Details
| Stereochemistry | RACEMIC |
| Molecular Formula | 2C17H23NO.2BrH.H2O |
| Molecular Weight | 694.58 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Br.Br.[H][C@@]12CC3=C(C=C(O)C=C3)[C@]4(CCCC[C@@]14[H])CCN2C.[H][C@@]56CC7=C(C=C(O)C=C7)[C@]8(CCCC[C@@]58[H])CCN6C
InChI
InChIKey=YJHAKXBQBWSVOL-BYVCFMHPSA-N
InChI=1S/2C17H23NO.2BrH.H2O/c2*1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17;;;/h2*5-6,11,14,16,19H,2-4,7-10H2,1H3;2*1H;1H2/t2*14-,16+,17+;;;/m00.../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 |
|
| Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine. | 1984 |
|
| Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence. | 1984 Jun 25 |
|
| 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 |
|
| Clinical pharmacology of opioids for pain. | 2002 Jul-Aug |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis. | 2004 May |
|
| [Fundamentals of modern treatment of myopia]. | 2005 |
|
| Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey: a further characterization. | 2005 Jul |
|
| Restless legs syndrome: diagnosis and review of management options. | 2006 Jun |
|
| Chronic exercise decreases sensitivity to mu opioids in female rats: correlation with exercise output. | 2006 Sep |
|
| Current aproach to cancer pain management: Availability and implications of different treatment options. | 2007 Jun |
|
| 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 |
|
| Opiates and elderly: use and side effects. | 2008 |
|
| Challenges in using opioids to treat pain in persons with substance use disorders. | 2008 Jun |
|
| Preoperative oral dextromethorphan does not reduce pain or morphine consumption after open cholecystectomy. | 2009 Jul |
|
| 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 |
|
| Acute pain management in children. | 2010 Jul 15 |
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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5964-68-1
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121493154
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V6H50N056L
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
