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

Stem definition	Drug id	CAS RN
opioid receptor agonists, analgesics, fentanyl derivatives	1164	437-38-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: fentanyl fentanil fentanyl citrate effentora instanyl fentanyl hydrochloride fentanyl HCl	A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. Molecular weight: 336.48 Formula: C22H28N2O CLOGP: 3.62 LIPINSKI: 0 HAC: 3 HDO: 0 TPSA: 23.55 ALOGS: -4.15 ROTB: 6 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

fentanyl
fentanil
fentanyl citrate
effentora
instanyl
fentanyl hydrochloride
fentanyl HCl

A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance.

Molecular weight: 336.48
Formula: C22H28N2O
CLOGP: 3.62
LIPINSKI: 0
HAC: 3
HDO: 0
TPSA: 23.55
ALOGS: -4.15
ROTB: 6

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.60	mg	N
0.60	mg	SL
1.20	mg	TD

ADMET properties:

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Property	Value	Reference
EoM (Fraction excreted unchanged in urine)	8 %	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	4.70 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	3 hours	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	1 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	0.89 L/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.74 mg/mL	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	0.16 %	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.00 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

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Approvals:

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Date	Agency	Company
Feb. 19, 1968	FDA	AKORN
Jan. 24, 2006	EMA	Janssen-Cilag International NV
June 29, 2020	PMDA	Hisamitsu Pharmaceutical Co., Inc.

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FDA Adverse Event Reporting System (Female)

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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
Drug abuse	3845.32	10.22	2255	140609	70263	63275895
Toxicity to various agents	1270.23	10.22	2112	140752	245138	63101020
Respiratory arrest	764.18	10.22	614	142250	32031	63314127
Product adhesion issue	760.39	10.22	314	142550	4405	63341753
Cardiac arrest	711.19	10.22	956	141908	91589	63254569
Death	647.80	10.22	2080	140784	372301	62973857
Cardio-respiratory arrest	601.77	10.22	708	142156	59251	63286907
Serotonin syndrome	599.14	10.22	505	142359	28177	63317981
Respiratory depression	553.16	10.22	359	142505	13356	63332802
Drug withdrawal syndrome	444.89	10.22	417	142447	26777	63319381

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FDA Adverse Event Reporting System (Male)

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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
Drug abuse	9364.54	10.97	5075	108003	94021	34749832
Toxicity to various agents	2479.33	10.97	3133	109945	197229	34646624
Respiratory arrest	863.99	10.97	720	112358	27323	34816530
Cardio-respiratory arrest	693.83	10.97	874	112204	54399	34789454
Cardiac arrest	682.39	10.97	1161	111917	94998	34748855
Overdose	661.42	10.97	1111	111967	89948	34753905
Respiratory depression	655.16	10.97	489	112589	15756	34828097
Accidental overdose	626.19	10.97	520	112558	19620	34824233
Incorrect route of product administration	612.40	10.97	453	112625	14392	34829461
Product adhesion issue	584.16	10.97	213	112865	1387	34842466

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FDA Adverse Event Reporting System (Geriatric)

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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
Drug abuse	13324.16	10.12	7139	207754	155552	79373943
Toxicity to various agents	3058.70	10.12	4643	210250	416897	79112598
Respiratory arrest	1615.75	10.12	1297	213596	56253	79473242
Cardiac arrest	1452.99	10.12	2041	212852	170055	79359440
Cardio-respiratory arrest	1343.01	10.12	1557	213336	106953	79422542
Serotonin syndrome	1090.99	10.12	932	213961	44095	79485400
Respiratory depression	1044.06	10.12	744	214149	26886	79502609
Incorrect route of product administration	907.95	10.12	753	214140	34176	79495319
Overdose	896.22	10.12	1703	213190	182503	79346992
Drug withdrawal syndrome	698.42	10.12	647	214246	34071	79495424

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FDA Adverse Event Reporting System (Pediatric)

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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
Muscle rigidity	48.98	30.68	11	298	3	89480
Intraventricular haemorrhage	32.49	30.68	14	295	142	89341

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Pharmacologic Action:

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Source	Code	Description
ATC	N01AH01	NERVOUS SYSTEM ANESTHETICS ANESTHETICS, GENERAL Opioid anesthetics
ATC	N01AH51	NERVOUS SYSTEM ANESTHETICS ANESTHETICS, GENERAL Opioid anesthetics
ATC	N02AB03	NERVOUS SYSTEM ANALGESICS OPIOIDS Phenylpiperidine derivatives
CHEBI has role	CHEBI:35482	narcotic analgesic
CHEBI has role	CHEBI:55322	mu-opioid agonists
CHEBI has role	CHEBI:38867	anaesthetic
CHEBI has role	CHEBI:38877	intravenous anesthetics
CHEBI has role	CHEBI:60807	anaesthestic adjuvant
CHEBI has role	CHEBI:60809	adjuvants
FDA EPC	N0000175690	Opioid Agonist

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

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Disease	Relation	SNOMED_ID
Pain	indication	22253000
General anesthesia	indication	50697003
Local anesthesia	indication	386761002
Breakthrough cancer pain	indication	879973007
Acute postoperative pain	indication	107401000119105
Regional Anesthesia for Surgery	indication
Chronic Pain with Opioid Tolerance	indication
Regional Anesthesia for Postoperative Pain	indication
Breakthrough Pain in Opioid Tolerant Patients	indication
Anesthesia for cesarean section	off-label use	4847005

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🐶 Veterinary Drug Use

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Species	Use	Relation
Dogs	Postoperative pain associated with surgical procedures	Indication
Dogs	Analgesia and tranquilizers	Indication

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🐶 Veterinary products

Product	Applicant	Ingredients
Innovar-Vet Injection	Intervet Inc.	2

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.62	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.1MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	8835460	Jan. 25, 2027	TREATMENT OF PAIN
0.1MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	9289387	Jan. 25, 2027	TREATMENT OF PAIN
0.1MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	9642797	Jan. 25, 2027	TREATMENT OF PAIN
0.1MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	8486973	April 27, 2030	TREATMENT OF PAIN
0.2MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	8835460	Jan. 25, 2027	TREATMENT OF PAIN
0.2MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	9289387	Jan. 25, 2027	TREATMENT OF PAIN
0.2MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	9642797	Jan. 25, 2027	TREATMENT OF PAIN
0.2MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	8486973	April 27, 2030	TREATMENT OF PAIN
0.4MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	8835460	Jan. 25, 2027	TREATMENT OF PAIN
0.4MG	SUBSYS	BTCP PHARMA	N202788	Jan. 4, 2012	DISCN	SPRAY	SUBLINGUAL	9289387	Jan. 25, 2027	TREATMENT OF PAIN

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Mu-type opioid receptor	GPCR	P35372	OPRM_HUMAN	AGONIST	EC50	9.00	WOMBAT-PK	CHEMBL
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		Ki	4.68	CHEMBL
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN		IC50	6.45	CHEMBL
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	5.74	CHEMBL
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN		Ki	4.58	CHEMBL
D(4) dopamine receptor	GPCR	P21917	DRD4_HUMAN		Ki	6.26	CHEMBL
Kappa-type opioid receptor	GPCR	P41145	OPRK_HUMAN		Ki	6.71	CHEMBL
Delta-type opioid receptor	GPCR	P41143	OPRD_HUMAN		Ki	6.17	CHEMBL
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	4.34	CHEMBL
Monoamine oxidase	Enzyme	P21397 P27338	AOFA_HUMAN AOFB_HUMAN		Ki	5.26	CHEMBL

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External reference:

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ID	Source
001568	NDDF
003571	NDDF
011514	NDDF
142436	RXNORM
1443-54-5	SECONDARY_CAS_RN
1608	INN_ID
1626	IUPHAR_LIGAND_ID
29190006	SNOMEDCT_US
29441	MMSL
3345	PUBCHEM_CID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9119	PATCH	12 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9119	PATCH	12 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9121	PATCH	25 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9121	PATCH	25 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9122	PATCH	50 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9122	PATCH	50 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9123	PATCH	75 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9123	PATCH	75 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9124	PATCH	100 ug	TRANSDERMAL	ANDA	34 sections
FENTANYL	HUMAN PRESCRIPTION DRUG LABEL	1	0378-9124	PATCH	100 ug	TRANSDERMAL	ANDA	34 sections

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