NEFOPAM

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H19NO
Molecular Weight	253.3389
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCOC(C2=CC=CC=C2)C3=C(C1)C=CC=C3

InChI

InChIKey=RGPDEAGGEXEMMM-UHFFFAOYSA-N

InChI=1S/C17H19NO/c1-18-11-12-19-17(14-7-3-2-4-8-14)16-10-6-5-9-15(16)13-18/h2-10,17H,11-13H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.medicines.org.uk/emc/medicine/31120
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68009340

Nefopam (nefopam hydrochloride) is a potent, rapidly-acting non-narcotic analgesic. It is totally distinct from other centrally-acting analgesics such as morphine, codeine, pentazocine and propoxyphene. Unlike the narcotic agents, nefopam (nefopam hydrochloride) has been shown not to cause respiratory depression. It is indicated for the relief of acute and chronic pain, including post-operative pain, dental pain, musculo-skeletal pain, acute traumatic pain and cancer pain. Its mechanism of action is unclear.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26475417	Inhibitor 8297	6.27 null [pKi]
Serotonin transporter 178 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26475417	Inhibitor 8297	7.53 null [pKi]
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26475417	Inhibitor 8297	7.48 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.medicines.org.uk/emc/medicine/31120	Primary		Approved 8429	Nefopam Hydrochloride Approved Use Nefopam is indicated for the relief of acute and chronic pain, including post-operative pain, dental pain, musculo-skeletal pain, acute traumatic pain and cancer pain. Launch Date 2015

PubMed

Title	Date	PubMed
Preoperative peribulbar block in patients undergoing retinal detachment surgery under general anesthesia: a randomized double-blind study.	2006 Apr	16551903
Efficacy of low-dose intrathecal morphine for postoperative analgesia after abdominal aortic surgery: a double-blind randomized study.	2006 Mar-Apr	16543098
Specific and sensitive analysis of nefopam and its main metabolite desmethyl-nefopam in human plasma by liquid chromatography-ion trap tandem mass spectrometry.	2006 Nov 16	16842961
Cyclodextrin inclusion complexes of the central analgesic drug nefopam.	2006 Nov-Dec	17090434
[What are the cardiovascular complications of the analgesics and glucocorticoids?].	2006 Sep	17078595
Role of catecholamines and serotonin receptor subtypes in nefopam-induced antinociception.	2006 Sep	16750379
Recent advances in the pharmacological management of pain.	2007	17927280
Meperidine and skin surface warming additively reduce the shivering threshold: a volunteer study.	2007	17316456
Nefopam is more potent than carbamazepine for neuroprotection against veratridine in vitro and has anticonvulsant properties against both electrical and chemical stimulation.	2007	17021653
The immunopotentiator effects of nefopam.	2007 Feb	17178394
Uterus, fallopian tube, ovary and vagina-sparing laparoscopic cystectomy: technical description and results.	2007 Feb	16939698
[Nefopam by continuous intravenous injection and adverse drug reactions: which causality assessment?].	2007 Jan	17158020
Hiccup during weaning from mechanical ventilation: the use of nefopam.	2007 Nov	17933805
Effective dose of nefopam in 80% of patients (ED80): a study using the continual reassessment method.	2007 Nov	17578479
[Prevention and relief of pain induced by otolaryngological and cervicofacial surgery].	2007 Oct	18047861
A review of the literature on post-operative pain in older cancer patients.	2007 Oct	17869093
Overview of adverse reactions to nefopam: an analysis of the French Pharmacovigilance database.	2007 Oct	17868209
Analgesic efficacy of bilateral superficial cervical plexus block administered before thyroid surgery under general anaesthesia.	2007 Oct	17681971
Nefopam and ketoprofen synergy in rodent models of antinociception.	2008 Apr 28	18316069
Genetic and chemical modifiers of a CUG toxicity model in Drosophila.	2008 Feb 13	18270582
A patient-based national survey on postoperative pain management in France reveals significant achievements and persistent challenges.	2008 Jul 15	18417292
Nefopam for the prevention of postoperative pain: quantitative systematic review.	2008 Nov	18796441
Cross-reactivity of nefopam and its metabolites with benzodiazepine EMIT immunoassay.	2008 Nov-Dec	19021938
[Physico-chemical stability and sterility of non-opioid analgesics in solution].	2008 Oct	18930626
[A national survey of postoperative pain management in France: influence of type of surgical centres].	2008 Sep	18722079
B-type natriuretic peptide release and left ventricular filling pressure assessed by echocardiographic study after subarachnoid hemorrhage: a prospective study in non-cardiac patients.	2009	19454040
Modulation of paracetamol and nefopam antinociception by serotonin 5-HT(3) receptor antagonists in mice.	2009	19270466
Contribution of transient receptor potential vanilloid subtype 1 to the analgesic and antihyperalgesic activity of nefopam in rodents.	2009	19096234
Investigation of enantiomeric separation of basic drugs by capillary electrophoresis using clindamycin phosphate as a novel chiral selector.	2009 Aug	19621372
Long-term pain vulnerability after surgery in rats: prevention by nefopam, an analgesic with antihyperalgesic properties.	2009 Aug	19608840
Anaesthetic practices for scheduled caesarean delivery: a 2005 French national survey.	2009 Aug	19412111
Predictive risk factors for pain during extracorporeal shockwave lithotripsy.	2009 Dec	19821695
Nefopam hydrochloride compatibility and stability with selected proton pump inhibitors in bionolyte G5 injection for intravenous infusion.	2009 Feb	19125900
Compatibility and stability of binary mixtures of acetaminophen, nefopam, ketoprofen and ketamine in infusion solutions.	2009 Jan	19122547
Nefopam and alfentanil additively reduce the shivering threshold in humans whereas nefopam and clonidine do not.	2009 Jul	19512866
Postoperative analgesia and early rehabilitation after total knee replacement: a comparison of continuous low-dose intravenous ketamine versus nefopam.	2009 Jul	18793861
Enatiomeric determination of tramadol and O-desmethyltramadol in human urine by gas chromatography-mass spectrometry.	2009 Jul 1	19482526
Single dose oral nefopam for acute postoperative pain in adults.	2009 Jul 8	19588431
Perioperative ketamine does not prevent chronic pain after thoracotomy.	2009 May	18783971
Positive interference of the analgesic nefopam in the urine immunoassay for benzodiazepines in a secure setting.	2009 Nov	18635712
Development and evaluation of nefopam transdermal matrix patch system in human volunteers.	2009 Nov-Dec	20169860
Managing severe cancer pain: the role of transdermal buprenorphine: a systematic review.	2009 Oct	19774212
High-yielding synthesis of Nefopam analogues (functionalized benzoxazocines) by sequential one-pot cascade operations.	2009 Sep 7	19675887
[Watch out for headaches at the end of a pregnancy! Do not miss an autoimmune hypositys].	2010 Apr	20363658
The effects of nefopam on the gain and maximum intensity of shivering in healthy volunteers.	2010 Aug	20529984
Nefopam but not physostigmine affects the thermoregulatory response in mice via alpha(2)-adrenoceptors.	2010 Feb	19744502
Glycogen: a novel branched polysaccharide chiral selector in CE.	2010 Mar	20309915
Evaluation of the enantioseparation capability of the novel chiral selector clindamycin phosphate towards basic drugs by micellar electrokinetic chromatography.	2010 Mar 12	20132938
Fatal nefopam overdose.	2010 May	20360495
Prolonged withdrawal delirium in concomitant diphenhydramine and nefopam dependence: A case report.	2010 May 30	20193724

Patents

Sample Use Guides

In Vivo Use Guide

Dosage may range from 1 to 3 tablets three times daily depending on response. The recommended starting dosage is 2 tablets three times daily.

Route of Administration: Oral

In Vitro Use Guide

The effects of nefopam on human serotonin receptors (5-HT2A, 5-HT2B, 5-HT2C) were tested. Nefopam had Ki values for 5-HT2A, 5-HT2B, and 5-HT2C of 1,685, 329.5, and 56 nM, respectively.

Name

Type

Language

NEFOPAM

Official Name

English

Nefopam [WHO-DD]

Common Name

English

3,4,5,6-TETRAHYDRO-5-METHYL-1-PHENYL-1H-2,5-BENZOXAZOCINE

Systematic Name

English

1H-2,5-BENZOXAZOCINE, 3,4,5,6-TETRAHYDRO-5-METHYL-1-PHENYL-

Systematic Name

English

NEFOPAM [MI]

Common Name

English

nefopam [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N02BG06