Buy Cas 76-42-6 Oxycodone. Oxycodone, sold under various brand names such as Roxicodone and OxyContin (which is the extended release form), is a semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive[14] and is a commonly abused drug.[15][16] It is usually taken by mouth, and is available in immediate-release and controlled-release formulations.[15] Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation.[15] In the United Kingdom, it is available by injection.[17] Combination products are also available with paracetamol (acetaminophen), ibuprofen, naloxone, naltrexone, and aspirin.[15]
Common side effects include euphoria, constipation, nausea, vomiting, loss of appetite, drowsiness, dizziness, itching, dry mouth, and sweating.[15] Side effects may also include addiction and dependence, substance abuse, irritability, depression or mania, delirium, hallucinations, hypoventilation, gastroparesis, bradycardia, and hypotension.[15] Those allergic to codeine may also be allergic to oxycodone.[15] Use of oxycodone in early pregnancy appears relatively safe.[15] Opioid withdrawal may occur if rapidly stopped.[15] Oxycodone acts by activating the μ-opioid receptor.[18] When taken by mouth, it has roughly 1.5 times the effect of the equivalent amount of morphine.[19]
Oxycodone was originally produced from the opium poppy opiate alkaloid thebaine in 1916. It was first used medically in Germany in 1917.[20] It is on the World Health Organization’s List of Essential Medicines.[21] It is available as a generic medication.[15] In 2021, it was the 59th most commonly prescribed medication in the United States, with more than 11 million prescriptions.[22][23] A number of abuse-deterrent formulations are available, such as in combination with naloxone or naltrexone.
Synonyms
- Dihydro-14-hydroxycodeinone
- NSC 19043
Technical Information
Formal Name 4,5α-epoxy-14-hydroxy-3-methoxy-17-methyl-morphinan-6-one
CAS Number 76-42-6
Molecular Formula C18H21NO4
Formula Weight 315.4
Purity ≥98%
Formulation(Request formulation change)
A neat solid
Solubility(Learn about Variance in Solubility)
- DMF: 20 mg/ml
- DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml
- DMSO: 10 mg/ml
SMILES
CN1[C@H]2[C@@]3(O)[C@]4(CC1)[C@](OC5=C4C(C2)=CC=C5OC)([H])C(CC3)=O
InChi Code
InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
InChi Key
BRUQQQPBMZOVGD-XFKAJCMBSA-N
Regulatory Information
DEA Schedule
II
Shipping & Storage Information
Storage -20°C
Shipping Room Temperature in continental US; may vary elsewhere
Stability ≥ 4 years
Medical uses
Oxycodone is used for managing moderate to severe acute or chronic pain when other treatments are not sufficient.[15] It may improve quality of life in certain types of pain.[25] Numerous studies have been completed, and the appropriate use of this compound does improve the quality of life of patients with long term chronic pain syndromes.[26][27][28]
Oxycodone is available as a controlled-release tablet, intended to be taken every 12 hours.[29] A 2006 review found that controlled-release oxycodone is comparable to immediate-release oxycodone, morphine, and hydromorphone in management of moderate to severe cancer pain, with fewer side effects than morphine. The author concluded that the controlled-release form is a valid alternative to morphine and a first-line treatment for cancer pain.[29] In 2014, the European Association for Palliative Care recommended oxycodone by mouth as a second-line alternative to morphine by mouth for cancer pain.[30]
In children between 11 and 16, the extended release formulation is FDA approved for the relief of cancer pain, trauma pain, or pain due to major surgery (for those already treated with opioids, who can tolerate at least 20 mg per day of oxycodone) – this provides an alternative to Duragesic (fentanyl), the only other extended-release opioid analgesic approved for children.[31]
Oxycodone, in its extended-release form and/or in combination with naloxone, is sometimes used off-label in the treatment of severe and refractory restless legs syndrome.
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76-42-6 Oxycodone
Available forms
[edit]
See also: Oxycodone/paracetamol, Oxycodone/aspirin, Oxycodone/ibuprofen, and Oxycodone/naloxone
Both sides of a single 10mg OxyContin pill.
Oxycodone is available in a variety of formulations for by mouth or under the tongue:[8][33][34][35]
- Immediate-release oxycodone (OxyFast, OxyIR, OxyNorm, Roxicodone)
- Controlled-release oxycodone (OxyContin, Xtampza ER) – 10–12 hour duration[13]
- Oxycodone tamper-resistant (OxyContin OTR)[36]
- Immediate-release oxycodone with paracetamol (acetaminophen) (Percocet, Endocet, Roxicet, Tylox)
- Immediate-release oxycodone with aspirin (Endodan, Oxycodan, Percodan, Roxiprin)
- Immediate-release oxycodone with ibuprofen (Combunox)[37]
- Controlled-release oxycodone with naloxone (Targin, Targiniq, Targinact)[38] – 10–12 hour duration[13]
- Controlled-release oxycodone with naltrexone (Troxyca) – 10–12 hour duration[13][39]
In the US, oxycodone is only approved for use by mouth, available as tablets and oral solutions. Parenteral formulations of oxycodone (brand name OxyNorm) are also available in other parts of the world, however, and are widely used in the European Union.[40][41][42] In Spain, the Netherlands and the United Kingdom, oxycodone is approved for intravenous (IV) and intramuscular (IM) use. When first introduced in Germany during World War I, both IV and IM administrations of oxycodone were commonly used for postoperative pain management of Central Powers soldiers.[5]
Side effects
[edit]
Most common side effects of oxycodone include reduced sensitivity to pain, delayed gastric emptying, euphoria, anxiolysis (a reduction in anxiety), feelings of relaxation, and respiratory depression.[44] Common side effects of oxycodone include constipation (23%), nausea (23%), vomiting (12%), somnolence (23%), dizziness (13%), itching (13%), dry mouth (6%), and sweating (5%).[44][45] Less common side effects (experienced by less than 5% of patients) include loss of appetite, nervousness, abdominal pain, diarrhea, urinary retention, dyspnea, and hiccups.[46]
Most side effects generally become less intense over time, although issues related to constipation are likely to continue for the duration of use.[47] Chronic use of this compound and associated constipation issues can become very serious, and have been implicated in life-threatening bowel perforations,[48] a number of specific medications including naloxegol[49] have been developed to address opioid induced constipation.
Oxycodone in combination with naloxone in managed-release tablets, has been formulated to both deter abuse and reduce opioid-induced constipation.[50]
Dependence and withdrawal
[edit]
See also: Opioid dependence
The risk of experiencing severe withdrawal symptoms is high if a patient has become physically dependent and discontinues oxycodone abruptly. Medically, when the drug has been taken regularly over an extended period, it is withdrawn gradually rather than abruptly. People who regularly use oxycodone recreationally or at higher than prescribed doses are at even higher risk of severe withdrawal symptoms. The symptoms of oxycodone withdrawal, as with other opioids, may include “anxiety, panic attack, nausea, insomnia, muscle pain, muscle weakness, fevers, and other flu-like symptoms“.[51][52]
Withdrawal symptoms have also been reported in newborns whose mothers had been either injecting or orally taking oxycodone during pregnancy.[53]
Hormone levels
[edit]
See also: Opioid § Low sex hormone levels
As with other opioids, chronic use of oxycodone (particularly with higher doses) can often cause concurrent hypogonadism (low sex hormone levels).[54][55]
Overdose
[edit]
In high doses, overdoses, or in some persons not tolerant to opioids, oxycodone can cause shallow breathing, slowed heart rate, cold/clammy skin, pauses in breathing, low blood pressure, constricted pupils, circulatory collapse, respiratory arrest, and death.[46]
In 2011, it was the leading cause of drug-related deaths in the U.S.[56] However, from 2012 onwards, heroin and fentanyl have become more common causes of drug-related deaths.[56]
Oxycodone overdose has also been described to cause spinal cord infarction in high doses and ischemic damage to the brain, due to prolonged hypoxia from suppressed breathing.[57]
Interactions
[edit]
Oxycodone is metabolized by the enzymes CYP3A4 and CYP2D6. Therefore, its clearance can be altered by inhibitors and inducers of these enzymes, increasing and decreasing half-life, respectively.[41] (For lists of CYP3A4 and CYP2D6 inhibitors and inducers, see here and here, respectively.) Natural genetic variation in these enzymes can also influence the clearance of oxycodone, which may be related to the wide inter-individual variability in its half-life and potency.[41]
Ritonavir or lopinavir/ritonavir greatly increase plasma concentrations of oxycodone in healthy human volunteers due to inhibition of CYP3A4 and CYP2D6.[58] Rifampicin greatly reduces plasma concentrations of oxycodone due to strong induction of CYP3A4.[59] There is also a case report of fosphenytoin, a CYP3A4 inducer, dramatically reducing the analgesic effects of oxycodone in a chronic pain patient.[60] Dosage or medication adjustments may be necessary in each case
Opioids
Opioid painkillers are a common treatment for cancer pain. There are different types of opioid painkillers. The type and amount (dose) you take depends on how severe your pain is and what kind of pain you have. You can take opioid painkillers for mild, moderate and severe pain.
Opioids
Opioids for mild to moderate pain include codeine. Some types are available over the counter.
Opioids for severe pain include:
- morphine
- oxycodone
- diamorphine
- fentanyl and alfentanil
- buprenorphine
- hydromorphone
- methadone
- tramadol
You can only get these drugs on prescription from your doctor.
Side effects of opioids
The most common side effects of opioid drugs are:
- constipation
- feeling or being sick
The side effects are different for everyone. They can depend on the type of drug and the dose.
Tell your doctor or nurse if you have any side effects so they can help you manage them. Your nurse will give you a contact number to ring if you have any questions or problems. If in doubt, call them.
We have more detailed information about opioid drugs, how you have them and any possible side effects you might have.
Worries about addiction
You might worry that you will become addicted to morphine and other opioid drugs. This is a common fear. But it’s unlikely that you’ll get addicted to painkillers if you’re taking them for cancer pain.
Doctors usually start you on a weaker opioid and then move on to a stronger one if needed. They will increase the dose slowly until your pain is better controlled.
Sometimes, you might need very high dose of these drugs to control your pain. It is quite safe to take high doses if you need them to feel comfortable. Your nurse and doctor will keep a close watch for side effects.
Your doctor might prescribe you non opioid drugs to take alongside opioids. This is to give you the best pain relief possible.
Morphine
There are lots of different preparations of morphine that you can take in different ways. They include:
- an immediate release liquid or capsule that you take every 2 to 4 hours
- slow release tablets, or powder that you take every 12 hours
- a liquid that can be injected into a vein or given through a drip (intravenous)
- a liquid that can be given through a small needle under the skin (subcutaneous injection)
- tablets you dissolve under your tongue (transmucosal tablets)
Adjusting your dose
Breakthrough pain
Oxycodone
This opioid is a man made (synthetic) form of morphine. It’s helpful particularly if morphine hasn’t helped or has given you unpleasant side effects.
Oxycodone is still a strong opioid and works in a similar way to morphine. It is available as:
- an injectable liquid
- a liquid that you drink
- tablets or capsules to swallow
There are slow release tablets for example:
- OxyContin
- Longtec
- Oxylan
- Ixyldone
- Oxeltra
Some people might have a slow release tablet that is a combination of oxycodone and naloxone. You might have this to prevent the side effect constipation. Examples of these include:
- Myloxifin
- Sofonac
- Targinact
You should have a supply of the immediate release oxycodone one of these is known as Oxynorm. You take this if you have any extra pain while you’re taking slow release tablets.
Diamorphine
Diamorphine is a form of morphine that’s very easy to dissolve in very small amounts of water.
Doctors might use it when you need to have morphine by injection, especially in a syringe driver. A syringe driver is a small battery operated pump. It gives liquid from a syringe through a small fine tube placed just under the skin.
The pump can give small amounts continuously. Doctors use it when they need to give regular pain control to people who have sickness or find it difficult to swallow tablets.
They might also use the pump for people who are terminally ill, but being cared for at home. A nurse changes the syringe every 12 to 24 hours.
Fentanyl and alfentanil
Fentanyl is a man made (synthetic), slow release opioid. Alfentanil is a type of fentanyl. It is also called Rapifen.
How you have fentanyl
How you have alfentanil
Buprenorphine
Buprenorphine is a medium to strong opioid painkiller.
You can have it as stick on patches which you put on every 4 days, examples of these are:
- Bupeaze
- Carlosafine
- Relevtec
- Transtec
And some you change once a week. These include:
- Butec
- Bunov
- BuTrans
- Panitaz
- Rebrikel
- Reletrans
- Sevodyne
They’re useful if you find swallowing pills and medicines difficult.
More information about buprenorphine
Hydromorphone
Hydromorphone is a strong opioid. It is also known as Palladone. It’s available as:
- immediate release capsules
- slow release capsules that you take every 12 hours (Palladone SR)
- an injectable liquid
With slow release tablets, you should also have a supply of the immediate release type hydromorphone. You then take these if you have any extra pain.
Methadone
Methadone is a strong opioid. It works very well at controlling nerve pain. It’s available as:
- tablets
- a liquid that you swallow
- an injectable liquid
Codeine
Codeine is a weak opioid. It’s usually the first choice of drug if non opioid drugs are not enough to control your pain.
A number of tablets combine codeine and paracetamol, such as co-codamol or co-dydramol.
Tramadol
Tramadol is a weak opioid. It’s available as:
- tablets or capsules (such as Zamadol)
- slow release tablets or capsules that you take every 12 hours (such as Tramquel or Zeridame)
- tablets that dissolve on your tongue (Zamadol melt)
- tablets that you dissolve in water then drink (effervescent tablets)
- drops that you mix with water and then drink
While you are taking slow release tablets, you should also have a supply of the immediate release type tramadol. You take this if you have any extra pain.
- Go to information about other types of painkillers
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