sufentanil Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
opioid receptor agonists, analgesics, fentanyl derivatives	2491	56030-54-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: sulfentanyl sulfentanil sulfentanil citrate sufentanil sufentanil citrate	An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. Molecular weight: 386.55 Formula: C22H30N2O2S CLOGP: 3.59 LIPINSKI: 0 HAC: 4 HDO: 0 TPSA: 32.78 ALOGS: -4.51 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

sulfentanyl
sulfentanil
sulfentanil citrate
sufentanil
sufentanil citrate

An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent.

Molecular weight: 386.55
Formula: C22H30N2O2S
CLOGP: 3.59
LIPINSKI: 0
HAC: 4
HDO: 0
TPSA: 32.78
ALOGS: -4.51
ROTB: 8

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)	6 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.06 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	0 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	9.40 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	15 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.08 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	14 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
May 4, 1984	FDA	AKORN

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	1257.88	29.72	317	4955	19957	46660833
Hypotension	264.58	29.72	214	5058	232375	46448415
Bronchospasm	242.47	29.72	84	5188	15623	46665167
Exposure during pregnancy	144.85	29.72	110	5162	108102	46572688
Maternal exposure during delivery	115.23	29.72	25	5247	791	46679999
Anaphylactoid shock	113.75	29.72	21	5251	284	46680506
Anaphylactic reaction	113.36	29.72	72	5200	53040	46627750
Tachycardia	100.71	29.72	86	5186	99536	46581254
Circulatory collapse	94.63	29.72	47	5225	21577	46659213
Cardiac arrest	75.32	29.72	70	5202	90329	46590461
Shock	74.04	29.72	40	5232	21805	46658985
Oliguria	70.03	29.72	29	5243	8730	46672060
Hepatocellular injury	67.89	29.72	42	5230	29480	46651310
Hepatorenal failure	65.45	29.72	15	5257	611	46680179
Respiratory depression	65.33	29.72	30	5242	11570	46669220
Peripheral nerve injury	61.44	29.72	13	5259	364	46680426
Delayed recovery from anaesthesia	60.70	29.72	15	5257	846	46679944
Haemodynamic instability	59.81	29.72	25	5247	7700	46673090
Suspected product quality issue	58.32	29.72	11	5261	168	46680622
Spinal epidural haemorrhage	56.93	29.72	10	5262	100	46680690
Hypocapnia	55.88	29.72	12	5260	361	46680429
Type I hypersensitivity	54.04	29.72	17	5255	2329	46678461
Erythema	50.65	29.72	71	5201	142749	46538041
Ventricular fibrillation	47.36	29.72	24	5248	11472	46669318
Unwanted awareness during anaesthesia	47.05	29.72	10	5262	286	46680504
Bradycardia	46.98	29.72	47	5225	66251	46614539
Stress cardiomyopathy	46.56	29.72	21	5251	7763	46673027
Patent ductus arteriosus	45.73	29.72	17	5255	3845	46676945
Fatigue	43.88	29.72	8	5264	608689	46072101
Foetal exposure during pregnancy	42.62	29.72	32	5240	30715	46650075
Serotonin syndrome	42.27	29.72	29	5243	24191	46656599
Oxygen saturation decreased	40	29.72	44	5228	69120	46611670
Cauda equina syndrome	39.03	29.72	10	5262	653	46680137
Anaesthetic complication	37.04	29.72	12	5260	1805	46678985
Acute generalised exanthematous pustulosis	36.89	29.72	19	5253	9386	46671404
Epidural haemorrhage	36.35	29.72	7	5265	120	46680670
Cardio-respiratory arrest	36.21	29.72	39	5233	59830	46620960
Myoglobin blood increased	35.56	29.72	11	5261	1425	46679365
Paralysis	35.31	29.72	18	5254	8703	46672087
Cholestasis	35.09	29.72	27	5245	26866	46653924
Post procedural stroke	34.25	29.72	6	5266	59	46680731
Foetal growth restriction	33.91	29.72	16	5256	6551	46674239
Eosinophilia	33.51	29.72	23	5249	19194	46661596
Suspected product contamination	32.21	29.72	5	5267	21	46680769
Metabolic acidosis	32.17	29.72	30	5242	38750	46642040
Carcinoid crisis	31.63	29.72	7	5265	243	46680547
Diarrhoea	31.51	29.72	12	5260	559590	46121200
Haemodilution	31.26	29.72	6	5266	101	46680689
Foetal heart rate abnormal	30.89	29.72	8	5264	545	46680245
Maternal exposure during pregnancy	30.54	29.72	47	5225	102502	46578288

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	811.05	31.83	216	3907	13777	29934578
Bronchospasm	170.10	31.83	61	4062	10277	29938078
Hypertransaminasaemia	133.32	31.83	40	4083	3845	29944510
Anaphylactic reaction	111.75	31.83	61	4062	27921	29920434
Hypotension	105.08	31.83	133	3990	200432	29747923
Hyperthermia malignant	104.19	31.83	28	4095	1806	29946549
Tachycardia	75.76	31.83	70	4053	73669	29874686
Circulatory collapse	69.57	31.83	40	4083	20174	29928181
Toxic epidermal necrolysis	68.50	31.83	38	4085	17902	29930453
Septic shock	58.82	31.83	57	4066	63550	29884805
Haemodynamic instability	57.33	31.83	26	4097	7989	29940366
Rhabdomyolysis	56.97	31.83	56	4067	63524	29884831
Multiple organ dysfunction syndrome	53.33	31.83	54	4069	63433	29884922
Shock	52.59	31.83	35	4088	22824	29925531
Victim of crime	50.75	31.83	11	4112	282	29948073
Hepatorenal failure	47.77	31.83	12	4111	592	29947763
Anaphylactoid shock	46.86	31.83	11	4112	407	29947948
Hepatocellular injury	44.60	31.83	33	4090	25438	29922917
Type I hypersensitivity	42.40	31.83	12	4111	936	29947419
Patent ductus arteriosus	42.10	31.83	16	4107	3153	29945202
Erythema	41.27	31.83	52	4071	77399	29870956
Suspected product contamination	39.13	31.83	7	4116	63	29948292
Coma	38.76	31.83	37	4086	40412	29907943
Infantile apnoea	38.62	31.83	11	4112	878	29947477
Suspected product quality issue	38.52	31.83	8	4115	166	29948189
Stress cardiomyopathy	36.59	31.83	12	4111	1537	29946818
Fear	36.10	31.83	21	4102	10804	29937551
Injury	35.47	31.83	27	4096	21704	29926651
Post procedural haemorrhage	33.62	31.83	18	4105	7892	29940463
Fibrinolysis increased	33.06	31.83	5	4118	13	29948342
Agitation neonatal	32.76	31.83	10	4113	1015	29947340
Anaesthetic complication	32.35	31.83	10	4113	1059	29947296

Pharmacologic Action:

Source	Code	Description
ATC	N01AH03	NERVOUS SYSTEM ANESTHETICS ANESTHETICS, GENERAL Opioid anesthetics
MeSH PA	D000759	Adjuvants, Anesthesia
FDA MoA	N0000175684	Full Opioid Agonists
FDA EPC	N0000175690	Opioid Agonist
MeSH PA	D000700	Analgesics
MeSH PA	D000701	Analgesics, Opioid
MeSH PA	D000777	Anesthetics
MeSH PA	D018686	Anesthetics, Intravenous
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 analgesics
CHEBI has role	CHEBI:38877	intravenous anesthetics
CHEBI has role	CHEBI:55322	mu opioid agonist
CHEBI has role	CHEBI:60807	anaesthesia adjuvants

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
General anesthesia	indication	50697003
Postoperative pain	indication	213299007
Asthenia	contraindication	13791008
Chronic disease of respiratory system	contraindication	17097001
Decreased cardiac function	contraindication	43650005
Bradycardia	contraindication	48867003
Injury of head	contraindication	82271004
Kidney disease	contraindication	90708001	DOID:557
Disease of liver	contraindication	235856003	DOID:409

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.37	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
EQ 0.03MG BASE	DSUVIA	ACELRX PHARMS	N209128	Nov. 2, 2018	RX	TABLET	SUBLINGUAL	Nov. 2, 2021	NEW PRODUCT

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Mu-type opioid receptor	GPCR	P35372	OPRM_HUMAN	AGONIST	EC50	8.13	WOMBAT-PK	CHEMBL
Delta-type opioid receptor	GPCR	P41143	OPRD_HUMAN		Ki	7.30	PDSP
Kappa-type opioid receptor	GPCR	P41145	OPRK_HUMAN		EC50	6.70	WOMBAT-PK
Opioid receptor	GPCR		OPRD_RAT OPRK_RAT OPRM_RAT SGMR1_RAT		Ki	10.70	CHEMBL
Mu-type opioid receptor	GPCR		OPRM_RAT		Ki	9.66	CHEMBL

External reference:

ID	Source
4019936	VUID
N0000148021	NUI
D00845	KEGG_DRUG
60561-17-3	SECONDARY_CAS_RN
4019269	VANDF
4019936	VANDF
C0143993	UMLSCUI
CHEBI:9316	CHEBI
CHEMBL658	ChEMBL_ID
CHEMBL1201163	ChEMBL_ID
D017409	MESH_DESCRIPTOR_UI
3534	IUPHAR_LIGAND_ID
4048	INN_ID
DB00708	DRUGBANK_ID
AFE2YW0IIZ	UNII
41693	PUBCHEM_CID
56795	RXNORM
10199	MMSL
32203	MMSL
5519	MMSL
d00378	MMSL
001570	NDDF
004630	NDDF
370275005	SNOMEDCT_US
37527009	SNOMEDCT_US
49998007	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Sufentanil Citrate	HUMAN PRESCRIPTION DRUG LABEL	1	0409-3382	INJECTION, SOLUTION	50 ug	EPIDURAL	ANDA	32 sections
Sufentanil Citrate	HUMAN PRESCRIPTION DRUG LABEL	1	0641-6110	INJECTION	0.05 mg	EPIDURAL	ANDA	27 sections
Sufentanil Citrate	HUMAN PRESCRIPTION DRUG LABEL	1	0641-6111	INJECTION	0.05 mg	EPIDURAL	ANDA	27 sections
Sufentanil Citrate	HUMAN PRESCRIPTION DRUG LABEL	1	0641-6112	INJECTION	0.05 mg	EPIDURAL	ANDA	27 sections
Sufentanil Citrate	HUMAN PRESCRIPTION DRUG LABEL	1	17478-050	INJECTION	50 ug	INTRAVENOUS	NDA	29 sections
Dsuvia	Human Prescription Drug Label	1	61621-430	TABLET	30 ug	SUBLINGUAL	NDA	30 sections