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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO
Molecular Weight 257.3706
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVORPHANOL

SMILES

[H][C@@]12CCCC[C@@]13CCN(C)[C@@H]2CC4=C3C=C(O)C=C4

InChI

InChIKey=JAQUASYNZVUNQP-USXIJHARSA-N
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

HIDE SMILES / InChI
Levorphanol, brand name Levo-Dromoran, is an opioid medication used to treat moderate to severe pain. Levorphanol is indicated for the management of moderate to severe pain where an opioid analgesic is appropriate. It is a potent synthetic opioid mu-receptor agonist similar in action to morphine. Like other opioid mu-receptor agonists, it is believed to act at receptors in both the brain and spinal cord to alter the transmission and perception of pain. The onset and peak analgesic effects following administration of levorphanol are similar to morphine when administered at equal analgesic doses. Levorphanol produces a degree of respiratory depression similar to that produced by morphine at equal analgesic doses, and like many opioid mu-receptor agonists, levorphanol produces euphoria or has a positive effect on mood in many individuals.

Originator

Curator's Comment: Levorphanol was initially synthesized in Germany in 1946

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Levorphanol Tartrate

Approved Use

Levorphanol Tartrate Tablets are indicated for the management of pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate.

Launch Date

-5.3585281E11
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 11.5 uM]
yes [IC50 >50 uM]
Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates.
1982 Jan
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.
1991 Mar-Apr
Pitfalls of opioid rotation: substituting another opioid for methadone in patients with cancer pain.
2002 Apr
Antidepressant-like effects of tramadol and other central analgesics with activity on monoamines reuptake, in helpless rats.
2002 Nov 29
Sex-related differences in mechanical nociception and antinociception produced by mu- and kappa-opioid receptor agonists in rats.
2002 Oct 4
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence.
2003 Aug
Differential effects of agonists on adenylyl cyclase superactivation mediated by the kappa opioid receptors: adenylyl cyclase superactivation is independent of agonist-induced phosphorylation, desensitization, internalization, and down-regulation.
2003 Dec
Opioids and chronic neuropathic pain.
2003 Mar 27
Oral opioid therapy for chronic peripheral and central neuropathic pain.
2003 Mar 27
Opioids ease neuropathic pain, but..
2003 May
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor.
2003 May
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey.
2003 May
Differential regulation of the human kappa opioid receptor by agonists: etorphine and levorphanol reduced dynorphin A- and U50,488H-induced internalization and phosphorylation.
2003 May
The competitive N-methyl-D-aspartate receptor antagonist (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959) potentiates the antinociceptive effects of opioids that vary in efficacy at the mu-opioid receptor.
2003 Nov
10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.
2004 Jan 1
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis.
2004 May
Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor.
2005 Aug
Analgesic therapy in postherpetic neuralgia: a quantitative systematic review.
2005 Jul
Restless legs syndrome: diagnosis and review of management options.
2006 Jun
Can levorphanol be used like methadone for intractable refractory pain?
2007 Apr
Role of atypical opiates in OCD. Experimental approach through the study of 5-HT(2A/C) receptor-mediated behavior.
2007 Feb
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
Does purity of supplements count?
2007 Jan
Current aproach to cancer pain management: Availability and implications of different treatment options.
2007 Jun
Chronic morphine treatment up-regulates mu opioid receptor binding in cells lacking filamin A.
2007 Oct 26
Opiates and elderly: use and side effects.
2008
Challenges in using opioids to treat pain in persons with substance use disorders.
2008 Jun
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.
2009 Jun 30
Somatostatin and opioid receptors do not regulate proliferation or apoptosis of the human multiple myeloma U266 cells.
2009 Jun 7
Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: ligands for mu, kappa, and delta opioid receptors.
2010 Jan 14
Patents

Sample Use Guides

Usual Adult Dose for Light Sedation Premedication for Anesthesia: 1 to 2 mg IM or subcutaneously, administered 60 to 90 minutes before surgery. Older or debilitated patients usually require less drug. Two mg of levorphanol is approximately equivalent to 10 to 15 mg of morphine or 100 mg of meperidine. Usual Adult Dose for Pain IV: 1 mg every 3 to 6 hours as needed. IM or subcutaneous: 1 to 2 mg every 6 to 8 hours as needed. Oral: 2 mg every 6 to 8 hours as needed. May be increased to 3 mg every 6 to 8 hours.
Route of Administration: Other
In Vitro Use Guide
Levorphanol (5-100 uM), consistently depressed the responses evoked by the putative inhibitory amino acid neurotransmitters glycine and beta-alanine but not GABA in cultured mouse spinal cord neurons.
Name Type Language
LEVORPHANOL
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Levorphanol [WHO-DD]
Common Name English
LEVORPHANOL [HSDB]
Common Name English
LEVORPHANOL [MI]
Common Name English
RO 1-5431
Code English
levorphanol [INN]
Common Name English
IDS-NL-007
Code English
LEVORPHANOL [VANDF]
Common Name English
LEVORPHAN
Common Name English
17-METHYLMORPHINAN-3-OL
Systematic Name English
2H-10,4A-IMINOETHANOPHENANTHREN-6-OL, 1,3,4,9,10,10A-HEXAHYDRO-11-METHYL-
Systematic Name English
(-)-3-HYDROXY-N-METHYLMORPHINAN
Systematic Name English
N-METHYL-3-HYDROXYMORPHINAN
Systematic Name English
AROMARONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
DEA NO. 9220
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
NDF-RT N0000175684
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
LIVERTOX NBK547967
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
NDF-RT N0000175690
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
NCI_THESAURUS C1506
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
Code System Code Type Description
CAS
77-07-6
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
HSDB
3349
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
RXCUI
6378
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL592
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
DAILYMED
27618J1N2X
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
WIKIPEDIA
LEVORPHANOL
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
FDA UNII
27618J1N2X
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
INN
91
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
NCI_THESAURUS
C61810
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
DRUG CENTRAL
1574
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
DRUG BANK
DB00854
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID3023213
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
PUBCHEM
5359272
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
MERCK INDEX
M6794
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY Merck Index
SMS_ID
100000082303
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
IUPHAR
7595
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
MESH
D007981
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
EVMPD
SUB08490MIG
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-002-6
Created by admin on Thu Jul 06 22:59:42 UTC 2023 , Edited by admin on Thu Jul 06 22:59:42 UTC 2023
PRIMARY