Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C17H19NO.ClH |
| Molecular Weight | 289.8 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1CCOC(C2=CC=CC=C2)C3=CC=CC=C3C1
InChI
InChIKey=CNNVSINJDJNHQK-UHFFFAOYSA-N
InChI=1S/C17H19NO.ClH/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;1H
| Molecular Formula | C17H19NO |
| Molecular Weight | 253.3389 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://www.medicines.org.uk/emc/medicine/31120Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009340
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 | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26475417 |
6.27 null [pKi] | ||
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26475417 |
7.53 null [pKi] | ||
Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26475417 |
7.48 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Nefopam Hydrochloride Approved UseNefopam 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 Date2015 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
48.5 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
47.4 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
183.1 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
31 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
50.89 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26796604/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
41.45 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26796604/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
377 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
748 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1029 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
787 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
410.45 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26796604/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
672.93 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26796604/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12787260/ |
20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26796604/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
NEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26796604/ |
75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered: |
N-DESMETHYLNEFOPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
25% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20971961/ |
NEFOPAM plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
120 mg single, oral Higher than recommended |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
|
0.4 mg/kg single, intramuscular Highest studied dose Dose: 0.4 mg/kg Route: intramuscular Route: single Dose: 0.4 mg/kg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
1.8 g single, oral Lethal dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Disc. AE: Seizures, Cardiorespiratory arrest... AEs leading to discontinuation/dose reduction: Seizures (grade 5) Sources: Cardiorespiratory arrest (grade 5) |
1.8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Sweating, Drowsiness... AEs leading to discontinuation/dose reduction: Sweating Sources: Drowsiness Hyperreflexia Tachycardia Convulsions grand mal |
90 mg single, oral Recommended |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Cardiorespiratory arrest | grade 5 Disc. AE |
1.8 g single, oral Lethal dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Seizures | grade 5 Disc. AE |
1.8 g single, oral Lethal dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Convulsions grand mal | Disc. AE | 1.8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Drowsiness | Disc. AE | 1.8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Hyperreflexia | Disc. AE | 1.8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Sweating | Disc. AE | 1.8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Tachycardia | Disc. AE | 1.8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The effects of nefopam on the gain and maximum intensity of shivering in healthy volunteers. | 2010-08 |
|
| Prolonged withdrawal delirium in concomitant diphenhydramine and nefopam dependence: A case report. | 2010-05-30 |
|
| Fatal nefopam overdose. | 2010-05 |
|
| [Watch out for headaches at the end of a pregnancy! Do not miss an autoimmune hypositys]. | 2010-04 |
|
| Evaluation of the enantioseparation capability of the novel chiral selector clindamycin phosphate towards basic drugs by micellar electrokinetic chromatography. | 2010-03-12 |
|
| Glycogen: a novel branched polysaccharide chiral selector in CE. | 2010-03 |
|
| Development and evaluation of nefopam transdermal matrix patch system in human volunteers. | 2010-02-23 |
|
| Nefopam but not physostigmine affects the thermoregulatory response in mice via alpha(2)-adrenoceptors. | 2010-02 |
|
| Predictive risk factors for pain during extracorporeal shockwave lithotripsy. | 2009-12 |
|
| Positive interference of the analgesic nefopam in the urine immunoassay for benzodiazepines in a secure setting. | 2009-11 |
|
| Managing severe cancer pain: the role of transdermal buprenorphine: a systematic review. | 2009-10 |
|
| High-yielding synthesis of Nefopam analogues (functionalized benzoxazocines) by sequential one-pot cascade operations. | 2009-09-07 |
|
| Investigation of enantiomeric separation of basic drugs by capillary electrophoresis using clindamycin phosphate as a novel chiral selector. | 2009-08 |
|
| Long-term pain vulnerability after surgery in rats: prevention by nefopam, an analgesic with antihyperalgesic properties. | 2009-08 |
|
| Anaesthetic practices for scheduled caesarean delivery: a 2005 French national survey. | 2009-08 |
|
| Single dose oral nefopam for acute postoperative pain in adults. | 2009-07-08 |
|
| Enatiomeric determination of tramadol and O-desmethyltramadol in human urine by gas chromatography-mass spectrometry. | 2009-07-01 |
|
| Nefopam and alfentanil additively reduce the shivering threshold in humans whereas nefopam and clonidine do not. | 2009-07 |
|
| Postoperative analgesia and early rehabilitation after total knee replacement: a comparison of continuous low-dose intravenous ketamine versus nefopam. | 2009-07 |
|
| Perioperative ketamine does not prevent chronic pain after thoracotomy. | 2009-05 |
|
| Nefopam hydrochloride compatibility and stability with selected proton pump inhibitors in bionolyte G5 injection for intravenous infusion. | 2009-02 |
|
| Compatibility and stability of binary mixtures of acetaminophen, nefopam, ketoprofen and ketamine in infusion solutions. | 2009-01 |
|
| 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 |
|
| Modulation of paracetamol and nefopam antinociception by serotonin 5-HT(3) receptor antagonists in mice. | 2009 |
|
| Contribution of transient receptor potential vanilloid subtype 1 to the analgesic and antihyperalgesic activity of nefopam in rodents. | 2009 |
|
| Cross-reactivity of nefopam and its metabolites with benzodiazepine EMIT immunoassay. | 2008-11-22 |
|
| Nefopam for the prevention of postoperative pain: quantitative systematic review. | 2008-11 |
|
| [Physico-chemical stability and sterility of non-opioid analgesics in solution]. | 2008-10 |
|
| [A national survey of postoperative pain management in France: influence of type of surgical centres]. | 2008-09 |
|
| A patient-based national survey on postoperative pain management in France reveals significant achievements and persistent challenges. | 2008-07-15 |
|
| Nefopam and ketoprofen synergy in rodent models of antinociception. | 2008-04-28 |
|
| Genetic and chemical modifiers of a CUG toxicity model in Drosophila. | 2008-02-13 |
|
| Hiccup during weaning from mechanical ventilation: the use of nefopam. | 2007-11 |
|
| Effective dose of nefopam in 80% of patients (ED80): a study using the continual reassessment method. | 2007-11 |
|
| [Prevention and relief of pain induced by otolaryngological and cervicofacial surgery]. | 2007-10 |
|
| A review of the literature on post-operative pain in older cancer patients. | 2007-10 |
|
| Overview of adverse reactions to nefopam: an analysis of the French Pharmacovigilance database. | 2007-10 |
|
| Analgesic efficacy of bilateral superficial cervical plexus block administered before thyroid surgery under general anaesthesia. | 2007-10 |
|
| The immunopotentiator effects of nefopam. | 2007-02 |
|
| Uterus, fallopian tube, ovary and vagina-sparing laparoscopic cystectomy: technical description and results. | 2007-02 |
|
| [Nefopam by continuous intravenous injection and adverse drug reactions: which causality assessment?]. | 2007-01 |
|
| Recent advances in the pharmacological management of pain. | 2007 |
|
| Meperidine and skin surface warming additively reduce the shivering threshold: a volunteer study. | 2007 |
|
| Nefopam is more potent than carbamazepine for neuroprotection against veratridine in vitro and has anticonvulsant properties against both electrical and chemical stimulation. | 2007 |
|
| Specific and sensitive analysis of nefopam and its main metabolite desmethyl-nefopam in human plasma by liquid chromatography-ion trap tandem mass spectrometry. | 2006-11-16 |
|
| Cyclodextrin inclusion complexes of the central analgesic drug nefopam. | 2006-11-09 |
|
| [What are the cardiovascular complications of the analgesics and glucocorticoids?]. | 2006-09 |
|
| Role of catecholamines and serotonin receptor subtypes in nefopam-induced antinociception. | 2006-09 |
|
| Preoperative peribulbar block in patients undergoing retinal detachment surgery under general anesthesia: a randomized double-blind study. | 2006-04 |
|
| Efficacy of low-dose intrathecal morphine for postoperative analgesia after abdominal aortic surgery: a double-blind randomized study. | 2005-08-03 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/31120
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22711801
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:00:24 GMT 2025
by
admin
on
Mon Mar 31 18:00:24 GMT 2025
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| Record UNII |
685J48E13W
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C1012
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757856
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245-585-5
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C83995
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100000091067
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685J48E13W
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DBSALT002173
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4324
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31872
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SUB03400MIG
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CHEMBL465026
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23327-57-3
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88312
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DTXSID7045441
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m7795
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PRIMARY | Merck Index |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |