(RS)-nefopam

Also known as nefopam

Nefopam, sold under the brand name Acupan among others, is a centrally acting, non-opioid analgesic medication, with stimulant and sympathomimetic properties that is primarily used to treat moderate to severe pain.

In the Vinony graph

Vinony's link graph records 1,378 inbound references to (RS)-nefopam, and connects out to valproic acid, N-methylserotonin and liver.

It is catalogued under topics including Analgesics, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.

Vinony links it to 15 Wikipedia language editions.

Key facts

Drug.UNII: 4UP8060B7J
Drug.KEGG: D08258
Drug.ChEBI: 88316
Drug.PubChem: 4450
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 445783136
Drug.IUPAC_name: (RS)-5-methyl-1-phenyl-1,3,4,6-tetrahydro-2,5-benzoxazocine
Drug.image: Nefopam enantiomers labelled.svg
Drug.image_class: skin-invert-image
Drug.width: 250px
Drug.image2: Nefopam enantiomers ball-and-stick models from xtal labelled.png
Drug.image_class2: bg-transparent
Drug.width2: 250px
Drug.tradename: nefopam medisol
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.routes_of_administration: intramuscular, intravenous, oral

via Wikipedia infobox

Chemical data

Formula: C17H19NO
Molecular weight: 253.34 g/mol
IUPAC name: 5-methyl-1-phenyl-1,3,4,6-tetrahydro-2,5-benzoxazocine
SMILES: CN1CCOC(C2=CC=CC=C2C1)C3=CC=CC=C3
InChIKey: RGPDEAGGEXEMMM-UHFFFAOYSA-N
XLogP: 2.9
Polar surface area: 12.5 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
Indications: pain, Fever, gastric cancer, burn

via ChEMBL · EBI

Research

8 papers

Antinociceptive effects of nefopam modulating serotonergic, adrenergic, and glutamatergic neurotransmission in the spinal cord.Neuroscience letters · 2020
Enantiomeric separation of nefopam and cathinone derivatives using a supramolecular deep eutectic solvent as a chiral selector in capillary electrophoresis.Electrophoresis · 2024
Pharmacologically targeting beta-catenin for NF1 associated deficiencies in fracture repair.Bone · 2017
Development and statistical optimization of nefopam hydrochloride loaded nanospheres for neuropathic pain using Box-Behnken design.Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society · 2016
Synergistic enantioseparation systems with either cyclodextrins or cyclofructans and L-alanine Tert butyl ester lactate.Electrophoresis · 2019

via PubMed

Wikidata facts

Mass: 253.147

Show 4 more facts

significant drug interaction: clomipramine
chemical formula: C₁₇H₁₉NO
canonical SMILES: CN1CCOC(C2=CC=CC=C2C1)C3=CC=CC=C3
Commons category: Nefopam

Sources (2)

via Wikidata · CC0

~6 min read

Encyclopedic overview

23 sections

Contents

History
Medical uses
Analgesic
Postoperative pain
Chronic pain
Other medical uses
Dosage
Contraindications
Side effects
CNS side effects
Overdose
Interactions
Mechanisms of action
Analgesic mechanisms of action
Pharmacology
Pharmacokinetics
Chemistry
Manufacture
Use by country
Society and culture
Recreational use
See also
References

==History== Nefopam is based on a benzoxazocine compound. It was developed in the 1960s and marketed under the name fenazocine. It was initially used in shivering, as a muscle relaxant and as an antidepressant, but then increasingly as an analgesic.

Excerpted from Wikipedia’s “(RS)-nefopam” article, available under the CC BY-SA 4.0 licence.