Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00148)
Name
Codeine
Synonyms    Click to Show/Hide the Synonyms of This API
codeine; Methylmorphine; Codeine anhydrous; Codicept; l-Codeine; Coducept; Morphine monomethyl ether; 76-57-3; Morphine 3-methyl ether; (-)-Codeine; O3-Methylmorphine; codeinum; Morphine-3-methyl ether; Codein; Norcodine, N-methyl; Norcodeine, N-methyl; CODEINE BASE; Codeine polistirex; codeina; CCRIS 7555; HSDB 3043; UNII-UX6OWY2V7J; O(3)-methylmorphine; CHEBI:16714; UX6OWY2V7J; Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-; 7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol; Codeine Anhydrate; 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol; (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol; Morphine-3-methyl ester; CHEMBL369475; (5alpha,6alpha)-17-methyl-3-(methyloxy)-7,8-didehydro-4,5-epoxymorphinan-6-ol; (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol; Codeine [INN:BAN]; EINECS 200-969-1; Codeine Alkaloid; Codeine USP; (Codeine); 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol(Codeine); 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol[codeine]; DSSTox_CID_341; Morphinan-6alpha-ol, 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl-; CHEMBL485; Epitope ID:120369; Codeine polistirex [USAN]; SCHEMBL3257; DSSTox_RID_75524; DSSTox_GSID_20341; GTPL1673; Codeine 0.1 mg/ml in Methanol; Codeine 1.0 mg/ml in Methanol; DTXSID2020341; IDS-NC-005(SECT.-2); ZINC3806721; Tox21_200082; BDBM50019351; BDBM50105098; AKOS015955539; Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-; DB00318; CAS-76-57-3; NCGC00248518-01; NCGC00257636-01; AC-11114; C06174; Q174723; Codeine, European Pharmacopoeia (EP) Reference Standard; 3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-ol; Codeine solution, 1 mg/mL in methanol, ampule of 1 mL, certified reference material; Codeine solution, analytical standard, for drug analysis, 1.0 mg/mL in methanol; Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha,6-alpha)- (9CI); Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)- (9CI); Morphinan-6alpha-ol, 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl- (8CI); (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-ol; (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; (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-7,9,11(18),15-tetraen-14-ol; (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol; (codeine)10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol; 10-methoxy-4-methyl-(13R,14S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-ol(Dihydrocodeine); 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol; 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol phosphate(codeine); 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol(codeine (H3PO4)); 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol(codeine phosphate)
Clinical Status
Approved
Disease Indication Anaesthesia ICD-11: 8E22 [1]
PubChem CID
5284371
Formula
C18H21NO3
Canonical SMILES
CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
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
InChIKey
OROGSEYTTFOCAN-DNJOTXNNSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5284371"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 299.4 Topological Polar Surface Area 41.9
XlogP 1.1 Complexity 509
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Codeine 15 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Magnesium stearate; Talc; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Lannett Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Silicon dioxide; Cellulose, microcrystalline; Starch, corn
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Silicon dioxide; Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Codeine 30 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Magnesium stearate; Talc; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Lannett Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Silicon dioxide; Cellulose, microcrystalline; Starch, corn
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Silicon dioxide; Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Codeine 60 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Magnesium stearate; Talc; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Lannett Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Silicon dioxide; Cellulose, microcrystalline; Starch, corn
                   Dosage Form Oral Tablet
                   Company Physicians Total Care; West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Silicon dioxide; Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved codeine from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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