Identification
- Summary
Levorphanol is an opioid analgesic used to treat moderate to severe pain.
- Generic Name
- Levorphanol
- DrugBank Accession Number
- DB00854
- Background
A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Levorphanol (DB00854)
- Weight
- Average: 257.3706
Monoisotopic: 257.177964363 - Chemical Formula
- C17H23NO
- Synonyms
- Levorfanol
- Levorfanolo
- Lévorphanol
- Levorphanol
- Levorphanolum
- External IDs
- Dea No. 9220
- Dea No. 9733
- IDS-NL-007
- RO 1-5431
Pharmacology
- Indication
For the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Levorphanol is a potent synthetic opioid analgesic indicated for the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate. Levorphanol is similar to morphine in its actions, however it is up to 8 times more potent than morphine. Levorphanol produces a degree of respiratory depression similar to that produced by morphine at equianalgesic doses, and like many mu-opioid drugs, levorphanol produces euphoria or has a positive effect on mood in many individuals.
- Mechanism of action
Like other mu-agonist opioids it is believed to act at receptors in the periventricular and periaqueductal gray matter in both the brain and spinal cord to alter the transmission and perception of pain.
Target Actions Organism AMu-type opioid receptor agonistHumans UDelta-type opioid receptor agonistHumans UKappa-type opioid receptor agonistHumans - Absorption
Levorphanol is well absorbed after PO administration with peak plasma concentrations occurring approximately 1 hour after dosing.
- Volume of distribution
- 10 to 13 L/kg
- Protein binding
40%
- Metabolism
Levorphanol is extensively metabolized in the liver and is eliminated as the glucuronide metabolite.
- Route of elimination
Not Available
- Half-life
11-16 hours
- Clearance
- 0.78 to 1.1 L/kg/hr
- Adverse Effects
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LD50=150 mg/kg (orally in rats). Signs of overdose include nausea, emesis, dizziness, respiratory depression, hypotension, urinary retention, cardiac arrhythmias, allergic reactions, skin rash, and uticaria.
- Pathways
Pathway Category Levorphanol Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Levorphanol is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Levorphanol. Acetophenazine The risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Levorphanol. Aclidinium The risk or severity of adverse effects can be increased when Aclidinium is combined with Levorphanol. Agomelatine The risk or severity of adverse effects can be increased when Levorphanol is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Levorphanol. Alimemazine The risk or severity of hypotension and CNS depression can be increased when Alimemazine is combined with Levorphanol. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Levorphanol. Almotriptan The risk or severity of adverse effects can be increased when Levorphanol is combined with Almotriptan. Alosetron The risk or severity of adverse effects can be increased when Levorphanol is combined with Alosetron. 
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- Avoid alcohol.
- Take with or without food. Food does not significantly affect absorption.
Products
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Ingredient UNII CAS InChI Key Levorphanol tartrate 04WQU6T9QI Not Available UMZNDVASJKIQCB-QLFXFZCRSA-N - International/Other Brands
- Aromarone
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Levo-Dromoran Injection, solution 2 mg/1mL Parenteral Valeant Pharmaceuticals North America 1953-01-08 2014-12-04 US 
Levo-Dromoran Injection, solution 2 mg/1mL Parenteral Valeant Pharmaceuticals North America 1953-01-08 2014-12-04 US Levo-Dromoran Tablet 2 mg/1 Oral Valeant Pharmaceuticals North America 1953-01-08 2014-12-04 US Levorphanol Tartrate Tablet 2 mg/1 Oral Roxane Laboratories, Inc. 2006-06-02 2006-06-02 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Levorphanol Tartrate Tablet 2 mg/1 Oral Virtus Pharmaceuticals, LLC 2018-12-13 2024-02-28 US Levorphanol Tartrate Tablet 2 mg/1 Oral SpecGx LLC 2019-12-13 Not applicable US Levorphanol Tartrate Tablet 2 mg/1 Oral bryant ranch prepack 2019-05-20 Not applicable US Levorphanol Tartrate Tablet 2 mg/1 Oral Lannett Company, Inc. 2019-05-20 Not applicable US Levorphanol Tartrate Tablet 1 mg/1 Oral Sentynl Therapeutics, Inc. 2018-06-18 2018-12-03 US Levorphanol Tartrate Tablet 3 mg/1 Oral Sentynl Therapeutics, Inc. 2018-06-18 2023-02-28 US Levorphanol Tartrate Tablet 2 mg/1 Oral Hikma Pharmaceuticals USA Inc. 2000-03-31 Not applicable US Levorphanol Tartrate Tablet 3 mg/1 Oral Lannett Company, Inc. 2020-01-12 Not applicable US Levorphanol Tartrate Tablet 2 mg/1 Oral Novitium Pharma Llc 2019-05-20 Not applicable US Levorphanol Tartrate Tablet 2 mg/1 Oral Sentynl Therapeutics, Inc. 2000-03-31 2023-10-31 US
Categories
- Drug Categories
- Alkaloids
- Analgesics
- Central Nervous System Agents
- Central Nervous System Depressants
- Heterocyclic Compounds, Fused-Ring
- Morphinans
- Narcotics
- Opiate Alkaloids
- Opioid Agonist
- Opioids
- Peripheral Nervous System Agents
- Phenanthrenes
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Morphinans
- Sub Class
- Not Available
- Direct Parent
- Morphinans
- Alternative Parents
- Phenanthrenes and derivatives / Benzazocines / Tetralins / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds show 1 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzazocine / Benzenoid / Hydrocarbon derivative / Morphinan / Organic nitrogen compound show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- morphinane alkaloid (CHEBI:6444)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 27618J1N2X
- CAS number
- 77-07-6
- InChI Key
- JAQUASYNZVUNQP-USXIJHARSA-N
- InChI
- 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
- IUPAC Name
- (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol
- SMILES
- [H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2
References
- Synthesis Reference
Joseph P. Haar, "Process for the Production of Levorphanol and Related Compounds." U.S. Patent US20080146805, issued June 19, 2008.
US20080146805- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014992
- KEGG Drug
- D08123
- KEGG Compound
- C08014
- PubChem Compound
- 5359272
- PubChem Substance
- 46506558
- ChemSpider
- 16736212
- BindingDB
- 50369518
- 6378
- ChEBI
- 6444
- ChEMBL
- CHEMBL592
- ZINC
- ZINC000003812984
- Therapeutic Targets Database
- DAP000268
- PharmGKB
- PA164744368
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Levorphanol
- MSDS
- Download (5.23 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Active Not Recruiting Supportive Care Hematopoietic and Lymphoid Cell Neoplasm / Malignant Solid Neoplasms / Metastatic Malignant Solid Neoplasms 1 Not Available Completed Not Available Pain, Chronic 1
Pharmacoeconomics
- Manufacturers
- Valeant pharmaceuticals international
- Roxane laboratories inc
- Packagers
- Cardinal Health
- Legacy Pharmaceuticals Packaging LLC
- Roxane Labs
- Valeant Ltd.
- Dosage Forms
Form Route Strength Injection, solution Parenteral 2 mg/1mL Tablet Oral 2 mg/1 Tablet Oral 1 mg/1 Tablet Oral 3 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 198-199 °C PhysProp water solubility 1840 mg/L Not Available logP 3.11 HANSCH,C ET AL. (1995) pKa 9.58 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.173 mg/mL ALOGPS logP 3.29 ALOGPS logP 2.9 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 10.46 Chemaxon pKa (Strongest Basic) 9.66 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 23.47 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 78.08 m3·mol-1 Chemaxon Polarizability 29.84 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9924 Blood Brain Barrier + 0.9953 Caco-2 permeable + 0.8767 P-glycoprotein substrate Substrate 0.8217 P-glycoprotein inhibitor I Non-inhibitor 0.7866 P-glycoprotein inhibitor II Non-inhibitor 0.935 Renal organic cation transporter Inhibitor 0.7666 CYP450 2C9 substrate Non-substrate 0.7467 CYP450 2D6 substrate Substrate 0.78 CYP450 3A4 substrate Substrate 0.7112 CYP450 1A2 substrate Non-inhibitor 0.6437 CYP450 2C9 inhibitor Non-inhibitor 0.9139 CYP450 2D6 inhibitor Inhibitor 0.7703 CYP450 2C19 inhibitor Non-inhibitor 0.8908 CYP450 3A4 inhibitor Non-inhibitor 0.8856 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9051 Ames test Non AMES toxic 0.5661 Carcinogenicity Non-carcinogens 0.9694 Biodegradation Not ready biodegradable 0.9681 Rat acute toxicity 2.9455 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6841 hERG inhibition (predictor II) Non-inhibitor 0.5153
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-0a4i-5930000000-4593c62f1e2a0579a248 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Allen RM, Granger AL, Dykstra LA: 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. J Pharmacol Exp Ther. 2003 Nov;307(2):785-92. Epub 2003 Sep 15. [Article]
- Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [Article]
Drug created at June 13, 2005 13:24 / Updated at March 03, 2023 17:46