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
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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 |
0.21 nM [Ki] | ||
Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381 |
4.2 nM [Ki] | ||
Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17039381 |
2.3 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Levorphanol Tartrate Approved UseLevorphanol 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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator​
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 11.5 uM] | ||||
yes [IC50 >50 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys. | 1981 |
|
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 |
|
Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence. | 1984 Jun 25 |
|
Baclofen-induced catatonia. | 1986 Dec |
|
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist. | 1991 Mar-Apr |
|
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. | 1995 Sep |
|
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 |
|
Central discriminative effects of morphine in rats: training via intracerebroventricular administration. | 2001 Dec |
|
The safety of dextromethorphan in pregnancy : results of a controlled study. | 2001 Feb |
|
Sex-related differences in mechanical nociception and antinociception produced by mu- and kappa-opioid receptor agonists in rats. | 2002 Oct 4 |
|
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 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 |
|
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 |
|
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis. | 2004 May |
|
Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates. | 2004 Sep |
|
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 |
|
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 |
|
Can levorphanol be used like methadone for intractable refractory pain? | 2007 Apr |
|
Levorphanol revisited. | 2007 Dec |
|
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 |
|
High-affinity carbamate analogues of morphinan at opioid receptors. | 2007 Mar 15 |
|
Morphine reduces local cytokine expression and neutrophil infiltration after incision. | 2007 Oct 2 |
|
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 |
|
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 |
|
Opioid pharmacology. | 2008 Mar |
|
Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor. | 2009 Sep |
|
Acute pain management in children. | 2010 Jul 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/levorphanol.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7284815
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
Edited
Wed Jul 05 23:18:01 UTC 2023
by
admin
on
Wed Jul 05 23:18:01 UTC 2023
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Record UNII |
WCB1I20F1K
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Record Status |
Validated (UNII)
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Record Version |
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |