicit, experimental

Description

A narcotic antagonist similar in action to naloxone. It is used to remobilize animals after etorphine neuroleptanalgesia and is considered a specific antagonist to etorphine. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Brand names

Not Available

Brand name mixtures

Not Available

Categories

Narcotic Antagonists

CAS number

14357-78-9

Weight

Average: 425.5604
Monoisotopic: 425.256608613

Chemical Formula

C₂₆H₃₅NO₄

InChI Key

InChIKey=OIJXLIIMXHRJJH-USQHPYHMSA-N

InChI

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

Plain Text

IUPAC Name

(1S,2R,6S)-3-(cyclopropylmethyl)-16-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol

SMILES

[H][C@]12CC3=C4C(OC5[C@@]4(CCN1CC1CC1)[C@@]21CCC5(OC)C(C1)C(C)(C)O)=C(O)C=C3

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Diprenorphine is used to reverse the effects of the super-potent opioid analgesics such as etorphine and carfentanil that are used for tranquilizing large animals in veterinary medicine. Not used in humans.

Pharmacodynamics

Not Available

Mechanism of action

Diprenorphine binds approximately equally to the three subtypes of opioid receptorsand antagonizes them.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	1.04e-01 g/l	ALOGPS
logP	3.52	ALOGPS
logP	2.27	ChemAxon Molconvert
logS	-3.61	ALOGPS
pKa	14.97	ChemAxon Molconvert
hydrogen acceptor count	5	ChemAxon Molconvert
hydrogen donor count	2	ChemAxon Molconvert
polar surface area	62.16	ChemAxon Molconvert
rotatable bond count	4	ChemAxon Molconvert
refractivity	118.37	ChemAxon Molconvert
polarizability	47.44	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C11794
PubChem Compound	26644
PubChem Substance	46506559
ChemSpider	24820
BindingDB	21865
Drug Product Database	0
Wikipedia	http://en.wikipedia.org/wiki/Diprenorphine

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Not Available

Targets
1. Mu-type opioid receptor Pharmacological action: yes Actions: antagonist Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin Organism class: human UniProt ID: P35372 Gene: OPRM1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Leung K: [6-O-methyl-11C]Diprenorphine Pubmed 2. Delta-type opioid receptor Pharmacological action: yes Actions: antagonist Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins Organism class: human UniProt ID: P41143 Gene: OPRD1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Willoch F, Tolle TR, Wester HJ, Munz F, Petzold A, Schwaiger M, Conrad B, Bartenstein P: Central pain after pontine infarction is associated with changes in opioid receptor binding: a PET study with 11C-diprenorphine. AJNR Am J Neuroradiol. 1999 Apr;20(4):686-90. Pubmed Jones AK, Kitchen ND, Watabe H, Cunningham VJ, Jones T, Luthra SK, Thomas DG: Measurement of changes in opioid receptor binding in vivo during trigeminal neuralgic pain using [11C] diprenorphine and positron emission tomography. J Cereb Blood Flow Metab. 1999 Jul;19(7):803-8. Pubmed Kampa M, Hatzoglou A, Notas G, Niniraki M, Kouroumalis E, Castanas E: Opioids are non-competitive inhibitors of nitric oxide synthase in T47D human breast cancer cells. Cell Death Differ. 2001 Sep;8(9):943-52. Pubmed Marie N, Lecoq I, Jauzac P, Allouche S: Differential sorting of human delta-opioid receptors after internalization by peptide and alkaloid agonists. J Biol Chem. 2003 Jun 20;278(25):22795-804. Epub 2003 Apr 2. Pubmed Webster JM, Bentley MT, Wojcikiewicz RJ: N,N,N’,N’-tetrakis(2-pyridylmethyl)ethylenediamine inhibits ligand binding to certain G protein-coupled receptors. Eur J Pharmacol. 2003 Aug 1;474(1):1-5. Pubmed Leung K: [6-O-methyl-11C]Diprenorphine Pubmed 3. Kappa-type opioid receptor Pharmacological action: unknown Actions: antagonist Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions Organism class: human UniProt ID: P41145 Gene: OPRK1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Leung K: [6-O-methyl-11C]Diprenorphine Pubmed 4. Tripartite motif-containing protein 13 Pharmacological action: unknown May act as a tumor suppressor Organism class: human UniProt ID: O60858 Gene: TRIM13 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Law PY, Hom DS, Loh HH: Multiple affinity states of opiate receptor in neuroblastoma x glioma NG108-15 hybrid cells. Opiate agonist association rate is a function of receptor occupancy. J Biol Chem. 1985 Mar 25;260(6):3561-9. Pubmed Pfeiffer A, Herz A: Discrimination of three opiate receptor binding sites with the use of a computerized curve-fitting technique. Mol Pharmacol. 1982 Mar;21(2):266-71. Pubmed Chang KJ, Hazum E, Cuatrecasas P: Novel opiate binding sites selective for benzomorphan drugs. Proc Natl Acad Sci U S A. 1981 Jul;78(7):4141-5. Pubmed Pfeiffer A, Herz A: Enhancement of delta- but not mu-opiate agonist binding by calcium. Naunyn Schmiedebergs Arch Pharmacol. 1982 May;319(2):147-53. Pubmed Cvejic S, Trapaidze N, Cyr C, Devi LA: Thr353, located within the COOH-terminal tail of the delta opiate receptor, is involved in receptor down-regulation. J Biol Chem. 1996 Feb 23;271(8):4073-6. Pubmed

Targets

1. Mu-type opioid receptor

Pharmacological action: yes
Actions: antagonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Organism class: human
UniProt ID: P35372 Link_out

Gene: OPRM1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Leung K: [6-O-methyl-11C]Diprenorphine Pubmed

2. Delta-type opioid receptor

Pharmacological action: yes
Actions: antagonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins

Organism class: human
UniProt ID: P41143 Link_out

Gene: OPRD1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Willoch F, Tolle TR, Wester HJ, Munz F, Petzold A, Schwaiger M, Conrad B, Bartenstein P: Central pain after pontine infarction is associated with changes in opioid receptor binding: a PET study with 11C-diprenorphine. AJNR Am J Neuroradiol. 1999 Apr;20(4):686-90. Pubmed
Jones AK, Kitchen ND, Watabe H, Cunningham VJ, Jones T, Luthra SK, Thomas DG: Measurement of changes in opioid receptor binding in vivo during trigeminal neuralgic pain using [11C] diprenorphine and positron emission tomography. J Cereb Blood Flow Metab. 1999 Jul;19(7):803-8. Pubmed
Kampa M, Hatzoglou A, Notas G, Niniraki M, Kouroumalis E, Castanas E: Opioids are non-competitive inhibitors of nitric oxide synthase in T47D human breast cancer cells. Cell Death Differ. 2001 Sep;8(9):943-52. Pubmed
Marie N, Lecoq I, Jauzac P, Allouche S: Differential sorting of human delta-opioid receptors after internalization by peptide and alkaloid agonists. J Biol Chem. 2003 Jun 20;278(25):22795-804. Epub 2003 Apr 2. Pubmed
Webster JM, Bentley MT, Wojcikiewicz RJ: N,N,N’,N’-tetrakis(2-pyridylmethyl)ethylenediamine inhibits ligand binding to certain G protein-coupled receptors. Eur J Pharmacol. 2003 Aug 1;474(1):1-5. Pubmed
Leung K: [6-O-methyl-11C]Diprenorphine Pubmed

3. Kappa-type opioid receptor

Pharmacological action: unknown
Actions: antagonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Organism class: human
UniProt ID: P41145 Link_out

Gene: OPRK1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Leung K: [6-O-methyl-11C]Diprenorphine Pubmed

4. Tripartite motif-containing protein 13

Pharmacological action: unknown

May act as a tumor suppressor

Organism class: human
UniProt ID: O60858 Link_out

Gene: TRIM13 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Law PY, Hom DS, Loh HH: Multiple affinity states of opiate receptor in neuroblastoma x glioma NG108-15 hybrid cells. Opiate agonist association rate is a function of receptor occupancy. J Biol Chem. 1985 Mar 25;260(6):3561-9. Pubmed
Pfeiffer A, Herz A: Discrimination of three opiate receptor binding sites with the use of a computerized curve-fitting technique. Mol Pharmacol. 1982 Mar;21(2):266-71. Pubmed
Chang KJ, Hazum E, Cuatrecasas P: Novel opiate binding sites selective for benzomorphan drugs. Proc Natl Acad Sci U S A. 1981 Jul;78(7):4141-5. Pubmed
Pfeiffer A, Herz A: Enhancement of delta- but not mu-opiate agonist binding by calcium. Naunyn Schmiedebergs Arch Pharmacol. 1982 May;319(2):147-53. Pubmed
Cvejic S, Trapaidze N, Cyr C, Devi LA: Thr353, located within the COOH-terminal tail of the delta opiate receptor, is involved in receptor down-regulation. J Biol Chem. 1996 Feb 23;271(8):4073-6. Pubmed

Comments

Drug created on July 31, 2007 07:10 / Updated on November 10, 2010 13:49

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.