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Naloxegol

Medication used in the treatment for Opioid-Induced Constipation

Summary

Medication used in the treatment for Opioid-Induced Constipation

FieldValue
imageNaloxegol.svg
image_classskin-invert-image
tradenameMovantik, Moventig
Drugs.com
DailyMedIDNaloxegol
pregnancy_AU
routes_of_administrationBy mouth
ATC_prefixA06
ATC_suffixAH03
legal_AUS4
legal_AU_comment
legal_CARx-only
legal_CA_comment
legal_UK
legal_USRx only
legal_EURx only
legal_EU_comment
CAS_number854601-70-0
PubChem56959087
ChemSpiderID28651656
ChEBI82975
UNII44T7335BKE
KEGGD10479
IUPAC_name(5α,6α)-4,5-epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)-17-(2-propen-1-yl)morphinan-3,14-diol
C34H= 53N=1O= 11
smilesCOCCOCCOCCOCCOCCOCCOCCO[C@H]1CC[C@]2([C@H]3Cc4ccc(c5c4[C@]2([C@H]1O5)CCN3CC=C)O)O
StdInChI1S/C34H53NO11/c1-3-9-35-10-8-33-30-26-4-5-27(36)31(30)46-32(33)28(6-7-34(33,37)29(35)25-26)45-24-23-44-22-21-43-20-19-42-18-17-41-16-15-40-14-13-39-12-11-38-2/h3-5,28-29,32,36-37H,1,6-25H2,2H3/t28-,29+,32-,33-,34+/m0/s1
StdInChIKeyXNKCCCKFOQNXKV-ZRSCBOBOSA-N
synonymsNKTR-118
protein_bound~4.2%
metabolismLiver (CYP3A)
elimination_half-life6–11 h
excretionFeces (68%), urine (16%)

| Drugs.com =

| elimination_half-life = 6–11 h

Naloxegol (INN; PEGylated naloxol; trade names Movantik and Moventig) is a peripherally acting μ-opioid receptor antagonist developed by AstraZeneca, licensed from Nektar Therapeutics, for the treatment of opioid-induced constipation. It was approved in 2014 in adult patients with chronic, non-cancer pain. Doses of 25 mg were found safe and well tolerated for 52 weeks. When given concomitantly with opioid analgesics, naloxegol reduced constipation-related side effects, while maintaining comparable levels of analgesia.

The most common side effects are abdominal pain, diarrhea, nausea, flatulence, vomiting, and headache.

Naloxegol was previously a Schedule II drug in the United States because of its chemical similarity to noroxymorphone. It was officially decontrolled in January 2015. It was reclassified as a prescription drug after the FDA and DEA concluded that the impermeability of the blood–brain barrier to this compound made it non-habit-forming, and so without the potential for abuse.

Medical use

Naloxegol is indicated for the treatment of opioid-induced constipation (OIC) in people with chronic non-cancer pain.

Side effects

The most common side effects are abdominal pain, diarrhea, nausea, flatulence, vomiting, and headache.

Pharmacodynamic properties

Naloxegol inhibits opioid binding in μ-opioid receptors in the gastrointestinal tract, thus decreasing the constipating effects (slowing of gastrointestinal motility and transit, hypertonicity, increased fluid reabsorption) associated with opioids.

If naloxegol is coadministered with other opioid antagonists, there is a potential for additive effect and increased risk of opioid withdrawal.

Mechanism of action

Chemically, naloxegol is a pegylated (polyethylene glycol-modified) derivative of α-naloxol. Specifically, the 6-α-hydroxyl group of α-naloxol is connected via an ether linkage to the free hydroxyl group of a monomethoxy-terminated n=7 oligomer of PEG, shown extending at the lower left of the molecule image at right. The "n=7" defines the number of two-carbon ethylenes, and so the chain length, of the attached PEG chain, and the "monomethoxy" indicates that the terminal hydroxyl group of the PEG is "capped" with a methyl group. The pegylation of the 6-α-hydroxyl side chain of naloxol prevents the drug from crossing the blood–brain barrier (BBB).

References

References

  1. (21 June 2022). "Prescription medicines: registration of new chemical entities in Australia, 2016".
  2. (4 May 2016). "Health Canada New Drug Authorizations: 2015 Highlights".
  3. (8 December 2014). "Moventig EPAR".
  4. (17 July 2006). "G Protein-Coupled Receptors as Drug Targets: Analysis of Activation and Constitutive Activity". John Wiley & Sons.
  5. "Nektar | R&D Pipeline | Products in Development | CNS/Pain | Oral Naloxegol (NKTR-118) and Oral NKTR-119".
  6. (16 September 2014). "FDA approves MOVANTIK™ (naloxegol) Tablets C-II for the treatment of opioid-induced constipation in adult patients with chronic non-cancer pain".
  7. (October 2014). "Randomised clinical trial: the long-term safety and tolerability of naloxegol in patients with pain and opioid-induced constipation". Alimentary Pharmacology & Therapeutics.
  8. (March 2015). "Naloxegol: a review of its use in patients with opioid-induced constipation". Drugs.
  9. (16 September 2024). "FDA approves MOVANTIK™ (naloxegol) tablets C-II for the treatment of opioid-induced constipation in adult patients with chronic non-cancer pain". AstraZeneca.
  10. "Schedules of Controlled Substances: Removal of Naloxegol From Control".
  11. "Movantik prescribing information highlights".
  12. "Naloxegol for Opioid-Induced Constipation in Patients with Noncancer Pain".
  13. (2016). "PubChem Compound Database". [[National Center for Biotechnology Information.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

allylamines daiichi-sankyo 4,5-epoxymorphinans drugs-developed-by-astrazeneca mu-opioid-receptor-antagonists peripherally-selective-drugs synthetic-opioids
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