U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C17H23NO
Molecular Weight 257.3706
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1953
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
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.
1984
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
1995 Sep
Pitfalls of opioid rotation: substituting another opioid for methadone in patients with cancer pain.
2002 Apr
Opioids and chronic neuropathic pain.
2003 Mar 27
Oral opioid therapy for chronic peripheral and central neuropathic pain.
2003 Mar 27
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey.
2003 May
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
[Fundamentals of modern treatment of myopia].
2005
Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor.
2005 Aug
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization.
2005 Jul
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.
2005 Oct
Opioid peptides and receptors in joint tissues: study in the rat.
2006 Jun
Levorphanol revisited.
2007 Dec
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
The effect of opiates on the activity of human placental aromatase/CYP19.
2007 Jan 15
Current aproach to cancer pain management: Availability and implications of different treatment options.
2007 Jun
Levorphanol: the forgotten opioid.
2007 Mar
High-affinity carbamate analogues of morphinan at opioid receptors.
2007 Mar 15
Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.
2007 May 31
Opiates and elderly: use and side effects.
2008
Effects of environmental enrichment on sensitivity to mu, kappa, and mixed-action opioids in female rats.
2008 Jul 5
Challenges in using opioids to treat pain in persons with substance use disorders.
2008 Jun
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.
2009 Sep
Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy.
2010 Feb
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.
2010 Jan
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:38:10 GMT 2023
Edited
by admin
on Sat Dec 16 17:38:10 GMT 2023
Record UNII
27618J1N2X
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
DEA NO. 9220
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
NDF-RT N0000175684
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
LIVERTOX NBK547967
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
NDF-RT N0000175690
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
NCI_THESAURUS C1506
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
Code System Code Type Description
CAS
77-07-6
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
HSDB
3349
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
RXCUI
6378
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL592
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
DAILYMED
27618J1N2X
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
WIKIPEDIA
LEVORPHANOL
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
FDA UNII
27618J1N2X
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
INN
91
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
NCI_THESAURUS
C61810
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
DRUG CENTRAL
1574
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
DRUG BANK
DB00854
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID3023213
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
PUBCHEM
5359272
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
MERCK INDEX
m6794
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY Merck Index
SMS_ID
100000082303
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
IUPHAR
7595
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
MESH
D007981
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
EVMPD
SUB08490MIG
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-002-6
Created by admin on Sat Dec 16 17:38:12 GMT 2023 , Edited by admin on Sat Dec 16 17:38:12 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY