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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-16 11:18:23 UTC
Update Date2022-03-07 02:49:24 UTC
HMDB IDHMDB0004995
Secondary Accession Numbers
  • HMDB0014463
  • HMDB04995
  • HMDB14463
Metabolite Identification
Common NameCodeine
DescriptionIn the United States, codeine is regulated by the Controlled Substances Act. It is a Schedule II controlled substance for pain-relief products containing codeine alone. In combination with aspirin or acetaminophen (paracetamol/tylenol) it is listed as Schedule III. Codeine is also available outside the United States as an over-the-counter drug (Schedule V) in liquid cough-relief formulations. Internationally, codeine is a Schedule II drug under the Single Convention on Narcotic Drugs. In the United Kingdom, codeine is regulated by the Misuse of Drugs Act 1971; it is a Class B Drug, except for concentrations of less than 8mg when combined with paracetamol - or 12.5mg when combined with ibuprofen - which are available in many over the counter preparations. it is a Class B Drug, except for concentrations of less than 8mg when combined with paracetamol - or 12.5mg when combined with ibuprofen - which are available in many over the counter preparations. An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. Codeine or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. It is marketed as the salts codeine sulfate and codeine phosphate. Codeine hydrochloride is more commonly marketed in contintental Europe and other regions. Codeine is an alkaloid found in opium in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. In the United Kingdom, codeine is regulated by the Misuse of Drugs Act 1971; Codeine or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. It is marketed as the salts codeine sulfate and codeine phosphate. Codeine hydrochloride is more commonly marketed in contintental Europe and other regions. Codeine is an alkaloid found in opium in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. Theoretically, a dose of approximately 200 mg (oral) of codeine must be administered to give equivalent analgesia to 30 mg (oral) of morphine (Rossi, 2004). It is not used, however, in single doses of greater than 60mg (and no more than 240 mg in 24 hours) since there is a ceiling effect. [PubChem]Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Codeine's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Structure
Data?1582752338
Synonyms
ValueSource
(-)-CodeineChEBI
(1S,13R,14S,17R)-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-14-olChEBI
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-olChEBI
7,8-Didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-olChEBI
CodeinChEBI
CodeinaChEBI
Codeine anhydrousChEBI
CodiceptChEBI
CoduceptChEBI
L-CodeineChEBI
MethylmorphineChEBI
Morphine 3-methyl etherChEBI
Morphine monomethyl etherChEBI
Morphine-3-methyl etherChEBI
O(3)-MethylmorphineChEBI
(5a,6a)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-olGenerator
(5Α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-olGenerator
7,8-Didehydro-4,5a-epoxy-3-methoxy-17-methylmorphinan-6a-olGenerator
7,8-Didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-olGenerator
Norcodeine, N-methylHMDB
Norcodine, N-methylHMDB
O3-MethylmorphineHMDB
Codeine phosphateMeSH, HMDB
IsocodeineMeSH, HMDB
N-MethylmorphineMeSH, HMDB
ArdinexMeSH, HMDB
N MethylmorphineMeSH, HMDB
Chemical FormulaC18H21NO3
Average Molecular Weight299.3642
Monoisotopic Molecular Weight299.152143543
IUPAC Name(1S,5R,13R,14S,17R)-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-14-ol
Traditional Name(1S,5R,13R,14S,17R)-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-14-ol
CAS Registry Number76-57-3
SMILES
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O
InChI Identifier
InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)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-/m0/s1
InChI KeyOROGSEYTTFOCAN-DNJOTXNNSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Piperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point157.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.58 g/LNot Available
LogP1.19AVDEEF,A ET AL. (1996)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM168.230932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP1.2ALOGPS
logP1.34ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity84.6 m³·mol⁻¹ChemAxon
Polarizability31.95 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]+169.18131661259
DarkChem[M-H]-169.42531661259
DeepCCS[M-2H]-208.35130932474
DeepCCS[M+Na]+184.39230932474
AllCCS[M+H]+173.432859911
AllCCS[M+H-H2O]+170.132859911
AllCCS[M+NH4]+176.432859911
AllCCS[M+Na]+177.332859911
AllCCS[M-H]-178.232859911
AllCCS[M+Na-2H]-177.732859911
AllCCS[M+HCOO]-177.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Codeine[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O3769.2Standard polar33892256
Codeine[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O2323.0Standard non polar33892256
Codeine[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O2437.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Codeine,1TMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C2436.8Semi standard non polar33892256
Codeine,1TBDMS,isomer #1COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C2711.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Codeine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-3090000000-38668348c3e45e16a9e72017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Codeine GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9135000000-5476697a08758d9606ba2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Codeine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Codeine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01ot-3950000000-e80ecb11646b4da6aa922014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT (LTQ Orbitrap XL Thermo Scientific) 60V, Positive-QTOFsplash10-0uxr-0973000000-87d07ddd2ed24b9598d72015-11-06HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0009000000-d68b67071bf467a42afa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0009000000-a298cedb776a11677cf72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0459000000-1a92521b38ba51a7fa812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOFsplash10-0gc1-0940000000-68cae285315cfe9c7d0e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOFsplash10-0uxs-0910000000-b0c288c76c616e1a54d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0159-0390000000-ac30542a576060b3373c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0009000000-870de7833257cd3428102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0009000000-8ece718ed46e5e4391122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0139000000-7880499a47dbd2f412292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0973000000-87d07ddd2ed24b9598d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-015a-0920000000-4f676c9e2b42320493af2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0910000000-e67964930533268605cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0009000000-99b083bf48ae39e3cec62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0009000000-efebfbff05a4cb72fe322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0139000000-be0f9b6eaa028b54ad6c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0973000000-89bc81638a52beefd8902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-015a-0920000000-7eccc8e19d8d88b181282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0910000000-5809a9ed32210bcfa2312017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine 10V, Positive-QTOFsplash10-0udi-0029000000-426a3155887524f062f82017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine 20V, Positive-QTOFsplash10-0udi-1098000000-e16cf5105c8be7f2dd002017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine 40V, Positive-QTOFsplash10-0a4i-4090000000-7d22a9e9b2e7b780b7b62017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine 10V, Negative-QTOFsplash10-0002-0090000000-d34a35c4caed20d97ad02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine 20V, Negative-QTOFsplash10-0002-0090000000-16ee1c88e7d182e8ebf42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Codeine 40V, Negative-QTOFsplash10-003f-1290000000-b1e3ca03a80d7ea7edab2017-07-26Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Epidermis
  • Hair
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.006 (0.002-0.015) uMInfant (0-1 year old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00318
Phenol Explorer Compound IDNot Available
FooDB IDFDB012162
KNApSAcK IDC00001837
Chemspider ID4447447
KEGG Compound IDC06174
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCodeine
METLIN ID498
PubChem Compound5284371
PDB IDNot Available
ChEBI ID16714
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGates, Marshall. The conversion of codeinone to codeine. Journal of the American Chemical Society (1953), 75 4340-1.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wilkins DG, Haughey HM, Krueger GG, Rollins DE: Disposition of codeine in female human hair after multiple-dose administration. J Anal Toxicol. 1995 Oct;19(6):492-8. [PubMed:8926744 ]
  2. Ammon S, von Richter O, Hofmann U, Thon KP, Eichelbaum M, Mikus G: In vitro interaction of codeine and diclofenac. Drug Metab Dispos. 2000 Oct;28(10):1149-52. [PubMed:10997932 ]
  3. Ropero-Miller JD, Lambing MK, Winecker RE: Simultaneous quantitation of opioids in blood by GC-EI-MS analysis following deproteination, detautomerization of keto analytes, solid-phase extraction, and trimethylsilyl derivatization. J Anal Toxicol. 2002 Oct;26(7):524-8. [PubMed:12423011 ]
  4. Joseph RE Jr, Hold KM, Wilkins DG, Rollins DE, Cone EJ: Drug testing with alternative matrices II. Mechanisms of cocaine and codeine deposition in hair. J Anal Toxicol. 1999 Oct;23(6):396-408. [PubMed:10517543 ]
  5. Paul BD, Shimomura ET, Smith ML: A practical approach to determine cutoff concentrations for opiate testing with simultaneous detection of codeine, morphine, and 6-acetylmorphine in urine. Clin Chem. 1999 Apr;45(4):510-9. [PubMed:10102911 ]
  6. Skopp G, Potsch L, Moeller MR: On cosmetically treated hair--aspects and pitfalls of interpretation. Forensic Sci Int. 1997 Jan 17;84(1-3):43-52. [PubMed:9042709 ]
  7. Piekoszewski W, Janowska E, Stanaszek R, Pach J, Winnik L, Karakiewicz B, Kozielec T: Determination of opiates in serum, saliva and hair addicted persons. Przegl Lek. 2001;58(4):287-9. [PubMed:11450354 ]
  8. Hebden JM, Gilchrist PJ, Perkins AC, Wilson CG, Spiller RC: Stool water content and colonic drug absorption: contrasting effects of lactulose and codeine. Pharm Res. 1999 Aug;16(8):1254-9. [PubMed:10468028 ]
  9. Huestis MA, Oyler JM, Cone EJ, Wstadik AT, Schoendorfer D, Joseph RE Jr: Sweat testing for cocaine, codeine and metabolites by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Oct 15;733(1-2):247-64. [PubMed:10572984 ]
  10. Sindrup SH, Hofmann U, Asmussen J, Mikus G, Brosen K, Nielsen F, Ingwersen SH, Broen Christensen C: Impact of quinidine on plasma and cerebrospinal fluid concentrations of codeine and morphine after codeine intake. Eur J Clin Pharmacol. 1996;49(6):503-9. [PubMed:8706777 ]
  11. Klein G, Barkworth MF, Birkenfeld A, Dyde CJ, Rehm KD, Toberich H, Cierpka H: [Relative bioavailability of paracetamol from tablets and suppositories as well as of paracetamol and codeine in a combination tablet]. Arzneimittelforschung. 1986 Mar;36(3):496-9. [PubMed:3518729 ]
  12. O'Neal CL, Crouch DJ, Rollins DE, Fatah A, Cheever ML: Correlation of saliva codeine concentrations with plasma concentrations after oral codeine administration. J Anal Toxicol. 1999 Oct;23(6):452-9. [PubMed:10517550 ]
  13. Hill V, Cairns T, Cheng CC, Schaffer M: Multiple aspects of hair analysis for opiates: methodology, clinical and workplace populations, codeine, and poppy seed ingestion. J Anal Toxicol. 2005 Oct;29(7):696-703. [PubMed:16419403 ]
  14. Yue QY, Hasselstrom J, Svensson JO, Sawe J: Effect of codeine on oro-cecal transit time in Chinese healthy volunteers in comparison with Caucasian subjects. Eur J Clin Pharmacol. 1999 Jan;54(11):839-42. [PubMed:10027657 ]
  15. Jonasson U, Jonasson B, Saldeen T, Thuen F: The prevalence of analgesics containing dextropropoxyphene or codeine in individuals suspected of driving under the influence of drugs. Forensic Sci Int. 2000 Aug 14;112(2-3):163-9. [PubMed:10940601 ]
  16. Kintz P, Tracqui A, Mangin P: Analysis of opiates in fly larvae sampled on a putrefied cadaver. J Forensic Sci Soc. 1994 Apr-Jun;34(2):95-7. [PubMed:8035160 ]
  17. Hofmann U, Seefried S, Schweizer E, Ebner T, Mikus G, Eichelbaum M: Highly sensitive gas chromatographic-tandem mass spectrometric method for the determination of morphine and codeine in serum and urine in the femtomolar range. J Chromatogr B Biomed Sci Appl. 1999 Apr 30;727(1-2):81-8. [PubMed:10360425 ]
  18. Hepler BR, Sutheimer C, Sunshine I, Sebrosky GF: Combined enzyme immunoassay-LCEC method for the identification, confirmation, and quantitation of opiates in biological fluids. J Anal Toxicol. 1984 Mar-Apr;8(2):78-90. [PubMed:6371380 ]
  19. Joseph RE Jr, Oyler JM, Wstadik AT, Ohuoha C, Cone EJ: Drug testing with alternative matrices I. Pharmacological effects and disposition of cocaine and codeine in plasma, sebum, and stratum corneum. J Anal Toxicol. 1998 Jan-Feb;22(1):6-17. [PubMed:9491963 ]
  20. Pascual JA, Sanagustin J: Fully automated analytical method for codeine quantification in human plasma using on-line solid-phase extraction and high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 1999 Mar 19;724(2):295-302. [PubMed:10219671 ]
  21. Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. [PubMed:15102399 ]
  22. Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. [PubMed:11092114 ]
  23. Schroeder K, Fahey T: Over-the-counter medications for acute cough in children and adults in ambulatory settings. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD001831. [PubMed:15495019 ]

Only showing the first 10 proteins. There are 49 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
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 IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
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 IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
Reactions
Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronidedetails

Only showing the first 10 proteins. There are 49 proteins in total.