Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H23NO.ClH |
| Molecular Weight | 293.832 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]12CC3=C(C=C(O)C=C3)[C@]4(CCCC[C@@]14[H])CCN2C
InChI
InChIKey=MKMAMQPDRUXVSS-DYWKTHLTSA-N
InChI=1S/C17H23NO.ClH/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;1H/t14-,16+,17+;/m0./s1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| 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 Date-5.3585281E11 |
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 |
|
| Effect of prolyl-leucyl-glycinamide and alpha-melanocyte-stimulating hormone on levorphanol-induced analgesia, tolerance and dependence. | 1984 Jun 25 |
|
| 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 |
|
| Age-related differences in sensitivity to the antinociceptive effects of opioids in male rats. Influence of nociceptive intensity and intrinsic efficacy at the mu receptor. | 2001 Aug |
|
| Central discriminative effects of morphine in rats: training via intracerebroventricular administration. | 2001 Dec |
|
| The safety of dextromethorphan in pregnancy : results of a controlled study. | 2001 Feb |
|
| 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 |
|
| 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 |
|
| Antidepressant-like effect of tramadol and its enantiomers in reserpinized mice: comparative study with desipramine, fluvoxamine, venlafaxine and opiates. | 2004 Sep |
|
| 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 |
|
| Can levorphanol be used like methadone for intractable refractory pain? | 2007 Apr |
|
| 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 |
|
| High-affinity carbamate analogues of morphinan at opioid receptors. | 2007 Mar 15 |
|
| 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 |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
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| Record UNII |
1TNM58GT5U
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| Record Status |
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| Record Version |
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61734-47-2
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