Hydrocodone 14413 225524010 2008-07-14T03:40:53Z ClueBot 4928500 Reverting possible vandalism by [[Special:Contributions/75.108.126.218|75.108.126.218]] to version by Excirial. False positive? [[User:ClueBot/FalsePositives|Report it]]. Thanks, [[User:ClueBot]]. (439720) (Bot) {{Drugbox| | image=Hydrocodone.png | width=155 | IUPAC_name = 4,5a-Epoxy-3-methoxy-17-methylmorphinan-6-one tartrate (1:1) hydrate (2:5) | CAS_number=125-29-1 | ATC_prefix=R05 | ATC_suffix=DA03 | PubChem=5284569 | DrugBank=APRD00591 | C=18 | H=21 | N=1 | O=3 | | molecular_weight = 299.368 | smiles = COc1ccc2C[C@@H]3N(C)CC[C@]45[C@@H](Oc1c25)C(=O)CC[C@@H]34 | bioavailability= High | metabolism = [[Hepatic]] | elimination_half-life= 3.8 hours | Excretion = Renal | pregnancy_category = Category B (USA) | legal_status = [[Controlled Substances Act#Schedule III drugs|Schedule III]] when in [[Hydrocodone#Commercial medications containing hydrocodone|combination product]] ([[United States of America|USA]]) | legal_UK = Class A | dependence_liability= Moderate | routes_of_administration= Oral, intravenous, intramuscular, subcutaneous, sublingual, intranasal }} '''Hydrocodone''' or '''dihydrocodeinone''' is a semi-synthetic [[opioid]] derived from two of the naturally occurring [[opiate]]s, [[codeine]] and [[thebaine]]. Hydrocodone is an orally active [[narcotic]] [[analgesic]] and [[Cough medicine|antitussive]]. It is commonly available in tablet, capsule, and syrup form and is often compounded with other analgesics like [[acetaminophen]] or [[ibuprofen]]. It is marketed, in its varying forms, under a number of [[trademarks]], including '''[[Vicodin]]''', Symtan, '''Anexsia''', '''Dicodid''', '''Hycodan''' (or generically '''Hydromet'''), '''Hycomine''', '''Lorcet''', '''Lortab''', '''Norco''', '''Novahistex''', '''Hydroco''', '''Tussionex''', '''Gentex''', '''Vicoprofen''', '''Xodol''', '''Bekadid''', '''Calmodid''', '''Codinovo''', '''Duodin''', '''Kolikodol''', '''Orthoxycol''', '''Mercodinone''', '''Synkonin''', '''Norgan''', and '''Hydrokon'''. Hydrocodone was first synthesized in Germany in 1920<ref>{{cite journal | author = [[Carl Mannich|Mannich, C.]]; Löwenheim, H. | title = Ueber zwei neue Reduktionsprodukte des Kodeins | journal = Archiv der Pharmazie | year = 1920 | volume = 258 | pages = 295–316 | doi = 10.1002/ardp.19202580218}}</ref> and was approved by the [[Food and Drug Administration|FDA]] on [[23 March]] [[1943]] for sale in the United States under the [[brand name]] Hycodan.<ref>{{cite web | url = http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=HYCODAN | title = Drugs@FDA - Approval History: Hycodan | accessdate = 2006-01-07| publisher = FDA }}</ref><ref>{{cite web | url = http://www.fda.gov/OHRMS/DOCKETS/98fr/E7-19340.htm | title = FDA Docket No. 2007N-0353, Drug Products Containing Hydrocodone; Enforcement Action Dates | accessdate = 2006-01-07| publisher = FDA }} See section I. B., ''DESI Review of Hydrocodone Products</ref> ==Overview== [[Image:650.jpg|thumb|left|180px|Hydrocodone Bitartrate 10mg/<br>Acetaminophen 650mg]] As a narcotic, hydrocodone relieves [[pain]] by binding to [[opioid receptor]]s in the [[brain]] and [[spinal cord]]. It can be taken with or without food as desired. When taken with alcohol, it can intensify drowsiness. It may interact with [[monoamine oxidase inhibitors]], as well as other drugs that cause drowsiness. It is in [[Food and Drug Administration|FDA]] [[pregnancy category]] B: its effect on an [[embryo]] or [[fetus]] is not clearly known and pregnant women should consult their physicians before taking it. Common [[Adverse drug reaction|side effects]] include [[dizziness]], [[lightheadedness]], [[nausea]], [[sedative|drowsiness]], [[constipation]], [[vomit]]ing, and [[Euphoria (emotion)|euphoria]]. Some less common side effects are [[allergy|allergic reaction]], [[blood]] disorders, changes in mood, mental fogginess, [[anxiety]], [[lethargy]], difficulty [[urination|urinating]], [[spasm]] of the [[ureter]], irregular or depressed [[Respiration (physiology)|respiration]], and [[rash]]. Hydrocodone is habit-forming, and can lead to physical and psychological addiction, but the potential for addiction varies from individual to individual depending on unique biological differences. Sales and production of this [[medication|drug]] have increased significantly in recent years, as have diversion and illicit use. In the [[United States|U.S.]], pure hydrocodone and forms containing more than 15 mg per dosage unit are considered [[Controlled Substances Act#Schedule II drugs|Schedule II]] drugs. Those containing less than or equal to 15 mg per dosage unit in combination with acetaminophen or another non-controlled drug are called [[hydrocodone compound]]s and are considered [[Controlled Substances Act#Schedule III drugs|Schedule III]] drugs. Hydrocodone is typically found in combination with other drugs such as [[paracetamol]], [[aspirin]], [[ibuprofen]] and [[homatropine|homatropine methylbromide]]. The purpose of the non-controlled drugs in combination is often twofold. 1) To provide increased analgesia via drug [[synergy]]. 2) To limit the intake of hydrocodone by causing unpleasant and often unsafe side effects at higher than prescribed doses (See Below). In the [[United Kingdom|UK]] it is listed as a [[Class A drug]] under the [[Misuse of Drugs Act 1971]]. Hydrocodone is not available in pure form in the United States due to a separate regulation, and is always sold with an [[Non-steroidal anti-inflammatory drug|NSAID]], acetaminophen or an antihistamine. The cough preparation Codiclear DH is the purest US hydrocodone item, containing guaifenesin and small amounts of [[ethanol]] as active ingredients. In Germany and elsewhere, hydrocodone is available as single-active-ingredient tablets as Dicodid (by analogy to the original manufacturer's other products Dilaudid and Dinarkon and others) available in 5 and 10 mg strengths. ==Overdosing risks== The presence of [[acetaminophen]] in hydrocodone-containing products deters many drug users from taking excessive amounts. However, some users will get around this by [[Cold water extraction|extracting]] a portion of the acetaminophen using cold water, taking advantage of the water-soluble element of the drug. It is not uncommon for addicts to have liver problems from consuming excessive amounts of acetaminophen over a long period of time; taking 10,000 to 15,000 milligrams (10 to 15 grams) of acetaminophen in a period of 24 hours typically results in severe [[hepatotoxicity]], and doses in the range of 15,000–20,000 milligrams a day have been reported as fatal.<ref name="rxlist">[http://www.rxlist.com/cgi/generic4/hydrocodone_od.htm Rx List]</ref> It is this factor that leads many recreational users to use only single entity opiates such as [[Oxycodone|OxyContin]]. One of the major problems today with the illicit use of hydrocodone, especially in younger populations, is that users may not be aware that hydrocodone pills contain acetaminophen. Consuming more than 4,000 milligrams of acetaminophen a day can cause liver damage, jaundice, and even liver failure<ref name="MedicineNet">[http://www.medicinenet.com/acetaminophen/article.htm Acetaminophen (Tylenol) - side effects, drug class, medical uses, and drug interactions by MedicineNet.com<!-- Bot generated title -->]</ref> if the drug is being taken in narcotic effect seeking dosages for an extended period of time. Daily consumption of hydrocodone should not exceed 40 milligrams in patients not tolerant to opiates. However, the 2006 PDR (''[[Physicians Desk Reference]]'') clearly states that Norco 10, containing 10 milligrams of hydrocodone and 325 milligrams of [[Paracetamol|APAP]] (viz., acetaminophen or paracetamol), can be taken at a dosage of up to twelve tablets per day (120 milligrams of hydrocodone). Such high amounts of hydrocodone are ''only'' intended for opiate-tolerant patients, and titration to such levels must be monitored very carefully. This restriction is only limited by the fact that twelve tablets, each containing 325 milligrams of APAP, puts the patient right below the 24-hour FDA maximum of 4,000 mg of APAP. Some specially compounded products are routinely given to chronic pain patients in doses of up to 180 mg of hydrocodone per day. Symptoms of hydrocodone overdosage include respiratory depression, extreme [[somnolence]], coma, stupor, cold and/or clammy skin, sometimes [[bradycardia]], and [[hypotension]]. A severe overdose may involve [[circulatory collapse]] [[cardiac arrest]] and/or [[death]]. Mixing hydrocodone with alcohol, cocaine, amphetamines, methylphenidate, benzodiazapines, barbiturates, and a number of other medication can have severe adverse reactions including but not limited to: heart failure, heart attack, respiratory distress, pulmonary failure, liver or kidney failure, jaundice, amnesia, seizures, blackouts and coma. Mixing acetaminophen with other NSAID analgesics like sulindac can cause serious damage to organs. ==Alcohol== It is not recommended to mix any amounts of hydrocodone and [[ethanol|alcohol]] as doing so could cause health problems. APAP is metabolized solely by the liver. Therefore the risk of fatal overdose due to [[hepatotoxicity]] can occur with significantly lower levels of APAP when mixed with ethanol. Also the mixture causes serious damage to the liver, kidneys, and stomach wall. It also increases the potential for coma, respiratory problems, and can damage the CNS.<ref>{{cite journal |journal= Postgraduate Medicine |volume= 107 |issue= 1 |month= January |year= 2000 |title= Alcohol-acetaminophen syndrome |author= Draganov, P.; Durrence, H.; Cox, C.; Reuben, A. |url= http://www.postgradmed.com/issues/2000/01_00/draganov.shtml }}</ref> Due to the feeling of euphoria it provides, these potentially negative consequences are often ignored by physically and/or psychologically dependent users. ==Hydrocodone compounds== [[Image:Hydrocodone-paracetamol-5-500.jpg|thumb|left|Hydrocodone and acetaminophen (also known as paracetamol or abbreviated as APAP) 5-500 tablets (Mallinckrodt).]]When sold commercially in the [[United States]], hydrocodone is always combined with another medication. Those combined with [[acetaminophen]] are known by various trademark names, such as Vicodin and Lortab. Hydrocodone also can be combined with [[aspirin]] (e.g., Lortab ASA), [[ibuprofen]] (e.g., Vicoprofen), and certain [[antihistamines]] (e.g., Chemdal HD). Pure hydrocodone tablets or capsules are not offered currently by any USA drug company. {{Fact|date=September 2007}} However according to the DEA there have been reports of 8 mg. makeshift Hydrocodone capsules. Combining an opioid such as hydrocodone with another [[analgesic]] can increase the effectiveness of the drug without increasing opioid-related side effects (e.g., nausea, constipation, sedation). Another argument for combining hydrocodone with acetaminophen is that it limits the potential for abuse. In tolerant users, hydrocodone can be taken in large doses relatively safely, but acetaminophen is fatally toxic to the liver in large quantities. == See also == * [[Codeine]] * [[Drug addiction]] * [[Hydrocodone compound]] * [[Hydromorphone]] * [[Opioid]] * [[Oxycodone]] * [[Vicodin]] * [[Gregory House|Dr.Gregory House]] == References == {{reflist}} == External links == * [http://www.deadiversion.usdoj.gov/drugs_concern/hydrocodone/hydrocodone.htm DEA Scheduling Information] * [http://www.erowid.org/pharms/hydrocodone/hydrocodone.shtml Erowid Hydrocodone (Vicodin) Vault] * [http://www.druglib.com/druginfo/lortab-elixir/ Lortab Elixir (Hydrocodone Bitartrate / Acetaminophen) - Drug label ] * [http://www.myaddiction.com/hydrocodone_addiction.html Hydrocodone Addiction Resource] {{Opioids}} {{Analgesics}} {{Cough and cold preparations}} [[Category:Analgesics]] [[Category:Semisynthetic opioids]] [[de:Hydrocodon]] [[es:Hidrocodona]] [[fr:Hydrocodone]] [[ko:하이드로콘]] [[it:Idrocodone]] [[hu:Hidrokodon]] [[nl:Hydrocodon]] [[pl:Hydrokodon]] [[pt:Di-hidrocodeína]] [[ru:Дигидроксикодеинон]] [[fi:Hydrokodoni]] [[sv:Hydrokodon]] [[th:ไฮโดรโคโดน]]