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Identification
NameCodeine
Accession NumberDB00318  (APRD00120, DB09471)
TypeSmall Molecule
GroupsApproved, Illicit
Description

An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. [PubChem]

Structure
Thumb
Synonyms
(−)-Codeine
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
(5α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
3-Methylmorphin
3-methylmorphine
7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol
7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol
Codein
Codeína
Codéine
Codeine anhydrous
Codeinum
L-Codeine
Methylmorphine
morphine 3-methyl ether
Morphine monomethyl ether
morphine monomethyl ether
morphine-3-methyl ether
O(3)-methylmorphine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Codeine 15tablet15 mgoralLaboratoire Riva Inc1994-12-31Not applicableCanada
Codeine 30tablet30 mgoralLaboratoire Riva Inc1994-12-31Not applicableCanada
Codeine Contin 100mg Controlled Release Tabtablet (extended-release)100 mgoralPurdue Pharma1995-12-31Not applicableCanada
Codeine Contin 150mg Controlled Release Tabtablet (extended-release)150 mgoralPurdue Pharma1995-12-31Not applicableCanada
Codeine Contin 200mg Controlled Release Tabtablet (extended-release)200 mgoralPurdue Pharma1995-12-31Not applicableCanada
Codeine Contin 50mg Controlled Release Tabtablet (extended-release)50 mgoralPurdue Pharma1997-03-13Not applicableCanada
Codeine Phosphate Inj 30mg/mlsolution30 mgintramuscular; subcutaneousHospira Healthcare Corporation1981-12-31Not applicableCanada
Codeine Phosphate Inj 60mg/mlsolution60 mgintramuscular; subcutaneousHospira Healthcare Corporation1981-12-31Not applicableCanada
Codeine Phosphate Injection USPliquid30 mgintramuscular; subcutaneousSandoz Canada Incorporated1978-12-31Not applicableCanada
Codeine Phosphate Syrupsyrup5 mgoralD.C. Labs Limited1951-12-312005-07-19Canada
Codeine Phosphate Syrupsyrup5.0 mgoralLaboratoire Atlas Inc1986-12-18Not applicableCanada
Codeine Phosphate Tab 15mgtablet15 mgoralD.C. Labs Limited1951-12-312003-07-11Canada
Codeine Phosphate Tab 30mgtablet30 mgoralD.C. Labs Limited1951-12-312003-07-11Canada
Codeine Phosphate Tab 60mgtablet60 mgoralD.C. Labs Limited1951-12-312003-07-11Canada
Codeine Sulfatetablet15 mg/1oralRoxane Laboratories, Inc2009-07-16Not applicableUs
Codeine Sulfatesolution30 mg/5mLoralPrecision Dose Inc.2013-02-262016-01-16Us
Codeine Sulfatesolution15 mg/2.5mLoralPrecision Dose Inc.2013-02-252016-01-16Us
Codeine Sulfatetablet60 mg/1oralPhysicians Total Care, Inc.2009-07-15Not applicableUs
Codeine Sulfatesolution30 mg/5mLoralTAGI Pharma, Inc.2012-06-012017-01-07Us
Codeine Sulfatetablet60 mg/1oralRoxane Laboratories, Inc2009-07-16Not applicableUs
Codeine Sulfatetablet30 mg/1oralRoxane Laboratories, Inc2009-07-16Not applicableUs
Codeine Tab 15mgtablet15 mgoralRougier Pharma Division Of Ratiopharm Inc1951-12-312015-10-01Canada
Codeine Tab 30mgtablet30 mgoralRougier Pharma Division Of Ratiopharm Inc1951-12-311999-09-27Canada
Linctus Codeine Blancliquid.2 %oralLaboratoire Atlas Inc1978-12-31Not applicableCanada
Paveral Liq 10mg/mlliquid10 mgoralRougier Pharma Division Of Ratiopharm Inc1990-12-311999-09-27Canada
PMS-codeinetablet15 mgoralPharmascience Inc2001-11-16Not applicableCanada
PMS-codeinetablet30 mgoralPharmascience Inc2001-12-16Not applicableCanada
Ratio-codeinetablet30 mgoralTeva Canada Limited1983-12-31Not applicableCanada
Ratio-codeinetablet15 mgoralTeva Canada Limited1983-12-31Not applicableCanada
Ratio-codeinesyrup5 mgoralTeva Canada Limited1977-12-31Not applicableCanada
Stanley Syrup W Codeine Phosphatesyrup5 mgoralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1965-12-311997-08-08Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acetaminophen and Codeine Phosphatetablet300 mg/1oralREMEDYREPACK INC.2013-04-04Not applicableUs
Codeine Sulfatetablet30 mg/1oralLannett Company, Inc.2014-06-13Not applicableUs
Codeine Sulfatetablet15 mg/1oralLannett Company, Inc.2014-06-13Not applicableUs
Codeine Sulfatetablet60 mg/1oralLannett Company, Inc.2014-06-13Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ActacodeSigma
BisoltusBoehringer Ingelheim
BromopharQualiphar
BronchicumSanofi-Aventis
BronchodinePharmacobel
CodantAntigen
CodedrillPierre Fabre
CodeinCristália
CodeisanBelmac
CoderpinaFrycia Centro América
CodicalmWelti
CodiceptNot Available
CodinexPinewood
CoduceptNot Available
CougelHwang's
CoutanMey See
DincoCenter
FarmacodFarmacom
GalcodineThornton & Ross
PectoralSiphat
TussoretMaxMedic
Brand mixtures
NameLabellerIngredients
(extra Strength) Acetaminophen, Caffeine & 8mg Codeine Phosphate CapletsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
222 TabletsMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
282 Mep TabMerck Frosst Canada & Cie, Merck Frosst Canada & Co.
282 TabMerck Frosst Canada & Cie, Merck Frosst Canada & Co.
282 TabletsPendopharm Division Of De Pharmascience Inc
292 TabMerck Frosst Canada & Cie, Merck Frosst Canada & Co.
292 TabletsPendopharm Division Of De Pharmascience Inc
A & C Tablets With Codeine 15mgD.C. Labs Limited
A & C Tablets With Codeine 30mgD.C. Labs Limited
A.C. & C 8mg TabVita Health Products Inc
A.C. & C. 8 mgLaboratoires Confab Inc
A.C. & C. 8mgWestcan Pharmaceuticals Ltd.
A.C.& C TabletsPharmascience Inc
Ac and C Tab 1/8grPharmascience Inc
Ac&c TabletsPharmascience Inc
Acet 2Pharmascience Inc
Acet 3Pharmascience Inc
Acet Codeine 30 TabPharmascience Inc
Acet Codeine 60 TabPharmascience Inc
Acetaminophen 300 Mg With 15 Mg Caffeine and 8 Mg Codeine PhosphateVita Health Products Inc
Acetaminophen 300mg, Caffeine & CodeineTanta Pharmaceuticals Inc
Acetaminophen 325 C & CTechnilab Pharma Inc.
Acetaminophen 325 Mg Caffeine and CodeineTanta Pharmaceuticals Inc
Acetaminophen 325 Mg With 15 Mg Caffeine and 8 Mg Codeine PhosphateVita Health Products Inc
Acetaminophen 500 Mg Compound Tablets With CodeinePharmascience Inc
Acetaminophen 500 Mg With 15 Mg Caffeine and 8 Mg Codeine PhosphateVita Health Products Inc
Acetaminophen 500mg, Caffeine and 8mg Codeine PhosphatePharmetics (2011) Inc
Acetaminophen and CodeineLiberty Pharmaceuticals, Inc.
Acetaminophen and Codeine PhosphateTeva Pharmaceuticals USA Inc
Acetaminophen Caffeine & 8mg Cod Phos TabStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Acetaminophen Caffeine & 8mg Cod. Phos. TabNovopharm Limited
Acetaminophen Compound Tablets With Codeine 8mgD.C. Labs Limited
Acetaminophen Elixir With 8mg Codeine Phosphate SyrupJamp Pharma Corporation
Acetaminophen W Codeine TabPharmascience Inc
Acetaminophen With CodeinePharm Pak, Inc.
Acetaminophen With Codeine - CapletTeva Canada Limited
Acetaminophen-caffeine-codeineLaboratoires Confab Inc
Acetaminophen, Caffeine & 8mg Codeine PhosphatePharmascience Inc
Acetaminophen, Caffeine & 8mg Codeine Phosphate TabletsJamp Pharma Corporation
Acetaminophen, Caffeine & CodeinePharmascience Inc
Acetaminophen, Caffeine & Codeine TabletsPharmascience Inc
Acetaminophen, Caffeine and 8 Mg Of Codeine Phosphate TabletsPharmetics (2011) Inc
Acetaminophen, Caffeine, and 8mg Of Codeine Phosphate TabletsPharmetics (2011) Inc
Acetaminophene Codeine Et Cafeine CapletsLaboratoires Trianon Inc
Acetaminophene Codeine Et Cafeine FortLaboratoires Trianon Inc
Acetazone Forte C8Teva Canada Limited
Acetylsalicylic Acid, Caffeine & 8 Mg Codeine Phosphate TabletsJamp Pharma Corporation
Acetylsalicylic Acid, Caffeine and 8mg Codeine PhosphatePharmetics (2011) Inc
AiracofCenturion Labs, Llc
Ala-hist AcPoly Pharmaceuticals
Anacin With Codeine TabWhitehall Robins Inc.
Apo-acetaco #1Apotex Inc
Asa-caffeine-codeineLaboratoires Confab Inc
Asa, Caffeine & 8mg Codeine PhosphateCanapharm Manufacturing Inc
Ascomp With CodeineNexgen Pharma, Inc.
Atasol 15 TabChurch & Dwight Canada Corp
Atasol 30 TabChurch & Dwight Canada Corp
Atasol 8 TabChurch & Dwight Canada Corp
Axacet-C1/8Technilab Pharma Inc.
Axisal-C1/8Technilab Pharma Inc.
Balminil Codeine + Decongestant + ExpectorantRougier Pharma Division Of Ratiopharm Inc
Balminil Codeine Night Time + ExpectorantRougier Pharma Division Of Ratiopharm Inc
Benylin 2 Cold and Flu With CodeineMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
Benylin Codeine 3.3mg De SyrPfizer Canada Inc., Consumer Healthcare Division
Butalbital, Acetaminophen and Caffeine With Codeine PhosphateWest Ward Pharmaceuticals Corp
Butalbital, Acetaminophen, Caffeine and Codeine PhosphateBreckenridge Pharmaceutical, Inc.
Butalbital, Acetaminophen, Caffeine, and Codeine PhosphateActavis Pharma, Inc.
Butalbital, Aspirin, Caffeine and Codeine PhosphateLannett Company, Inc.
Butalbital, Aspirin, Caffeine, and Codeine PhosphateMayne Pharma Inc.
C T Acetylsalicylic Acid Codeine and Caf TabPharmavite Laboratories (1987) Inc.
C-2 Buffered With CodeinePharmascience Inc
C2 Buffered With Codeine TabWampole Brands, A Division Of Pangeo Pharma (Canada) Inc.
C2 Tab With CodeineWampole Brands, A Division Of Pangeo Pharma (Canada) Inc.
CalmylinTeva Canada Limited
Calmylin AceTeva Canada Limited
Calmylin Codeine D-E SyrTechnilab Pharma Inc.
Calmylin Pse With CodeineTeva Canada Limited
CapcofCapital Pharmaceutical, Llc
Capital and CodeineValeant Pharmaceuticals International
Carisoprodol, Aspirin and Codeine PhosphateEon Labs, Inc.
Cheracol Cough SyrupShire Pharma Canada Ulc
Cheratussin AcQualitest Pharmaceuticals
Cheratussin DacQualitest Pharmaceuticals
CoactifedGlaxosmithkline Inc
Codar ArRespa Pharmaceuticals, Inc.
Codar DRespa Pharmaceuticals
Codar GfRespa Pharmaceuticals, Inc.
Codeine and Chlorpheniramine Maleate ERNexgen Pharma, Inc.
Codeine-guaifenesinMethod Pharmaceuticals, Llc
Coryphen 325 Codeine 30 TabRougier Pharma Division Of Ratiopharm Inc
Coryphen 650 Codeine 30 TabRougier Pharma Division Of Ratiopharm Inc
CotabsPharmavite Laboratories (1987) Inc.
CotrifedTechnilab Pharma Inc.
Cough Syr W Codeine Diphenhyd HCl & Ammon ClStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Cough Syr W.cod. Pseudoephed.hcl GuaifenesinStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Cough SyrupTeva Canada Limited
Cough Syrup With CodeineTeva Canada Limited
Covan SyrupPharmascience Inc
Damylin Avec Codeine SiropLaboratoire Atlas Inc
Damylin With Codeine SyrupLaboratoire Riva Inc
Dimetane Expectorant CPfizer Consumer Healthcare A Division Of Pfizer Canada Inc
Dimetane Expectorant-C SyrWhitehall Robins Inc.
Dimetapp-CPfizer Consumer Healthcare A Division Of Pfizer Canada Inc
Dimetapp-C SyrWhitehall Robins Inc.
Empracet-30Glaxosmithkline Inc
Empracet-60Glaxosmithkline Inc
Endacof CLarken Laboratories, Inc.
Exdol 15tabMerck Frosst Canada & Cie, Merck Frosst Canada & Co.
Exdol 30tabMerck Frosst Canada & Cie, Merck Frosst Canada & Co.
Exdol 8 TabMerck Frosst Canada & Cie, Merck Frosst Canada & Co.
Exdol-15Pharmascience Inc
Exdol-30Pharmascience Inc
Exdol-8Pharmascience Inc
Execlear CLarken Laboratories, Inc.
Fioricet With CodeineWatson Pharma, Inc.
Fiorinal C1/2Tribute Pharmaceuticals Canada Inc
Fiorinal C1/4Tribute Pharmaceuticals Canada Inc
Fiorinal With CodeineActavis Pharma, Inc.
Guaiatussin AcHi Tech Pharmacal Co., Inc.
Guaifenesin AcRising Pharmaceuticals
Guaifenesin and Codeine PhosphatePharmaceutical Associates, Inc.
Guaifenesin and Codeine Phosphate SfPhysicians Total Care, Inc.
Guaifenesin DacRising Pharmaceuticals
Histex AcAllegis Pharmaceuticals, LLC
Iophen C NrQualitest Pharmaceuticals
Lexuss 210Centurion Labs
Lortuss EXSallus Laboratories, Llc
M-clear WcR.A. Mc Neil Company
M-end Max DR.A. Mc Neil Company
M-end PER.A. Mc Neil Company
M-end WcR.A. Mc Neil Company
Mar-cof BPMarnel Pharmaceutcals, Inc.
Mar-cof Cg ExpectorantMarnel Pharmaceutcals, Inc.
Mersyndol With CodeineSanofi Aventis Canada Inc
Methoxacet-C 1/8Teva Canada Limited
Methoxisal-C 1/2Teva Canada Limited
Methoxisal-C 1/4Teva Canada Limited
Methoxisal-C 1/8Teva Canada Limited
Muscle & Back Pain Relief - 8Vita Health Products Inc
Muscle & Back Pain Relief-8Pharmascience Inc
Muscle and Back Pain Relief - 8 TabletsPharmetics (2011) Inc
Muscle and Back Pain Relief CapletsJamp Pharma Corporation
Muscle and Back Pain Relief-8Teva Canada Limited
Neo AcLaser Pharmaceuticals Llc
Ninjacof-XGCenturion Labs, Llc
Notuss PESj Pharmaceuticals, Llc
Notuss-NXSj Pharmaceuticals, Llc
Notuss-nxdSj Pharmaceuticals, Llc
Novahistex CAventis Pharma Inc
Novo Ac and C 8mg TabNovopharm Limited
Novo-gesic C15Novopharm Limited
Novo-gesic C30Novopharm Limited
Novo-gesic-C8Novopharm Limited
Nu-acetaco #1Nu Pharm Inc
Oradrine TabletsPharmavite Laboratories (1987) Inc.
Painex Tab 0.25grIcn Canada Ltd.
Painex Tab 0.5grIcn Canada Ltd.
Parafon Forte C8 W Codeine TabMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.
Pentuss SrsRhone Poulenc Rorer Canada Inc.
Phenaphen No 2 CapAyerst Laboratories
Phenaphen No 3 CapAyerst Laboratories
Phenaphen No 4 CapAyerst Laboratories
Phenaphen No.2 CapWyeth Ayerst Canada Inc.
Phenaphen No.3 CapWyeth Ayerst Canada Inc.
Phenaphen No.4 CapWyeth Ayerst Canada Inc.
Phenylhistine DhQualitest Pharmaceuticals
PHL-acet-codeine 30Pharmel Inc
PHL-acet-codeine 60Pharmel Inc
PluratussCreekwood Pharmaceutical, Inc.
PMS-acetaminophen W Codeine ElixirPharmascience Inc
PMS-pharnal-C 1/4 CapsulesPharmascience Inc
PMS-pharnal-C1/2 CapsulesPharmascience Inc
Poly Hist NcPoly Pharmaceuticals, Inc.
Poly-tussinPoly Pharmaceuticals
Poly-tussin AcPoly Pharmaceuticals, Inc.
Poly-tussin DPoly Pharmaceuticals
Pracet 30Laboratoire Riva Inc
Pro-clear AcPro Pharma Llc
Pro-red AcPro Pharma, Llc
Procet-30Pro Doc Limitee
Prometh With CodeineActavis Mid Atlantic LLC
Promethazine HCl, Phenylephrine HCl, Codeine PhosphateAmneal Pharmaceuticals of New York, LLC
Promethazine Hydrochloride and Codeine PhosphatePharmaceutical Associates, Inc.
Promethazine Hydrochloride Phenylephrine Hydrochloride and Codeine Phosphatebryant ranch prepack
Promethazine Hydrochloride, Phenylephrine Hydrochloride, and Codeine PhosphateHi Tech Pharmacal Co., Inc.
Promethazine Vc With CodeineActavis Mid Atlantic LLC
Promethazine With CodeineQualitest Pharmaceuticals
Promethazine With Codeine CoughMorton Grove Pharmaceuticals, Inc.
Pronal - C1/2 CapsulesPro Doc Limitee
Pronal C1/4 CapsulesPro Doc Limitee
Ratio-cotridinTeva Canada Limited
Ratio-cotridin ExpectorantTeva Canada Limited
Ratio-emtec-30Teva Canada Limited
Ratio-lenoltec No 1Teva Canada Limited
Ratio-lenoltec No 2Teva Canada Limited
Ratio-lenoltec No 3Teva Canada Limited
Ratio-lenoltec No 4Teva Canada Limited
Ratio-tecnal C 1/2Teva Canada Limited
Ratio-tecnal C 1/4Teva Canada Limited
Relcof-CBurel Pharmaceuticals, Llc
Robafen AcMajor Pharmaceuticals
Robaxacet-8Pfizer Consumer Healthcare A Division Of Pfizer Canada Inc
Robaxisal C 1/2Pfizer Consumer Healthcare A Division Of Pfizer Canada Inc
Robaxisal C 1/4Pfizer Consumer Healthcare A Division Of Pfizer Canada Inc
Robaxisal C-1/8 TabletsWyeth Consumer Healthcare Inc.
Robitussin AcPfizer Consumer Healthcare A Division Of Pfizer Canada Inc
Robitussin Syrup With CodeineWyeth Consumer Healthcare Inc.
Rounox Avec Codeine 15tabRougier Pharma Division Of Ratiopharm Inc
Rounox Codeine 30 TabRougier Pharma Division Of Ratiopharm Inc
Rounox Codeine 60 TabRougier Pharma Division Of Ratiopharm Inc
Routec and Codeine 30 - TabRougier Pharma Division Of Ratiopharm Inc
RydexCenturion Labs
Sinutab With Codeine TabletsMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
Spasmhalt-8Pendopharm Division Of De Pharmascience Inc
Spasmhalt-asa-8Pendopharm Division Of De Pharmascience Inc
Statuss GreenMagna Pharmaceuticals, Inc.
Suppress Cough Syr W.cod.diphen.hcl Amm.chl.Stanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Tamicode TabletsViva Pharmaceutical Inc.
Theracodeine-300Physician Therapeutics Llc
Triacin-CSTI Pharma LLC
Trianal C½Laboratoire Riva Inc
Trianal C¼Laboratoire Riva Inc
Triatec-30Laboratoire Riva Inc
Triatec-8Laboratoire Riva Inc
Triatec-8 FortLaboratoire Riva Inc
Tricode ArRespa Pharmaceuticals, Inc.
Tricode GfRespa Pharmaceuticals, Inc.
Tusnel CLlorens Pharmaceutical International Division
Tussaminic C Forte SyrupNovartis Consumer Health Canada Inc.
Tussaminic C Pediatric SyrupNovartis Consumer Health Canada Inc.
Tylenol No 1 TabMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.
Tylenol No.1 CapletsMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
Tylenol No.1 Forte CapletsMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
Tylenol No1 Forte Tablets With CodeineMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.
Tylenol W Codeine No2 TabMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.
Tylenol W Codeine No3 TabMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.
Tylenol W Codeine No4 TabMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.
Tylenol With CodeineA S Medication Solutions Llc
Tylenol With Codeine ElixirJanssen Inc
Tylenol With Codeine No. 2 - TabJanssen Inc
Tylenol With Codeine No. 3 - TabJanssen Inc
Tylenol With Codeine No. 4 - TabJanssen Inc
Virtussin A/cVirtus Pharmaceuticals
Virtussin AcPreferred Pharmaceuticals, Inc.
Virtussin DacVirtus Pharmaceuticals
Wampole-acetaminophen/codeine/caffeineJamp Pharma Corporation
Z-tuss AcMagna Pharmaceuticals, Inc.
Z-tuss EMagna Pharmaceuticals, Inc.
Zodryl Ac 25Coda Dose, Inc.
Zodryl Ac 30Coda Dose, Inc.
Zodryl Ac 40Coda Dose, Inc.
Zodryl Ac 50Coda Dose, Inc.
Zodryl Ac 60Coda Dose, Inc.
Zodryl Ac 80Coda Dose, Inc.
Zodryl Dec 25Coda Dose, Inc.
Zodryl Dec 30Coda Dose, Inc.
Zodryl Dec 40Coda Dose, Inc.
Zodryl Dec 50Coda Dose, Inc.
Zodryl Dec 60Coda Dose, Inc.
Zodryl Dec 80Coda Dose, Inc.
Zotex-CVertical Pharmaceuticals, Inc.
Salts
Name/CASStructureProperties
Codeine hydrochloride
1422-07-7
Thumb
  • InChI Key: NUXLENPAZQNFAM-FFHNEAJVSA-N
  • Monoisotopic Mass: 335.1288213
  • Average Mass: 335.83
DBSALT001068
Codeine monohydrate
6059-47-8
Thumb
  • InChI Key: WRRSFOZOETZUPG-FFHNEAJVSA-N
  • Monoisotopic Mass: 317.162708225
  • Average Mass: 317.385
DBSALT001844
Codeine phosphate
52-28-8
Thumb
  • InChI Key: WUXLCJZUUHIXFY-FFHNEAJVSA-N
  • Monoisotopic Mass: 397.129038639
  • Average Mass: 397.3594
DBSALT000030
Codeine phosphate hemihydrate
41444-62-6
Thumb
  • InChI Key: DKSZLDSPXIWGFO-BLOJGBSASA-N
  • Monoisotopic Mass: 812.268642914
  • Average Mass: 812.743
DBSALT001592
Codeine sulfate
1420-53-7
Thumb
  • InChI Key: BCXHDORHMMZBBZ-DORFAMGDSA-N
  • Monoisotopic Mass: 696.271666799
  • Average Mass: 696.81
DBSALT000031
Codeine sulfate trihydrate
6854-40-6
Thumb
  • InChI Key: BOLDZXRCJAJADM-AAXBYHQXSA-N
  • Monoisotopic Mass: 750.303360852
  • Average Mass: 750.86
DBSALT001843
Categories
UNIIUX6OWY2V7J
CAS number76-57-3
WeightAverage: 299.3642
Monoisotopic: 299.152143543
Chemical FormulaC18H21NO3
InChI KeyOROGSEYTTFOCAN-DNJOTXNNSA-N
InChI
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
IUPAC Name
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-ol
SMILES
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Benzylisoquinoline
  • Phenanthrene
  • Tetralin
  • Benzofuran
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Piperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor treatment and management of pain (systemic). It is also used as an antidiarrheal and as a cough suppressant.
PharmacodynamicsCodeine, an opiate agonist in the CNS, is similar to other phenanthrene derivatives such as morphine. It is selective for the mu receptor, but with a much weaker affinity than morphine. The analgesic properties of codeine have been speculated to come from its conversion to morphine. The principle therapeutic action is analgesia. Codeine concentrations do not correlate with brain concentration or relief of pain. The minimum effective concentration is highly variable is influenced by numerous factors, including but not limited to, age, previous opioid use, age, and general medical condition. However, the effective dose for patients that have developed tolerance is significantly higher than the opioid-naive patients.
Mechanism of actionOpiate 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.
Related Articles
AbsorptionWell absorbed following oral administration with a bioavailability of approximately 90%. Maximum plasma concentration occurs 60 minutes post-administration. Food does not effect the rate or extent of absorption of codeine.
Volume of distribution

Apparent volume of distribution = 3-6 L/kg

Protein binding7-25% bound to plasma proteins.
Metabolism

Hepatic. Codeine is a prodrug, itself inactive, but demethylated to the active morphine by the liver enzyme CYP2D6 to morphine. 70-80% of the dose undergoes glucuronidation to form codeine-6-glucuronide. This process is mediated by UDP-glucuronosyltransferase UGT2B7 and UGT2B4. 5-10% of the dose undergoes O-demethylation to morphine and 10% undergoes N-demethylation to form norcodeine. CYP2D6 mediates the biotransformation to morphine. CYP3A4 is the enzymes that mediates the conversion to norcodiene. Morphine and norcodeine are further metabolized and undergo glucuronidation. The glucuronide metabolites of morphine are morphine-3-glucuronide (M3G) and morphine-6-glucuronide (M6G). Both morphine and morphine-6-glucuronide are active and have analgesic activity. Norcodiene and M3G do not have any analgesic properties.

SubstrateEnzymesProduct
Codeine
morphineDetails
Codeine
norcodeineDetails
Codeine
Codeine-6-glucuronideDetails
Route of elimination90% of the total dose of codeine is excreted through the kidneys, of which 10% is unchanged codeine.
Half lifePlasma half-lives of codeine and its metabolites have been reported to be approximately 3 hours.
ClearanceNot Available
ToxicityRespiratory depression, sedation and miosis and common symptoms of overdose. Other symptoms include nausea, vomiting, skeletal muscle flaccidity, bradycardia, hypotension, and cool, clammy skin. Apnea and death may ensue.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Codeine Metabolism PathwayDrug metabolismSMP00621
Codeine Action PathwayDrug actionSMP00405
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2D6
Gene symbol: CYP2D6
UniProt: P10635
rs3892097 CYP2D6*4A Allele, homozygotePoor drug metabolizer, lower dose requirements1782973
Cytochrome P450 2D6
Gene symbol: CYP2D6
UniProt: P10635
rs5030655 CYP2D6*6T deletion, homozygotePoor drug metabolizer, lower dose requirements1782973
Cytochrome P450 2D6
Gene symbol: CYP2D6
UniProt: P10635
Not AvailableCYP2D6*5Deletion, homozygotePoor drug metabolizer, lower dose requirements1782973
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.9979
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.8631
P-glycoprotein inhibitor IInhibitor0.5435
P-glycoprotein inhibitor IINon-inhibitor0.8724
Renal organic cation transporterInhibitor0.638
CYP450 2C9 substrateNon-substrate0.7698
CYP450 2D6 substrateSubstrate0.9274
CYP450 3A4 substrateSubstrate0.7796
CYP450 1A2 substrateNon-inhibitor0.6494
CYP450 2C9 inhibitorNon-inhibitor0.8866
CYP450 2D6 inhibitorInhibitor0.6978
CYP450 2C19 inhibitorNon-inhibitor0.8256
CYP450 3A4 inhibitorNon-inhibitor0.8899
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.747
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9567
BiodegradationNot ready biodegradable0.9935
Rat acute toxicity2.8450 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8556
hERG inhibition (predictor II)Non-inhibitor0.8615
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Roxane laboratories inc
Packagers
Dosage forms
FormRouteStrength
Solutionoral
Tabletoral
Tabletoral300 mg/1
Capsuleoral
Suspensionoral
Liquidoral
Tablet, extended releaseoral
Tablet (extended-release)oral100 mg
Tablet (extended-release)oral150 mg
Tablet (extended-release)oral200 mg
Tablet (extended-release)oral50 mg
Solutionintramuscular; subcutaneous30 mg
Solutionintramuscular; subcutaneous60 mg
Liquidintramuscular; subcutaneous30 mg
Syruporal5.0 mg
Tabletoral60 mg
Solutionoral15 mg/2.5mL
Solutionoral30 mg/5mL
Tabletoral15 mg/1
Tabletoral30 mg/1
Tabletoral60 mg/1
Liquidoral.2 %
Liquidoral10 mg
Syrup (extended-release)oral
Elixiroral
Syruporal
Syruporal5 mg
Tabletoral15 mg
Tabletoral30 mg
Kitoral
Prices
Unit descriptionCostUnit
Codeine phosphate powder8.25USD g
Codeine Phosphate 30 mg/ml1.31USD ml
Codeine sulfate 60 mg tablet0.86USD tablet
Codeine sulfate 30 mg tablet0.76USD tablet
Codeine ph 30 mg/ml syringe0.54USD ml
Codeine ph 15 mg/ml syringe0.49USD ml
Codeine sulfate 15 mg tablet0.43USD tablet
Ratio-Codeine 30 mg Tablet0.09USD tablet
Ratio-Codeine 15 mg Tablet0.07USD tablet
Ratio-Codeine 5 mg/ml Syrup0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6248363 No1999-11-232019-11-23Us
US6383471 No1999-04-062019-04-06Us
US9066942 No2012-01-032032-01-03Us
US9107921 No2012-01-032032-01-03Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point157.5 °CPhysProp
boiling point250 °C at 2.20E+01 mm HgPhysProp
water solubility9000 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.19AVDEEF,A ET AL. (1996)
logS-1.52ADME Research, USCD
pKa8.21 (at 25 °C)LIDE,DR (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.577 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity84.6 m3·mol-1ChemAxon
Polarizability31.95 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL Thermo Scientific) 60V, Positivesplash10-0uxr-0973000000-87d07ddd2ed24b9598d7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01ot-3950000000-e80ecb11646b4da6aa92View in MoNA
References
Synthesis Reference

Nagaraj R. Ayyangar, Anil R. Choudhary, Uttam R. Kalkote, Vasant K. Sharma, “Process for the preparation of codeine from morphine.” U.S. Patent US4764615, issued May, 1912.

US4764615
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
External Links
ATC CodesN02AA59N02AA79R05DA04
AHFS Codes
  • 28:08.08
  • 48:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.5 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe therapeutic efficacy of Codeine can be decreased when used in combination with Abiraterone.
AcepromazineAcepromazine may increase the hypotensive activities of Codeine.
AcetazolamideThe risk or severity of adverse effects can be increased when Codeine is combined with Acetazolamide.
AmilorideThe risk or severity of adverse effects can be increased when Codeine is combined with Amiloride.
AmiodaroneThe therapeutic efficacy of Codeine can be decreased when used in combination with Amiodarone.
AmphetamineAmphetamine may increase the analgesic activities of Codeine.
AzelastineCodeine may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Codeine.
BendroflumethiazideThe risk or severity of adverse effects can be increased when Codeine is combined with Bendroflumethiazide.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Codeine.
BumetanideThe risk or severity of adverse effects can be increased when Codeine is combined with Bumetanide.
BupropionThe therapeutic efficacy of Codeine can be decreased when used in combination with Bupropion.
ButorphanolButorphanol may decrease the analgesic activities of Codeine.
CathinoneCathinone may increase the analgesic activities of Codeine.
CelecoxibThe therapeutic efficacy of Codeine can be decreased when used in combination with Celecoxib.
ChloroquineThe therapeutic efficacy of Codeine can be decreased when used in combination with Chloroquine.
ChlorothiazideThe risk or severity of adverse effects can be increased when Codeine is combined with Chlorothiazide.
ChlorpromazineThe therapeutic efficacy of Codeine can be decreased when used in combination with Chlorpromazine.
ChlorthalidoneThe risk or severity of adverse effects can be increased when Codeine is combined with Chlorthalidone.
CimetidineThe therapeutic efficacy of Codeine can be decreased when used in combination with Cimetidine.
Cimetropium BromideCodeine may increase the anticholinergic activities of Cimetropium Bromide.
CinacalcetThe therapeutic efficacy of Codeine can be decreased when used in combination with Cinacalcet.
ClobazamThe therapeutic efficacy of Codeine can be decreased when used in combination with Clobazam.
ClomipramineThe therapeutic efficacy of Codeine can be decreased when used in combination with Clomipramine.
ClozapineThe therapeutic efficacy of Codeine can be decreased when used in combination with Clozapine.
CocaineThe therapeutic efficacy of Codeine can be decreased when used in combination with Cocaine.
CyclothiazideThe risk or severity of adverse effects can be increased when Codeine is combined with Cyclothiazide.
DarifenacinThe therapeutic efficacy of Codeine can be decreased when used in combination with Darifenacin.
DelavirdineThe therapeutic efficacy of Codeine can be decreased when used in combination with Delavirdine.
DesipramineThe therapeutic efficacy of Codeine can be decreased when used in combination with Desipramine.
DiphenhydramineThe therapeutic efficacy of Codeine can be decreased when used in combination with Diphenhydramine.
DronedaroneThe therapeutic efficacy of Codeine can be decreased when used in combination with Dronedarone.
DuloxetineThe therapeutic efficacy of Codeine can be decreased when used in combination with Duloxetine.
EliglustatThe therapeutic efficacy of Codeine can be decreased when used in combination with Eliglustat.
EluxadolineCodeine may increase the activities of Eluxadoline.
Etacrynic acidThe risk or severity of adverse effects can be increased when Codeine is combined with Ethacrynic acid.
EthanolCodeine may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
EthoxzolamideThe risk or severity of adverse effects can be increased when Codeine is combined with Ethoxzolamide.
FluoxetineThe therapeutic efficacy of Codeine can be decreased when used in combination with Fluoxetine.
FurosemideThe risk or severity of adverse effects can be increased when Codeine is combined with Furosemide.
HaloperidolThe therapeutic efficacy of Codeine can be decreased when used in combination with Haloperidol.
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Codeine is combined with Hydrochlorothiazide.
HydroflumethiazideThe risk or severity of adverse effects can be increased when Codeine is combined with Hydroflumethiazide.
ImipramineThe therapeutic efficacy of Codeine can be decreased when used in combination with Imipramine.
IndapamideThe risk or severity of adverse effects can be increased when Codeine is combined with Indapamide.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Codeine.
IsoniazidThe therapeutic efficacy of Codeine can be decreased when used in combination with Isoniazid.
KetoconazoleThe therapeutic efficacy of Codeine can be decreased when used in combination with Ketoconazole.
LanreotideThe metabolism of Codeine can be decreased when combined with Lanreotide.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Codeine.
LorcaserinThe therapeutic efficacy of Codeine can be decreased when used in combination with Lorcaserin.
MethadoneThe therapeutic efficacy of Codeine can be decreased when used in combination with Methadone.
MethotrimeprazineThe therapeutic efficacy of Codeine can be decreased when used in combination with Methotrimeprazine.
MetolazoneThe risk or severity of adverse effects can be increased when Codeine is combined with Metolazone.
MirabegronThe therapeutic efficacy of Codeine can be decreased when used in combination with Mirabegron.
MorphineThe risk or severity of adverse effects can be increased when Codeine is combined with Morphine.
NicardipineThe therapeutic efficacy of Codeine can be decreased when used in combination with Nicardipine.
NilotinibThe therapeutic efficacy of Codeine can be decreased when used in combination with Nilotinib.
OctreotideThe metabolism of Codeine can be decreased when combined with Octreotide.
PanobinostatThe therapeutic efficacy of Codeine can be decreased when used in combination with Panobinostat.
ParoxetineThe therapeutic efficacy of Codeine can be decreased when used in combination with Paroxetine.
PasireotideThe metabolism of Codeine can be decreased when combined with Pasireotide.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Codeine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Codeine.
PromazineThe therapeutic efficacy of Codeine can be decreased when used in combination with Promazine.
QuinidineThe therapeutic efficacy of Codeine can be decreased when used in combination with Quinidine.
QuinineThe therapeutic efficacy of Codeine can be decreased when used in combination with Quinine.
RamosetronCodeine may increase the activities of Ramosetron.
RitonavirThe therapeutic efficacy of Codeine can be decreased when used in combination with Ritonavir.
RolapitantThe therapeutic efficacy of Codeine can be decreased when used in combination with Rolapitant.
SertralineThe therapeutic efficacy of Codeine can be decreased when used in combination with Sertraline.
SpironolactoneThe risk or severity of adverse effects can be increased when Codeine is combined with Spironolactone.
StiripentolThe therapeutic efficacy of Codeine can be decreased when used in combination with Stiripentol.
TacrineThe therapeutic efficacy of Codeine can be decreased when used in combination with Tacrine.
TerbinafineThe therapeutic efficacy of Codeine can be decreased when used in combination with Terbinafine.
ThioridazineThe therapeutic efficacy of Codeine can be decreased when used in combination with Thioridazine.
TiclopidineThe therapeutic efficacy of Codeine can be decreased when used in combination with Ticlopidine.
TicrynafenThe risk or severity of adverse effects can be increased when Codeine is combined with Ticrynafen.
TipranavirThe therapeutic efficacy of Codeine can be decreased when used in combination with Tipranavir.
TorasemideThe risk or severity of adverse effects can be increased when Codeine is combined with Torasemide.
TranylcypromineThe therapeutic efficacy of Codeine can be decreased when used in combination with Tranylcypromine.
TriamtereneThe risk or severity of adverse effects can be increased when Codeine is combined with Triamterene.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Codeine.
Food Interactions
  • Avoid alcohol.
  • Take with food, food reduces irritation.
  • To avoid constipation: increase your daily intake of fiber (beans, whole grains, vegetables).

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
partial agonist
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. Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociati...
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular Weight:
44778.855 Da
References
  1. Grond S, Sablotzki A: Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923. [PubMed:15509185 ]
  2. Takahama K, Shirasaki T: Central and peripheral mechanisms of narcotic antitussives: codeine-sensitive and -resistant coughs. Cough. 2007 Jul 9;3:8. [PubMed:17620111 ]
  3. Freissmuth M, Beindl W, Kratzel M: Binding and structure-activity-relation of benzo[f]isoquinoline- and norcodeinone-derivatives at mu-opioid receptors in the rat cerebral cortex. Br J Pharmacol. 1993 Dec;110(4):1429-36. [PubMed:8306082 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
partial agonist
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 synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates th...
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular Weight:
42644.665 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Takahama K, Shirasaki T: Central and peripheral mechanisms of narcotic antitussives: codeine-sensitive and -resistant coughs. Cough. 2007 Jul 9;3:8. [PubMed:17620111 ]
  4. Mignat C, Wille U, Ziegler A: Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes. Life Sci. 1995;56(10):793-9. [PubMed:7885194 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
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 nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurot...
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular Weight:
40368.235 Da
References
  1. Ortiz MI, Castro-Olguin J, Pena-Samaniego N, Castaneda-Hernandez G: Probable activation of the opioid receptor-nitric oxide-cyclic GMP-K+ channels pathway by codeine. Pharmacol Biochem Behav. 2005 Dec;82(4):695-703. Epub 2006 Jan 4. [PubMed:16386786 ]
  2. Mignat C, Wille U, Ziegler A: Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes. Life Sci. 1995;56(10):793-9. [PubMed:7885194 ]
  3. Loghin F, Popa DS, Socaciu C: Influence of glutethimide on rat brain mononucleotides by sub-chronic codeine treatment. J Cell Mol Med. 2001 Oct-Dec;5(4):409-16. [PubMed:12067475 ]
  4. Advenier C, Girard V, Naline E, Vilain P, Emonds-Alt X: Antitussive effect of SR 48968, a non-peptide tachykinin NK2 receptor antagonist. Eur J Pharmacol. 1993 Nov 30;250(1):169-71. [PubMed:8119316 ]
  5. Karlsson JA, Lanner AS, Persson CG: Airway opioid receptors mediate inhibition of cough and reflex bronchoconstriction in guinea pigs. J Pharmacol Exp Ther. 1990 Feb;252(2):863-8. [PubMed:2156065 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Zhou SF: Polymorphism of human cytochrome P450 2D6 and its clinical significance: Part I. Clin Pharmacokinet. 2009;48(11):689-723. doi: 10.2165/11318030-000000000-00000. [PubMed:19817501 ]
  2. Duquette PH, Peterson FJ, Crankshaw DL, Lindemann NJ, Holtzman JL: Studies of the metabolic N- and O-demethylation of [6-3H]codeine. Drug Metab Dispos. 1983 Sep-Oct;11(5):477-80. [PubMed:6138234 ]
  3. 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 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Duquette PH, Peterson FJ, Crankshaw DL, Lindemann NJ, Holtzman JL: Studies of the metabolic N- and O-demethylation of [6-3H]codeine. Drug Metab Dispos. 1983 Sep-Oct;11(5):477-80. [PubMed:6138234 ]
  2. 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 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
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 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
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...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 Da
References
  1. FDA label
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
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-hydr...
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular Weight:
60512.035 Da
References
  1. FDA label

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Tzvetkov MV, dos Santos Pereira JN, Meineke I, Saadatmand AR, Stingl JC, Brockmoller J: Morphine is a substrate of the organic cation transporter OCT1 and polymorphisms in OCT1 gene affect morphine pharmacokinetics after codeine administration. Biochem Pharmacol. 2013 Sep 1;86(5):666-78. doi: 10.1016/j.bcp.2013.06.019. Epub 2013 Jul 5. [PubMed:23835420 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 25, 2016 02:18