Identification

Name
Naloxone
Accession Number
DB01183  (APRD00025)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

Naloxone is an opioid antagonist medication used to block or reverse the effects of opioid drugs, particularly within the setting of drug overdoses which are rapidly becoming a leading cause of death worldwide. More specifically, naloxone has a high affinity for μ-opioid receptors, where it acts as an inverse agonist, causing the rapid removal of any other drugs bound to these receptors. When taken in large quantities, opioid medications such as morphine, hydromorphone, methadone, heroin, or fentanyl are capable of causing life-threatening symptoms such as respiratory depression, reduced heart rate, slurred speech, drowsiness, and constricted pupils. If untreated, this can progress to vomiting, absent pulse and breathing, loss of consciousness, and even death. Naloxone is indicated for the rapid reversal of these symptoms of central nervous system depression in opioid overdose. It's important to note that naloxone only works on opioid receptors within the body, and is therefore not capable of reversing the effects of non-opioid medications such as stimulants like methamphetamine or cocaine, or benzodiazepines like lorazepam or diazepam.

Also known as the brand name product Narcan, naloxone is currently available by intramuscular (IM) or subcutaneous (SubQ) injection, nasal spray, or intravenous (IV) infusion. Naloxone IM injections are commonly available in the form of "kits", which is ideal for making overdose treatment accessible and readily available for administration by minimally trained individuals within the community. Kits commonly include the supplies necessary to treat an overdose in a non-medical setting such as alcohol swabs, syringes, a rescue breathing mask, and instructions for use. Frequently also carried by medical and emergency personnel and at events known to be associated with heavy drug use like music festivals, naloxone kits are considered a key component of harm reduction strategies.

When injected intramuscularly (IM), naloxone acts within 3-5 minutes and can last from 30-60 minutes before its effects wear off. Administration of naloxone is associated with very few side effects. Notably, if injected into a person not currently using opioid medications, there would be no noticeable effects at all. However, for individuals using opioid medications or experiencing an overdose, IM injection of naloxone rapidly reverses opioid effects and can cause the injected individual to immediately experience withdrawal symptoms. Common symptoms of opioid withdrawal include nausea, vomiting, sweating, runny nose, aches, and diarrhea. Although certainly physically uncomfortable, opioid withdrawal symptoms are not life-threatening like they are for alcohol withdrawals. Administration of naloxone is therefore appropriate for any person appearing to have any symptoms of an opioid overdose. Due to its short duration of action, person's injected with naloxone should be monitored for responsiveness and potentially injected a second time or taken to the hospital.

Naloxone is also available within the combination product Suboxone with the opioid medication buprenorphine. Suboxone is used for the maintentance treatment of opioid dependence and addiction. When taken orally, naloxone has no pharmacological effect and does not reduce the effectiveness of the opioid effect of buprenorphine. The primary purpose of including naloxone within Suboxone is to act as a deterrent to injection, as injected naloxone would rapidly reverse the effects of buprenorphine.

Structure
Thumb
Synonyms
  • (−)-naloxone
  • 1-N-Allyl-14-hydroxynordihydromorphinone
  • 17-allyl-3,14-dihydroxy-4,5α-epoxymorphinan-6-one
  • Nalossone
  • Naloxona
  • Naloxone
  • Naloxonum
External IDs
EN 1530 Base
Product Ingredients
IngredientUNIICASInChI Key
Naloxone hydrochlorideF850569PQR357-08-4RGPDIGOSVORSAK-STHHAXOLSA-N
Naloxone hydrochloride dihydrate5Q187997EE51481-60-8TXMZWEASFRBVKY-IOQDSZRYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EvzioInjection, solution.4 mg/1Intramuscular; SubcutaneousKaleo, Inc2014-04-03Not applicableUs
EvzioInjection, solution2 mg/.4mLIntramuscular; SubcutaneousKaleo, Inc2016-10-19Not applicableUs
Injectable Naloxone HydrochlorideSolution0.4 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2016-08-05Not applicableCanada
Injectable Naloxone HydrochlorideSolution1 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories LtdNot applicableNot applicableCanada
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 InjectionSolution0.4 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2013-10-03Not applicableCanada
Naloxone Hydrochloride InjectionSolution1 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2013-10-10Not 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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Naloxone HydrochlorideInjection1 mg/mLParenteralInternational Medication Systems, Limited2001-06-01Not applicableUs
Naloxone HydrochlorideInjection.4 mg/mLIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceutical1986-09-24Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.1987-01-072016-10-13Us
Naloxone HydrochlorideInjection1 mg/mLParenteralCardinal Health2001-06-01Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousMc Kesson Packaging Services A Buisness Unit Of Mc Kesson Corporation2010-05-03Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines2010-03-01Not applicableUs
Naloxone HydrochlorideInjection1 mg/mLParenteralRemedy Repack2015-03-072017-03-17Us
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousMylan Institutional2014-03-06Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousSomerset Therapeutics, Llc2017-08-03Not applicableUs
Naloxone HydrochlorideInjection, solution.4 mg/mLIntramuscular; Intravenous; SubcutaneousCardinal Health2012-03-06Not applicableUs
International/Other Brands
Nalone / Narcan / Narcanti / Narcon
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Act Buprenorphine/naloxoneNaloxone (2 mg) + Buprenorphine (8 mg)TabletSublingualActavis Pharma CompanyNot applicableNot applicableCanada
Act Buprenorphine/naloxoneNaloxone (0.5 mg) + Buprenorphine (2 mg)TabletSublingualActavis Pharma CompanyNot applicableNot applicableCanada
BunavailNaloxone hydrochloride dihydrate (.7 mg/1) + Buprenorphine Hydrochloride (4.2 mg/1)FilmBuccalBio Delivery Sciences International2014-08-05Not applicableUs
BunavailNaloxone hydrochloride dihydrate (.3 mg/1) + Buprenorphine Hydrochloride (2.1 mg/1)FilmBuccalBio Delivery Sciences International2014-08-05Not applicableUs
BunavailNaloxone hydrochloride dihydrate (1 mg/1) + Buprenorphine Hydrochloride (6.3 mg/1)FilmBuccalBio Delivery Sciences International2014-08-05Not applicableUs
Buprenorphine and NaloxoneNaloxone (2 mg/1) + Buprenorphine (8 mg/1)TabletSublingualLannett Company, Inc..2016-09-19Not applicableUs
Buprenorphine and NaloxoneNaloxone hydrochloride (.5 mg/1) + Buprenorphine Hydrochloride (2 mg/1)TabletSublingualGolden State Medical Supply2016-01-19Not applicableUs
Buprenorphine and NaloxoneNaloxone hydrochloride dihydrate (.5 mg/1) + Buprenorphine Hydrochloride (2 mg/1)TabletSublingualTeva2014-12-102018-10-31Us
Buprenorphine and NaloxoneNaloxone (.5 mg/1) + Buprenorphine (2 mg/1)TabletSublingualLannett Company, Inc..2016-09-19Not applicableUs
Buprenorphine and NaloxoneNaloxone hydrochloride dihydrate (2 mg/1) + Buprenorphine Hydrochloride (8 mg/1)TabletSublingualActavis Pharma Company2013-03-04Not applicableUs
Categories
UNII
36B82AMQ7N
CAS number
465-65-6
Weight
Average: 327.3743
Monoisotopic: 327.147058165
Chemical Formula
C19H21NO4
InChI Key
UZHSEJADLWPNLE-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[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
SMILES
OC1=CC=C2C[C@H]3N(CC=C)CC[C@@]45[C@@H](OC1=C24)C(=O)CC[C@@]35O

Pharmacology

Indication

For 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
Pharmacodynamics

Naloxone is an opiate antagonist and prevents or reverses the effects of opioids including respiratory depression, sedation and hypotension. In the absence of narcotics or agonistic effects of other narcotic antagonists, it exhibits essentially no pharmacologic activity.

Mechanism of action

While 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 mu-opioid 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.

TargetActionsOrganism
AMu-type opioid receptor
antagonist
Human
ADelta-type opioid receptor
antagonist
Human
AKappa-type opioid receptor
antagonist
Human
NCyclic AMP-responsive element-binding protein 1
other/unknown
Human
NEstrogen receptor alpha
antagonist
other/unknown
Human
UToll-like receptor 4
inhibitor
Human
ULiver carboxylesterase 1Not AvailableHuman
Absorption

Tmax: 0.4mg IM injection = 0.38 hr Nasal spray (one 2mg spray) = 0.33 hr Nasal spray (one 4mg spray) = 0.50 hr

Cmax: 0.4mg IM injection = 0.88 ng/mL Nasal spray (one 2mg spray) = 2.91 ng/mL Nasal spray (one 4mg spray) = 4.83 ng/mL

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 binding

Plasma 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 elimination

Urine (25%- 40% is excreted as metabolites within 6 hours)

Half life

0.4mg IM injection = 1.24 hr Nasal spray (one 2mg spray) = 1.85 hr Nasal spray (one 4mg spray) = 2.08 hr

Clearance
Not Available
Toxicity

LD50, IV administration, mouse = 150 ± 5 mg/kg; LD50, IV administration, rat = 109 ± 4 mg/kg;

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Naloxone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Naloxone can be increased when it is combined with Abiraterone.Approved
AmiodaroneThe metabolism of Naloxone can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Naloxone can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Naloxone can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Naloxone can be decreased when combined with Atomoxetine.Approved
BoceprevirThe metabolism of Naloxone can be decreased when combined with Boceprevir.Approved, Withdrawn
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
CarbamazepineThe metabolism of Naloxone can be increased when combined with Carbamazepine.Approved, Investigational
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
ClarithromycinThe metabolism of Naloxone can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Naloxone can be decreased when combined with Clemastine.Approved
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
ConivaptanThe serum concentration of Naloxone can be increased when it is combined with Conivaptan.Approved, Investigational
CrisaboroleThe metabolism of Naloxone can be decreased when combined with Crisaborole.Approved
CrizotinibThe metabolism of Naloxone can be decreased when combined with Crizotinib.Approved
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
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
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
DihydroergotamineThe metabolism of Naloxone can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Naloxone can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Naloxone can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Naloxone can be decreased when combined with Dronedarone.Approved
EfavirenzThe metabolism of Naloxone can be decreased when combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Naloxone can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Naloxone can be decreased when combined with Erythromycin.Approved, Vet Approved
FelodipineThe metabolism of Naloxone can be decreased when combined with Felodipine.Approved, Investigational
FluconazoleThe metabolism of Naloxone can be decreased when combined with Fluconazole.Approved
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
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
IndinavirThe metabolism of Naloxone can be decreased when combined with Indinavir.Approved
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
KetoconazoleThe metabolism of Naloxone can be decreased when combined with Ketoconazole.Approved, Investigational
LapatinibThe metabolism of Naloxone can be decreased when combined with Lapatinib.Approved, Investigational
LopinavirThe metabolism of Naloxone can be decreased when combined with Lopinavir.Approved
LosartanThe metabolism of Naloxone can be decreased when 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
MethylnaltrexoneThe risk or severity of adverse effects can be increased when Methylnaltrexone is combined with Naloxone.Approved
MifepristoneThe serum concentration of Naloxone can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Naloxone can be decreased when it is combined with Mitotane.Approved
NaloxegolThe risk or severity of adverse effects can be increased when Naloxone is combined with Naloxegol.Approved
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
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
NilotinibThe metabolism of Naloxone can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Naloxone can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Naloxone can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Naloxone can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Naloxone can be increased when combined with Pentobarbital.Approved, Vet 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
PioglitazoneThe metabolism of Naloxone can be decreased when combined with Pioglitazone.Approved, Investigational
PosaconazoleThe metabolism of Naloxone can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Naloxone can be increased when combined with Primidone.Approved, Vet Approved
QuinineThe metabolism of Naloxone can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Naloxone can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe serum concentration of Naloxone can be increased when it is combined with Ranolazine.Approved, Investigational
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
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
SecobarbitalThe metabolism of Naloxone can be increased when combined with Secobarbital.Approved, Vet 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
St. John's WortThe serum concentration of Naloxone can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Naloxone can be increased when it is combined with Stiripentol.Approved
SulfamethoxazoleThe metabolism of Naloxone can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Naloxone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TamoxifenThe metabolism of Naloxone can be decreased when combined with Tamoxifen.Approved
TelaprevirThe metabolism of Naloxone can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Naloxone can be decreased when combined with Telithromycin.Approved
TeriflunomideThe metabolism of Naloxone can be decreased when combined with Teriflunomide.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
TopiroxostatThe metabolism of Naloxone can be decreased when combined with Topiroxostat.Approved, Investigational
TrimethoprimThe metabolism of Naloxone can be decreased when combined with Trimethoprim.Approved, Vet 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
VoriconazoleThe metabolism of Naloxone can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Naloxone can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not 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
Human Metabolome Database
HMDB15314
KEGG Drug
D08249
KEGG Compound
C07252
PubChem Compound
5284596
PubChem Substance
46508816
ChemSpider
4447644
BindingDB
54795
ChEBI
7459
ChEMBL
CHEMBL80
Therapeutic Targets Database
DAP000097
PharmGKB
PA450586
IUPHAR
1676
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Naloxone
ATC Codes
V03AB15 — Naloxone
AHFS Codes
  • 28:10.00 — Opiate Antagonists
MSDS
Download (74 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentOpioid Use Disorders1
1Active Not RecruitingBasic ScienceHealthy Volunteers1
1CompletedNot AvailableChronic Hepatitis C Infection1
1CompletedNot AvailableDrug Dependence1
1CompletedBasic ScienceHyperalgesia / Naloxone / Opioid Antagonist / Pain1
1CompletedBasic ScienceIntestinal Obstruction1
1CompletedOtherPain, Chronic1
1CompletedTreatmentAddictions / Opioid Dependence / Pain1
1CompletedTreatmentChronic Hepatitis C Infection / Opioid-Related Disorders1
1CompletedTreatmentCocaine-Related Disorders1
1CompletedTreatmentDrug Overdose1
1CompletedTreatmentDrug Overdose / Opioid-Related Disorders1
1CompletedTreatmentHIV Risk Behaviors / Substance-Related Disorders1
1CompletedTreatmentHealthy Males1
1CompletedTreatmentHepatitis C Virus (HCV)1
1CompletedTreatmentHeroin Dependence / Opioid-Related Disorders1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Opioid Dependency1
1CompletedTreatmentOpiate Addiction1
1CompletedTreatmentOpioid Use Disorders1
1CompletedTreatmentOpioid-Related Disorders / Pain, Chronic1
1CompletedTreatmentPain2
1CompletedTreatmentTreatment of Menopausal Hot Flashes1
1Not Yet RecruitingNot AvailableDrug Overdose / Opioid-Related Disorders1
1RecruitingPreventionIdiopathic Hypogonadotropic Hypogonadism1
1RecruitingTreatmentHeroin Dependence / Opioid Use Disorders1
1, 2Active Not RecruitingPreventionDiabetes, Diabetes Mellitus Type 1 / Hypoglycemia Unawareness1
1, 2Active Not RecruitingTreatmentDepression / Major Depressive Disorder (MDD)1
1, 2CompletedTreatmentDrug Overdose1
1, 2CompletedTreatmentOpiate Addiction1
1, 2CompletedTreatmentOpioid Addiction / Opioid Dependence / Opioid Related Disorders1
1, 2CompletedTreatmentOpioid-Related Disorders1
1, 2RecruitingTreatmentDepression / Major Depressive Disorder (MDD)1
1, 2RecruitingTreatmentDrug; Withdrawal Symptoms, Neonatal / Fetus and Newborn Affected by Other Maternal Medication / Withdrawal1
1, 2RecruitingTreatmentOpioid Dependence1
2CompletedBasic ScienceDrug Overdose1
2CompletedBasic ScienceHealthy Volunteers1
2CompletedTreatmentCancers / Occasional Constipation / Pain1
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2CompletedTreatmentMorphinan Opioid Overdose1
2CompletedTreatmentNausea / Pain / Pruritus1
2CompletedTreatmentOccasional Constipation1
2CompletedTreatmentOpiate Dependence2
2CompletedTreatmentOpiate withdrawal symptoms / Opioid Dependence / Opioid Detoxification1
2CompletedTreatmentOpioid Dependence1
2CompletedTreatmentOpioid Related Disorders1
2CompletedTreatmentOpioid Use Disorders1
2CompletedTreatmentOpioid-Related Disorders5
2CompletedTreatmentOpioid-Related Disorders / Substance-Related Disorders2
2Not Yet RecruitingBasic ScienceMaternal Opioid Use Disorder / Opioid Exposed Infant1
2Not Yet RecruitingTreatmentGambling Disorder / Gambling Urge / Naloxone / Opioid Antagonist / Pathological Gambling1
2Not Yet RecruitingTreatmentHigh Dosage Buprenorphine1
2RecruitingNot AvailableHealthy Volunteers1
2RecruitingBasic ScienceBMI >30 kg/m21
2RecruitingBasic ScienceHealthy Volunteers / Hyperalgesia / Inflammations, Endodontic / Pain, Acute / Sensitization, Central1
2RecruitingPreventionPain, Neuropathic1
2RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
2TerminatedTreatmentOpioid-Related Disorders1
2Unknown StatusTreatmentPain, Chronic1
2, 3CompletedPreventionPruritus1
2, 3CompletedTreatmentBrain Death / Organ Donors / Transplantation, Lung1
2, 3CompletedTreatmentDependence, Cocaine1
2, 3CompletedTreatmentMalignant Pain / Non-malignant Pain1
2, 3RecruitingTreatmentOpioid Dependence1
2, 3Unknown StatusTreatmentBinge Eating Disorder (BED)1
2, 3Unknown StatusTreatmentOpioid Dependence1
3Active Not RecruitingTreatmentDepression / Major Depressive Disorder (MDD)1
3Active Not RecruitingTreatmentOpioid Dependence1
3CompletedNot AvailableSubjects With Moderate to Severe, Chronic Nonmalignant Pain1
3CompletedBasic ScienceHeroin Dependence1
3CompletedBasic ScienceOpioid-Related Disorders1
3CompletedHealth Services ResearchHeroin Addiction1
3CompletedTreatmentAlcohol Abuse / Alcohol Drinking / Alcohol-Related Disorders / Alcoholism1
3CompletedTreatmentCancers / Pain1
3CompletedTreatmentDepression / Depressive Disorders / Major Depressive Disorder (MDD)1
3CompletedTreatmentHeroin Dependence / Morphine Dependence / Substance Withdrawal Syndrome2
3CompletedTreatmentHeroin Dependence / Substance-Related Disorders1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentOpiate Dependence / Opioid-Related Disorders1
3CompletedTreatmentOpioid Dependence, on Agonist Therapy1
3CompletedTreatmentOpioid Dependence / Opioid Related Disorders1
3CompletedTreatmentOpioid Dependency1
3CompletedTreatmentOpioid Tolerance1
3CompletedTreatmentOpioid Use Disorders / Opioid-Related Disorders1
3CompletedTreatmentOpioid-Related Disorders1
3CompletedTreatmentPain1
3Enrolling by InvitationTreatmentOpioid Dependence1
3Not Yet RecruitingTreatmentPain, Chronic1
3RecruitingOtherOpioid Addiction1
3RecruitingTreatmentEpilepsies1
3TerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections / Opioid-Related Disorders1
3Unknown StatusSupportive CareConstipation, Impaction, and Bowel Obstruction / Unspecified Adult Solid Tumor, Protocol Specific1
3Unknown StatusTreatmentHip Arthroplasty / Knee Replacement Surgery / Spinal Anaesthesia1
3WithdrawnNot AvailableOpioid Dependence1
3WithdrawnTreatmentOpioid Dependence1
4CompletedSupportive CareCancers1
4CompletedSupportive CarePain, Chronic1
4CompletedSupportive CareSpinal Disorders / Spinal Disorders Related Pain1
4CompletedTreatmentBack Pain / Low Back Pain (LBP) / Pain, Neuropathic1
4CompletedTreatmentBack Pain / Osteoarthritis (OA)1
4CompletedTreatmentCancers2
4CompletedTreatmentChronic Hepatitis C Infection With Hepatic Coma / Hepatic Failure / Hepatic Impairment1
4CompletedTreatmentDrug Abuse / Opiate Dependence / Opiate-Related Disorders1
4CompletedTreatmentDrug Dependence / Opiate Dependence1
4CompletedTreatmentDrug Dependence / Opiate Dependence / Substance Dependence1
4CompletedTreatmentHeart; Dysfunction Postoperative, Cardiac Surgery1
4CompletedTreatmentHeroin Dependence / Opioid Dependence / Substance-Related Disorders1
4CompletedTreatmentLow Back Pain (LBP)1
4CompletedTreatmentOpiate Addiction1
4CompletedTreatmentOpiate Dependence2
4CompletedTreatmentOpiate-Related Disorders1
4CompletedTreatmentOpioid Dependence, on Agonist Therapy1
4CompletedTreatmentOpioid Dependency1
4CompletedTreatmentOpioid Induced Pharyngeal and Esophageal Dysfunction1
4CompletedTreatmentOpioid Related Disorders / Postoperative pain1
4CompletedTreatmentOpioid Use Disorders1
4CompletedTreatmentLumbar epidural anesthesia / Oral Oxycodone With/Without Naloxone / Postoperative Pain Management / Radical Cystectomy / Return of the Bowel Function1
4Not Yet RecruitingTreatmentGeneral Surgery / Opioid-use Disorder / Pain, Acute1
4RecruitingPreventionRespiratory Depression1
4RecruitingTreatmentDrug Dependence1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Substance Related Disorders1
4RecruitingTreatmentOpioid Use Disorders1
4SuspendedBasic SciencePain1
4TerminatedPreventionAnalgesia / Occasional Constipation1
4TerminatedTreatmentOpiate Addiction / Refractory Pains1
4TerminatedTreatmentPain1
4Unknown StatusNot AvailableOpioid Induced Constipation (OIC) / Postoperative pain1
4Unknown StatusTreatmentDrug Overdose1
4Unknown StatusTreatmentOpioid Dependence1
4WithdrawnTreatmentOpiate Addiction1
4WithdrawnTreatmentPain, Chronic1
Not AvailableActive Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Drug Dependence / Human Immunodeficiency Virus (HIV) / Opiate Addiction1
Not AvailableCompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Opiate Dependence / Post-Traumatic Stress Disorder (PTSD)1
Not AvailableCompletedNot AvailableChronic Severe Pain1
Not AvailableCompletedNot AvailableDrug Abuse / Opiate Dependence / Opioid-Related Disorders2
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableSevere Pain1
Not AvailableCompletedBasic ScienceAutonomic Failure / Diabetes Mellitus (DM) / Hypoglycemia1
Not AvailableCompletedBasic ScienceDrug Overdose1
Not AvailableCompletedBasic ScienceEndogenous and Esophageal Sensitivity1
Not AvailableCompletedDiagnosticChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedOtherHealthy Volunteers1
Not AvailableCompletedPreventionPain1
Not AvailableCompletedPreventionProphylaxis against postoperative nausea and vomiting1
Not AvailableCompletedSupportive CarePostoperative pain / Prophylaxis against postoperative nausea and vomiting / Scoliosis1
Not AvailableCompletedTreatmentChronic Hepatitis C Infection / Heroin Dependence1
Not AvailableCompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedTreatmentMorphine Adverse Reaction1
Not AvailableCompletedTreatmentOpiate Addiction1
Not AvailableCompletedTreatmentOpioid-Related Disorders2
Not AvailableEnrolling by InvitationPreventionDrug Abuse / Drug Dependence / Drug Overdose / Opioid-Related Disorders / Substance Abuse1
Not AvailableNot Yet RecruitingHealth Services ResearchBuprenorphine / Endocardits, Bacterial / Opioid-use Disorder / Outpatient Parenteral Antibiotic Therapy1
Not AvailableRecruitingNot AvailableBuprenorphine / Pain1
Not AvailableRecruitingTreatmentPain, Chronic1
Not AvailableSuspendedNot AvailableIschemia-Reperfusion Injury1
Not AvailableTerminatedBasic ScienceHealthy Volunteers1
Not AvailableTerminatedTreatmentOpioid-Related Disorders1
Not AvailableUnknown StatusSupportive CarePain1
Not AvailableUnknown StatusTreatmentOpioid Use Disorders1
Not AvailableWithdrawnBasic ScienceExperimental Pain Perception1
Not AvailableWithdrawnTreatmentOpiate Dependence1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
FilmBuccal
PillSublingual
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
SprayNasal2 mg/.1mL
SprayNasal4 mg/.1mL
LiquidIntramuscular; Intravenous; Subcutaneous0.02 mg
Spray, meteredNasal2 mg
Spray, meteredNasal4 mg
TabletOral
Film, solubleSublingual
TabletSublingual
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)
US9205082No2002-05-102022-05-10Us
US7579019No2000-01-222020-01-22Us
US6159498No1996-10-182016-10-18Us
US9073933No2005-03-302025-03-30Us
US7674800No2005-03-302025-03-30Us
US7683072No2005-03-302025-03-30Us
US7674799No2005-03-302025-03-30Us
US8475832No2010-03-262030-03-26Us
US8603514No2004-04-032024-04-03Us
US8017150No2003-02-132023-02-13Us
US8425462No2004-11-232024-11-23Us
US8231573No2008-11-252028-11-25Us
US8016788No2005-03-212025-03-21Us
US8206360No2007-02-272027-02-27Us
US9238108No2007-01-222027-01-22Us
US8226610No2009-04-102029-04-10Us
US7918823No2004-11-232024-11-23Us
US8608698No2004-11-232024-11-23Us
US8021344No2009-11-022029-11-02Us
US8361029No2004-11-232024-11-23Us
US8313466No2004-11-232024-11-23Us
US7731690No2005-01-152025-01-15Us
US9278182No2006-02-012026-02-01Us
US7731686No2006-06-012026-06-01Us
US8926594No2006-03-312026-03-31Us
US7749194No2008-10-302028-10-30Us
US9056170No2004-11-232024-11-23Us
US7947017No2008-03-122028-03-12Us
US8939943No2011-02-282031-02-28Us
US8627816No2012-02-042032-02-04Us
US9022022No2011-02-282031-02-28Us
US8147866No2007-07-232027-07-23Us
US8703177No2012-08-202032-08-20Us
US8470361No2010-05-222030-05-22Us
US8454996No1999-09-242019-09-24Us
US8658198No2007-12-032027-12-03Us
US8940330No2012-09-182032-09-18Us
US9259421No2012-09-182032-09-18Us
US9168252No2002-05-102022-05-10Us
US9161937No2002-05-102022-05-10Us
US8969369No2002-05-102022-05-10Us
US9084729No2002-05-102022-05-10Us
US9283216No2002-05-102022-05-10Us
US9056051No2002-05-102022-05-10Us
US8846090No2003-04-042023-04-04Us
US6277384No1998-12-222018-12-22Us
US8822487No1998-12-222018-12-22Us
US8673355No1998-12-222018-12-22Us
US6696066No1998-12-222018-12-22Us
US8846091No2003-04-042023-04-04Us
US9211253No2015-03-162035-03-16Us
US9522919No2005-03-302025-03-30Us
US9517307No2014-07-182034-07-18Us
US9474869No2011-02-282031-02-28Us
US9522188No2015-04-242035-04-24Us
US9655843No2007-07-232027-07-23Us
US9439900No2012-09-182032-09-18Us
US9345701No2002-05-102022-05-10Us
US9511066No2002-05-102022-05-10Us
US9555000No2003-04-042023-04-04Us
US9474750No1998-12-222018-12-22Us
US9283221No2002-05-102022-05-10Us
US9480644No2015-03-162035-03-16Us
US9629965No2015-03-162035-03-16Us
US9561177No2015-03-162035-03-16Us
US9468747No2015-03-162035-03-16Us
US9707226No2015-03-162035-03-16Us
US9687454No2009-08-072029-08-07Us
US9724471No2007-05-232027-05-23Us
US9775838No2015-03-162035-03-16Us
US9737669No2004-11-232024-11-23Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)200-205 °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)10.07ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.72 m3·mol-1ChemAxon
Polarizability33.83 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0139000000-e70921e0765c3389ce85

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenanthrenes and derivatives
Sub Class
Not Available
Direct Parent
Phenanthrenes and derivatives
Alternative Parents
Isoquinolones and derivatives / Tetralins / Coumarans / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Aralkylamines / Piperidines / Tertiary alcohols / Trialkylamines / 1,2-aminoalcohols
show 7 more
Substituents
Phenanthrene / Isoquinolone / Tetralin / Coumaran / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Aralkylamine / Piperidine / Cyclic alcohol / Tertiary alcohol
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
morphinane alkaloid, organic heteropentacyclic compound (CHEBI:7459)

Targets

Details
1. Mu-type opioid receptor
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...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
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 n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
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 synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
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. Transcript...
Gene Name
CREB1
Uniprot ID
P16220
Uniprot Name
Cyclic AMP-responsive element-binding protein 1
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
Antagonist
Other/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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
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 ...
Gene Name
TLR4
Uniprot ID
O00206
Uniprot Name
Toll-like receptor 4
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Bencharit S, Morton CL, Xue Y, Potter PM, Redinbo MR: Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat Struct Biol. 2003 May;10(5):349-56. [PubMed:12679808]

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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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 inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
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
Uniprot Name
Multidrug resistance protein 1
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]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34