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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/25 19:55:39」(JST)

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Diprenorphine (diprenorfin, Revivon, M5050)^[1] is an non-selective opioid antagonist, though it may have some slight partial agonist activity at the kappa-opioid receptor.^[2]^[3] It is used to reverse the effects of super-potent opioid analgesics such as etorphine and carfentanil that are used for tranquilizing large animals in veterinary medicine.

Diprenorphine is the strongest opiate antagonist that is commercially available (some 100 times more potent as an antagonist than nalorphine),^[4] and is used for reversing the effects of very strong opioids for which the binding affinity is so high that naloxone does not effectively or reliably reverse the narcotic effects.^[5] These super-potent opioids, with the single exception of buprenorphine, are not used in humans because the dose for a human is so small that it would be difficult to measure properly, so there is an excessive risk of overdose leading to fatal respiratory depression. However conventional opioid derivatives are not strong enough to rapidly tranquilize large animals such as elephants and rhinos, so drugs such as etorphine or carfentanil are available for this purpose.

Diprenorphine is considered the specific antagonist for etorphine and carfentanil,^[6] and is normally used to remobilise animals once veterinary procedures have been completed.^[7] Because diprenorphine also has some agonistic properties of its own, it should not be used on humans in the event that they are accidentally exposed to etorphine or carfentanil. Naloxone or naltrexone are the preferred human antagonists.^[8]

In theory, diprenorphine could also be used as an antidote for treating overdose of certain opioid derivatives which are used in humans, such as buprenorphine, for which the binding affinity is so high that naloxone does not reliably reverse the narcotic effects. However, diprenorphine is not generally available in hospitals; instead a vial of diprenorphine is supplied with etorphine or carfentanil specifically for reversing the effects of these drugs, so use of diprenorphine for treating e.g. a buprenorphine overdose is not carried out in practice, although it would work in theory.

References

^ US Patent 3433791 - Endoethano Nor Oripavines & Nor Thebaines
^ Lewis JW, Husbands SM. The orvinols and related opioids--high affinity ligands with diverse efficacy profiles. Current Pharmaceutical Design. 2004;10(7):717-32.
^ Traynor JR, Corbett AD, Kosterlitz HW (May 1987). "Diprenorphine has agonist activity at opioid kappa-receptors in the myenteric plexus of the guinea-pig ileum". Eur. J. Pharmacol. 137 (1): 85–9. PMID 3038579.
^ Furst S, Hosztafi S, Friedmann T. Structure-Activity Relationships of Synthetic and Semisynthetic Opioid Agonists and Antagonists. Current Medicinal Chemistry, 1995; 1(6):423-440. ISSN:0929-8673
^ Takemori AE, Hayashi G, Smits SE. Studies on the quantitative antagonism of analgesics by naloxone and diprenorphine. European Journal of Pharmacology. 1972 Oct;20(1):85-92. Abstract.
^ Jessup DA, Clark WE, Jones KR, Clark R, Lance WR. Immobilization of free-ranging desert bighorn sheep, tule elk, and wild horses, using carfentanil and xylazine: reversal with naloxone, diprenorphine, and yohimbine. Journal of the American Veterinary Medical Association. 1985 Dec 1;187(11):1253-4.
^ Alford BT, Burkhart RL, Johnson WP. Etorphine and diprenorphine as immobilizing and reversing agents in captive and free-ranging mammals. Journal of the American Veterinary Medical Association. 1974 Apr 1;164(7):702-5.
^ Caulkett NA, Arnemo JM. Chemical Immobilization of Free-Ranging Terrestrial Mammals. In: Tranquilli WJ, Thurmon JC, Grimm KA, eds. Lumb and Jones' Veterinary Anesthesia and Analgesia. 4th ed. Philadelphia: Lippincott, Williams and Wilkins, 2007. 815.

English Journal

Multi-Scale hierarchical generation of PET parametric maps: application and testing on a [11C]DPN study.

Rizzo G, Turkheimer FE, Keihaninejad S, Bose SK, Hammers A, Bertoldo A.SourceDepartment of Information Engineering, University of Padova, Padova, Italy.
NeuroImage.Neuroimage.2012 Feb 1;59(3):2485-93. Epub 2011 Sep 8.
We propose a general approach to generate parametric maps. It consists in a multi-stage hierarchical scheme where, starting from the kinetic analysis of the whole brain, we then cascade the kinetic information to anatomical systems that are akin in terms of receptor densities, and then down to the v
PMID 21924366

Structural basis for μ-opioid receptor binding and activation.

Serohijos AW, Yin S, Ding F, Gauthier J, Gibson DG, Maixner W, Dokholyan NV, Diatchenko L.SourceBiochemistry and Biophysics Department, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA.
Structure (London, England : 1993).Structure.2011 Nov 9;19(11):1683-90.
Opioids that stimulate the μ-opioid receptor (MOR1) are the most frequently prescribed and effective analgesics. Here we present a structural model of MOR1. Molecular dynamics simulations show a ligand-dependent increase in the conformational flexibility of the third intracellular loop that couples
PMID 22078567

Japanese Journal

オピオイド受容体活性における加齢の影響 : [^<11>C]diprenorphine PET による定量的検討

上間武,RAKSHI James S.,伊藤健吾,西川隆,武田雅俊,BROOKS David J.
Psychogeriatrics : the official journal of the Japanese Psychogeriatric Society 1(4), 309-316, 2001-12-20
NAID 10019049972

^<11>C-diprenorphine binding in Huntington's disease : a comparison of region of interest analysis with statistical parametric mapping

WEEKS RA
J Cereb Blood Flow Metab 17, 943-949, 1997
NAID 30009335006

Related Pictures

★リンクテーブル★

リンク元

「オピオイド」

Diprenorphine
Systematic (IUPAC) name
	(5α,7α)-17-(Cyclopropylmethyl)- 4,5-epoxy- 18,19-dihydro- 3-hydroxy- 6-methoxy- α,α-dimethyl- 6,14-ethenomorphinan- 7-methanol
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	?
Identifiers
CAS number	14357-78-9
ATCvet code	QV03AB92
PubChem	CID 443408
IUPHAR ligand	1617
DrugBank	DB01548
ChemSpider	391634
UNII	1F0L5N25ZZ
KEGG	D07863
ChEMBL	CHEMBL281786
Chemical data
Formula	C26H35NO4
Mol. mass	425.56 g/mol
	SMILES CC(C)([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O;
	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 ; Key:OIJXLIIMXHRJJH-KNLIIKEYSA-N ;
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　　[★]

英: opioid
同: 類麻薬
関: オピオイド受容体

オピオイド受容体に結合するモルフィン様物質のことを指す。

内因性のオピオイドペプチドが発見され、これらは内因性オピオイドペプチドと呼ばれるようになった。

作用

縮瞳

モルフィンと多くのμ,κアゴニストは瞳孔の縮小を引き起こす。これは瞳孔を支配する副交感神経の興奮による。μアゴニストを中毒量投与すると縮瞳し、pinpoints pupupilsはpathognomonicである。(GOO.559)

オピオイドとオピオイド類似物質の作用

GOO.552

Drugs	RECEPTOR TYPES
Drugs	μ受容体	δ受容体	κ受容体
morphine	＋＋＋		＋
methadone	＋＋＋
etorphine	＋＋＋	＋＋＋	＋＋＋
levorphanol	＋＋＋
fentanyl	＋＋＋
sufentanil	＋＋＋	＋	＋
DAMGO	＋＋＋
butorphanol	P		＋＋＋
buprenorphine	P		ーー
naloxone	ーーー	ー	ーー
naltrexone	ーーー	ー	ーーー
CTOP	ーーー
diprenorphine	ーーー	ーー	ーーー
β-funaltrexamine	ーーー	ー	＋＋
naloxonazine	ーーー	ー	ー
nalorphine	ーーー		＋
pentazocine	P		＋＋
nalbuphine	ーー		＋＋
naloxone benzoylhydrazone	ーーー	ー	ー
bremazocine	＋＋＋	＋＋	＋＋＋
ethylketocyclazocine	P	＋	＋＋＋
U50,488			＋＋＋
U69,593			＋＋＋
spiradoline	＋		＋＋＋
nor-Binaltorphimine	ー	ー	ーーー
naltrindole	ー	ーーー	ー
DPDPE		＋＋
[[［[D-Ala2,Glu4］deltorphin]]		＋＋

DSLET	＋	＋＋
endogenous Peptides
met-enkephalin	＋＋	＋＋＋
leu-enkephalin	＋＋	＋＋＋
β-endorphin	＋＋＋	＋＋＋
dynorphin A	＋＋		＋＋＋
dynorphin B	＋	＋	＋＋＋
α-neoendorphin	＋	＋	＋＋＋

＋アゴニスト　ーアンタゴニスト　P partial agonist

各鎮痛薬のオピオイド受容体への作用

　　　　　　　　　μ受容体　κ受容体

レミフェンタニル　＋＋＋　　ー

フェンタニル　　　＋＋＋　　－

モルヒネ　　　　　＋＋＋　　＋

ペチジン　　　　　＋＋　　　＋

トラマドール　　　＋　　　　－

ペンタゾシン　　　ー　　　　＋＋

ブプレノルフィン　Ｐ　　　　ー

ナロキソン　　　　ー　　　　－

[1] US Patent 3433791 - Endoethano Nor Oripavines & Nor Thebaines

[2] Lewis JW, Husbands SM. The orvinols and related opioids--high affinity ligands with diverse efficacy profiles. Current Pharmaceutical Design. 2004;10(7):717-32.

[pmid3038579-3] Traynor JR, Corbett AD, Kosterlitz HW (May 1987). "Diprenorphine has agonist activity at opioid kappa-receptors in the myenteric plexus of the guinea-pig ileum". Eur. J. Pharmacol. 137 (1): 85–9. PMID 3038579.

[4] Furst S, Hosztafi S, Friedmann T. Structure-Activity Relationships of Synthetic and Semisynthetic Opioid Agonists and Antagonists. Current Medicinal Chemistry, 1995; 1(6):423-440. ISSN:0929-8673

[5] Takemori AE, Hayashi G, Smits SE. Studies on the quantitative antagonism of analgesics by naloxone and diprenorphine. European Journal of Pharmacology. 1972 Oct;20(1):85-92. Abstract.

[6] Jessup DA, Clark WE, Jones KR, Clark R, Lance WR. Immobilization of free-ranging desert bighorn sheep, tule elk, and wild horses, using carfentanil and xylazine: reversal with naloxone, diprenorphine, and yohimbine. Journal of the American Veterinary Medical Association. 1985 Dec 1;187(11):1253-4.

[7] Alford BT, Burkhart RL, Johnson WP. Etorphine and diprenorphine as immobilizing and reversing agents in captive and free-ranging mammals. Journal of the American Veterinary Medical Association. 1974 Apr 1;164(7):702-5.

[8] Caulkett NA, Arnemo JM. Chemical Immobilization of Free-Ranging Terrestrial Mammals. In: Tranquilli WJ, Thurmon JC, Grimm KA, eds. Lumb and Jones' Veterinary Anesthesia and Analgesia. 4th ed. Philadelphia: Lippincott, Williams and Wilkins, 2007. 815.

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案内

diprenorphine