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

Stem definition	Drug id	CAS RN
analgesics	4283	175591-09-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: tapentadol tapentadol hydrochloride nucynta tapentadol HCl	An opioid analgesic, MU OPIOID RECEPTOR agonist, and noradrenaline reuptake inhibitor that is used in the treatment of moderate to severe pain, and of pain associated with DIABETIC NEUROPATHIES. Molecular weight: 221.34 Formula: C14H23NO CLOGP: 3.15 LIPINSKI: 0 HAC: 2 HDO: 1 TPSA: 23.47 ALOGS: -2.45 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

tapentadol
tapentadol hydrochloride
nucynta
tapentadol HCl

An opioid analgesic, MU OPIOID RECEPTOR agonist, and noradrenaline reuptake inhibitor that is used in the treatment of moderate to severe pain, and of pain associated with DIABETIC NEUROPATHIES.

Molecular weight: 221.34
Formula: C14H23NO
CLOGP: 3.15
LIPINSKI: 0
HAC: 2
HDO: 1
TPSA: 23.47
ALOGS: -2.45
ROTB: 5

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.40	g	O

ADMET properties:

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Property	Value	Reference
Vd (Volume of distribution)	4.64 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	21.33 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	2.39 hours	Lombardo F, Berellini G, Obach RS
S (Water solubility)	1.16 mg/mL	Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
Nov. 20, 2008	FDA	JANSSEN PHARMS

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 interaction	130.26	15.29	183	11369	228948	63248522
Sopor	108.88	15.29	61	11491	22103	63455367
Serotonin syndrome	101.79	15.29	64	11488	28618	63448852
Toxicity to various agents	101.67	15.29	170	11382	247080	63230390
Paroxysmal extreme pain disorder	72.46	15.29	13	11539	87	63477383
Degenerative bone disease	71.25	15.29	14	11538	161	63477309
Chronic respiratory disease	70.10	15.29	14	11538	176	63477294
Confusional arousal	68.70	15.29	14	11538	196	63477274
Drug abuse	66.95	15.29	74	11478	72444	63405026
Post procedural hypothyroidism	64.73	15.29	14	11538	265	63477205

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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
Serotonin syndrome	116.81	18.80	62	6418	19871	34930580
Delirium	106.67	18.80	78	6402	43913	34906538
Quality of life decreased	85.53	18.80	31	6449	3970	34946481
Hyperaesthesia	77.55	18.80	30	6450	4600	34945851
Drug abuse	75.01	18.80	92	6388	99004	34851447
Constipation	72.82	18.80	107	6373	136875	34813576
Suicide attempt	61.84	18.80	54	6426	39062	34911389
Toxicity to various agents	60.80	18.80	122	6358	200240	34750211
Sopor	55.28	18.80	32	6448	12104	34938347
Overdose	54.00	18.80	75	6405	90984	34859467

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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
Toxicity to various agents	154.81	15.54	279	14561	421261	79308287
Sopor	149.97	15.54	87	14753	32923	79696625
Serotonin syndrome	129.90	15.54	89	14751	44938	79684610
Delirium	129.72	15.54	115	14725	84512	79645036
Drug abuse	128.93	15.54	155	14685	162536	79567012
Drug interaction	125.42	15.54	253	14587	414930	79314618
Confusional state	87.89	15.54	187	14653	317810	79411738
Suicide attempt	84.32	15.54	90	14750	82842	79646706
Intentional overdose	79.06	15.54	98	14742	105862	79623686
Respiratory depression	78.21	15.54	54	14786	27576	79701972

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N02AX06	NERVOUS SYSTEM ANALGESICS OPIOIDS Other opioids
FDA EPC	N0000175690	Opioid Agonist
FDA MoA	N0000000174	Opioid Agonists
MeSH PA	D018663	Adrenergic Agents
MeSH PA	D018759	Adrenergic Uptake Inhibitors
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	D049990	Membrane Transport Modulators

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

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Disease	Relation	SNOMED_ID	DOID
Pain	indication	22253000
Chronic obstructive lung disease	contraindication	13645005	DOID:3083
Asthenia	contraindication	13791008
Alcohol intoxication	contraindication	25702006
Hypercapnia	contraindication	29596007
Myxedema	contraindication	43153006	DOID:11634
Paralytic ileus	contraindication	55525008	DOID:8442
Substance abuse	contraindication	66214007
Benign intracranial hypertension	contraindication	68267002	DOID:11459
Sleep apnea	contraindication	73430006	DOID:0050847

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.76	acidic
pKa2	9.12	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
EQ 100MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8309060	Nov. 20, 2023	MANAGEMENT OF NEUROPATHIC PAIN ASSOCIATED WITH DIABETIC PERIPHERAL NEUROPATHY
EQ 100MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8309060	Nov. 20, 2023	RELIEF OF MODERATE TO SEVERE CHRONIC PAIN
EQ 100MG BASE	NUCYNTA	COLLEGIUM PHARM INC	N022304	Nov. 20, 2008	RX	TABLET	ORAL	7994364	June 27, 2025	RELIEF OF MODERATE TO SEVERE ACUTE PAIN
EQ 100MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	7994364	June 27, 2025	MANAGEMENT OF NEUROPATHIC PAIN ASSOCIATED WITH DIABETIC PERIPHERAL NEUROPATHY
EQ 100MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	7994364	June 27, 2025	RELIEF OF MODERATE TO SEVERE CHRONIC PAIN
EQ 100MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	11344512	April 21, 2028	A METHOD OF TITRATING AN OPIOID TO MANAGE NEUROPATHIC PAIN ASSOCIATED WITH DIABETIC PERIPHERAL NEUROPATHY SEVERE ENOUGH TO REQUIRE DAILY, AROUND-THE-CLOCK, LONG-TERM OPIOID TREATMENT AND FOR WHICH ALTERNATIVE TREATMENT OPTIONS ARE INADEQUATE
EQ 100MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	11344512	April 21, 2028	A METHOD OF TITRATING AN OPIOID TO MANAGE PAIN SEVERE ENOUGH TO REQUIRE DAILY, AROUND-THE-CLOCK, LONG-TERM OPIOID TREATMENT AND FOR WHICH ALTERNATIVE TREATMENTS ARE INADEQUATE
EQ 100MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8536130	Sept. 22, 2028	MANAGEMENT OF NEUROPATHIC PAIN ASSOCIATED WITH DIABETIC PERIPHERAL NEUROPATHY
EQ 150MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8309060	Nov. 20, 2023	MANAGEMENT OF NEUROPATHIC PAIN ASSOCIATED WITH DIABETIC PERIPHERAL NEUROPATHY
EQ 150MG BASE	NUCYNTA ER	COLLEGIUM PHARM INC	N200533	Aug. 25, 2011	RX	TABLET, EXTENDED RELEASE	ORAL	8309060	Nov. 20, 2023	RELIEF OF MODERATE TO SEVERE CHRONIC PAIN

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
EQ 100MG BASE	NUCYNTA	COLLEGIUM PHARM INC	N022304	Nov. 20, 2008	RX	TABLET	ORAL	July 3, 2026	NEW PATIENT POPULATION
EQ 20MG BASE/ML	NUCYNTA	COLLEGIUM PHARM INC	N203794	Oct. 15, 2012	DISCN	SOLUTION	ORAL	July 3, 2026	NEW PATIENT POPULATION
EQ 50MG BASE	NUCYNTA	COLLEGIUM PHARM INC	N022304	Nov. 20, 2008	RX	TABLET	ORAL	July 3, 2026	NEW PATIENT POPULATION
EQ 75MG BASE	NUCYNTA	COLLEGIUM PHARM INC	N022304	Nov. 20, 2008	RX	TABLET	ORAL	July 3, 2026	NEW PATIENT POPULATION

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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	Ki	7.02	WOMBAT-PK	CHEMBL
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN	INHIBITOR	Ki	6.32	WOMBAT-PK	CHEMBL
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	4.66	CHEMBL

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External reference:

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ID	Source
013168	NDDF
013169	NDDF
165888	MMSL
175591-23-8	SECONDARY_CAS_RN
26545	MMSL
35753	MMSL
4029061	VUID
4029061	VANDF
4029062	VANDF
441757005	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
NUCYNTA	HUMAN PRESCRIPTION DRUG LABEL	1	16590-289	TABLET, FILM COATED	100 mg	ORAL	NDA	35 sections
NUCYNTA	HUMAN PRESCRIPTION DRUG LABEL	1	16590-863	TABLET, FILM COATED	50 mg	ORAL	NDA	35 sections
NUCYNTA	HUMAN PRESCRIPTION DRUG LABEL	1	16590-889	TABLET, FILM COATED	75 mg	ORAL	NDA	32 sections
NUCYNTA	HUMAN PRESCRIPTION DRUG LABEL	1	21695-069	TABLET, FILM COATED	50 mg	ORAL	NDA	34 sections
Nucynta	HUMAN PRESCRIPTION DRUG LABEL	1	24510-050	TABLET, FILM COATED	50 mg	ORAL	NDA	39 sections
Nucynta	HUMAN PRESCRIPTION DRUG LABEL	1	24510-050	TABLET, FILM COATED	50 mg	ORAL	NDA	39 sections
Nucynta	HUMAN PRESCRIPTION DRUG LABEL	1	24510-075	TABLET, FILM COATED	75 mg	ORAL	NDA	39 sections
Nucynta	HUMAN PRESCRIPTION DRUG LABEL	1	24510-075	TABLET, FILM COATED	75 mg	ORAL	NDA	39 sections
Nucynta	HUMAN PRESCRIPTION DRUG LABEL	1	24510-100	TABLET, FILM COATED	100 mg	ORAL	NDA	39 sections
Nucynta	HUMAN PRESCRIPTION DRUG LABEL	1	24510-100	TABLET, FILM COATED	100 mg	ORAL	NDA	39 sections

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