loading...| Preferred Name |
codeine |
|
| Synonyms |
Methylmorphine Morphine monomethyl ether L-Codeine Norcodeine Norcodine N-Methyl Codeine anhydrous morphine-3-methyl ether codeina codeine anhydrous methylmorphine (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol l-codeine codeine (-)-Codeine 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol morphine 3-methyl ether morphine monomethyl ether Coducept Codicept Codein O(3)-methylmorphine (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 Codeine 3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-ol |
|
| Definitions |
An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. (PubChem) Pharmacology: Codeine, an opiate agonist in the CNS, is similar to other phenanthrene derivatives such as morphine. Codeine, in combination with guaifenesin or iodinated glycerol, is used as a cough suppressant and, as a single agent or in combination with acetaminophen or other products, is used for pain control and as an antidiarrheal agent. Mechanism of action: 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. Drug type: Approved. Illicit. Small Molecule. Drug category: Analgesics. Analgesics, Opioid. Antitussive Agents. Antitussives. Narcotics. Opiate Agonists A morphinane alkaloid found in the opium poppy, Papaver somniferum var. album; has analgesic, anti-tussive and anti-diarrhoeal properties. |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_16714 |
|
| alternative label |
morphine-3-methyl ether codeina codeine anhydrous methylmorphine (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol l-codeine codeine (-)-Codeine 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol morphine 3-methyl ether morphine monomethyl ether Coducept Codicept Codein O(3)-methylmorphine (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 Codeine 3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-ol |
|
| charge |
0 |
|
| createdDate |
March 5, 2010 |
|
| database_cross_reference |
PMID:23507688 Reaxys:94996 CAS:76-57-3 Wikipedia:Codeine Beilstein:5303198 PMID:24517264 Drug_Central:725 PMID:24458010 KNApSAcK:C00001837 PMID:9776433 KEGG:C06174 Beilstein:5768734 PMID:24324229 PMID:24396053 PMID:24069665 PMID:24176887 DrugBank:DB00318 Gmelin:232454 Beilstein:94996 PMID:2215478 PMID:24491926 |
|
| definition |
An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. (PubChem) Pharmacology: Codeine, an opiate agonist in the CNS, is similar to other phenanthrene derivatives such as morphine. Codeine, in combination with guaifenesin or iodinated glycerol, is used as a cough suppressant and, as a single agent or in combination with acetaminophen or other products, is used for pain control and as an antidiarrheal agent. Mechanism of action: 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. Drug type: Approved. Illicit. Small Molecule. Drug category: Analgesics. Analgesics, Opioid. Antitussive Agents. Antitussives. Narcotics. Opiate Agonists A morphinane alkaloid found in the opium poppy, Papaver somniferum var. album; has analgesic, anti-tussive and anti-diarrhoeal properties. |
|
| formula |
C18H21NO3 |
|
| has characteristic |
http://uri.neuinfo.org/nif/nifstd/nlx_chem_090801 http://purl.obolibrary.org/obo/CHEBI_60606 http://purl.obolibrary.org/obo/CHEBI_35703 http://purl.obolibrary.org/obo/CHEBI_88188 http://purl.obolibrary.org/obo/CHEBI_78298 http://purl.obolibrary.org/obo/CHEBI_50266 |
|
| has exact synonym |
Codeine 3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-ol |
|
| has functional parent | ||
| has role |
http://purl.obolibrary.org/obo/CHEBI_60606 http://purl.obolibrary.org/obo/CHEBI_35703 http://purl.obolibrary.org/obo/CHEBI_88188 http://purl.obolibrary.org/obo/CHEBI_78298 http://purl.obolibrary.org/obo/CHEBI_50266 |
|
| has_alternative_id |
CHEBI:23348 CHEBI:3803 CHEBI:14006 |
|
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
morphine-3-methyl ether codeina codeine anhydrous methylmorphine (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol l-codeine codeine (-)-Codeine 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol morphine 3-methyl ether morphine monomethyl ether Coducept Codicept Codein O(3)-methylmorphine (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 |
|
| id |
CHEBI:16714 |
|
| in_subset | ||
| 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 |
|
| inchikey |
OROGSEYTTFOCAN-DNJOTXNNSA-N |
|
| is conjugate base of | ||
| label |
codeine |
|
| mass |
299.36420 |
|
| monoisotopicmass |
299.15214 |
|
| notation |
CHEBI:16714 |
|
| note |
An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. (PubChem) Pharmacology: Codeine, an opiate agonist in the CNS, is similar to other phenanthrene derivatives such as morphine. Codeine, in combination with guaifenesin or iodinated glycerol, is used as a cough suppressant and, as a single agent or in combination with acetaminophen or other products, is used for pain control and as an antidiarrheal agent. Mechanism of action: 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. Drug type: Approved. Illicit. Small Molecule. Drug category: Analgesics. Analgesics, Opioid. Antitussive Agents. Antitussives. Narcotics. Opiate Agonists A morphinane alkaloid found in the opium poppy, Papaver somniferum var. album; has analgesic, anti-tussive and anti-diarrhoeal properties. |
|
| preferred label |
codeine |
|
| prefLabel |
codeine |
|
| smiles |
[H][C@]12C=C[C@H](O)[C@@H]3Oc4c(OC)ccc5C[C@H]1N(C)CC[C@@]23c45 |
|
| synonym |
Methylmorphine Morphine monomethyl ether L-Codeine Norcodeine Norcodine N-Methyl Codeine anhydrous |
|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_38164 |