levorphanol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
opioid receptor antagonists/agonists, morphinan derivates 1574 77-07-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • levorphanol
  • racemorphan
  • aromarone
  • levorphan
  • N-Methyl-3-hydroxymorphinan
  • levorphanol tartrate
  • levo-dromoran
A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection.
  • Molecular weight: 257.38
  • Formula: C17H23NO
  • CLOGP: 3.53
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 23.47
  • ALOGS: -3.17
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.58 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 11.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 15.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.60 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 13.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 8, 1953 FDA VALEANT PHARM INTL

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009294 Narcotics
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
General anesthesia indication 50697003
Local anesthesia indication 386761002
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
Alcohol withdrawal delirium contraindication 8635005
Asthenia contraindication 13791008
Constipation contraindication 14760008 DOID:2089
Mood swings contraindication 18963009
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Hypercapnia contraindication 29596007
Dehydration contraindication 34095006
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Bradycardia contraindication 48867003
Ulcerative colitis contraindication 64766004 DOID:8577
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Urethral stricture contraindication 76618002
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Cor pulmonale contraindication 83291003 DOID:8515
Pulmonary emphysema contraindication 87433001
Kidney disease contraindication 90708001 DOID:557
Acute abdominal pain contraindication 116290004
Neoplasm of brain contraindication 126952004 DOID:1319
Seizure disorder contraindication 128613002
Drug-induced psychosis contraindication 191483003 DOID:1742
Disease of liver contraindication 235856003 DOID:409
Morbid obesity contraindication 238136002 DOID:11981
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Exacerbation of asthma contraindication 281239006
Lesion of brain contraindication 301766008
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Central nervous system depression contraindication 418072004
Dysfunction of sphincter of Oddi contraindication 430887001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.05 acidic
pKa2 9.55 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Mu-type opioid receptor GPCR AGONIST Ki 9.68 CHEMBL CHEMBL
Delta-type opioid receptor GPCR Ki 8.38 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 4.60 CHEMBL
Glutamate [NMDA] receptor Ion channel IC50 5.60 CHEMBL
Kappa-type opioid receptor GPCR Ki 8.64 CHEMBL
Kappa-type opioid receptor GPCR Ki 8.64 CHEMBL
Acetylcholinesterase Enzyme Ki 4.60 CHEMBL
Mu-type opioid receptor GPCR Ki 9.52 CHEMBL
Kappa-type opioid receptor GPCR Ki 8 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 8.72 CHEMBL
Glutamate NMDA receptor Ion channel IC50 5.92 CHEMBL
Mu-type opioid receptor GPCR Ki 9.68 CHEMBL
Opioid receptor GPCR EC50 9.15 CHEMBL

External reference:

IDSource
4019801 VUID
N0000147890 NUI
D00841 KEGG_DRUG
5985-38-6 SECONDARY_CAS_RN
4017787 VANDF
4019801 VANDF
C1450007 UMLSCUI
CHEBI:6444 CHEBI
CHEMBL2062261 ChEMBL_ID
CHEMBL3989768 ChEMBL_ID
CHEMBL592 ChEMBL_ID
CHEMBL20803 ChEMBL_ID
5359272 PUBCHEM_CID
D007981 MESH_DESCRIPTOR_UI
DB00854 DRUGBANK_ID
7595 IUPHAR_LIGAND_ID
91 INN_ID
28 INN_ID
27618J1N2X UNII
153973 RXNORM
1811 MMSL
1836 MMSL
4975 MMSL
d00825 MMSL
001563 NDDF
004625 NDDF
387275004 SNOMEDCT_US
50335004 SNOMEDCT_US
67347006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 0406-2224 TABLET 2 mg ORAL ANDA 30 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 0527-3236 TABLET 2 mg ORAL ANDA 26 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 0527-3237 TABLET 3 mg ORAL ANDA 26 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 42358-101 TABLET 1 mg ORAL ANDA 30 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 42358-102 TABLET 2 mg ORAL ANDA 30 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 42358-103 TABLET 3 mg ORAL ANDA 30 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 57664-762 TABLET 2 mg ORAL ANDA 25 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 63629-2093 TABLET 2 mg ORAL ANDA 26 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 69543-412 TABLET 2 mg ORAL ANDA 29 sections
Levorphanol Tartrate HUMAN PRESCRIPTION DRUG LABEL 1 69543-417 TABLET 2 mg ORAL ANDA 29 sections