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
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
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 Date1953 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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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 |
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Comparison of opioid agonists in maintaining responding and in suppressing morphine withdrawal in rhesus monkeys. | 1981 |
|
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine. | 1984 |
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Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist. | 1991 Mar-Apr |
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Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. | 1995 Sep |
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Central discriminative effects of morphine in rats: training via intracerebroventricular administration. | 2001 Dec |
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Pitfalls of opioid rotation: substituting another opioid for methadone in patients with cancer pain. | 2002 Apr |
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Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence. | 2003 Aug |
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Opioids and chronic neuropathic pain. | 2003 Mar 27 |
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Oral opioid therapy for chronic peripheral and central neuropathic pain. | 2003 Mar 27 |
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Opioids ease neuropathic pain, but.. | 2003 May |
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Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor. | 2003 May |
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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 |
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Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates. | 2004 Sep |
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Analgesic therapy in postherpetic neuralgia: a quantitative systematic review. | 2005 Jul |
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Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization. | 2005 Jul |
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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 |
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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 |
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Does purity of supplements count? | 2007 Jan |
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The effect of opiates on the activity of human placental aromatase/CYP19. | 2007 Jan 15 |
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Levorphanol: the forgotten opioid. | 2007 Mar |
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Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol. | 2007 May 31 |
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Morphine reduces local cytokine expression and neutrophil infiltration after incision. | 2007 Oct 2 |
|
Opiates and elderly: use and side effects. | 2008 |
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An evaluation of the genotoxicity of the antitussive drug Dextromethorphan. | 2008 Apr |
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Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2009 Jul |
|
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 |
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.
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C67413
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9220
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N0000175684
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NBK547967
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C1506
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27618J1N2X
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LEVORPHANOL
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ACTIVE MOIETY
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