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
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 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 |
---|---|---|---|
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 |
---|---|---|
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 |
|
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 |
|
Opioids and chronic neuropathic pain. | 2003 Mar 27 |
|
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 |
|
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis. | 2004 May |
|
[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 |
|
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 |
|
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 |
|
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 |
|
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
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
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Record UNII |
27618J1N2X
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Record Status |
Validated (UNII)
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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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3349
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6378
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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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201-002-6
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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Related Record | Type | Details | ||
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ACTIVE MOIETY |