nefopam 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	1891	13669-70-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: nefopam fenazoxine (+/-)-Nefopam nefopam hydrochloride nefopam HCl	Non-narcotic analgesic chemically similar to ORPHENADRINE. Its mechanism of action is unclear. It is used for the relief of acute and chronic pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p26) Molecular weight: 253.35 Formula: C17H19NO CLOGP: 2.91 LIPINSKI: 0 HAC: 2 HDO: 0 TPSA: 12.47 ALOGS: -3.50 ROTB: 1

Molecule

Description

Molfile Inchi Smiles

Synonyms:

nefopam
fenazoxine
(+/-)-Nefopam
nefopam hydrochloride
nefopam HCl

Non-narcotic analgesic chemically similar to ORPHENADRINE. Its mechanism of action is unclear. It is used for the relief of acute and chronic pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p26)

Molecular weight: 253.35
Formula: C17H19NO
CLOGP: 2.91
LIPINSKI: 0
HAC: 2
HDO: 0
TPSA: 12.47
ALOGS: -3.50
ROTB: 1

Drug dosage:

None

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	34 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	3 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	1.04 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	36 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	5.60 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	12 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	5 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Jan. 1, 1978	YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hepatocellular injury	327.78	25.85	114	4654	25833	50574523
Cholestasis	299.35	25.85	106	4662	25295	50575061
Acute kidney injury	107.18	25.85	119	4649	227939	50372417
Drug reaction with eosinophilia and systemic symptoms	99.26	25.85	50	4718	28374	50571982
Foetal megacystis	69.90	25.85	10	4758	26	50600330
Drug dependence	69.66	25.85	35	4733	19724	50580632
Coma	69.48	25.85	51	4717	56828	50543528
Tonic clonic movements	62.90	25.85	16	4752	1221	50599135
Pancreatitis acute	60.77	25.85	34	4734	23778	50576578
Acute generalised exanthematous pustulosis	60.67	25.85	25	4743	8913	50591443
Hepatic cytolysis	59.57	25.85	24	4744	8079	50592277
Peripheral nerve injury	57.15	25.85	12	4756	390	50599966
Anticholinergic syndrome	56.99	25.85	16	4752	1779	50598577
Thrombocytopenia	56.98	25.85	65	4703	127608	50472748
Fatigue	54.80	25.85	3	4765	707598	49892758
Shock haemorrhagic	48.82	25.85	21	4747	8323	50592033
Miosis	47.45	25.85	19	4749	6291	50594065
Mixed liver injury	46.69	25.85	16	4752	3435	50596921
Spinal epidural haemorrhage	45.21	25.85	8	4760	102	50600254
Hyperkalaemia	41.18	25.85	35	4733	48054	50552302
Encephalopathy	40.62	25.85	30	4738	33681	50566675
Eosinophilia	37.95	25.85	23	4745	18629	50581727
Epidural haemorrhage	37.67	25.85	7	4761	119	50600237
Urinary bladder rupture	36.99	25.85	7	4761	132	50600224
Hyperlactacidaemia	35.74	25.85	12	4756	2421	50597935
Granulomatous liver disease	34.79	25.85	9	4759	734	50599622
Metabolic acidosis	34.77	25.85	29	4739	38796	50561560
Cutaneous T-cell lymphoma	34.43	25.85	10	4758	1254	50599102
Poisoning deliberate	33.83	25.85	16	4752	7896	50592460
Pancreatic pseudoaneurysm	33.80	25.85	6	4762	78	50600278
Cell death	32.83	25.85	11	4757	2204	50598152
Foetal heart rate abnormal	32.73	25.85	8	4760	518	50599838
Stevens-Johnson syndrome	32.31	25.85	22	4746	21730	50578626
Prescription drug used without a prescription	31.51	25.85	10	4758	1690	50598666
Blood phosphorus decreased	30.55	25.85	12	4756	3777	50596579
Somnolence	30.08	25.85	53	4715	154932	50445424
Myoclonus	29.84	25.85	18	4750	14452	50585904
Porphyria	29.58	25.85	6	4762	164	50600192
Epidural analgesia	29.55	25.85	5	4763	48	50600308
Drug ineffective	29.19	25.85	21	4747	819312	49781044
Livedo reticularis	29.11	25.85	10	4758	2162	50598194
Autonomic nervous system imbalance	28.19	25.85	10	4758	2375	50597981
Porphyria acute	28.10	25.85	7	4761	490	50599866
Agranulocytosis	27.92	25.85	20	4748	21401	50578955
Hepatitis	27.14	25.85	23	4745	31430	50568926
Shock	26.27	25.85	19	4749	20631	50579725
Folate deficiency	26.19	25.85	9	4759	1946	50598410
Naevus haemorrhage	26.00	25.85	5	4763	103	50600253

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Agranulocytosis	150.96	28.76	64	3322	20276	29550865
Hepatocellular injury	138.49	28.76	61	3325	21182	29549959
Cholestasis	114.15	28.76	55	3331	23407	29547734
Rash maculo-papular	106.38	28.76	53	3333	24236	29546905
Drug reaction with eosinophilia and systemic symptoms	99.27	28.76	53	3333	27939	29543202
Eosinophilia	87.21	28.76	45	3341	22116	29549025
Alveolar lung disease	85.04	28.76	17	3369	352	29570789
Pulmonary interstitial emphysema syndrome	81.09	28.76	17	3369	449	29570692
Confusional state	76.35	28.76	83	3303	127794	29443347
Hyperleukocytosis	64.42	28.76	18	3368	1617	29569524
Diffuse alveolar damage	60.46	28.76	18	3368	2025	29569116
Pancytopenia	58.50	28.76	59	3327	83109	29488032
Urethral valves	53.15	28.76	11	3375	272	29570869
Acute kidney injury	52.71	28.76	102	3284	265165	29305976
Eosinophilic pneumonia	50.60	28.76	17	3369	2829	29568312
Hyperammonaemia	49.29	28.76	20	3366	5643	29565498
Oesophageal achalasia	45.78	28.76	10	3376	322	29570819
Haemolytic anaemia	42.49	28.76	21	3365	9398	29561743
Toxic skin eruption	38.87	28.76	20	3366	9737	29561404
Generalised oedema	36.33	28.76	20	3366	11145	29559996
Hepatitis	36.26	28.76	25	3361	20758	29550383
Hepatic encephalopathy	33.45	28.76	20	3366	13015	29558126
Pancreatitis acute	32.67	28.76	25	3361	24360	29546781
Eczema	32.36	28.76	20	3366	13806	29557335
Thrombocytopenia	31.85	28.76	56	3330	134767	29436374
Mixed liver injury	31.57	28.76	11	3375	2040	29569101
Neutropenia	31.49	28.76	55	3331	131656	29439485
Cholestatic liver injury	29.62	28.76	10	3376	1687	29569454

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hepatocellular injury	428.86	23.55	175	8090	45060	64445407
Cholestasis	376.01	23.55	159	8106	44713	64445754
Drug reaction with eosinophilia and systemic symptoms	182.23	23.55	103	8162	54114	64436353
Agranulocytosis	154.31	23.55	82	8183	38147	64452320
Acute kidney injury	134.14	23.55	220	8045	449020	64041447
Eosinophilia	116.27	23.55	68	8197	38008	64452459
Rash maculo-papular	105.49	23.55	69	8196	46957	64443510
Pancreatitis acute	86.75	23.55	59	8206	42796	64447671
Thrombocytopenia	79.51	23.55	119	8146	223682	64266785
Pulmonary interstitial emphysema syndrome	79.26	23.55	17	8248	446	64490021
Confusional state	77.73	23.55	128	8137	261016	64229451
Alveolar lung disease	76.75	23.55	17	8248	520	64489947
Coma	73.25	23.55	72	8193	87543	64402924
Mixed liver injury	72.27	23.55	27	8238	5454	64485013
Fatigue	68.54	23.55	8	8257	748722	63741745
Tonic clonic movements	63.19	23.55	19	8246	1970	64488497
Drug dependence	63.01	23.55	44	8221	33268	64457199
Hepatic cytolysis	61.95	23.55	32	8233	14017	64476450
Hepatitis	59.05	23.55	48	8217	45534	64444933
Hyperleukocytosis	58.46	23.55	18	8247	2022	64488445
Acute generalised exanthematous pustulosis	56.23	23.55	30	8235	14028	64476439
Encephalopathy	54.16	23.55	51	8214	58768	64431699
Toxic skin eruption	52.48	23.55	32	8233	19252	64471215
Pancytopenia	51.95	23.55	77	8188	143232	64347235
Diffuse alveolar damage	50.31	23.55	18	8247	3217	64487250
Peripheral nerve injury	48.00	23.55	12	8253	624	64489843
Haemolytic anaemia	47.20	23.55	28	8237	16025	64474442
Anticholinergic syndrome	45.89	23.55	16	8249	2653	64487814
Febrile bone marrow aplasia	42.16	23.55	23	8242	11232	64479235
Eosinophilic pneumonia	40.84	23.55	17	8248	4560	64485907
Hyperammonaemia	39.22	23.55	21	8244	9883	64480584
Neutropenia	38.79	23.55	91	8174	239533	64250934
Oesophageal achalasia	37.38	23.55	10	8255	680	64489787
Drug ineffective	37.19	23.55	32	8233	840215	63650252
Foetal heart rate abnormal	36.01	23.55	8	8257	248	64490219
Hyperbilirubinaemia	35.47	23.55	26	8239	21179	64469288
Hyperthermia	35.28	23.55	23	8242	15527	64474940
Anaphylactic shock	35.24	23.55	30	8235	30298	64460169
Spinal epidural haemorrhage	34.12	23.55	7	8258	147	64490320
Epidural haemorrhage	33.03	23.55	7	8258	173	64490294
Pancreatic pseudoaneurysm	31.95	23.55	6	8259	78	64490389
Gamma-glutamyltransferase increased	31.75	23.55	35	8230	48475	64441992
Prothrombin time ratio decreased	31.69	23.55	9	8256	764	64489703
Urinary retention	31.35	23.55	35	8230	49166	64441301
Shock haemorrhagic	31.32	23.55	22	8243	16769	64473698
Hepatic encephalopathy	31.17	23.55	24	8241	21042	64469425
Transaminases increased	30.63	23.55	33	8232	44561	64445906
Hyperlactacidaemia	30.26	23.55	14	8251	4830	64485637
Cell death	29.39	23.55	13	8252	4041	64486426
Generalised oedema	29.21	23.55	23	8242	20830	64469637
Pneumonia	29.00	23.55	18	8247	559558	63930909
Miosis	28.58	23.55	19	8246	13247	64477220
Poisoning deliberate	28.33	23.55	19	8246	13439	64477028
Epidural analgesia	27.83	23.55	5	8260	50	64490417
Myoclonus	27.46	23.55	24	8241	25094	64465373
Porphyria	26.62	23.55	6	8259	199	64490268
Metabolic acidosis	25.49	23.55	38	8227	70920	64419547
Cutaneous T-cell lymphoma	25.33	23.55	10	8255	2342	64488125
Blood phosphorus decreased	25.16	23.55	13	8252	5692	64484775
Pain	24.52	23.55	21	8244	553490	63936977
Naevus haemorrhage	24.46	23.55	5	8260	103	64490364
Hallucinations, mixed	24.43	23.55	13	8252	6039	64484428
Symmetrical drug-related intertriginous and flexural exanthema	24.42	23.55	7	8258	614	64489853
Prescription drug used without a prescription	24.36	23.55	10	8255	2590	64487877
Hepatitis acute	23.72	23.55	17	8248	13372	64477095
Granulomatous liver disease	23.63	23.55	8	8257	1214	64489253
Headache	23.56	23.55	20	8245	529447	63961020

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	N02BG06	NERVOUS SYSTEM ANALGESICS OTHER ANALGESICS AND ANTIPYRETICS Other analgesics and antipyretics
MeSH PA	D000700	Analgesics
MeSH PA	D018712	Analgesics, Non-Narcotic
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D018689	Sensory System Agents
CHEBI has role	CHEBI:35640	adrenergic uptake inhibitors
CHEBI has role	CHEBI:50949	SSRI
CHEBI has role	CHEBI:51039	dopamine reuptake inhibitor

Drug Use (View source of the data)

None

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.85	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Type	Activity value (-log[M])	Bioact source
Sodium channel protein type 5 subunit alpha	Ion channel	Q14524	SCN5A_HUMAN			WOMBAT-PK
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN	Ki	7.54	PDSP
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN	Ki	7.48	PDSP
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN	Ki	5.77	PDSP
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN	Ki	6.48	PDSP
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN	Ki	7.25	PDSP
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN	Ki	6.28	PDSP

External reference:

ID	Source
N0000167217	NUI
D05133	KEGG_DRUG
23327-57-3	SECONDARY_CAS_RN
C0027556	UMLSCUI
CHEBI:88316	CHEBI
CHEMBL465026	ChEMBL_ID
DB12293	DRUGBANK_ID
D009340	MESH_DESCRIPTOR_UI
4450	PUBCHEM_CID
3018	INN_ID
4UP8060B7J	UNII
4324	RXNORM
001582	NDDF
004636	NDDF
322300008	SNOMEDCT_US
350324006	SNOMEDCT_US
419768004	SNOMEDCT_US
CHEMBL1407915	ChEMBL_ID

Pharmaceutical products:

None