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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/30 09:35:17」(JST)

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Levorphanol /lɛvaʊrfɑːnɒl/ (Levo-Dromoran) is an opioid medication used to treat moderate to severe pain. Chemically it is (-)-3-hydroxy-N-methyl-morphinan.^[1] It is the levorotatory stereoisomer of the synthetic morphinan (Dromoran) and a pure opioid agonist, first described in Germany in 1948 as an orally active morphine-like analgesic.^[2] It has been in clinical use in the U.S. since the 1950s.^[1] Levorphanol has opioid, NMDA antagonist and monoamine reuptake inhibitor activity; it binds strongly to the mu opioid receptor and less strongly to the kappa and delta opioid receptors but lacks complete cross-tolerance with morphine.^[1] It possesses greater intrinsic activity at the MOR than morphine.^[1] The duration of action is generally long compared to other comparable analgesics and varies from 4 hours to as much as 15 hours. For this reason levorphanol is useful in palliation of chronic pain and similar conditions. Levorphanol has an oral to parenteral effectiveness ratio of 2:1, one of the most favourable of the strong narcotics. Its NMDA actions, similar to those of the phenylheptylamine open-chain narcotics such as methadone or the phenylpiperidine ketobemidone, make levorphanol useful for types of pain that other analgesics may not be as effective against, such as neuropathic pain.^[3]

Levorphanol is listed under the Single Convention On Narcotic Drugs 1961 and is regulated like morphine in most countries. In the United States it is a Schedule II Narcotic controlled substance with a DEA ACSCN of 9220 and 2013 annual aggregate manufacturing quota of 4.5 kilos. The salts in use are the tartrate (free base conversion ratio 0.58) and hydrobromide (0.76) ^[4]

Synthesis

By the resolution of the racemate (i.e. racemorphan):^[5]

References

^ ^a ^b ^c ^d Davis, MP; Glare, PA; Hardy, J (2009) [2005]. Opioids in Cancer Pain (2nd ed.). Oxford, UK: Oxford University Press. ISBN 978-0-19-157532-7. edit
^ DE 1014545
^ Prommer, E (2007). "Levorphanol: the forgotten opioid.". Supportive Care in Cancer 15 (3): 259–264. doi:10.1007/s00520-006-0146-2. PMID 17039381.
^ http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html
^ Schnider, O.; Gr�Ssner, A. (1951). "Oxy-morphinane. (3. Mitteilung). Optisch aktive 3-Oxy-morphinane". Helvetica Chimica Acta 34 (7): 2211. doi:10.1002/hlca.19510340715. edit

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English Journal

Sulfation of opioid drugs by human cytosolic sulfotransferases: metabolic labeling study and enzymatic analysis.

Kurogi K1, Chepak A1, Hanrahan MT1, Liu MY2, Sakakibara Y3, Suiko M3, Liu MC4.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2014 Oct 1;62:40-8. doi: 10.1016/j.ejps.2014.05.003. Epub 2014 May 14.
The current study was designed to examine the sulfation of eight opioid drugs, morphine, hydromorphone, oxymorphone, butorphanol, nalbuphine, levorphanol, nalorphine, and naltrexone, in HepG2 human hepatoma cells and human organ samples (lung, liver, kidney, and small intestine) and to identify the
PMID 24832963

Point-of-care detection and real-time monitoring of intravenously delivered drugs via tubing with an integrated SERS sensor.

Wu HY1, Cunningham BT.
Nanoscale.Nanoscale.2014 May 21;6(10):5162-71. doi: 10.1039/c4nr00027g.
We demonstrate an approach for detection, identification, and kinetic monitoring of drugs flowing within tubing, through the use of a plasmonic nanodome array (PNA) surface. The PNA structures are fabricated using a low-cost nanoreplica molding process upon a flexible plastic substrate that is subse
PMID 24699532

Medication pain management in the elderly: unique and underutilized analgesic treatment options.

Atkinson TJ1, Fudin J, Pandula A, Mirza M.
Clinical therapeutics.Clin Ther.2013 Nov;35(11):1669-89. doi: 10.1016/j.clinthera.2013.09.008. Epub 2013 Oct 22.
BACKGROUND: By 2030, the US population of adults aged ≥65 years will increase by >80%, and these adults will account for nearly 20% of the US population. In this population, the decline of multiple physiologic processes and diseases collectively influence treatment options. Physiologic changes,
PMID 24161287

Japanese Journal

オピエートのフロンティア電子密度の統計解析

滋賀大学教育学部紀要. 3, 自然科学 54, 35-39, 2004
NAID 110001183530

オピエート分子の構造に関する理論的研究

情報化学討論会・構造活性相関シンポジウム講演要旨集 tokusi(0), JP31-JP31, 2001
NAID 130004575375

オピエート分子の構造に関する理論的研究

情報化学討論会講演要旨集 tokusi(0), JP31-JP31, 2001
NAID 130004575179

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★リンクテーブル★

リンク元	「オピオイド」「麻薬」「レボルファノール」
関連記事	「levorphan」

「オピオイド」

Levorphanol
Systematic (IUPAC) name
	17-methylmorphinan-3-ol
Clinical data
Trade names	Levo-dromoran
AHFS/Drugs.com	monograph
MedlinePlus	a682020
Pregnancy cat.	US: C;
Legal status	AU: Controlled (S8); CA: Schedule I; US: Schedule II; Class A (UK);
Dependence; liability	High
Routes	oral, intravenous, subcutaneous, intramuscular
Pharmacokinetic data
Bioavailability	70% (oral); 100% (IV)
Protein binding	40%
Metabolism	Hepatic
Half-life	11-16 hours
Identifiers
CAS number	77-07-6
ATC code	None
PubChem	CID 5359272
DrugBank	DB00854
ChemSpider	16736212
UNII	27618J1N2X
KEGG	D08123
ChEMBL	CHEMBL592
Chemical data
Formula	C17H23NO
Mol. mass	257.371 g/mol
	SMILES CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(O)C=C4;
	InChI InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1 ; Key:JAQUASYNZVUNQP-USXIJHARSA-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)