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 |
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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 |
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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 |
---|---|---|
Prostaglandin hyperalgesia, V: a peripheral analgesic receptor for opiates. | 1982 Jan |
|
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. | 1995 Sep |
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Clinical pharmacology of opioids for pain. | 2002 Jul-Aug |
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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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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 |
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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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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 |
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Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis. | 2004 May |
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[Fundamentals of modern treatment of myopia]. | 2005 |
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Social and environmental influences on opioid sensitivity in rats: importance of an opioid's relative efficacy at the mu-receptor. | 2005 Aug |
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Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output. | 2006 Sep |
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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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The effect of opiates on the activity of human placental aromatase/CYP19. | 2007 Jan 15 |
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Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol. | 2007 May 31 |
|
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.
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NCI_THESAURUS |
C67413
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DEA NO. |
9220
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N0000175684
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NBK547967
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N0000175690
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C1506
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CHEMBL592
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27618J1N2X
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LEVORPHANOL
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m6794
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100000082303
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7595
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201-002-6
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ACTIVE MOIETY
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