Nefopam

Structural formula
General
Non-proprietary name	Nefopam
other names	( RS ) -3,4,5,6-tetrahydro-5-methyl-1-phenyl-1 H -2,5-benzoxazocine
Molecular formula	C 17 H 19 NO
External identifiers / databases
EC number	237-148-2
ECHA InfoCard	100,033,757
PubChem	4450
ChemSpider	4295
DrugBank	DB12293
Wikidata	Q599052
Drug information
ATC code	N02 BG06
Drug class	non-opioid analgesic
properties
Molar mass	253.34 g · mol -1
Physical state	firmly
Melting point	238-242 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301 + 311 + 331
	P: 261-280-301 + 310-311
Toxicological data	80 mg kg −1 ( LD 50 , rat , oral , hydrochloride) ; 44.5 mg kg −1 ( LD 50 , mouse , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nefopam (trade names Ajan , Silentan ) is a drug from the group of non-opioid analgesics. It does not have any anti-inflammatory or fever-lowering effects and thus differs significantly from other representatives of the active ingredient group. The mechanism of action is still partly unclear. A classification in the group of serotonin-norepinephrine -dopamine reuptake inhibitors ( English serotonin – norepinephrine – dopamine reuptake inhibitor , SNDRI) is possible. The drug is no longer used in Germany. It was first mentioned in the literature as an antidepressant under the name Fanazoxin.

Clinical information

Contraindications (contraindications)

Nefopam is contraindicated for celebratory seizure disorders. It must not be used in combination with paracetamol as it increases its hepatotoxicity . It should only be used under strict control in patients with poor bladder emptying, glaucoma, or tachycardia .

Adverse effects (side effects)

Side effects include nausea, vomiting, arterial hypertension , sweating, and sleep and vision disorders. The occurrence of motor restlessness was also observed.

Pharmacological properties

Mechanism of action (pharmacodynamics)

The exact mechanism of action is still unclear. Influencing the serotonergic and noradrenergic system is discussed. There is no affinity for opioid receptors. Nefopam's analgesic potency is somewhere between aspirin and morphine. There is hardly any abuse of the drug.

Absorption and distribution in the body (pharmacokinetics)

After oral ingestion, 50% of the drug is rapidly absorbed and over 90% is excreted renally .

synthesis

Nefopam is produced via a multi-stage synthesis starting from 2-benzoylbenzoic acid and N -methylaminoethanol .

Individual evidence

↑ ^a ^b Entry on Nefopam. In: Römpp Online . Georg Thieme Verlag, accessed on July 30, 2014.
↑ ^a ^b ^c Data sheet Nefopam hydrochloride from Sigma-Aldrich , accessed on April 30, 2014 ( PDF ).
↑ Ernst Mutschler, Monika Schäfer-Korting: Textbook of Pharmacology and Toxicology. 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001, ISBN 3-8047-1763-2 , p. 221.
^ A New Class of Antidepressant Drugs in the Treatment of Psychiatric Disorders: The Triple Reuptake Inhibitors (PDF).
↑ S. Ebel, H. Schütz: On the analysis of Nefopam (Ajan®), a new analgesic with a morphine-like effect. In: Archives of Toxicology . Volume 38, 1977, pp. 239-250.
↑ ^a ^b Ernst Mutschler, Monika Schäfer-Korting: Textbook of Pharmacology and Toxicology. 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001, ISBN 3-8047-1763-2 , p. 241.
↑ Deutsches Ärzteblatt, September 5, 1984, p. 2565.
^ E. Nuremberg, P. Surmann: Hager's Handbook of Pharmaceutical Practice, Volume 2. 5th Edition. Springer-Verlag, Berlin 2000, ISBN 3-540-52459-2 , p. 1125.

[Römpp-1] Entry on Nefopam. In: Römpp Online . Georg Thieme Verlag, accessed on July 30, 2014.

[Sigma-Aldrich-2] Data sheet Nefopam hydrochloride from Sigma-Aldrich , accessed on April 30, 2014 ( PDF ).

[3] Ernst Mutschler, Monika Schäfer-Korting: Textbook of Pharmacology and Toxicology. 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001, ISBN 3-8047-1763-2 , p. 221.

[4] A New Class of Antidepressant Drugs in the Treatment of Psychiatric Disorders: The Triple Reuptake Inhibitors (PDF).

[5] S. Ebel, H. Schütz: On the analysis of Nefopam (Ajan®), a new analgesic with a morphine-like effect. In: Archives of Toxicology . Volume 38, 1977, pp. 239-250.

[Mutschler-6] Ernst Mutschler, Monika Schäfer-Korting: Textbook of Pharmacology and Toxicology. 8th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft Stuttgart 2001, ISBN 3-8047-1763-2 , p. 241.

[7] Deutsches Ärzteblatt, September 5, 1984, p. 2565.

[Hager-8] E. Nuremberg, P. Surmann: Hager's Handbook of Pharmaceutical Practice, Volume 2. 5th Edition. Springer-Verlag, Berlin 2000, ISBN 3-540-52459-2 , p. 1125.