Overview
| Generic Names: | Dihydrocodeinone; Hidrocodona [INN-Spanish]; Hydrocodon; Hydrocodonum [INN-Latin]; Hydrocone; Hydroconum; Idrocodone [Dcit] |
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| IUPAC Name: | 4,5-epoxy-3-methoxy-17-methylmorphinan-6-one |
| Trade Names: | Bekadid; Codinovo; Dico; Dicodid; Multacodin |
| Brand Mixtures: | Amacodone (acetaminophen + hydrocodone bitartrate); Anexsia (acetaminophen + hydrocodone bitartrate); Anodynos (acetaminophen + hydrocodone bitartrate); Bancap (acetaminophen + hydrocodone bitartrate); Caldomine DH Adulte (Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate); Caldomine DH Enfant (Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate); CoGesic (acetaminophen + hydrocodone bitartrate); Coristine-DH Liq (Hydrocodone Bitartrate + Phenylephrine Hydrochloride); Dalmacol (Alcohol Anhydrous + Doxylamine Succinate + Etafedrin Hydrochloride + Hydrocodone Bitartrate + Sodium Citrate); Dimetane Expectorant-DC Syr (Brompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride); Dimetane Expectorant-DC Syrup (Brompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride); Dolacet (acetaminophen + hydrocodone bitartrate); Duradyne (acetaminophen + hydrocodone bitartrate); Hycomine-S (Ammonium Chloride + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Pyrilamine Maleate); Hydrocet (acetaminophen + hydrocodone bitartrate); Hydrogesic (acetaminophen + hydrocodone bitartrate); Lorcet (acetaminophen + hydrocodone bitartrate); Lortab (acetaminophen + hydrocodone bitartrate); Margesic (acetaminophen + hydrocodone bitartrate); Mercodol with Decapryn (Doxylamine Succinate + Etafedrin Hydrochloride + Hydrocodone Bitartrate + Sodium Citrate); Norcet (acetaminophen + hydrocodone bitartrate); Novahistex Dh Expectorant (Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride); Novahistex Dh Syrup (Hydrocodone Bitartrate + Phenylephrine Hydrochloride); Ratio-Calmydone (Doxylamine Succinate + Etafedrin Hydrochloride + Hydrocodone Bitartrate + Sodium Citrate); Ratio-Coristex-DH (Hydrocodone Bitartrate + Phenylephrine Hydrochloride); Solucodan Syrup (Hydrocodone Bitartrate + Menthol + Potassium Guaiacol Sulphonate + Sodium Citrate); Solucodan-H (Diphenylpyraline Hydrochloride + Hydrocodone Bitartrate + Menthol + Potassium Guaiacol Sulphonate + Sodium Citrate); Stagesic (acetaminophen + hydrocodone bitartrate); TGesic (acetaminophen + hydrocodone bitartrate); Triaminic Expectorant DH Syrup (Guaifenesin + Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate); Tussaminic DH Forte Syrup (Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate); Tussaminic DH Pediatric Syrup (Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate); Vicodin (acetaminophen + hydrocodone bitartrate); Zydone (acetaminophen + hydrocodone bitartrate) |
| PharmGKB Accession Id: | PA449900 |
Description
Narcotic analgesic related to codeine, but more potent and more addicting by weight. It is used also as cough suppressant. [PubChem]
Indication
For relief of moderate to moderately severe pain.
ATC Therapeutic Category
- R05DA:Opium alkaloids and derivatives
Pharmacology and Interactions
Mechanism Of Action
Hydrocodone acts as a weak agonist at OP1, OP2, and OP3 opiate receptors within the central nervous system (CNS). Hydrocodone primarily affects OP3 receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, 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 such as hydrocodone also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. 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.
Pharmacology
Hydrocodone, a semisynthetic opiate agonist and hydrogenated ketone derivative, is similar to other phenanthrene derivatives, such as codeine. Used as an analgesic, hydrocodone is combined with acetaminophen, ibuprofen, or aspirin to treat pain. Used as an antitussive, hydrocodone is combined with phenylephrine, pseudoephedrine, phenylpropanolamine, guaifenesin, pyrilamine, pheniramine, or chlorpheniramine.
Food Interactions
Avoid alcohol. Take with food. To avoid constipation: increase your daily intake of fiber (beans, whole grains, vegetables).
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Hepatic and also in intestinal mucosa.
Protein Binding
As most agents in the 5-ring morphinan group of semi-synthetic opioids bind plasma protein to a similar degree (range 19% [hydromorphone] to 45% [oxycodone]), hydrocodone is expected to fall within this range.
Absorption
Well absorbed from the gastrointestinal tract.
Half Life
1.25-3 hours
Toxicity
Symptoms of overdose include respiratory depression (a decrease in respiratory rate and/or tidal volume, Cheyne-Stokes respiration, cyanosis), extreme somnolence progressing to stupor or coma, skeletal muscle flaccidity, dizziness, ringing in the ears, confusion, blurred vision, eye problems, cold and clammy skin, and sometimes bradycardia and hypotension. In severe overdose, apnea, circulatory collapse, cardiac arrest and death may occur. LD50=85.7mg/kg (subcutaneous, in mice).
Chemical Properties
Chemical Formula:
C18H21NO3
SMILES Code:
CN1CC[C@]23c4c5ccc(c4O[C@H]2C(=O)CC[C@H]3[C@H]1C5)OC
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
299.3642 / 299.1521
Curated Information
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
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CYP2D6 |
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CYP3A |
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CYP3A4 |
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CYP3A5 |
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Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
Curated Information
The following drugs are in curated knowledge about this drug.
| Drug | Relationship | Evidence | |
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ketoconazole |
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quinidine |
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troleandomycin |
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Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| cimetidine | Cimetidine increases the effect of the narcotic |
| naltrexone | Naltrexone may precipitate a withdrawal syndrome in opiod-dependent individual |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
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Pain |
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Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
LinkOuts
Common Searches
Search PubMed
Search Medline Plus
Search PubChem
Search CTD
Non-Curated Publications
A list of non-curated publications that mention this drug is available.