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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO.C4H6O6
Molecular Weight 407.4575
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVORPHANOL TARTRATE ANHYDROUS

SMILES

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

InChI

InChIKey=RWTWIZDKEIWLKQ-IWWMGODWSA-N
InChI=1S/C17H23NO.C4H6O6/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17;5-1(3(7)8)2(6)4(9)10/h5-6,11,14,16,19H,2-4,7-10H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t14-,16+,17+;1-,2-/m01/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

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
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
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.
1991 Mar-Apr
Age-related differences in sensitivity to the antinociceptive effects of opioids in male rats. Influence of nociceptive intensity and intrinsic efficacy at the mu receptor.
2001 Aug
Clinical pharmacology of opioids for pain.
2002 Jul-Aug
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
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
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
Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output.
2006 Sep
Levorphanol revisited.
2007 Dec
Does purity of supplements count?
2007 Jan
A retrospective study on the impact of comorbid depression or anxiety on healthcare resource use and costs among diabetic neuropathy patients.
2009 Jun 30
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.
2009 Sep
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.
2010 Jan
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 Fri Dec 15 15:49:33 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:33 GMT 2023
Record UNII
WCB1I20F1K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVORPHANOL TARTRATE ANHYDROUS
Common Name English
NSC-91012
Code English
Levorphanol tartrate [WHO-DD]
Common Name English
MORPHINAN-3-OL, 17-METHYL-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT)
Common Name English
17-METHYLMORPHINAN-3-OL, TARTRATE (1:1) (SALT)
Common Name English
Code System Code Type Description
CAS
125-72-4
Created by admin on Fri Dec 15 15:49:33 GMT 2023 , Edited by admin on Fri Dec 15 15:49:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID30924987
Created by admin on Fri Dec 15 15:49:33 GMT 2023 , Edited by admin on Fri Dec 15 15:49:33 GMT 2023
PRIMARY
FDA UNII
WCB1I20F1K
Created by admin on Fri Dec 15 15:49:33 GMT 2023 , Edited by admin on Fri Dec 15 15:49:33 GMT 2023
PRIMARY
NSC
91012
Created by admin on Fri Dec 15 15:49:33 GMT 2023 , Edited by admin on Fri Dec 15 15:49:33 GMT 2023
PRIMARY
PUBCHEM
5464027
Created by admin on Fri Dec 15 15:49:33 GMT 2023 , Edited by admin on Fri Dec 15 15:49:33 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-753-8
Created by admin on Fri Dec 15 15:49:33 GMT 2023 , Edited by admin on Fri Dec 15 15:49:33 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY