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
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 |
|---|---|---|
| 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 |
|
| 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 |
|
| Pitfalls of opioid rotation: substituting another opioid for methadone in patients with cancer pain. | 2002 Apr |
|
| Interface for coupling nonaqueous wide-bore capillary electrophoresis with mass spectrometry. | 2002 Feb |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Analgesic therapy in postherpetic neuralgia: a quantitative systematic review. | 2005 Jul |
|
| Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output. | 2006 Sep |
|
| Levorphanol revisited. | 2007 Dec |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2010 Feb |
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
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1506
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NCI_THESAURUS |
C67413
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5985-38-6
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100000086127
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m6794
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DTXSID30975252
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DBSALT000935
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04WQU6T9QI
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6700-40-9
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04WQU6T9QI
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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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1364007
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SUB02914MIG
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CHEMBL592
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
