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

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	679.25	30.56	178	3560	19977	50581409
Anaphylactic reaction	311.45	30.56	125	3613	53930	50547456
Cardiac arrest	124.10	30.56	77	3661	83574	50517812
Bronchospasm	123.48	30.56	45	3693	14809	50586577
Delayed recovery from anaesthesia	115.82	30.56	23	3715	726	50600660
Circulatory collapse	103.66	30.56	43	3695	19957	50581429
Hypotension	89.70	30.56	98	3640	235371	50366015
Bradycardia	84.70	30.56	55	3683	64371	50537015
Neuromuscular block prolonged	80.86	30.56	16	3722	495	50600891
Hyperthermia malignant	74.98	30.56	16	3722	723	50600663
Tachycardia	73.57	30.56	60	3678	99703	50501683
Serotonin syndrome	70.35	30.56	35	3703	24678	50576708
Blood pressure decreased	64.45	30.56	44	3694	55865	50545521
Stress cardiomyopathy	54.92	30.56	21	3717	7866	50593520
Anaphylactoid reaction	54.91	30.56	17	3721	3389	50597997
Patent ductus arteriosus	52.99	30.56	17	3721	3803	50597583
Exposure during pregnancy	52.34	30.56	54	3684	120961	50480425
Anaphylactoid shock	50.58	30.56	10	3728	308	50601078
Pulseless electrical activity	46.86	30.56	18	3720	6823	50594563
Hyperreflexia	44.34	30.56	16	3722	5102	50596284
Clonus	43.60	30.56	15	3723	4160	50597226
Premature baby	40.74	30.56	22	3716	18315	50583071
Dyskinesia	39.56	30.56	25	3713	27836	50573550
Diabetes insipidus	38.95	30.56	12	3726	2352	50599034
Toxic epidermal necrolysis	35.33	30.56	21	3717	20971	50580415
Drug interaction	33.70	30.56	56	3682	199565	50401821
Subcutaneous emphysema	31.77	30.56	8	3730	749	50600637
Fatigue	31.47	30.56	7	3731	707594	49893792
Trigemino-cardiac reflex	30.58	30.56	5	3733	50	50601336

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	499.38	31.67	143	3519	13193	29557672
Anaphylactic reaction	212.22	31.67	91	3571	27482	29543383
Cardiac arrest	143.01	31.67	103	3559	85488	29485377
Hypotension	109.79	31.67	127	3535	194227	29376638
Hyperthermia malignant	107.91	31.67	28	3634	1756	29569109
Delayed recovery from anaesthesia	104.78	31.67	23	3639	700	29570165
Neuromuscular block prolonged	103.09	31.67	21	3641	442	29570423
Trigemino-cardiac reflex	89.37	31.67	16	3646	163	29570702
Propofol infusion syndrome	86.14	31.67	20	3642	787	29570078
Bradycardia	82.95	31.67	67	3595	65562	29505303
Blood pressure decreased	76.31	31.67	55	3607	45422	29525443
Bronchospasm	74.66	31.67	32	3630	9577	29561288
Airway complication of anaesthesia	72.12	31.67	13	3649	138	29570727
Toxic epidermal necrolysis	69.05	31.67	37	3625	18116	29552749
Drug interaction	66.12	31.67	100	3562	197285	29373580
Ventricular fibrillation	59.45	31.67	32	3630	15801	29555064
Hypoventilation	57.19	31.67	19	3643	2822	29568043
Kounis syndrome	56.68	31.67	17	3645	1812	29569053
Diabetes insipidus	55.96	31.67	18	3644	2416	29568449
Seizure like phenomena	53.69	31.67	13	3649	613	29570252
Drug reaction with eosinophilia and systemic symptoms	47.23	31.67	34	3628	27958	29542907
Arteriospasm coronary	47.06	31.67	16	3646	2549	29568316
Circulatory collapse	46.75	31.67	29	3633	18644	29552221
Recurrence of neuromuscular blockade	41.22	31.67	8	3654	130	29570735
Cardio-respiratory arrest	40.57	31.67	40	3622	50561	29520304
Erythema	40.03	31.67	48	3614	75558	29495307
Anaesthetic complication neurological	39.74	31.67	9	3653	316	29570549
Sinus arrest	38.65	31.67	12	3650	1435	29569430
Anaphylactoid shock	38.58	31.67	9	3653	361	29570504
Status epilepticus	38.23	31.67	21	3641	10773	29560092
Rhabdomyolysis	36.17	31.67	41	3621	60767	29510098
Anaphylactoid reaction	35.16	31.67	12	3650	1933	29568932
Tachycardia	35.13	31.67	44	3618	72366	29498499

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	1132.77	26.86	319	7078	30009	64461326
Anaphylactic reaction	513.49	26.86	217	7180	68447	64422888
Cardiac arrest	245.63	26.86	175	7222	153889	64337446
Delayed recovery from anaesthesia	204.98	26.86	45	7352	1483	64489852
Bronchospasm	179.93	26.86	74	7323	21608	64469727
Hypotension	176.54	26.86	217	7180	380757	64110578
Neuromuscular block prolonged	166.24	26.86	35	7362	942	64490393
Hyperthermia malignant	158.58	26.86	40	7357	2419	64488916
Bradycardia	138.71	26.86	112	7285	118107	64373228
Circulatory collapse	136.86	26.86	70	7327	33662	64457673
Blood pressure decreased	128.07	26.86	94	7303	86105	64405230
Trigemino-cardiac reflex	118.09	26.86	21	7376	223	64491112
Tachycardia	95.69	26.86	101	7296	149478	64341857
Propofol infusion syndrome	92.94	26.86	24	7373	1593	64489742
Diabetes insipidus	92.32	26.86	30	7367	4491	64486844
Airway complication of anaesthesia	89.04	26.86	18	7379	394	64490941
Toxic epidermal necrolysis	87.55	26.86	54	7343	37112	64454223
Anaphylactoid reaction	86.94	26.86	29	7368	4709	64486626
Drug interaction	86.28	26.86	151	7246	361932	64129403
Anaphylactoid shock	83.57	26.86	19	7378	735	64490600
Ventricular fibrillation	72.82	26.86	41	7356	23819	64467516
Recurrence of neuromuscular blockade	69.20	26.86	13	7384	191	64491144
Hypoventilation	69.14	26.86	26	7371	5980	64485355
Kounis syndrome	65.54	26.86	21	7376	3004	64488331
Pulseless electrical activity	65.22	26.86	31	7366	12708	64478627
Erythema	63.73	26.86	92	7305	186978	64304357
Serotonin syndrome	60.89	26.86	44	7353	39238	64452097
Stress cardiomyopathy	58.26	26.86	26	7371	9231	64482104
Fatigue	56.97	26.86	9	7388	748721	63742614
Rhabdomyolysis	55.15	26.86	60	7337	91666	64399669
Post procedural complication	52.75	26.86	32	7365	21321	64470014
Upper airway obstruction	50.21	26.86	14	7383	1244	64490091
Respiratory depression	47.54	26.86	31	7366	23412	64467923
Sinus arrest	45.33	26.86	16	7381	3074	64488261
Seizure like phenomena	42.17	26.86	13	7384	1639	64489696
Clonus	41.27	26.86	18	7379	6049	64485286
Death	41.03	26.86	4	7393	482701	64008634
Arteriospasm coronary	39.75	26.86	17	7380	5448	64485887
Urticaria	39.63	26.86	65	7332	147252	64344083
Pain	39.12	26.86	8	7389	553503	63937832
Ventricular tachycardia	39.09	26.86	32	7365	34233	64457102
Arthralgia	36.71	26.86	4	7393	442256	64049079
Cardio-respiratory arrest	35.82	26.86	50	7347	98343	64392992
Anaesthetic complication neurological	35.80	26.86	9	7388	536	64490799
Nausea	33.35	26.86	25	7372	785775	63705560
Anaesthetic complication	32.74	26.86	12	7385	2567	64488768
Procedural hypotension	32.44	26.86	11	7386	1875	64489460
Respiratory arrest	32.42	26.86	35	7362	52950	64438385
Hyperreflexia	32.38	26.86	16	7381	7132	64484203
Type I hypersensitivity	32.36	26.86	13	7384	3561	64487774
Blood pressure immeasurable	32.32	26.86	11	7386	1897	64489438
Drug reaction with eosinophilia and systemic symptoms	31.75	26.86	35	7362	54182	64437153
Subcutaneous emphysema	30.12	26.86	10	7387	1599	64489736
Fall	29.47	26.86	6	7391	416820	64074515
Electrocardiogram ST segment elevation	29.22	26.86	15	7382	7244	64484091
Capillary nail refill test abnormal	28.67	26.86	5	7392	47	64491288
Oxygen saturation decreased	28.41	26.86	47	7350	107129	64384206
Dyskinesia	27.64	26.86	28	7369	39360	64451975

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
132539-07-2	SECONDARY_CAS_RN
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
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