Identification

Generic Name
Codeine-N-oxide
DrugBank Accession Number
DB01568
Background

Not Available

Type
Small Molecule
Groups
Experimental, Illicit
Structure
Weight
Average: 315.3636
Monoisotopic: 315.147058165
Chemical Formula
C18H21NO4
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Morphinans
Sub Class
Not Available
Direct Parent
Morphinans
Alternative Parents
Phenanthrenes and derivatives / Tetralins / Coumarans / Anisoles / Alkyl aryl ethers / Piperidines / Trialkyl amine oxides / Secondary alcohols / Trisubstituted amine oxides and derivatives / Oxacyclic compounds
show 5 more
Substituents
Alcohol / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Coumaran / Ether / Hydrocarbon derivative / Morphinan
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Z32OFX7V17
CAS number
3688-65-1
InChI Key
BDLSDHWCOJPHIE-KFUGMXNISA-N
InChI
InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-,19-/m0/s1
IUPAC Name
(1S,4S,5R,13R,14S,17R)-14-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-4-ium-4-olate
SMILES
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CC[N@+](C)([O-])[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

References

General References
Not Available
PubChem Compound
5359929
PubChem Substance
46504794
ChemSpider
4514400
ZINC
ZINC000247915557
Wikipedia
Codeine-N-oxide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)231.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.138 mg/mLALOGPS
logP-0.48ALOGPS
logP0.22Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.78Chemaxon
pKa (Strongest Basic)3.94Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area61.75 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity86.65 m3·mol-1Chemaxon
Polarizability32.6 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6433
Blood Brain Barrier+0.9939
Caco-2 permeable+0.6034
P-glycoprotein substrateSubstrate0.8477
P-glycoprotein inhibitor INon-inhibitor0.7436
P-glycoprotein inhibitor IINon-inhibitor0.9656
Renal organic cation transporterNon-inhibitor0.5157
CYP450 2C9 substrateNon-substrate0.8192
CYP450 2D6 substrateNon-substrate0.5
CYP450 3A4 substrateSubstrate0.7774
CYP450 1A2 substrateNon-inhibitor0.8243
CYP450 2C9 inhibitorNon-inhibitor0.8429
CYP450 2D6 inhibitorNon-inhibitor0.7587
CYP450 2C19 inhibitorNon-inhibitor0.7613
CYP450 3A4 inhibitorNon-inhibitor0.8591
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9033
Ames testNon AMES toxic0.7812
CarcinogenicityNon-carcinogens0.8989
BiodegradationNot ready biodegradable0.8248
Rat acute toxicity2.4831 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7675
hERG inhibition (predictor II)Non-inhibitor0.8397
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

Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51