Identification
- Name
- Naloxone
- Accession Number
- DB01183
- 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. 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; 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, persons 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 maintenance 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.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Naloxone (DB01183)
- Weight
- Average: 327.3743
Monoisotopic: 327.147058165 - Chemical Formula
- C19H21NO4
- 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
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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism AMu-type opioid receptor antagonistHumans ADelta-type opioid receptor antagonistHumans AKappa-type opioid receptor antagonistHumans NCyclic AMP-responsive element-binding protein 1 other/unknownHumans NEstrogen receptor alpha antagonistother/unknownHumans UToll-like receptor 4 inhibitorHumans ULiver carboxylesterase 1 Not Available Humans - 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
LD50, IV administration, mouse = 150 ± 5 mg/kg; LD50, IV administration, rat = 109 ± 4 mg/kg;
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Naloxone Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Abacavir may decrease the excretion rate of Naloxone which could result in a higher serum level. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Naloxone. Abiraterone The metabolism of Abiraterone can be decreased when combined with Naloxone. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Naloxone. Acarbose Acarbose may decrease the excretion rate of Naloxone which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Naloxone which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Naloxone which could result in a higher serum level. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Naloxone. Acetaminophen Acetaminophen may decrease the excretion rate of Naloxone which could result in a higher serum level. Acetazolamide Naloxone may increase the excretion rate of Acetazolamide which could result in a lower serum level and potentially a reduction in efficacy. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take separate from meals. When formulated as a buccal film or sublingual form, avoid eating or drinking until the film has completely dissolved.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Naloxone hydrochloride F850569PQR 357-08-4 RGPDIGOSVORSAK-STHHAXOLSA-N Naloxone hydrochloride dihydrate 5Q187997EE 51481-60-8 TXMZWEASFRBVKY-IOQDSZRYSA-N - Product Images
- International/Other Brands
- Narcanti / Narcon
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataEvzio Injection, solution 0.4 mg/1 Intramuscular; Subcutaneous Kaleo, Inc 2014-04-03 2018-05-31 US 
Evzio Injection, solution 2 mg/0.4mL Intramuscular; Subcutaneous Kaleo, Inc 2016-10-19 Not applicable US EVZIO(R) NALOXONE HCl Injection, solution 2 mg/0.4mL Intramuscular; Subcutaneous HF Acquisition Co LLC, DBA HealthFirst 2020-01-11 Not applicable US Injectable Naloxone Hydrochloride Solution Intramuscular; Intravenous; Subcutaneous Omega Laboratories Ltd 2016-08-05 Not applicable Canada 
Injectable Naloxone Hydrochloride Solution Intramuscular; Intravenous; Subcutaneous Omega Laboratories Ltd Not applicable Not applicable Canada Naloxone HCl Injection - 0.4mg/ml USP Liquid Intramuscular; Intravenous; Subcutaneous Sandoz Canada Incorporated 1995-12-31 Not applicable Canada Naloxone HCl Injection - 1mg/ml USP Liquid Intramuscular; Intravenous; Subcutaneous Sandoz Canada Incorporated 1995-12-31 Not applicable Canada Naloxone Hydrochloride Injection 0.4 mg/1mL Parenteral International Medication Systems, Limited 2006-04-13 2006-04-13 US Naloxone Hydrochloride Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous Hospira 2006-05-11 2006-05-11 US Naloxone Hydrochloride Injection, solution 0.02 mg/1mL Intramuscular; Intravenous; Subcutaneous Hospira 2006-05-11 2006-05-11 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataNaloxone Hci Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous Hf Acquisition Co. Llc, Dba Health First 2018-08-18 Not applicable US Naloxone HCl Injection 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous Renaissance Ssa, Llc 2019-12-28 Not applicable US Naloxone Hydrochloride Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous General Injectables & Vaccines, Inc 2010-03-01 Not applicable US Naloxone Hydrochloride Injection 1 mg/1mL Parenteral General Injectables & Vaccines, Inc. 2014-05-07 Not applicable US Naloxone Hydrochloride Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous TYA Pharmaceuticals 1986-09-24 Not applicable US Naloxone Hydrochloride Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous Hospira, Inc. 2005-09-02 Not applicable US Naloxone Hydrochloride Injection 1 mg/1mL Parenteral Amphastar Pharmaceuticals, Inc. 2001-06-01 2013-01-10 US Naloxone Hydrochloride Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous A-S Medication Solutions 2017-02-28 2019-05-31 US Naloxone Hydrochloride Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous Mylan Institutional LLC 2014-12-17 Not applicable US Naloxone Hydrochloride Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous Cardinal Health 2011-07-08 2019-09-30 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Act Buprenorphine/naloxone Naloxone (2 mg) + Buprenorphine (8 mg) Tablet Sublingual TEVA Canada Limited 2017-09-28 Not applicable Canada Act Buprenorphine/naloxone Naloxone (0.5 mg) + Buprenorphine (2 mg) Tablet Sublingual TEVA Canada Limited 2017-09-28 Not applicable Canada Bunavail Naloxone hydrochloride dihydrate (0.7 mg/1) + Buprenorphine hydrochloride (4.2 mg/1) Film Buccal BioDelivery Sciences International, Inc. 2014-09-30 2021-10-31 US Bunavail Naloxone hydrochloride dihydrate (0.3 mg/1) + Buprenorphine hydrochloride (2.1 mg/1) Film Buccal BioDelivery Sciences International, Inc. 2014-09-30 2021-02-28 US Bunavail Naloxone hydrochloride dihydrate (1 mg/1) + Buprenorphine hydrochloride (6.3 mg/1) Film Buccal BioDelivery Sciences International, Inc. 2014-09-30 2021-07-31 US Buprenorphine and Naloxone Naloxone hydrochloride (3 mg/1) + Buprenorphine hydrochloride (12 mg/1) Film, soluble Buccal; Sublingual Indivior Inc. 2019-02-19 2021-04-30 US Buprenorphine and Naloxone Naloxone hydrochloride dihydrate (0.5 mg/1) + Buprenorphine hydrochloride (2 mg/1) Tablet Sublingual Sun Pharmaceutical Industries, Inc. 2017-07-18 Not applicable US Buprenorphine and Naloxone Naloxone hydrochloride dihydrate (0.5 mg/1) + Buprenorphine hydrochloride (2 mg/1) Tablet Sublingual Rhodes Parmaceuticals L.P. 2020-04-13 Not applicable US Buprenorphine and Naloxone Naloxone hydrochloride (0.5 mg/1) + Buprenorphine hydrochloride (2 mg/1) Tablet Sublingual bryant ranch prepack 2016-01-07 Not applicable US Buprenorphine and Naloxone Naloxone (0.5 mg/1) + Buprenorphine (2 mg/1) Tablet Sublingual Lannett Company, Inc. 2016-09-19 Not applicable US
Categories
- ATC Codes
- A06AH04 — Naloxone
- A06AH — Peripheral opioid receptor antagonists
- A06A — DRUGS FOR CONSTIPATION
- A06 — DRUGS FOR CONSTIPATION
- A — ALIMENTARY TRACT AND METABOLISM
- V03AB — Antidotes
- V03A — ALL OTHER THERAPEUTIC PRODUCTS
- V03 — ALL OTHER THERAPEUTIC PRODUCTS
- V — VARIOUS
- Drug Categories
- Alimentary Tract and Metabolism
- Alkaloids
- Analgesics
- Antidotes
- Central Nervous System Agents
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strong)
- Cytochrome P-450 Enzyme Inhibitors
- Drugs for Constipation
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Morphinans
- Narcotics
- Natural Opium Alkaloids
- Nervous System
- Opiate Alkaloids
- Opiate Antagonists
- Opioid Antagonists
- P-glycoprotein substrates
- Peripheral Nervous System Agents
- Peripheral Opioid Receptor Antagonists
- Phenanthrenes
- Sensory System Agents
- UGT1A1 Substrates
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Coumaran show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- morphinane alkaloid, organic heteropentacyclic compound (CHEBI:7459)
Chemical Identifiers
- UNII
- 36B82AMQ7N
- CAS number
- 465-65-6
- 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[[email protected]]3N(CC=C)CC[[email protected]@]45[[email protected]@H](OC1=C24)C(=O)CC[[email protected]@]35O
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
- Link [Link]
- External Links
- Human Metabolome Database
- HMDB0015314
- KEGG Drug
- D08249
- KEGG Compound
- C07252
- PubChem Compound
- 5284596
- PubChem Substance
- 46508816
- ChemSpider
- 4447644
- BindingDB
- 54795
- 7242
- ChEBI
- 7459
- ChEMBL
- CHEMBL80
- ZINC
- ZINC000000389747
- Therapeutic Targets Database
- DAP000097
- PharmGKB
- PA450586
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Naloxone
- AHFS Codes
- 28:10.00 — Opiate Antagonists
- MSDS
- Download (74 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Supportive Care Back Pain Lower Back 1 4 Completed Prevention Opioid Induced Constipation (OIC) / Postoperative pain 1 4 Completed Prevention Respiratory Depression 1 4 Completed Supportive Care Malignancies 1 4 Completed Supportive Care Pain, Chronic 1 4 Completed Supportive Care Spinal Disorders 1 4 Completed Treatment Back Pain Lower Back 1 4 Completed Treatment Back Pain Lower Back / Back Pain, Unspecified / Pain, Neuropathic 1 4 Completed Treatment Back Pain, Unspecified / Osteoarthritis (OA) 1 4 Completed Treatment Chronic Hepatitis C Infection With Hepatic Coma / Hepatic Failure / Hepatic Impairment 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amphastar Pharmaceuticals
- A-S Medication Solutions LLC
- Bristol-Myers Squibb Co.
- Bryant Ranch Prepack
- Cardinal Health
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Endo Pharmaceuticals Inc.
- General Injectables and Vaccines Inc.
- Hospira Inc.
- Lake Erie Medical and Surgical Supply
- Letco Medical Inc.
- Mallinckrodt Inc.
- Mckesson Corp.
- Nucare Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Reckitt Benckiser Inc.
- Southwood Pharmaceuticals
- Stat Rx Usa
- Dosage Forms
Form Route Strength Film Buccal Tablet Oral 2 MG Tablet Oral 8 MG Film Buccal; Sublingual Film, soluble Buccal; Sublingual Injection, solution 400 mcg/1mL Injection, solution Intramuscular; Subcutaneous 0.4 mg/1 Injection, solution Intramuscular; Subcutaneous 2 mg/0.4mL Injection Injection Intramuscular; Intravenous; Subcutaneous 0.4 mg/ml Solution Intramuscular; Intravenous; Subcutaneous 0.4 mg Injection, solution Parenteral 0.4 MG/ML Injection, solution 0.04 MG/2ML Injection, solution 0.4 MG/ML Injection, solution 0.4 MG/1ML Liquid Intramuscular; Intravenous; Subcutaneous Injection Intramuscular; Intravenous; Subcutaneous 0.4 mg/1mL Injection Intramuscular; Intravenous; Subcutaneous 1 mg/1mL Injection Parenteral 0.4 mg/1mL Injection Parenteral 1 mg/1mL Injection Parenteral 4 mg/1mL Injection, solution Intramuscular; Intravenous; Subcutaneous 0.02 mg/1mL Injection, solution Intramuscular; Intravenous; Subcutaneous 0.4 mg/1mL Powder Not applicable 1 kg/1kg Solution Intramuscular; Intravenous; Subcutaneous Injection Intravenous 0.02 mg/1mL Injection Intravenous 0.4 mg/1mL Injection Intravenous 1 mg/1mL Spray Nasal 2 mg/0.1mL Spray Nasal 4 mg/0.1mL Spray, metered Nasal Injection, solution 40 mg/100mL Spray Nasal 1.8 MG Tablet, extended release Oral 5 mg Tablet, extended release Oral 10 mg Tablet, extended release Oral 20 mg Tablet, extended release Oral 15 mg Tablet, extended release Oral 2.5 mg Tablet, extended release Oral 30 mg Tablet, extended release Oral 40 mg Tablet Oral Film, soluble Sublingual Tablet Oral; Sublingual 16 MG Tablet Oral; Sublingual 2 MG Tablet Oral; Sublingual 8 MG Tablet Sublingual Tablet Sublingual 2 mg Tablet Sublingual 8 mg Tablet, extended release Oral Tablet, film coated, extended release Oral Tablet, extended release Oral 100 mg Tablet, extended release Oral 150 mg Tablet, extended release Oral 50 mg Tablet, extended release Oral 200 mg Solution Oral 50 mg/0.72mL Solution Oral 4 mg Tablet, extended release Oral 8 mg Tablet, extended release Oral 12 mg Tablet, extended release Oral 16 mg Tablet, extended release Oral 4 mg Tablet Sublingual 0.7 MG Tablet Sublingual 1.4 MG Tablet Sublingual 11.4 MG Tablet Sublingual 2.9 MG Tablet Sublingual 5.7 MG Tablet Sublingual 8.6 MG Tablet, orally disintegrating Sublingual - Prices
Unit description Cost Unit Naloxone hcl powder 70.9USD g Naloxone 0.4 mg/ml vial 7.07USD ml Naloxone 0.4 mg/ml ampul 4.78USD ml Narcan 0.4 mg/ml ampul 4.58USD ml Naloxone 0.02 mg/ml vial 0.84USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS9205082 No 2015-12-08 2022-05-10 US US7579019 No 2009-08-25 2020-01-22 US US6159498 No 2000-12-12 2016-10-18 US US9073933 No 2015-07-07 2025-03-30 US US7674800 No 2010-03-09 2025-03-30 US US7683072 No 2010-03-23 2025-03-30 US US7674799 No 2010-03-09 2025-03-30 US US8475832 No 2013-07-02 2030-03-26 US US8603514 No 2013-12-10 2024-04-03 US US8017150 No 2011-09-13 2023-02-13 US US8425462 No 2013-04-23 2024-11-23 US US8231573 No 2012-07-31 2028-11-25 US US8016788 No 2011-09-13 2025-03-21 US US8206360 No 2012-06-26 2027-02-27 US US9238108 No 2016-01-19 2027-01-22 US US8226610 No 2012-07-24 2029-04-10 US US7918823 No 2011-04-05 2024-11-23 US US8608698 No 2013-12-17 2024-11-23 US US8021344 No 2011-09-20 2029-11-02 US US8361029 No 2013-01-29 2024-11-23 US US8313466 No 2012-11-20 2024-11-23 US US7731690 No 2010-06-08 2025-01-15 US US9278182 No 2016-03-08 2026-02-01 US US7731686 No 2010-06-08 2026-06-01 US US8926594 No 2015-01-06 2026-03-31 US US7749194 No 2010-07-06 2028-10-30 US US9056170 No 2015-06-16 2024-11-23 US US7947017 No 2011-05-24 2028-03-12 US US8939943 No 2015-01-27 2031-02-28 US US8627816 No 2014-01-14 2032-02-04 US US9022022 No 2015-05-05 2031-02-28 US US8147866 No 2012-04-03 2027-07-23 US US8703177 No 2014-04-22 2032-08-20 US US8470361 No 2013-06-25 2030-05-22 US US8454996 No 2013-06-04 2019-09-24 US US8658198 No 2014-02-25 2027-12-03 US US8940330 No 2015-01-27 2032-09-18 US US9259421 No 2016-02-16 2032-09-18 US US9168252 No 2015-10-27 2022-05-10 US US9161937 No 2015-10-20 2022-05-10 US US8969369 No 2015-03-03 2022-05-10 US US9084729 No 2015-07-21 2022-05-10 US US9283216 No 2016-03-15 2022-05-10 US US9056051 No 2015-06-16 2022-05-10 US US8846090 No 2014-09-30 2023-04-04 US US6277384 No 2001-08-21 2018-12-22 US US8822487 No 2014-09-02 2018-12-22 US US8673355 No 2014-03-18 2018-12-22 US US6696066 No 2004-02-24 2018-12-22 US US8846091 No 2014-09-30 2023-04-04 US US9211253 No 2015-12-15 2035-03-16 US US9522919 No 2016-12-20 2025-03-30 US US9517307 No 2016-12-13 2034-07-18 US US9474869 No 2016-10-25 2031-02-28 US US9522188 No 2016-12-20 2035-04-24 US US9655843 No 2017-05-23 2027-07-23 US US9439900 No 2016-09-13 2032-09-18 US US9345701 No 2016-05-24 2022-05-10 US US9511066 No 2016-12-06 2022-05-10 US US9555000 No 2017-01-31 2023-04-04 US US9474750 No 2016-10-25 2018-12-22 US US9283221 No 2016-03-15 2022-05-10 US US9480644 No 2016-11-01 2035-03-16 US US9629965 No 2017-04-25 2035-03-16 US US9561177 No 2017-02-07 2035-03-16 US US9468747 No 2016-10-18 2035-03-16 US US9707226 No 2017-07-18 2035-03-16 US US9687454 No 2017-06-27 2029-08-07 US US9724471 No 2017-08-08 2027-05-23 US US9775838 No 2017-10-03 2035-03-16 US US9737669 No 2017-08-22 2024-11-23 US US9855221 No 2018-01-02 2022-02-14 US US9907793 No 2018-03-06 2023-04-04 US US9931305 No 2018-04-03 2022-02-14 US US10085937 No 2018-10-02 2035-03-16 US US10143972 No 2018-12-04 2031-05-24 US US10220158 No 2019-03-05 2035-03-20 US US10143792 No 2018-12-04 2031-05-24 US US10285910 No 2019-05-14 2022-10-11 US US10314977 No 2019-06-11 2024-11-23 US US10322239 No 2019-06-18 2031-02-28 US US10335549 No 2019-07-02 2025-04-30 US US10737028 No 2004-11-23 2024-11-23 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 200-205 °C Not Available water solubility Soluble Not Available logP 2.09 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 5.64 mg/mL ALOGPS logP 1.47 ALOGPS logP 1.62 ChemAxon logS -1.8 ALOGPS pKa (Strongest Acidic) 10.07 ChemAxon pKa (Strongest Basic) 7.84 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 70 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 88.72 m3·mol-1 ChemAxon Polarizability 33.83 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9729 Blood Brain Barrier + 0.9787 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.8788 P-glycoprotein inhibitor I Non-inhibitor 0.7922 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Inhibitor 0.5 CYP450 2C9 substrate Non-substrate 0.8522 CYP450 2D6 substrate Substrate 0.5296 CYP450 3A4 substrate Substrate 0.6107 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9303 CYP450 2D6 inhibitor Non-inhibitor 0.7886 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9153 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9523 Ames test Non AMES toxic 0.7182 Carcinogenicity Non-carcinogens 0.9583 Biodegradation Not ready biodegradable 0.9968 Rat acute toxicity 2.7231 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7798 hERG inhibition (predictor II) Non-inhibitor 0.8641
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-004i-0139000000-e70921e0765c3389ce85
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
- 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]
- 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]
- 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]
- Marek GJ: Behavioral evidence for mu-opioid and 5-HT2A receptor interactions. Eur J Pharmacol. 2003 Aug 1;474(1):77-83. [PubMed:12909198]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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]
- Goodman AJ, Le Bourdonnec B, Dolle RE: Mu opioid receptor antagonists: recent developments. ChemMedChem. 2007 Nov;2(11):1552-70. [PubMed:17918759]
- 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
- Humans
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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
- Humans
- 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
- Peng X, Neumeyer JL: Kappa receptor bivalent ligands. Curr Top Med Chem. 2007;7(4):363-73. [PubMed:17305578]
- 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]
- 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
- Humans
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- Humans
- 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 tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- 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
- Humans
- 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
- 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
- Humans
- 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
- 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
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Fang WB, Chang Y, McCance-Katz EF, Moody DE: Determination of naloxone and nornaloxone (noroxymorphone) by high-performance liquid chromatography-electrospray ionization- tandem mass spectrometry. J Anal Toxicol. 2009 Oct;33(8):409-17. doi: 10.1093/jat/33.8.409. [PubMed:19874646]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [PubMed:15304429]
Carriers
- Kind
- Protein
- Organism
- Humans
- 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
- Humans
- 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
- 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
- Humans
- 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
- 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 October 26, 2020 22:41
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