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Hydrocodone

Catalog No. DB00956 Name DrugBank
CAS Number 125-29-1 Website http://www.ualberta.ca/
M. F. C18H21NO3 Telephone (780) 492-3111
M. W. 299.36424 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 832

SYNONYMS

IUPAC name
(1S,5R,13R,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-trien-14-one
IUPAC Traditional name
hydrocodone
Brand Name
Bekadid
Dicodid
Codinovo
Dico
Multacodin
Synonyms
Idrocodone [Dcit]
Dihydrocodeinone
Hydrocone
Hydroconum
Hidrocodona [INN-Spanish]
Hydrocodon
Hydrocodonum [INN-Latin]

DATABASE IDS

PubChem SID 46506225
PubChem CID 5284569
CAS Number 125-29-1

PROPERTIES

Hydrophobicity(logP) 1.2
Solubility Insoluble

DETAILS

Description (English)
Item Information
Drug Groups illicit; approved
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. Also used for the symptomatic relief of nonproductive cough, alone or in combination with other antitussives or expectorants.
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. Opiate agonists exert their principal pharmacologic effect at specific receptor binding sites in the CNS and other tissues. There are several subtypes of opiate receptors including the mu receptor (localized in pain modulating regions of the CNS), the kappa receptor (localized in the deep layers of the cerebral cortex), the delta receptor (localized in the limbic regions of the CNS), and the sigma receptor (thought to mediate the dysphoric and psychotomimetic effects of some opiate partial agonists). Agonist activity at the mu or kappa receptor can result in analgesia, miosis, and/or decreased body temperature. Agonist activity at the mu receptor can also result in suppression of opiate withdrawal, whereas antagonist activity can result in precipitation of withdrawal. Opiate agonists act at several sites within the CNS involving several systems of neurotransmitters to produce analgesia, but the precise mechanism of action has not been fully determined. Opiate agonists do not alter the threshold or responsiveness of afferent nerve endings to noxious stimuli nor the conduction of impulses along peripheral nerves. Instead, they alter the perception of pain at the spinal cord and higher levels in the CNS and the person's emotional response to pain.
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).
Affected Organisms
Humans and other mammals
Biotransformation Hepatic and also in intestinal mucosa.
Absorption Well absorbed from the gastrointestinal tract.
Half Life 1.25-3 hours
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.
External Links
Wikipedia
RxList

REFERENCES