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Identification
NameNaloxone
Accession NumberDB01183  (APRD00025)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionA specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.
Structure
Thumb
Synonyms
1-N-Allyl-14-hydroxynordihydromorphinone
17-Allyl-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one
EN 1530 Base
L-Naloxone
N-Allylnoroxymorphone
Nalossone
Naloxona
Naloxone
Naloxonum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EvzioInjection, solution2 mg/.4mLIntramuscular; Subcutaneouskaleo, Inc.2016-10-19Not applicableUs
EvzioInjection, solution.4 mg/1Intramuscular; Subcutaneouskaleo, Inc.2014-04-03Not applicableUs
Naloxone HCl Injection - 0.4mg/ml USPLiquid0.4 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated1995-12-31Not applicableCanada
Naloxone HCl Injection - 1mg/ml USPLiquid1 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated1995-12-31Not applicableCanada
Naloxone Hydrochloride InjectionSolution1 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2013-10-10Not applicableCanada
Naloxone Hydrochloride InjectionSolution0.4 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2013-10-03Not applicableCanada
Naloxone Hydrochloride Injection Sdz Preservative FreeSolution0.4 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated2013-07-10Not applicableCanada
Naloxone Hydrochloride Injection USPSolution0.4 mgIntramuscular; Intravenous; SubcutaneousTeligent Ou2014-01-09Not applicableCanada
Naloxone Hydrochloride Nasal SpraySpray, metered2 mgNasalAdapt Pharma Operations LimitedNot applicableNot applicableCanada
Naloxone Hydrochloride Nasal SpraySpray, metered4 mgNasalAdapt Pharma Operations LimitedNot applicableNot applicableCanada
NarcanSpray4 mg/.1mLNasalLake Erie Medical DBA Quality Care Products LLC2015-11-18Not applicableUs
NarcanSpray4 mg/.1mLNasalAdapt Pharma, Inc.2015-11-18Not applicableUs
Narcan Injection 0.02mg/mlLiquid0.02 mgIntramuscular; Intravenous; SubcutaneousBristol Myers Squibb Canada1993-12-312004-08-05Canada
Narcan Injection 0.4mg/mlSolution0.4 mgIntramuscular; Intravenous; SubcutaneousBristol Myers Squibb Canada1992-12-312004-08-05Canada
Narcan Injection 1mg/mlLiquid1 mgIntramuscular; Intravenous; SubcutaneousBristol Myers Squibb Canada1992-12-312004-08-04Canada
S.O.S. Naloxone Hydrochloride InjectionSolution1 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada IncorporatedNot applicableNot applicableCanada
S.O.S. Naloxone Hydrochloride InjectionSolution0.4 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated2016-06-21Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousMylan Institutional LLC2014-12-17Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines, Inc.2014-05-07Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.1987-01-072016-10-13Us
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousA S Medication Solutions2005-07-12Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousCardinal Health2011-07-08Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousMylan Institutional LLC2016-09-14Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousPhysicians Total Care, Inc.2000-06-15Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousTYA Pharmaceuticals1986-09-24Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralREMEDYREPACK INC.2013-06-122016-04-05Us
Naloxone HydrochlorideInjection1 mg/mLParenteralGeneral Injectables & Vaccines, Inc.2010-12-27Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.1987-01-07Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralAmphastar Pharmaceuticals, Inc.1988-04-01Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousCardinal Health2012-03-06Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralInternational Medication Systems, Limited2016-07-28Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralPhysicians Total Care, Inc.2011-05-05Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousSina Health Inc1987-01-07Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralGeneral Injectables & Vaccines, Inc2012-08-29Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.1987-01-07Not applicableUs
Naloxone HydrochlorideInjection.4 mg/mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines, Inc2010-03-01Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralREMEDYREPACK INC.2015-03-07Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralAmphastar Pharmaceuticals, Inc.2001-06-01Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralInternational Medication Systems, Limited1988-04-01Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralCardinal Health2001-06-01Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousMylan Institutional LLC2014-03-06Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines, Inc2010-08-01Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.1986-09-24Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralGeneral Injectables & Vaccines, Inc2013-12-06Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousMc Kesson Packaging Services Business Unit Of Mc Kesson Corporation2010-05-03Not applicableUs
Naloxone HydrochlorideInjection.4 mg/mLIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceuticals Corp.1986-09-24Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralInternational Medication Systems, Limited2001-06-01Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousCardinal Health2011-07-08Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Injectable Naloxone HydrochlorideSolution0.4 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2016-08-05Not applicableCanada
Unapproved/Other Products Not Available
International Brands
NameCompany
NaloneNot Available
NarcanNot Available
NarcantiNot Available
NarconNot Available
Brand mixtures
NameLabellerIngredients
Act Buprenorphine/naloxoneActavis Pharma Company
BunavailBio Delivery Sciences International, Inc.
Buprenorphine and NaloxoneHi Tech Pharmacal Co., Inc.
Buprenorphine HCl and Naloxone HClMallinckrodt, Inc.
Buprenorphine Hydrochloride and Naloxone Hydrochloride DihydrateWest Ward Pharmaceuticals Corp
Mylan-buprenorphine/naloxoneMylan Pharmaceuticals Ulc
Pentazocine and NaloxoneLake Erie Medical & Surgical Supply DBA Quality Care Products LLC
Pentazocine HCl and Naloxone HClSTAT Rx USA LLC
Pentazocine Hydrochloride and Naloxone HydrochlorideGAVIS Pharmaceuticals, LLC
SuboxoneLake Erie Medical & Surgical Supply DBA Quality Care Products LLC
TarginPurdue Pharma
Teva-buprenorphine/naloxoneTeva Canada Limited
ZubsolvOrexo Us, Inc.
Salts
Name/CASStructureProperties
Naloxone Hydrochloride
Thumb
  • InChI Key: RGPDIGOSVORSAK-STHHAXOLSA-N
  • Monoisotopic Mass: 363.123735904
  • Average Mass: 363.835
DBSALT000126
Naloxone hydrochloride dihydrate
ThumbNot applicableDBSALT001497
Categories
UNII36B82AMQ7N
CAS number465-65-6
WeightAverage: 327.3743
Monoisotopic: 327.147058165
Chemical FormulaC19H21NO4
InChI KeyUZHSEJADLWPNLE-GRGSLBFTSA-N
InChI
InChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1
IUPAC Name
(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O
Pharmacology
IndicationFor the complete or partial reversal of narcotic depression, including respiratory depression, induced by opioids including natural and synthetic narcotics, propoxyphene, methadone and the narcotic-antagonist analgesics: nalbuphine, pentazocine and butorphanol. It is also indicated for the diagnosis of suspected acute opioid overdose. It may also be used as an adjunctive agent to increase blood pressure in the management of septic shock.
Structured Indications
PharmacodynamicsNaloxone is an opiate antagonist and prevents or reverses the effects of opioids including respiratory depression, sedation and hypotension. Also, it can reverse the psychotomimetic and dysphoric effects of agonist-antagonists such as pentazocine. Naloxone is an essentially pure narcotic antagonist, i.e., it does not possess the "agonistic" or morphine-like properties characteristic of other narcotic antagonists; naloxone does not produce respiratory depression, psychotomimetic effects or pupillary constriction. In the absence of narcotics or agonistic effects of other narcotic antagonists, it exhibits essentially no pharmacologic activity. When given intravenously, the onset of action is apparent within 2 minutes. The onset of action is slower if given subcutaneously or intramuscularly. The duration of action also differs between sites of injection and dose.
Mechanism of actionWhile the mechanism of action of naloxone is not fully understood, the preponderance of evidence suggests that naloxone antagonizes the opioid effects by competing for the same receptor sites, especially the opioid mu receptor. Recently, naloxone has been shown to bind all three opioid receptors (mu, kappa and gamma) but the strongest binding is to the mu receptor.
TargetKindPharmacological actionActionsOrganismUniProt ID
Mu-type opioid receptorProteinyes
antagonist
HumanP35372 details
Delta-type opioid receptorProteinyes
antagonist
HumanP41143 details
Kappa-type opioid receptorProteinyes
antagonist
HumanP41145 details
Cyclic AMP-responsive element-binding protein 1Proteinno
other/unknown
HumanP16220 details
Estrogen receptorProteinno
antagonist
other/unknown
HumanP03372 details
Toll-like receptor 4Proteinunknown
inhibitor
HumanO00206 details
Related Articles
AbsorptionWell absorbed following intramuscular injection.
Volume of distribution

Following parenteral administration naloxone hydrochloride is rapidly distributed in the body. Naloxone is also very lipophillic and easily crosses the blood-brain-barrier. It can also cross the placenta.

Protein bindingPlasma protein binding occurs but is relatively weak. Plasma albumin is the major binding constituent but significant binding of naloxone also occurs to plasma constituents other than albumin.
Metabolism

Naloxone is hepatically metabolized and primarily undergoes glucuronidation to form naloxone-3-glucuronide.

Route of eliminationUrine (25%- 40% is excreted as metabolites within 6 hours)
Half lifeAdults = 30-81 minutes; Neonates = 3.1 ± 0.5 hours.
ClearanceNot Available
ToxicityLD50, IV administration, mouse = 150 ± 5 mg/kg; LD50, IV administration, rat = 109 ± 4 mg/kg;
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Naloxone Action PathwayDrug actionSMP00688
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Naloxone can be increased when it is combined with Abiraterone.Approved
AcetaminophenThe serum concentration of Naloxone can be increased when it is combined with Acetaminophen.Approved
AfatinibThe serum concentration of Naloxone can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Naloxone can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Naloxone can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Naloxone can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Naloxone can be increased when it is combined with Alfentanil.Approved, Illicit
AmantadineThe serum concentration of Naloxone can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Naloxone can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe metabolism of Naloxone can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Naloxone can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Naloxone can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Naloxone can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Naloxone can be increased when it is combined with Amsacrine.Approved
AprepitantThe serum concentration of Naloxone can be increased when it is combined with Aprepitant.Approved, Investigational
AstemizoleThe serum concentration of Naloxone can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe metabolism of Naloxone can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Naloxone can be increased when it is combined with Atenolol.Approved
AtomoxetineThe metabolism of Naloxone can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe serum concentration of Naloxone can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Naloxone can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Naloxone can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Naloxone can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Naloxone can be increased when it is combined with Bepridil.Approved, Withdrawn
BexaroteneThe serum concentration of Naloxone can be decreased when it is combined with Bexarotene.Approved, Investigational
BiperidenThe serum concentration of Naloxone can be increased when it is combined with Biperiden.Approved
BoceprevirThe metabolism of Naloxone can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Naloxone can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Naloxone can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Naloxone can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Naloxone can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Naloxone can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Naloxone can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe serum concentration of Naloxone can be increased when it is combined with Cabazitaxel.Approved
CaffeineThe serum concentration of Naloxone can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Naloxone can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Naloxone can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Naloxone can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Naloxone can be increased when combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Naloxone can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Naloxone can be increased when it is combined with Caspofungin.Approved
CelecoxibThe metabolism of Naloxone can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Naloxone can be increased when it is combined with Ceritinib.Approved
ChloroquineThe serum concentration of Naloxone can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Naloxone can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Naloxone can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Naloxone can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
CholesterolThe serum concentration of Naloxone can be increased when it is combined with Cholesterol.Experimental
Cholic AcidThe serum concentration of Naloxone can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Naloxone can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Naloxone can be decreased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Naloxone can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Naloxone can be increased when it is combined with Citalopram.Approved
ClarithromycinThe metabolism of Naloxone can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Naloxone can be decreased when combined with Clemastine.Approved
ClofazimineThe serum concentration of Naloxone can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Naloxone can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClopidogrelThe metabolism of Naloxone can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Naloxone can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Naloxone can be decreased when combined with Cobicistat.Approved
ColchicineThe serum concentration of Naloxone can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Naloxone can be increased when it is combined with Colforsin.Experimental
ConivaptanThe serum concentration of Naloxone can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Naloxone can be decreased when combined with Crizotinib.Approved
CyclophosphamideThe serum concentration of Naloxone can be increased when it is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe metabolism of Naloxone can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Naloxone can be decreased when it is combined with Dabrafenib.Approved
DaclatasvirThe serum concentration of Naloxone can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Naloxone can be increased when it is combined with Dactinomycin.Approved
DarunavirThe metabolism of Naloxone can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Naloxone can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Naloxone can be decreased when it is combined with Daunorubicin.Approved
DeferasiroxThe serum concentration of Naloxone can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Naloxone can be decreased when combined with Delavirdine.Approved
DesipramineThe serum concentration of Naloxone can be increased when it is combined with Desipramine.Approved
DesloratadineThe serum concentration of Naloxone can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Naloxone can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Naloxone can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Naloxone can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigoxinThe serum concentration of Naloxone can be decreased when it is combined with Digoxin.Approved
DihydroergotamineThe metabolism of Naloxone can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Naloxone can be decreased when combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Naloxone can be increased when it is combined with Dipyridamole.Approved
DoxazosinThe serum concentration of Naloxone can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Naloxone can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Naloxone can be decreased when it is combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Naloxone can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronabinolThe serum concentration of Naloxone can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe metabolism of Naloxone can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Naloxone can be decreased when it is combined with Efavirenz.Approved, Investigational
ElbasvirThe serum concentration of Naloxone can be increased when it is combined with Elbasvir.Approved
EnalaprilThe serum concentration of Naloxone can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Naloxone can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Naloxone can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Naloxone can be increased when it is combined with Ergotamine.Approved
ErythromycinThe metabolism of Naloxone can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Naloxone can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstramustineThe serum concentration of Naloxone can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Naloxone can be decreased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Naloxone can be decreased when it is combined with Estrone.Approved
EtoposideThe serum concentration of Naloxone can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Naloxone can be decreased when it is combined with Etravirine.Approved
FelodipineThe serum concentration of Naloxone can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Naloxone can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Naloxone can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Naloxone can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe metabolism of Naloxone can be decreased when combined with Fluconazole.Approved
FluoxetineThe serum concentration of Naloxone can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Naloxone can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Naloxone can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Naloxone can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe metabolism of Naloxone can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Naloxone can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Naloxone can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Naloxone can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Naloxone can be increased when it is combined with Fusidic Acid.Approved
GefitinibThe serum concentration of Naloxone can be increased when it is combined with Gefitinib.Approved, Investigational
GemfibrozilThe metabolism of Naloxone can be decreased when combined with Gemfibrozil.Approved
GenisteinThe serum concentration of Naloxone can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Naloxone can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Naloxone can be increased when it is combined with Glycerol.Experimental
Gramicidin DThe serum concentration of Naloxone can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Naloxone can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolThe serum concentration of Naloxone can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Naloxone can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Naloxone can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Naloxone can be decreased when combined with Imatinib.Approved
ImipramineThe serum concentration of Naloxone can be increased when it is combined with Imipramine.Approved
IndinavirThe metabolism of Naloxone can be decreased when combined with Indinavir.Approved
IndomethacinThe serum concentration of Naloxone can be increased when it is combined with Indomethacin.Approved, Investigational
IrbesartanThe metabolism of Naloxone can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Naloxone can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Naloxone can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Naloxone can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Naloxone can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Naloxone can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Naloxone can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe metabolism of Naloxone can be decreased when combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Naloxone can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Naloxone can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinThe serum concentration of Naloxone can be increased when it is combined with Levofloxacin.Approved, Investigational
LevothyroxineThe serum concentration of Naloxone can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Naloxone can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Naloxone can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Naloxone can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Naloxone can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Naloxone can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Naloxone can be increased when it is combined with Loperamide.Approved
LopinavirThe metabolism of Naloxone can be decreased when combined with Lopinavir.Approved
LoratadineThe serum concentration of Naloxone can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Naloxone can be increased when it is combined with Losartan.Approved
LovastatinThe metabolism of Naloxone can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Naloxone can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Naloxone can be increased when it is combined with Lumacaftor.Approved
MaprotilineThe serum concentration of Naloxone can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Naloxone can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Naloxone can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Naloxone can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Naloxone can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Naloxone can be increased when it is combined with Methadone.Approved
MethylnaltrexoneThe risk or severity of adverse effects can be increased when Methylnaltrexone is combined with Naloxone.Approved
MetoprololThe serum concentration of Naloxone can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Naloxone can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Naloxone can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Naloxone can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Naloxone can be increased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Naloxone can be increased when it is combined with Mitomycin.Approved
MitotaneThe serum concentration of Naloxone can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Naloxone can be decreased when it is combined with Mitoxantrone.Approved, Investigational
ModafinilThe serum concentration of Naloxone can be decreased when it is combined with Modafinil.Approved, Investigational
MorphineThe serum concentration of Naloxone can be increased when it is combined with Morphine.Approved, Investigational
NafcillinThe serum concentration of Naloxone can be decreased when it is combined with Nafcillin.Approved
NaloxegolThe risk or severity of adverse effects can be increased when Naloxone is combined with Naloxegol.Approved
NaltrexoneThe serum concentration of Naloxone can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Naloxone can be increased when it is combined with Naringenin.Experimental
NefazodoneThe metabolism of Naloxone can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Naloxone can be decreased when combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Naloxone can be increased when it is combined with Neostigmine.Approved, Vet Approved
NetupitantThe serum concentration of Naloxone can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Naloxone can be increased when combined with Nevirapine.Approved
NicardipineThe serum concentration of Naloxone can be increased when it is combined with Nicardipine.Approved
NifedipineThe serum concentration of Naloxone can be decreased when it is combined with Nifedipine.Approved
NilotinibThe metabolism of Naloxone can be decreased when combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Naloxone can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Naloxone can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Naloxone can be increased when it is combined with Nitrendipine.Approved
NorethisteroneThe serum concentration of Naloxone can be decreased when it is combined with Norethisterone.Approved
OlaparibThe metabolism of Naloxone can be decreased when combined with Olaparib.Approved
OmeprazoleThe serum concentration of Naloxone can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Naloxone can be increased when it is combined with Osimertinib.Approved
P-NitrophenolThe serum concentration of Naloxone can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe serum concentration of Naloxone can be increased when it is combined with Paclitaxel.Approved, Vet Approved
PalbociclibThe serum concentration of Naloxone can be increased when it is combined with Palbociclib.Approved
Palmitic AcidThe serum concentration of Naloxone can be increased when it is combined with Palmitic Acid.Experimental
PantoprazoleThe serum concentration of Naloxone can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Naloxone can be increased when it is combined with Paroxetine.Approved, Investigational
PentobarbitalThe metabolism of Naloxone can be increased when combined with Pentobarbital.Approved, Vet Approved
PerindoprilThe serum concentration of Naloxone can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe metabolism of Naloxone can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Naloxone can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideThe serum concentration of Naloxone can be increased when it is combined with Pimozide.Approved
PioglitazoneThe metabolism of Naloxone can be decreased when combined with Pioglitazone.Approved, Investigational
Platelet Activating FactorThe serum concentration of Naloxone can be decreased when it is combined with Platelet Activating Factor.Experimental
PonatinibThe serum concentration of Naloxone can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe metabolism of Naloxone can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Naloxone can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Naloxone can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Naloxone can be increased when it is combined with Prednisone.Approved, Vet Approved
PrimidoneThe metabolism of Naloxone can be increased when combined with Primidone.Approved, Vet Approved
ProbenecidThe serum concentration of Naloxone can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Naloxone can be decreased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Naloxone can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Naloxone can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Naloxone can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Naloxone can be increased when it is combined with Protriptyline.Approved
QuercetinThe serum concentration of Naloxone can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Naloxone can be increased when it is combined with Quinacrine.Approved
QuinidineThe serum concentration of Naloxone can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Naloxone can be increased when it is combined with Quinine.Approved
RabeprazoleThe metabolism of Naloxone can be decreased when combined with Rabeprazole.Approved, Investigational
RanitidineThe serum concentration of Naloxone can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Naloxone can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Naloxone can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Naloxone can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Naloxone can be decreased when it is combined with Reserpine.Approved
RifabutinThe metabolism of Naloxone can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Naloxone can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Naloxone can be increased when combined with Rifapentine.Approved
RilpivirineThe serum concentration of Naloxone can be increased when it is combined with Rilpivirine.Approved
RitonavirThe metabolism of Naloxone can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Naloxone can be increased when it is combined with Rolapitant.Approved
RosiglitazoneThe metabolism of Naloxone can be decreased when combined with Rosiglitazone.Approved, Investigational
SaquinavirThe metabolism of Naloxone can be decreased when combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Naloxone can be increased when it is combined with Scopolamine.Approved
SecobarbitalThe metabolism of Naloxone can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Naloxone can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Naloxone can be increased when it is combined with Sertraline.Approved
SildenafilThe metabolism of Naloxone can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Naloxone can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Naloxone can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Naloxone can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Naloxone can be decreased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Naloxone can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Naloxone can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Naloxone can be decreased when it is combined with St. John's Wort.Nutraceutical
StaurosporineThe serum concentration of Naloxone can be increased when it is combined with Staurosporine.Experimental
StiripentolThe serum concentration of Naloxone can be increased when it is combined with Stiripentol.Approved
StreptozocinThe serum concentration of Naloxone can be decreased when it is combined with Streptozocin.Approved
SulfamethoxazoleThe metabolism of Naloxone can be decreased when combined with Sulfamethoxazole.Approved
SulfinpyrazoneThe serum concentration of Naloxone can be increased when it is combined with Sulfinpyrazone.Approved
SulfisoxazoleThe metabolism of Naloxone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SumatriptanThe serum concentration of Naloxone can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Naloxone can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Naloxone can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Naloxone can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Naloxone can be decreased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Naloxone can be increased when it is combined with Taurocholic Acid.Experimental
TelaprevirThe metabolism of Naloxone can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Naloxone can be decreased when combined with Telithromycin.Approved
TelmisartanThe serum concentration of Naloxone can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Naloxone can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Naloxone can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Naloxone can be increased when it is combined with Terfenadine.Withdrawn
TeriflunomideThe metabolism of Naloxone can be decreased when combined with Teriflunomide.Approved
TesmilifeneThe serum concentration of Naloxone can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Naloxone can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Naloxone can be increased when it is combined with Ticagrelor.Approved
TiclopidineThe metabolism of Naloxone can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Naloxone can be decreased when it is combined with Tocilizumab.Approved
TolvaptanThe serum concentration of Naloxone can be increased when it is combined with Tolvaptan.Approved
TrazodoneThe serum concentration of Naloxone can be decreased when it is combined with Trazodone.Approved, Investigational
TrifluoperazineThe serum concentration of Naloxone can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Naloxone can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Naloxone can be decreased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Naloxone can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Naloxone can be increased when it is combined with Troleandomycin.Approved
VenlafaxineThe metabolism of Naloxone can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Naloxone can be decreased when combined with Verapamil.Approved
VinblastineThe serum concentration of Naloxone can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Naloxone can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Naloxone can be increased when it is combined with Vinorelbine.Approved, Investigational
VoriconazoleThe metabolism of Naloxone can be decreased when combined with Voriconazole.Approved, Investigational
ZimelidineThe serum concentration of Naloxone can be increased when it is combined with Zimelidine.Withdrawn
ZiprasidoneThe metabolism of Naloxone can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

Bianca Brogmann, Silke Muhlau, Christof Spitzley, “Pharmaceutical preparation containing oxycodone and naloxone.” U.S. Patent US20050245556, issued November 03, 2005.

US20050245556
General References
  1. Link [Link]
External Links
ATC CodesV03AB15
AHFS Codes
  • 28:10.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9729
Blood Brain Barrier+0.9787
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.8788
P-glycoprotein inhibitor INon-inhibitor0.7922
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterInhibitor0.5
CYP450 2C9 substrateNon-substrate0.8522
CYP450 2D6 substrateSubstrate0.5296
CYP450 3A4 substrateSubstrate0.6107
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9303
CYP450 2D6 inhibitorNon-inhibitor0.7886
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9153
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9523
Ames testNon AMES toxic0.7182
CarcinogenicityNon-carcinogens0.9583
BiodegradationNot ready biodegradable0.9968
Rat acute toxicity2.7231 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7798
hERG inhibition (predictor II)Non-inhibitor0.8641
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
FilmBuccal
PillSublingual
TabletSublingual
Injection, solutionIntramuscular; Subcutaneous.4 mg/1
Injection, solutionIntramuscular; Subcutaneous2 mg/.4mL
LiquidIntramuscular; Intravenous; Subcutaneous0.4 mg
LiquidIntramuscular; Intravenous; Subcutaneous1 mg
InjectionIntramuscular; Intravenous; Subcutaneous.4 mg/mL
InjectionIntramuscular; Intravenous; Subcutaneous1 mg/mL
InjectionParenteral1 mg/mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous.4 mg/mL
SolutionIntramuscular; Intravenous; Subcutaneous1 mg
SolutionIntramuscular; Intravenous; Subcutaneous0.4 mg
Spray, meteredNasal2 mg
Spray, meteredNasal4 mg
SprayNasal4 mg/.1mL
LiquidIntramuscular; Intravenous; Subcutaneous0.02 mg
TabletOral
Film, solubleBuccal; Sublingual
Film, solubleSublingual
Tablet, extended releaseOral
Tablet, orally disintegratingSublingual
Prices
Unit descriptionCostUnit
Naloxone hcl powder70.9USD g
Naloxone 0.4 mg/ml vial7.07USD ml
Naloxone 0.4 mg/ml ampul4.78USD ml
Narcan 0.4 mg/ml ampul4.58USD ml
Naloxone 0.02 mg/ml vial0.84USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6159498 No1996-10-182016-10-18Us
US6277384 No1998-12-222018-12-22Us
US6696066 No1998-12-222018-12-22Us
US7579019 No2000-01-222020-01-22Us
US7674799 No2005-03-302025-03-30Us
US7674800 No2005-03-302025-03-30Us
US7683072 No2005-03-302025-03-30Us
US7731686 No2006-06-102026-06-10Us
US7731690 No2005-01-152025-01-15Us
US7749194 No2008-10-302028-10-30Us
US7918823 No2004-11-232024-11-23Us
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US8017150 No2003-02-132023-02-13Us
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US8147866 No2007-07-232027-07-23Us
US8206360 No2007-02-272027-02-27Us
US8226610 No2009-04-102029-04-10Us
US8231573 No2008-11-252028-11-25Us
US8313466 No2004-11-232024-11-23Us
US8361029 No2004-11-232024-11-23Us
US8425462 No2004-11-232024-11-23Us
US8454996 No1999-09-242019-09-24Us
US8470361 No2010-05-222030-05-22Us
US8475832 No2010-03-262030-03-26Us
US8603514 No2004-04-032024-04-03Us
US8608698 No2004-11-232024-11-23Us
US8627816 No2012-02-042032-02-04Us
US8658198 No2007-12-032027-12-03Us
US8673355 No1998-12-222018-12-22Us
US8703177 No2012-08-202032-08-20Us
US8822487 No1998-12-222018-12-22Us
US8846090 No2003-04-042023-04-04Us
US8846091 No2003-04-042023-04-04Us
US8926594 No2006-03-312026-03-31Us
US8939943 No2011-02-282031-02-28Us
US8940330 No2012-09-182032-09-18Us
US8969369 No2002-05-102022-05-10Us
US9022022 No2011-02-282031-02-28Us
US9056051 No2002-05-102022-05-10Us
US9056170 No2004-11-232024-11-23Us
US9073933 No2005-03-302025-03-30Us
US9084729 No2002-05-102022-05-10Us
US9161937 No2002-05-102022-05-10Us
US9168252 No2002-05-102022-05-10Us
US9205082 No2002-05-102022-05-10Us
US9211253 No2015-03-162035-03-16Us
US9238108 No2007-01-222027-01-22Us
US9259421 No2012-09-182032-09-18Us
US9278182 No2006-02-012026-02-01Us
US9283216 No2002-05-102022-05-10Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point200-205 °CNot Available
water solubilitySolubleNot Available
logP2.09HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility5.64 mg/mLALOGPS
logP1.47ALOGPS
logP1.62ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.27ChemAxon
pKa (Strongest Basic)10.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.72 m3·mol-1ChemAxon
Polarizability33.8 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Benzylisoquinoline
  • Phenanthrene
  • Isoquinolone
  • Tetralin
  • Benzofuran
  • Aralkylamine
  • Cyclohexanone
  • Alkyl aryl ether
  • Benzenoid
  • Piperidine
  • Tertiary alcohol
  • Cyclic alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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. Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociati...
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular Weight:
44778.855 Da
References
  1. Narita M, Suzuki M, Mizoguchi H, Narita M, Yajima Y, Sakurada S, Tseng LF, Suzuki T: Up-regulation of mu-opioid receptor-mediated G-protein activation in protein kinase Cgamma knockout mice following repeated naloxone treatment. Neurosci Lett. 2003 Feb 27;338(2):103-6. [PubMed:12566163 ]
  2. Freye E, Latasch L, Von Bredow G, Neruda B: [The opioid tramadol demonstrates excitatory properties of non-opioid character--a preclinical study using alfentanil as a comparison]. Schmerz. 1998 Feb 28;12(1):19-24. [PubMed:12799988 ]
  3. Neal CR Jr, Owens CE, Taylor LP, Hoversten MT, Akil H, Watson SJ Jr: Binding and GTPgammaS autoradiographic analysis of preproorphanin precursor peptide products at the ORL1 and opioid receptors. J Chem Neuroanat. 2003 Jul;25(4):233-47. [PubMed:12842269 ]
  4. Spetea M, Toth F, Schutz J, Otvos F, Toth G, Benyhe S, Borsodi A, Schmidhammer H: Binding characteristics of [3H]14-methoxymetopon, a high affinity mu-opioid receptor agonist. Eur J Neurosci. 2003 Jul;18(2):290-5. [PubMed:12887410 ]
  5. Marek GJ: Behavioral evidence for mu-opioid and 5-HT2A receptor interactions. Eur J Pharmacol. 2003 Aug 1;474(1):77-83. [PubMed:12909198 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Helm S, Trescot AM, Colson J, Sehgal N, Silverman S: Opioid antagonists, partial agonists, and agonists/antagonists: the role of office-based detoxification. Pain Physician. 2008 Mar-Apr;11(2):225-35. [PubMed:18354714 ]
  8. Goodman AJ, Le Bourdonnec B, Dolle RE: Mu opioid receptor antagonists: recent developments. ChemMedChem. 2007 Nov;2(11):1552-70. [PubMed:17918759 ]
  9. van Dorp E, Yassen A, Dahan A: Naloxone treatment in opioid addiction: the risks and benefits. Expert Opin Drug Saf. 2007 Mar;6(2):125-32. [PubMed:17367258 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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 nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurot...
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular Weight:
40368.235 Da
References
  1. Moncada A, Cendan CM, Baeyens JM, Del Pozo E: Effects of serine/threonine protein phosphatase inhibitors on morphine-induced antinociception in the tail flick test in mice. Eur J Pharmacol. 2003 Mar 28;465(1-2):53-60. [PubMed:12650833 ]
  2. Kakinohana M, Marsala M, Carter C, Davison JK, Yaksh TL: Neuraxial morphine may trigger transient motor dysfunction after a noninjurious interval of spinal cord ischemia: a clinical and experimental study. Anesthesiology. 2003 Apr;98(4):862-70. [PubMed:12657847 ]
  3. Breljak D, Boranic M, Horvat S: Oligopeptide fragments of the enkephalin molecule interfere with hematopoietic cell colony formation. Int J Immunopathol Pharmacol. 2000 Jan-Apr;13(1):13-19. [PubMed:12749773 ]
  4. Chudapongse N, Kim SY, Kramer RE, Ho IK: Nonspecific effects of the selective kappa-opioid receptor agonist U-50,488H on dopamine uptake and release in PC12 cells. J Pharmacol Sci. 2003 Nov;93(3):372-5. [PubMed:14646257 ]
  5. Osman AM, Gomma M, Saad AH: A possible role for an enkephalinergic system in the internal defense mechanism of Biomphalaria alexandrina exposed to Schistosoma mansoni. J Egypt Soc Parasitol. 2003 Dec;33(3):841-61. [PubMed:14708857 ]
  6. Helm S, Trescot AM, Colson J, Sehgal N, Silverman S: Opioid antagonists, partial agonists, and agonists/antagonists: the role of office-based detoxification. Pain Physician. 2008 Mar-Apr;11(2):225-35. [PubMed:18354714 ]
  7. van Dorp E, Yassen A, Dahan A: Naloxone treatment in opioid addiction: the risks and benefits. Expert Opin Drug Saf. 2007 Mar;6(2):125-32. [PubMed:17367258 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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 synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates th...
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular Weight:
42644.665 Da
References
  1. Peng X, Neumeyer JL: Kappa receptor bivalent ligands. Curr Top Med Chem. 2007;7(4):363-73. [PubMed:17305578 ]
  2. van Dorp E, Yassen A, Dahan A: Naloxone treatment in opioid addiction: the risks and benefits. Expert Opin Drug Saf. 2007 Mar;6(2):125-32. [PubMed:17367258 ]
  3. Helm S, Trescot AM, Colson J, Sehgal N, Silverman S: Opioid antagonists, partial agonists, and agonists/antagonists: the role of office-based detoxification. Pain Physician. 2008 Mar-Apr;11(2):225-35. [PubMed:18354714 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
other/unknown
General Function:
Transcriptional activator activity, rna polymerase ii transcription factor binding
Specific Function:
Phosphorylation-dependent transcription factor that stimulates transcription upon binding to the DNA cAMP response element (CRE), a sequence present in many viral and cellular promoters. Transcription activation is enhanced by the TORC coactivators which act independently of Ser-133 phosphorylation. Involved in different cellular processes including the synchronization of circadian rhythmicity ...
Gene Name:
CREB1
Uniprot ID:
P16220
Molecular Weight:
36687.86 Da
References
  1. Li J, Li YH, Yuan XR: Changes of phosphorylation of cAMP response element binding protein in rat nucleus accumbens after chronic ethanol intake: naloxone reversal. Acta Pharmacol Sin. 2003 Sep;24(9):930-6. [PubMed:12956944 ]
  2. Chartoff EH, Papadopoulou M, Konradi C, Carlezon WA Jr: Dopamine-dependent increases in phosphorylation of cAMP response element binding protein (CREB) during precipitated morphine withdrawal in primary cultures of rat striatum. J Neurochem. 2003 Oct;87(1):107-18. [PubMed:12969258 ]
  3. Gao C, Chen LW, Tao YM, Chen J, Xu XJ, Chi ZQ: Effects of ohmefentanyl stereoisomers on phosphorylation of cAMP- response element binding protein in cultured rat hippocampal neurons. Acta Pharmacol Sin. 2003 Dec;24(12):1253-8. [PubMed:14653953 ]
  4. Walters CL, Cleck JN, Kuo YC, Blendy JA: Mu-opioid receptor and CREB activation are required for nicotine reward. Neuron. 2005 Jun 16;46(6):933-43. [PubMed:15953421 ]
  5. Hawes JJ, Narasimhaiah R, Picciotto MR: Galanin attenuates cyclic AMP regulatory element-binding protein (CREB) phosphorylation induced by chronic morphine and naloxone challenge in Cath.a cells and primary striatal cultures. J Neurochem. 2006 Feb;96(4):1160-8. Epub 2006 Jan 17. [PubMed:16417577 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
antagonistother/unknown
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Farooqui M, Geng ZH, Stephenson EJ, Zaveri N, Yee D, Gupta K: Naloxone acts as an antagonist of estrogen receptor activity in MCF-7 cells. Mol Cancer Ther. 2006 Mar;5(3):611-20. [PubMed:16546975 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transmembrane signaling receptor activity
Specific Function:
Cooperates with LY96 and CD14 to mediate the innate immune response to bacterial lipopolysaccharide (LPS). Acts via MYD88, TIRAP and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response (PubMed:9237759, PubMed:10835634). Also involved in LPS-independent inflammatory responses triggered by free fatty acids, such as palmitate, and Ni(2+). Responses triggered b...
Gene Name:
TLR4
Uniprot ID:
O00206
Molecular Weight:
95679.19 Da
References
  1. Lewis SS, Loram LC, Hutchinson MR, Li CM, Zhang Y, Maier SF, Huang Y, Rice KC, Watkins LR: (+)-naloxone, an opioid-inactive toll-like receptor 4 signaling inhibitor, reverses multiple models of chronic neuropathic pain in rats. J Pain. 2012 May;13(5):498-506. doi: 10.1016/j.jpain.2012.02.005. Epub 2012 Apr 20. [PubMed:22520687 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibited by the grapefruit juice component naringin.
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular Weight:
74144.105 Da
References
  1. Gao B, Hagenbuch B, Kullak-Ublick GA, Benke D, Aguzzi A, Meier PJ: Organic anion-transporting polypeptides mediate transport of opioid peptides across blood-brain barrier. J Pharmacol Exp Ther. 2000 Jul;294(1):73-9. [PubMed:10871297 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
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Drug created on June 13, 2005 07:24 / Updated on December 02, 2016 03:19