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

Stem definition	Drug id	CAS RN
opioid receptor agonists, analgesics, fentanyl derivatives	2363	132875-61-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: remifentanil remifentanyl ramifentanyl remifentanil hydrochloride remifentanil HCl	Remifentanil is a mu-opioid agonist with rapid onset and peak effect, and short duration of action. Molecular weight: 376.45 Formula: C20H28N2O5 CLOGP: 1.96 LIPINSKI: 0 HAC: 7 HDO: 0 TPSA: 76.15 ALOGS: -2.80 ROTB: 9 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

remifentanil
remifentanyl
ramifentanyl
remifentanil hydrochloride
remifentanil HCl

Remifentanil is a mu-opioid agonist with rapid onset and peak effect, and short duration of action.

Molecular weight: 376.45
Formula: C20H28N2O5
CLOGP: 1.96
LIPINSKI: 0
HAC: 7
HDO: 0
TPSA: 76.15
ALOGS: -2.80
ROTB: 9

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.10 %	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	0.40 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	37 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.30 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.80 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
July 12, 1996	FDA	MYLAN INSTITUTIONAL
Oct. 20, 2006	PMDA	Janssen Pharmaceutical K.K.

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
Anaphylactic shock	748.04	33.93	193	3745	21547	56266582
Anaphylactic reaction	321.18	33.93	129	3809	58866	56229263
Cardiac arrest	143.96	33.93	84	3854	86230	56201899
Bronchospasm	131.01	33.93	47	3891	15622	56272507
Delayed recovery from anaesthesia	122.89	33.93	24	3914	734	56287395
Circulatory collapse	104.27	33.93	43	3895	20760	56267369
Bradycardia	97.64	33.93	60	3878	67444	56220685
Hypotension	94.32	33.93	101	3837	250407	56037722
Neuromuscular block prolonged	81.54	33.93	16	3922	501	56287628
Tachycardia	79.67	33.93	63	3875	105813	56182316
Hyperthermia malignant	75.59	33.93	16	3922	735	56287394
Serotonin syndrome	69.84	33.93	35	3903	26455	56261674
Blood pressure decreased	64.42	33.93	44	3894	59006	56229123
Exposure during pregnancy	58.36	33.93	59	3879	136283	56151846
Anaphylactoid reaction	55.34	33.93	17	3921	3489	56284640
Stress cardiomyopathy	54.90	33.93	21	3917	8315	56279814
Patent ductus arteriosus	53.34	33.93	17	3921	3934	56284195
Anaphylactoid shock	50.66	33.93	10	3928	323	56287806
Pulseless electrical activity	47.35	33.93	18	3920	7006	56281123
Hyperreflexia	44.79	33.93	16	3922	5234	56282895
Clonus	44.14	33.93	15	3923	4234	56283895
Premature delivery	44.09	33.93	26	3912	27034	56261095
Premature baby	40.90	33.93	22	3916	19183	56268946
Ventricular tachycardia	40.65	33.93	21	3917	16880	56271249
Dyskinesia	39.80	33.93	25	3913	29083	56259046
Diabetes insipidus	39.24	33.93	12	3926	2425	56285704
Toxic epidermal necrolysis	38.07	33.93	22	3916	22020	56266109
Drug interaction	38.02	33.93	59	3879	209696	56078433
Fatigue	34.01	33.93	7	3931	788545	55499584

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
Anaphylactic shock	514.71	32.08	148	3736	13997	31679463
Anaphylactic reaction	226.68	32.08	97	3787	29456	31664004
Cardiac arrest	149.38	32.08	107	3777	88955	31604505
Hyperthermia malignant	139.34	32.08	35	3849	1949	31691511
Hypotension	120.64	32.08	136	3748	204482	31488978
Delayed recovery from anaesthesia	110.15	32.08	24	3860	713	31692747
Neuromuscular block prolonged	103.31	32.08	21	3863	442	31693018
Bradycardia	99.62	32.08	76	3808	69251	31624209
Trigemino-cardiac reflex	89.18	32.08	16	3868	167	31693293
Bronchospasm	87.17	32.08	36	3848	9936	31683524
Propofol infusion syndrome	85.66	32.08	20	3864	815	31692645
Blood pressure decreased	80.87	32.08	58	3826	48033	31645427
Toxic epidermal necrolysis	78.08	32.08	41	3843	19483	31673977
Airway complication of anaesthesia	72.25	32.08	13	3871	138	31693322
Ventricular fibrillation	68.10	32.08	37	3847	18811	31674649
Drug interaction	64.11	32.08	101	3783	208442	31485018
Kounis syndrome	63.18	32.08	19	3865	2065	31691395
Diabetes insipidus	59.48	32.08	19	3865	2521	31690939
Hypoventilation	55.92	32.08	19	3865	3055	31690405
Drug reaction with eosinophilia and systemic symptoms	54.57	32.08	38	3846	29980	31663480
Seizure like phenomena	53.10	32.08	13	3871	649	31692811
Cardio-respiratory arrest	45.84	32.08	43	3841	51683	31641777
Circulatory collapse	45.54	32.08	29	3855	19715	31673745
Arteriospasm coronary	45.35	32.08	16	3868	2875	31690585
Anaesthetic complication neurological	39.84	32.08	9	3875	316	31693144
Recurrence of neuromuscular blockade	38.96	32.08	8	3876	177	31693283
Anaphylactoid shock	38.67	32.08	9	3875	361	31693099
Sinus arrest	38.34	32.08	12	3872	1489	31691971
Erythema	38.05	32.08	48	3836	80357	31613103
Neuromuscular blockade	36.50	32.08	8	3876	244	31693216
Status epilepticus	36.19	32.08	21	3863	12085	31681375
Rhabdomyolysis	35.02	32.08	41	3843	63540	31629920
Anaphylactoid reaction	34.33	32.08	12	3872	2097	31691363
Tachycardia	33.70	32.08	44	3840	76163	31617297
Death	33.33	32.08	3	3881	360566	31332894

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
Anaphylactic shock	1214.35	25.77	339	7481	32151	70888473
Anaphylactic reaction	533.02	25.77	226	7594	74748	70845876
Cardiac arrest	271.78	25.77	186	7634	159648	70760976
Delayed recovery from anaesthesia	217.09	25.77	47	7773	1510	70919114
Bronchospasm	199.75	25.77	80	7740	22712	70897912
Hypotension	192.51	25.77	229	7591	404152	70516472
Hyperthermia malignant	192.03	25.77	47	7773	2614	70918010
Bradycardia	167.77	25.77	126	7694	124489	70796135
Neuromuscular block prolonged	167.40	25.77	35	7785	948	70919676
Circulatory collapse	136.12	25.77	70	7750	35404	70885220
Blood pressure decreased	130.84	25.77	96	7724	91419	70829205
Trigemino-cardiac reflex	117.91	25.77	21	7799	235	70920389
Tachycardia	99.43	25.77	104	7716	158442	70762182
Toxic epidermal necrolysis	99.24	25.77	59	7761	39498	70881126
Diabetes insipidus	96.60	25.77	31	7789	4640	70915984
Propofol infusion syndrome	92.28	25.77	24	7796	1705	70918919
Drug interaction	90.07	25.77	155	7665	381286	70539338
Airway complication of anaesthesia	89.66	25.77	18	7802	396	70920228
Anaphylactoid reaction	86.49	25.77	29	7791	4978	70915646
Kounis syndrome	84.56	25.77	26	7794	3385	70917239
Anaphylactoid shock	84.06	25.77	19	7801	745	70919879
Ventricular fibrillation	82.86	25.77	46	7774	27065	70893559
Pulseless electrical activity	71.49	25.77	33	7787	13182	70907442
Hypoventilation	67.81	25.77	26	7794	6556	70914068
Recurrence of neuromuscular blockade	66.02	25.77	13	7807	258	70920366
Erythema	63.38	25.77	93	7727	199470	70721154
Fatigue	61.50	25.77	9	7811	824310	70096314
Stress cardiomyopathy	60.86	25.77	27	7793	9835	70910789
Serotonin syndrome	59.69	25.77	44	7776	42070	70878554
Ventricular tachycardia	58.36	25.77	41	7779	36382	70884242
Rhabdomyolysis	54.96	25.77	60	7760	95700	70824924
Post procedural complication	52.92	25.77	32	7788	22049	70898575
Upper airway obstruction	50.34	25.77	14	7806	1282	70919342
Sinus arrest	49.17	25.77	17	7803	3198	70917426
Respiratory depression	47.02	25.77	31	7789	24800	70895824
Neuromuscular blockade	45.89	25.77	11	7809	559	70920065
Clonus	44.68	25.77	19	7801	6249	70914375
Seizure like phenomena	42.20	25.77	13	7807	1702	70918922
Death	41.84	25.77	4	7816	510057	70410567
Cardio-respiratory arrest	41.07	25.77	53	7767	100624	70820000
Anaesthetic complication	40.55	25.77	14	7806	2622	70918002
Pain	40.19	25.77	10	7810	628806	70291818
Arteriospasm coronary	38.80	25.77	17	7803	6007	70914617
Arthralgia	38.63	25.77	5	7815	503385	70417239
Drug reaction with eosinophilia and systemic symptoms	37.97	25.77	39	7781	57974	70862650
Urticaria	36.66	25.77	65	7755	162984	70757640
Anaesthetic complication neurological	35.67	25.77	9	7811	566	70920058
Nausea	34.84	25.77	26	7794	852062	70068562
Respiratory arrest	33.04	25.77	35	7785	53898	70866726
Blood pressure immeasurable	32.50	25.77	11	7809	1941	70918683
Procedural hypotension	32.42	25.77	11	7809	1955	70918669
Hyperreflexia	32.36	25.77	16	7804	7426	70913198
Type I hypersensitivity	32.31	25.77	13	7807	3719	70916905
Postoperative delirium	32.16	25.77	7	7813	230	70920394
Electrocardiogram ST segment elevation	32.04	25.77	16	7804	7588	70913036
Fall	30.49	25.77	6	7814	444090	70476534
Subcutaneous emphysema	30.07	25.77	10	7810	1672	70918952
Oxygen saturation decreased	29.56	25.77	49	7771	116380	70804244
Dyskinesia	29.42	25.77	29	7791	41045	70879579
Capillary nail refill test abnormal	28.86	25.77	5	7815	47	70920577
Acute generalised exanthematous pustulosis	28.61	25.77	19	7801	15378	70905246
Exposure during pregnancy	27.96	25.77	41	7779	87676	70832948
Respiratory acidosis	27.50	25.77	16	7804	10265	70910359
Pulmonary alveolar haemorrhage	27.38	25.77	16	7804	10353	70910271
Hypoxic-ischaemic encephalopathy	26.79	25.77	14	7806	7294	70913330
Dizziness	26.65	25.77	9	7811	464132	70456492
Prinzmetal angina	26.51	25.77	9	7811	1603	70919021
Shock	26.13	25.77	27	7793	40398	70880226
Torsade de pointes	25.82	25.77	19	7801	18097	70902527

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	N01AH06	NERVOUS SYSTEM ANESTHETICS ANESTHETICS, GENERAL Opioid anesthetics
MeSH PA	D000700	Analgesics
MeSH PA	D000701	Analgesics, Opioid
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D002492	Central Nervous System Depressants
MeSH PA	D009294	Narcotics
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D018689	Sensory System Agents
CHEBI has role	CHEBI:35482	narcotic analgesic
CHEBI has role	CHEBI:35717	hypnotics
CHEBI has role	CHEBI:38877	intravenous anesthetics
CHEBI has role	CHEBI:55322	mu-opioid agonists
FDA MoA	N0000175684	Full Opioid Agonists
FDA EPC	N0000175690	Opioid Agonist

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID
General anesthesia	indication	50697003
Local anesthesia	indication	386761002
Acute postoperative pain	indication	107401000119105
Low blood pressure	contraindication	45007003
Bradycardia	contraindication	48867003
Decreased respiratory function	contraindication	80954004

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.07	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Mu-type opioid receptor	GPCR	P35372	OPRM_HUMAN	AGONIST				WOMBAT-PK	CHEMBL
Mu-type opioid receptor	GPCR		OPRM_RAT		IC50	9.22		CHEMBL

External reference:

ID	Source
4024040	VUID
N0000022045	NUI
D01177	KEGG_DRUG
4020990	VANDF
4024040	VANDF
C0246631	UMLSCUI
CHEBI:8802	CHEBI
CHEMBL1005	ChEMBL_ID
DB00899	DRUGBANK_ID
CHEMBL1201120	ChEMBL_ID
D000077208	MESH_DESCRIPTOR_UI
60815	PUBCHEM_CID
7292	IUPHAR_LIGAND_ID
6924	INN_ID
132539-07-2	SECONDARY_CAS_RN
P10582JYYK	UNII
236540	RXNORM
181723	MMSL
186043	MMSL
5415	MMSL
d04034	MMSL
006250	NDDF
006251	NDDF
108376001	SNOMEDCT_US
108379008	SNOMEDCT_US
386839004	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9391	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	ANDA	27 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9392	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 mg	INTRAVENOUS	ANDA	27 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9393	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	5 mg	INTRAVENOUS	ANDA	27 sections
Remifentanil Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	63323-723	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	ANDA	30 sections
Remifentanil Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	63323-723	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	ANDA	30 sections
Remifentanil Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	63323-724	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	ANDA	30 sections
Remifentanil Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	63323-725	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	ANDA	30 sections
Ultiva	HUMAN PRESCRIPTION DRUG LABEL	1	67457-198	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	NDA	30 sections
Ultiva	HUMAN PRESCRIPTION DRUG LABEL	1	67457-912	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	NDA	30 sections
Ultiva	HUMAN PRESCRIPTION DRUG LABEL	1	67457-913	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	NDA	30 sections
Ultiva	HUMAN PRESCRIPTION DRUG LABEL	1	67457-914	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	NDA	30 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	68475-505	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	ANDA	27 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	68475-506	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 mg	INTRAVENOUS	ANDA	27 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	68475-507	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	5 mg	INTRAVENOUS	ANDA	27 sections