Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H23NO.C4H6O6.2H2O |
| Molecular Weight | 443.488 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.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=UMZNDVASJKIQCB-QLFXFZCRSA-N
InChI=1S/C17H23NO.C4H6O6.2H2O/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);2*1H2/t14-,16+,17+;1-,2-;;/m01../s1
| 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 |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL233 |
0.21 nM [Ki] | ||
Target ID: CHEMBL236 |
4.2 nM [Ki] | ||
Target ID: CHEMBL237 |
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 |
|---|---|---|---|
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 |
|---|---|---|
| Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine. | 1984 |
|
| Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist. | 1991 Mar-Apr |
|
| Clinical pharmacology of opioids for pain. | 2002 Jul-Aug |
|
| 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 |
|
| The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity. | 2003 Jan 2 |
|
| Discrimination of a single dose of morphine followed by naltrexone: substitution of other agonists for morphine and other antagonists for naltrexone in a rat model of acute dependence. | 2003 Mar |
|
| 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 |
|
| Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates. | 2004 Sep |
|
| [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 |
|
| 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 |
|
| Restless legs syndrome: diagnosis and review of management options. | 2006 Jun |
|
| 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 |
|
| Can levorphanol be used like methadone for intractable refractory pain? | 2007 Apr |
|
| 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 |
|
| 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 |
|
| An evaluation of the genotoxicity of the antitussive drug Dextromethorphan. | 2008 Apr |
|
| 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 |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:33:59 GMT 2023
by
admin
on
Fri Dec 15 15:33:59 GMT 2023
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| Record UNII |
04WQU6T9QI
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| Record Status |
Validated (UNII)
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| Record Version |
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C1506
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C67413
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5985-38-6
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100000086127
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m6794
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6700-40-9
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153973
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5985-51-3
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5462348
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C47586
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CHEMBL592
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