Naloxone (CHEM016797)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:43:58 UTC
Update Date2016-11-09 01:15:28 UTC
Accession NumberCHEM016797
Identification
Common NameNaloxone
ClassSmall Molecule
DescriptionNaloxone 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 , , , , or 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 or , or benzodiazepines like or . 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 . 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-NaloxoneChEBI
1-N-Allyl-14-hydroxynordihydromorphinoneChEBI
17-Allyl-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-oneChEBI
NaloxonaChEBI
NaloxonumChEBI
DBL NaloxoneKegg
17-Allyl-3,14-dihydroxy-4,5a-epoxymorphinan-6-oneGenerator
17-Allyl-3,14-dihydroxy-4,5α-epoxymorphinan-6-oneGenerator
EN 1530 baseHMDB
L-NaloxoneHMDB
N-AllylnoroxymorphoneHMDB
NalossoneHMDB
Abello brand OF naloxone hydrochlorideHMDB
Abello, naloxoneHMDB
Boots brand OF naloxone hydrochlorideHMDB
Bristol-myers squibb brand OF naloxone hydrochlorideHMDB
Curamed brand OF naloxone hydrochlorideHMDB
endo Brand OF naloxone hydrochlorideHMDB
NarcantiHMDB
Ratiopharm brand OF naloxone hydrochlorideHMDB
Dihydride, naloxone hydrochlorideHMDB
Naloxon ratiopharmHMDB
Naloxone hydrochlorideHMDB
Naloxone hydrochloride, (5 beta,9 alpha,13 alpha,14 alpha)-isomerHMDB
SERB brand OF naloxone hydrochlorideHMDB
Bristol myers squibb brand OF naloxone hydrochlorideHMDB
Curamed, naloxonHMDB
Lamepro brand OF naloxone hydrochlorideHMDB
MRZ 2593BRHMDB
NaloneHMDB
Naloxon-ratiopharmHMDB
Hydrobromide, naloxoneHMDB
Hydrochloride dihydride, naloxoneHMDB
Hydrochloride, naloxoneHMDB
MRZ 2593 BRHMDB
MRZ 2593-BRHMDB
Naloxon curamedHMDB
Naloxone abelloHMDB
Naloxone hydrochloride dihydrideHMDB
Naloxone, (5 beta,9 alpha,13 alpha,14 alpha)-isomerHMDB
NaloxonratiopharmHMDB
Naloxone hydrobromideHMDB
NarcanHMDB
United drug brand OF naloxone hydrochlorideHMDB
Chemical FormulaC19H21NO4
Average Molecular Mass327.374 g/mol
Monoisotopic Mass327.147 g/mol
CAS Registry Number465-65-6
IUPAC Name(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
Traditional Namenaloxone
SMILES[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O
InChI IdentifierInChI=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
InChI KeyUZHSEJADLWPNLE-GRGSLBFTSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Isoquinolone
  • Tetralin
  • Coumaran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Cyclic alcohol
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.64 g/LALOGPS
logP1.47ALOGPS
logP1.62ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.27ChemAxon
pKa (Strongest Basic)10.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.72 m³·mol⁻¹ChemAxon
Polarizability33.8 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9042000000-3da4b2172456d62748f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9703600000-474943cf0224b80b9babSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0900000000-6b7de93b51a79132630fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0139000000-e70921e0765c3389ce85Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-0790000000-385321bfef7553f8994aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-2b2b5b609cf6e1a1d0a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0019000000-fdc81a17ea0adfa1d6b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0009000000-1e89424c27afc0579ffcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-5079000000-7ad11d1224dead9d51b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9030000000-102851f487961aeb63cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-8c2763e72d5fce389611Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0049000000-d9a6f9d54d49fda8a151Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2090000000-fbfe8d648c7bfc3bbe9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-354160c39518aa1987e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0019000000-c4826be6e2657469cceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-0096000000-16546df9ae1b2c3cee96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-82e8b7e0c70cdc0f9fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-ad63c6111240451f0f01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-0049000000-d10f137bf09021c8d430Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01183
HMDB IDHMDB0015314
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNaloxone
Chemspider ID4447644
ChEBI ID7459
PubChem Compound ID5284596
Kegg Compound IDC07252
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. FDA label
2. Medscape: http://www.medscape.com/viewarticle/441915_3
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17023477
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24868924
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25468814
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26469689
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26604818
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26634308