NEFOPAM

Possibly Marketed Outside US

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

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

Molecular Formula	C17H19NO
Molecular Weight	253.3389
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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	Inhibitor 8,297	6.27 null [pKi]
Serotonin transporter 178	Inhibitor 8,297	7.53 null [pKi]
Norepinephrine transporter 191	Inhibitor 8,297	7.48 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614	Primary		Approved 8,429	Nefopam Hydrochloride

C_max

Value	Dose	Analyte	Population
48.5 nM	20 mg single, oral	NEFOPAM plasma	Homo sapiens
47.4 nM	20 mg single, oral	N-DESMETHYLNEFOPAM plasma	Homo sapiens
183.1 nM	20 mg single, intravenous	NEFOPAM plasma	Homo sapiens
31 nM	20 mg single, intravenous	N-DESMETHYLNEFOPAM plasma	Homo sapiens
50.89 ng/mL	75 mg single, oral	NEFOPAM plasma	Homo sapiens
41.45 ng/mL	75 mg single, oral	N-DESMETHYLNEFOPAM plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
377 nM × h	20 mg single, oral	NEFOPAM plasma	Homo sapiens
748 nM × h	20 mg single, oral	N-DESMETHYLNEFOPAM plasma	Homo sapiens
1029 nM × h	20 mg single, intravenous	NEFOPAM plasma	Homo sapiens
787 nM × h	20 mg single, intravenous	N-DESMETHYLNEFOPAM plasma	Homo sapiens
410.45 ng × h/mL	75 mg single, oral	NEFOPAM plasma	Homo sapiens
672.93 ng × h/mL	75 mg single, oral	N-DESMETHYLNEFOPAM plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
5.1 h	20 mg single, oral	NEFOPAM plasma	Homo sapiens
10.6 h	20 mg single, oral	N-DESMETHYLNEFOPAM plasma	Homo sapiens
5.1 h	20 mg single, intravenous	NEFOPAM plasma	Homo sapiens
15 h	20 mg single, intravenous	N-DESMETHYLNEFOPAM plasma	Homo sapiens
8.08 h	75 mg single, oral	NEFOPAM plasma	Homo sapiens
10.25 h	75 mg single, oral	N-DESMETHYLNEFOPAM plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
25%			NEFOPAM plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
120 mg single, oral Higher than recommended	unhealthy, ADULT
0.4 mg/kg single, intramuscular Highest studied dose	unhealthy, ADULT
1.8 g single, oral Lethal dose	healthy, ADULT	Disc. AE: Seizures, Cardiorespiratory arrest...
1.8 g single, oral Overdose	healthy, ADULT	Disc. AE: Sweating, Drowsiness...
90 mg single, oral Recommended	unhealthy, ADULT

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AEs

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AE	Significance	Dose	Population
Cardiorespiratory arrest	grade 5 Disc. AE	1.8 g single, oral Lethal dose	healthy, ADULT
Seizures	grade 5 Disc. AE	1.8 g single, oral Lethal dose	healthy, ADULT
Convulsions grand mal	Disc. AE	1.8 g single, oral Overdose	healthy, ADULT
Drowsiness	Disc. AE	1.8 g single, oral Overdose	healthy, ADULT
Hyperreflexia	Disc. AE	1.8 g single, oral Overdose	healthy, ADULT

Showing 1 to 5 of 7 entries

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PubMed

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Title	Date	PubMed
Effect of a non-opiate analgesic, nefopam hydrochloride, on stress gastric ulcer in rats.	2001	11793953
Postanaesthetic shivering: epidemiology, pathophysiology, and approaches to prevention and management.	2001	11772130
Novel effect of nefopam preventing cGMP increase, oxygen radical formation and neuronal death induced by veratridine.	2001 Dec	11747898
Nefopam reduces thermal hypersensitivity in acute and postoperative pain models in the rat.	2001 Dec	11735363
Nefopam for refractory postoperative hiccups.	2001 Nov	11682430

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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.

Substance Class	Chemical
Record UNII	4UP8060B7J
Record Status	`Validated (UNII)`
Record Version

Show entries

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

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Classification Tree

Code System

Code

Other analgesics and antipyretics

WHO-ATC

N02BG06

Other analgesics and antipyretics

WHO-VATC

QN02BG06

Antianxiety Agent

NCI_THESAURUS

C1012

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Code System

Code

Type

Description

LACTMED

Nefopam

PRIMARY

FDA UNII

4UP8060B7J

PRIMARY

ECHA (EC/EINECS)

237-148-2

PRIMARY

DRUG BANK

DB12293

PRIMARY

NCI_THESAURUS

C83994

PRIMARY

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Related Record

Type

Details


					685J48E13W

NEFOPAM HYDROCHLORIDE

SALT/SOLVATE -> PARENT

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Related Record

Type

Details


					4UP8060B7J

NEFOPAM

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound