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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:56 UTC
HMDB IDHMDB0015314
Secondary Accession Numbers
  • HMDB15314
Metabolite Identification
Common NameNaloxone
DescriptionNaloxone is only found in individuals that have used or taken this drug. It is a specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors. [PubChem]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 opioid mu receptor. Recently, naloxone has been shown to bind all three opioid receptors (mu, kappa and gamma) but the strongest binding is to the mu receptor.
Structure
Data?1582753282
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 Weight327.3743
Monoisotopic Molecular Weight327.147058165
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
CAS Registry Number465-65-6
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O
InChI Identifier
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
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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point200 - 205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.64 g/LNot Available
LogP0.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM171.830932474
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.94931661259
DarkChem[M-H]-167.45331661259
DeepCCS[M-2H]-215.67930932474
DeepCCS[M+Na]+191.71430932474
AllCCS[M+H]+178.432859911
AllCCS[M+H-H2O]+175.432859911
AllCCS[M+NH4]+181.232859911
AllCCS[M+Na]+181.932859911
AllCCS[M-H]-181.532859911
AllCCS[M+Na-2H]-181.032859911
AllCCS[M+HCOO]-180.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Naloxone[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O4025.7Standard polar33892256
Naloxone[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O2639.3Standard non polar33892256
Naloxone[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O2780.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Naloxone,1TMS,isomer #1C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C52724.2Semi standard non polar33892256
Naloxone,1TMS,isomer #2C=CCN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(=O)CC[C@@]3(O[Si](C)(C)C)[C@H]1C52669.8Semi standard non polar33892256
Naloxone,1TMS,isomer #3C=CCN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@@]2(O)[C@H]1CC1=CC=C(O)C(=C13)O42717.1Semi standard non polar33892256
Naloxone,1TMS,isomer #4C=CCN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@@]3(O)[C@H]1C52677.6Semi standard non polar33892256
Naloxone,2TMS,isomer #1C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(=O)CC[C@@]3(O[Si](C)(C)C)[C@H]1C52693.0Semi standard non polar33892256
Naloxone,2TMS,isomer #2C=CCN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@@]2(O)[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O42724.8Semi standard non polar33892256
Naloxone,2TMS,isomer #3C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@@]3(O)[C@H]1C52693.9Semi standard non polar33892256
Naloxone,2TMS,isomer #4C=CCN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@@]2(O[Si](C)(C)C)[C@H]1CC1=CC=C(O)C(=C13)O42664.5Semi standard non polar33892256
Naloxone,2TMS,isomer #5C=CCN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@@]3(O[Si](C)(C)C)[C@H]1C52651.3Semi standard non polar33892256
Naloxone,3TMS,isomer #1C=CCN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@@]2(O[Si](C)(C)C)[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O42715.2Semi standard non polar33892256
Naloxone,3TMS,isomer #1C=CCN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@@]2(O[Si](C)(C)C)[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O42841.0Standard non polar33892256
Naloxone,3TMS,isomer #1C=CCN1CC[C@]23C4=C(O[Si](C)(C)C)CC[C@@]2(O[Si](C)(C)C)[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O43293.2Standard polar33892256
Naloxone,3TMS,isomer #2C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@@]3(O[Si](C)(C)C)[C@H]1C52726.8Semi standard non polar33892256
Naloxone,3TMS,isomer #2C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@@]3(O[Si](C)(C)C)[C@H]1C52793.8Standard non polar33892256
Naloxone,3TMS,isomer #2C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C)=CC[C@@]3(O[Si](C)(C)C)[C@H]1C53265.3Standard polar33892256
Naloxone,1TBDMS,isomer #1C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C52979.7Semi standard non polar33892256
Naloxone,1TBDMS,isomer #2C=CCN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(=O)CC[C@@]3(O[Si](C)(C)C(C)(C)C)[C@H]1C52910.7Semi standard non polar33892256
Naloxone,1TBDMS,isomer #3C=CCN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@@]2(O)[C@H]1CC1=CC=C(O)C(=C13)O42960.2Semi standard non polar33892256
Naloxone,1TBDMS,isomer #4C=CCN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@@]3(O)[C@H]1C52919.9Semi standard non polar33892256
Naloxone,2TBDMS,isomer #1C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(=O)CC[C@@]3(O[Si](C)(C)C(C)(C)C)[C@H]1C53146.5Semi standard non polar33892256
Naloxone,2TBDMS,isomer #2C=CCN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@@]2(O)[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O43191.7Semi standard non polar33892256
Naloxone,2TBDMS,isomer #3C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@@]3(O)[C@H]1C53153.0Semi standard non polar33892256
Naloxone,2TBDMS,isomer #4C=CCN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@@]2(O[Si](C)(C)C(C)(C)C)[C@H]1CC1=CC=C(O)C(=C13)O43114.6Semi standard non polar33892256
Naloxone,2TBDMS,isomer #5C=CCN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@@]3(O[Si](C)(C)C(C)(C)C)[C@H]1C53090.0Semi standard non polar33892256
Naloxone,3TBDMS,isomer #1C=CCN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@@]2(O[Si](C)(C)C(C)(C)C)[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O43348.2Semi standard non polar33892256
Naloxone,3TBDMS,isomer #1C=CCN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@@]2(O[Si](C)(C)C(C)(C)C)[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O43464.2Standard non polar33892256
Naloxone,3TBDMS,isomer #1C=CCN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)CC[C@@]2(O[Si](C)(C)C(C)(C)C)[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O43528.8Standard polar33892256
Naloxone,3TBDMS,isomer #2C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@@]3(O[Si](C)(C)C(C)(C)C)[C@H]1C53354.4Semi standard non polar33892256
Naloxone,3TBDMS,isomer #2C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@@]3(O[Si](C)(C)C(C)(C)C)[C@H]1C53339.5Standard non polar33892256
Naloxone,3TBDMS,isomer #2C=CCN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(O[Si](C)(C)C(C)(C)C)=CC[C@@]3(O[Si](C)(C)C(C)(C)C)[C@H]1C53474.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Naloxone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9042000000-3da4b2172456d62748f02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naloxone GC-MS (2 TMS) - 70eV, Positivesplash10-004i-9703600000-474943cf0224b80b9bab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naloxone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Naloxone LC-ESI-qTof , Positive-QTOFsplash10-00di-0900000000-6b7de93b51a79132630f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naloxone , positive-QTOFsplash10-004i-0139000000-e70921e0765c3389ce852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naloxone 40V, Positive-QTOFsplash10-03di-0790000000-385321bfef7553f8994a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naloxone 10V, Positive-QTOFsplash10-004i-0009000000-2b2b5b609cf6e1a1d0a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naloxone 20V, Positive-QTOFsplash10-03di-0019000000-fdc81a17ea0adfa1d6b12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 10V, Positive-QTOFsplash10-03fr-0009000000-1e89424c27afc0579ffc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 20V, Positive-QTOFsplash10-03dl-5079000000-7ad11d1224dead9d51b52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 40V, Positive-QTOFsplash10-0006-9030000000-102851f487961aeb63cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 10V, Negative-QTOFsplash10-004i-0009000000-8c2763e72d5fce3896112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 20V, Negative-QTOFsplash10-056r-0049000000-d9a6f9d54d49fda8a1512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 40V, Negative-QTOFsplash10-00ku-2090000000-fbfe8d648c7bfc3bbe9f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 10V, Positive-QTOFsplash10-004i-0009000000-354160c39518aa1987e32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 20V, Positive-QTOFsplash10-03fr-0019000000-c4826be6e2657469ccea2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 40V, Positive-QTOFsplash10-00b9-0096000000-16546df9ae1b2c3cee962021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 10V, Negative-QTOFsplash10-004i-0009000000-82e8b7e0c70cdc0f9fe62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 20V, Negative-QTOFsplash10-004i-0009000000-ad63c6111240451f0f012021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naloxone 40V, Negative-QTOFsplash10-00b9-0049000000-d10f137bf09021c8d4302021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01183 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01183 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01183
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447644
KEGG Compound IDC07252
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNaloxone
METLIN IDNot Available
PubChem Compound5284596
PDB IDNot Available
ChEBI ID7459
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). FDA label . .
  2. Medscape [Link]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
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 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular weight:
66215.4
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 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
This protein binds the cAMP response element (CRE), a sequence present in many viral and cellular promoters. CREB stimulates transcription on binding to the CRE. Transcription activation is enhanced by the TORC coactivators which act independently of Ser-133 phosphorylation. Implicated in synchronization of circadian rhythmicity
Gene Name:
CREB1
Uniprot ID:
P16220
Molecular weight:
36687.9
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular weight:
40412.3
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular weight:
44778.9
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular weight:
42644.7
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 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
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 ]
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
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 ]