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	805.66	33.23	206	4003	23427	63461386
Anaphylactic reaction	341.11	33.23	137	4072	65963	63418850
Cardiac arrest	150.63	33.23	87	4122	92458	63392355
Delayed recovery from anaesthesia	136.16	33.23	26	4183	745	63484068
Bronchospasm	132.70	33.23	48	4161	17232	63467581
Bradycardia	127.56	33.23	72	4137	73155	63411658
Hypotension	126.50	33.23	120	4089	272484	63212329
Circulatory collapse	111.12	33.23	45	4164	21893	63462920
Neuromuscular block prolonged	81.65	33.23	16	4193	526	63484287
Serotonin syndrome	74.88	33.23	37	4172	28645	63456168
Hyperthermia malignant	74.77	33.23	16	4193	818	63483995
Tachycardia	74.45	33.23	62	4147	118094	63366719
Blood pressure decreased	67.43	33.23	46	4163	64976	63419837
Exposure during pregnancy	63.49	33.23	64	4145	155483	63329330
Anaphylactoid reaction	59.50	33.23	18	4191	3705	63481108
Premature delivery	55.96	33.23	31	4178	30250	63454563
Stress cardiomyopathy	53.43	33.23	21	4188	9429	63475384
Patent ductus arteriosus	53.01	33.23	17	4192	4233	63480580
Anaphylactoid shock	51.07	33.23	10	4199	327	63484486
Pulseless electrical activity	47.09	33.23	18	4191	7503	63477310
Oxygen saturation decreased	44.69	33.23	41	4168	88544	63396269
Hyperreflexia	43.71	33.23	16	4193	5918	63478895
Clonus	43.65	33.23	15	4194	4621	63480192
Premature baby	40.43	33.23	22	4187	20713	63464100
Diabetes insipidus	38.99	33.23	12	4197	2613	63482200
Toxic epidermal necrolysis	38.92	33.23	23	4186	25311	63459502
Dyskinesia	38.85	33.23	25	4184	31977	63452836
Ventricular tachycardia	38.40	33.23	21	4188	19958	63464855
Drug interaction	37.85	33.23	60	4149	229071	63255742
Fatigue	37.29	33.23	7	4202	888021	62596792
Respiratory depression	36.68	33.23	18	4191	13697	63471116

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	595.90	30.48	171	4192	15770	34936798
Anaphylactic reaction	232.69	30.48	102	4261	32199	34920369
Hyperthermia malignant	200.90	30.48	48	4315	2129	34950439
Cardiac arrest	151.31	30.48	112	4251	96047	34856521
Diabetes insipidus	143.68	30.48	39	4324	2889	34949679
Hypotension	143.42	30.48	156	4207	221493	34731075
Bradycardia	130.24	30.48	93	4270	75325	34877243
Delayed recovery from anaesthesia	129.97	30.48	28	4335	773	34951795
Trigemino-cardiac reflex	107.80	30.48	19	4344	174	34952394
Neuromuscular block prolonged	101.26	30.48	21	4342	480	34952088
Toxic epidermal necrolysis	95.95	30.48	49	4314	21597	34930971
Propofol infusion syndrome	87.53	30.48	21	4342	945	34951623
Bronchospasm	83.97	30.48	36	4327	10695	34941873
Blood pressure decreased	76.31	30.48	58	4305	51457	34901111
Drug interaction	75.72	30.48	115	4248	225831	34726737
Drug reaction with eosinophilia and systemic symptoms	74.20	30.48	48	4315	32964	34919604
Airway complication of anaesthesia	71.51	30.48	13	4350	144	34952424
Ventricular fibrillation	68.48	30.48	40	4323	22914	34929654
Kounis syndrome	59.29	30.48	19	4344	2499	34950069
Recurrence of neuromuscular blockade	54.72	30.48	11	4352	214	34952354
Hypoventilation	53.62	30.48	19	4344	3395	34949173
Cardio-respiratory arrest	52.21	30.48	48	4315	55225	34897343
Seizure like phenomena	51.01	30.48	13	4350	751	34951817
Rhabdomyolysis	50.86	30.48	52	4311	68111	34884457
Respiratory depression	45.00	30.48	27	4336	16218	34936350
Circulatory collapse	43.36	30.48	29	4334	21009	34931559
Status epilepticus	43.01	30.48	24	4339	12590	34939978
Arteriospasm coronary	42.61	30.48	16	4347	3366	34949202
Sinus arrest	40.43	30.48	13	4350	1727	34950841
Anaesthetic complication neurological	39.29	30.48	9	4354	330	34952238
Anaphylactoid shock	38.08	30.48	9	4354	379	34952189
Erythema	36.60	30.48	50	4313	88730	34863838
Neuromuscular blockade	35.86	30.48	8	4355	260	34952308
Hypercapnia	35.67	30.48	15	4348	4240	34948328
Tachycardia	33.82	30.48	47	4316	84725	34867843
Anaphylactoid reaction	32.97	30.48	12	4351	2313	34950255
Fatigue	32.68	30.48	4	4359	370649	34581919

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	1353.28	26.47	375	8173	35621	79700219
Anaphylactic reaction	557.46	26.47	239	8309	83504	79652336
Cardiac arrest	282.74	26.47	194	8354	171902	79563938
Delayed recovery from anaesthesia	248.85	26.47	53	8495	1620	79734220
Hypotension	247.51	26.47	268	8280	440049	79295791
Hyperthermia malignant	240.22	26.47	57	8491	2860	79732980
Bradycardia	227.60	26.47	155	8393	135402	79600438
Bronchospasm	198.59	26.47	81	8467	24778	79711062
Diabetes insipidus	179.68	26.47	51	8497	5186	79730654
Neuromuscular block prolonged	166.74	26.47	35	8513	995	79734845
Circulatory collapse	139.74	26.47	72	8476	37596	79698244
Trigemino-cardiac reflex	137.44	26.47	24	8524	245	79735595
Blood pressure decreased	130.50	26.47	98	8450	99368	79636472
Toxic epidermal necrolysis	117.58	26.47	68	8480	44513	79691327
Drug interaction	99.23	26.47	167	8381	415016	79320824
Tachycardia	95.41	26.47	106	8442	177662	79558178
Propofol infusion syndrome	94.43	26.47	25	8523	1958	79733882
Kounis syndrome	91.74	26.47	29	8519	4253	79731587
Airway complication of anaesthesia	89.90	26.47	18	8530	402	79735438
Anaphylactoid reaction	88.95	26.47	30	8518	5392	79730448
Ventricular fibrillation	84.96	26.47	49	8499	31877	79703963
Anaphylactoid shock	84.18	26.47	19	8529	762	79735078
Recurrence of neuromuscular blockade	82.42	26.47	16	8532	303	79735537
Rhabdomyolysis	74.19	26.47	72	8476	103059	79632781
Hypoventilation	73.28	26.47	28	8520	7196	79728644
Pulseless electrical activity	70.19	26.47	33	8515	14127	79721713
Respiratory depression	69.79	26.47	41	8507	27589	79708251
Fatigue	69.50	26.47	9	8539	929718	78806122
Serotonin syndrome	60.39	26.47	45	8503	44982	79690858
Erythema	60.19	26.47	95	8453	223195	79512645
Stress cardiomyopathy	58.37	26.47	27	8521	11139	79724701
Ventricular tachycardia	56.43	26.47	42	8506	41893	79693947
Drug reaction with eosinophilia and systemic symptoms	54.14	26.47	49	8499	64195	79671645
Post procedural complication	54.05	26.47	33	8515	23796	79712044
Arteriospasm coronary	53.98	26.47	22	8526	6694	79729146
Cardio-respiratory arrest	51.86	26.47	61	8487	108449	79627391
Sinus arrest	51.46	26.47	18	8530	3604	79732236
Upper airway obstruction	49.39	26.47	14	8534	1414	79734426
Pain	47.57	26.47	9	8539	703793	79032047
Neuromuscular blockade	46.00	26.47	11	8537	569	79735271
Seizure like phenomena	45.68	26.47	14	8534	1853	79733987
Hypercapnia	44.82	26.47	21	8527	8914	79726926
Type I hypersensitivity	44.44	26.47	17	8531	4381	79731459
Arthralgia	43.95	26.47	5	8543	571798	79164042
Clonus	43.59	26.47	19	8529	6821	79729019
Nausea	41.26	26.47	26	8522	957170	78778670
Procedural hypotension	40.44	26.47	13	8535	2010	79733830
Anaesthetic complication	39.82	26.47	14	8534	2845	79732995
Haemodynamic instability	39.23	26.47	24	8524	17358	79718482
Status epilepticus	38.05	26.47	27	8521	25014	79710826
Oxygen saturation decreased	36.24	26.47	56	8492	128991	79606849
Anaesthetic complication neurological	34.91	26.47	9	8539	635	79735205
Death	34.70	26.47	9	8539	566505	79169335
Respiratory arrest	33.73	26.47	36	8512	57514	79678326
Fall	33.41	26.47	6	8542	487623	79248217
Urticaria	33.27	26.47	66	8482	185135	79550705
Shock	32.40	26.47	31	8517	43517	79692323
Blood pressure immeasurable	31.99	26.47	11	8537	2093	79733747
Exposure during pregnancy	31.40	26.47	46	8502	101086	79634754
Hyperreflexia	30.98	26.47	16	8532	8369	79727471
Electrocardiogram ST segment elevation	30.96	26.47	16	8532	8381	79727459
Hyperkalaemia	29.84	26.47	48	8500	114350	79621490
Dyskinesia	29.82	26.47	30	8518	44743	79691097
Subcutaneous emphysema	29.71	26.47	10	8538	1784	79734056
Acute generalised exanthematous pustulosis	29.49	26.47	20	8528	17234	79718606
Postoperative delirium	29.39	26.47	7	8541	356	79735484
Respiratory acidosis	29.27	26.47	17	8531	11183	79724657
Dizziness	29.25	26.47	10	8538	526431	79209409
Pulmonary alveolar haemorrhage	28.91	26.47	17	8531	11440	79724400
Capillary nail refill test abnormal	28.91	26.47	5	8543	48	79735792
Premature delivery	28.25	26.47	22	8526	23445	79712395
Diarrhoea	26.93	26.47	33	8515	880456	78855384

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	28 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9391	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	ANDA	28 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9392	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 mg	INTRAVENOUS	ANDA	28 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9392	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 mg	INTRAVENOUS	ANDA	28 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9393	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	5 mg	INTRAVENOUS	ANDA	28 sections
REMIFENTANIL HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9393	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	5 mg	INTRAVENOUS	ANDA	28 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	67457-198	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	67457-912	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	67457-913	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
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
Ultiva	HUMAN PRESCRIPTION DRUG LABEL	1	72078-034	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	NDA	32 sections
Ultiva	HUMAN PRESCRIPTION DRUG LABEL	1	72078-035	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	NDA	32 sections
Ultiva	HUMAN PRESCRIPTION DRUG LABEL	1	72078-036	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 mg	INTRAVENOUS	NDA	32 sections