CODEINE

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Search structure


Synonyms	Codeine Codeine monohydrate Codeinum Codeinum monohydricum Dea no. 9050 IDS-NC-005(SECT.-2)
Status
Molecule Category	Free-form
ATC	R05DA04
UNII	UX6OWY2V7J
EPA CompTox	DTXSID2020341


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	OROGSEYTTFOCAN-DNJOTXNNSA-N
Smiles	COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@@]341
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H21NO3
Molecular Weight	299.37
AlogP	1.5
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	1.0
Polar Surface Area	41.93
Molecular species	BASE
Aromatic Rings	1.0
Heavy Atoms	22.0

Assay Description	Organism	Bioactivity	Reference
In vitro binding affinity against cloned human Opioid receptor mu 1 expressed in HEK 293S cells	None	105.0 nM
Anti-inflammatory effect expressed as % inhibition at 50 mg/kg in acute carrageenan paw edema test in rats	Rattus norvegicus	20.0 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM	Cavia porcellus	5.7 %
Displacement of [3H]diprenorphine from recombinant mu opioid receptor expressed in C6 cells	None	727.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy	Homo sapiens	39.1 %
Inhibition of gastrointestinal transit of charcoal meal in rat at 55.2 mg/kg, po	Rattus norvegicus	70.0 %
Antitussive activity in Dunkin-Hartley guinea pig assessed as inhibition of electrically-stimulated vagus nerve-induced cough at 100 mg/kg, po administered compound prior to electrical stimulation of vagus nerve measured at 20 to 40 mins relative to control	Cavia porcellus	80.0 %

Related Entries

Environmental Exposure

Environmental Exposure Map

Countries
Croatia
Czech Republic
Germany
Hungary
Romania
Serbia
Slovakia
Slovenia

Cross References

Resources	Reference
ChEBI	16714
ChEMBL	CHEMBL485
DrugBank	DB00318
DrugCentral	725
FDA SRS	UX6OWY2V7J
Human Metabolome Database	HMDB0004995
Guide to Pharmacology	1673
KEGG	C06174
PharmGKB	PA449088
PubChem	5362471
SureChEMBL	SCHEMBL3257
ZINC	ZINC000003806721

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).