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

Stem definition	Drug id	CAS RN
local anaesthetics	2403	84057-95-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: ropivacaine (-)-Ropivacaine anapeine naropeine naropine S-Ropivacaine ropivacaine hydrochloride monohydrate ropivacaine hydrochloride ropivacaine HCl	An anilide used as a long-acting local anesthetic. It has a differential blocking effect on sensory and motor neurons. Molecular weight: 274.41 Formula: C17H26N2O CLOGP: 3.16 LIPINSKI: 0 HAC: 3 HDO: 1 TPSA: 32.34 ALOGS: -3.04 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

ropivacaine
(-)-Ropivacaine
anapeine
naropeine
naropine
S-Ropivacaine
ropivacaine hydrochloride monohydrate
ropivacaine hydrochloride
ropivacaine HCl

An anilide used as a long-acting local anesthetic. It has a differential blocking effect on sensory and motor neurons.

Molecular weight: 274.41
Formula: C17H26N2O
CLOGP: 3.16
LIPINSKI: 0
HAC: 3
HDO: 1
TPSA: 32.34
ALOGS: -3.04
ROTB: 4

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
S (Water solubility)	53.80 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	1 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	15.62 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.75 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	5.50 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.06 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	2.20 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Sept. 24, 1996	FDA	FRESENIUS KABI USA

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
Anaesthetic complication	127.93	38.29	28	3122	1702	50600272
Peripheral nerve injury	120.48	38.29	21	3129	381	50601593
Maternal exposure during delivery	118.92	38.29	24	3126	982	50600992
Cauda equina syndrome	113.43	38.29	22	3128	732	50601242
Anaphylactic shock	96.52	38.29	39	3111	20116	50581858
Maternal exposure during pregnancy	91.26	38.29	77	3073	159701	50442273
Myoclonus	83.31	38.29	32	3118	14438	50587536
Cardiac arrest	82.64	38.29	56	3094	83595	50518379
Neurotoxicity	75.67	38.29	30	3120	14710	50587264
Exposure during pregnancy	74.58	38.29	61	3089	120954	50481020
Generalised tonic-clonic seizure	70.93	38.29	34	3116	26276	50575698
Toxicity to various agents	68.98	38.29	75	3075	212424	50389550
Hypotension	66.02	38.29	77	3073	235392	50366582
Spinal epidural haemorrhage	55.65	38.29	9	3141	101	50601873
Seizure	55.52	38.29	51	3099	117823	50484151
Nerve block	54.09	38.29	11	3139	467	50601507
Respiratory depression	53.22	38.29	22	3128	11988	50589986
Oliguria	50.25	38.29	19	3131	8197	50593777
Vitamin K deficiency	49.44	38.29	10	3140	413	50601561
Paraplegia	49.44	38.29	14	3136	2440	50599534
Monoplegia	47.69	38.29	14	3136	2769	50599205
Hypoaesthesia	43.07	38.29	46	3104	127211	50474763
Epidural haemorrhage	40.57	38.29	7	3143	119	50601855

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	100.02	32.31	37	2055	13299	29559136
Anaesthetic complication	93.34	32.31	20	2072	966	29571469
Negative pressure pulmonary oedema	81.10	32.31	14	2078	209	29572226
Cardiac arrest	79.77	32.31	58	2034	85533	29486902
Local anaesthetic systemic toxicity	62.54	32.31	11	2081	184	29572251
Urethral valves	58.45	32.31	11	2081	272	29572163
Phrenic nerve paralysis	48.51	32.31	8	2084	89	29572346
Delayed recovery from anaesthesia	48.16	32.31	11	2081	712	29571723
Spinal cord infarction	46.17	32.31	9	2083	269	29572166
Neuromuscular block prolonged	41.60	32.31	9	2083	454	29571981
Incorrect route of product administration	39.71	32.31	18	2074	10783	29561652
Stress cardiomyopathy	39.32	32.31	11	2081	1613	29570822
Ventricular fibrillation	38.85	32.31	20	2072	15813	29556622
Respiratory depression	38.82	32.31	19	2073	13504	29558931
Bradycardia	38.55	32.31	34	2058	65595	29506840
Generalised tonic-clonic seizure	35.29	32.31	20	2072	19119	29553316
Product packaging confusion	32.92	32.31	5	2087	31	29572404
Recurrence of neuromuscular blockade	32.55	32.31	6	2086	132	29572303

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
Anaesthetic complication	186.87	28.76	43	5131	2536	64491022
Anaphylactic shock	178.22	28.76	73	5101	30255	64463303
Cardiac arrest	148.19	28.76	112	5062	153952	64339606
Cauda equina syndrome	116.25	28.76	25	5149	1078	64492480
Maternal exposure during delivery	109.95	28.76	23	5151	867	64492691
Maternal exposure during pregnancy	94.88	28.76	71	5103	95813	64397745
Generalised tonic-clonic seizure	93.67	28.76	51	5123	39806	64453752
Local anaesthetic systemic toxicity	86.34	28.76	18	5156	667	64492891
Negative pressure pulmonary oedema	79.07	28.76	14	5160	213	64493345
Phrenic nerve paralysis	79.00	28.76	14	5160	214	64493344
Neurotoxicity	78.38	28.76	40	5134	27364	64466194
Peripheral nerve injury	76.05	28.76	16	5158	620	64492938
Myoclonus	75.75	28.76	38	5136	25080	64468478
Respiratory depression	75.24	28.76	37	5137	23406	64470152
Hypotension	72.72	28.76	118	5056	380856	64112702
Incorrect route of product administration	72.48	28.76	36	5138	23262	64470296
Ventricular fibrillation	71.66	28.76	36	5138	23824	64469734
Paraplegia	68.87	28.76	22	5152	4468	64489090
Seizure	67.99	28.76	75	5099	166817	64326741
Stress cardiomyopathy	63.71	28.76	25	5149	9232	64484326
Exposure during pregnancy	62.64	28.76	51	5123	77624	64415934
Anaphylactic reaction	59.44	28.76	47	5127	68617	64424941
Bradycardia	58.57	28.76	59	5115	118160	64375398
Spinal cord paralysis	57.94	28.76	10	5164	130	64493428
Monoplegia	57.49	28.76	18	5156	3425	64490133
Nerve block	53.96	28.76	11	5163	364	64493194
Tachycardia	53.73	28.76	63	5111	149516	64344042
Delayed recovery from anaesthesia	52.48	28.76	14	5160	1514	64492044
Tonic clonic movements	48.82	28.76	14	5160	1975	64491583
Product packaging confusion	46.70	28.76	9	5165	222	64493336
Toxicity to various agents	45.60	28.76	94	5080	363419	64130139
Circulatory collapse	44.95	28.76	30	5144	33702	64459856
Spinal epidural haemorrhage	43.80	28.76	8	5166	146	64493412
Diarrhoea	43.56	28.76	4	5170	722700	63770858
Vitamin K deficiency	42.19	28.76	10	5164	669	64492889
Hypoaesthesia	40.91	28.76	53	5121	139055	64354503
Foetal heart rate abnormal	39.75	28.76	8	5166	248	64493310
Motor dysfunction	39.63	28.76	19	5155	11354	64482204
Neuromuscular block prolonged	38.58	28.76	10	5164	967	64492591
Spinal cord infarction	38.53	28.76	9	5165	565	64492993
Fatigue	38.29	28.76	7	5167	748723	63744835
Wrong product administered	36.67	28.76	16	5158	7704	64485854
Epidural haemorrhage	36.31	28.76	7	5167	173	64493385
Uterine hypotonus	34.76	28.76	6	5168	78	64493480
Diplegia	33.63	28.76	10	5164	1601	64491957
Anterior spinal artery syndrome	33.54	28.76	6	5168	97	64493461
Premature delivery	33.45	28.76	20	5154	18569	64474989
Post procedural complication	33.38	28.76	21	5153	21332	64472226
Paralysis	33.35	28.76	17	5157	11578	64481980
Diaphragmatic paralysis	33.27	28.76	9	5165	1025	64492533
Type I hypersensitivity	33.11	28.76	12	5162	3562	64489996
Oliguria	32.41	28.76	18	5156	14558	64479000
Tachypnoea	31.52	28.76	22	5152	26549	64467009
Caesarean section	30.90	28.76	16	5158	11258	64482300
Epidural analgesia	30.17	28.76	5	5169	50	64493508
Paraparesis	29.64	28.76	11	5163	3491	64490067
Myelitis transverse	29.26	28.76	9	5165	1614	64491944
Spinal anaesthesia	28.90	28.76	5	5169	66	64493492
Tracheal deviation	28.83	28.76	5	5169	67	64493491

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	N01BB09	NERVOUS SYSTEM ANESTHETICS ANESTHETICS, LOCAL Amides
FDA CS	M0000897	Amides
MeSH PA	D000777	Anesthetics
MeSH PA	D000779	Anesthetics, Local
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D002492	Central Nervous System Depressants
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D018689	Sensory System Agents
CHEBI has role	CHEBI:36333	local anesthetics
FDA EPC	N0000175682	Amide Local Anesthetic
FDA PE	N0000175976	Local Anesthesia

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

Disease	Relation	SNOMED_ID	DOID
Anesthesia for cesarean section	indication	4847005
Local anesthesia	indication	386761002
Regional Anesthesia for Labor Pain	indication
Major Nerve Block for Surgery	indication
Regional Anesthesia for Postoperative Pain	indication
Regional Anesthesia for Surgery	indication
Alcoholism	contraindication	7200002
Chronic obstructive lung disease	contraindication	13645005	DOID:3083
Chronic disease of respiratory system	contraindication	17097001
Inflammatory bowel disease	contraindication	24526004	DOID:0050589
Decreased cardiac function	contraindication	43650005
Bradycardia	contraindication	48867003
Disorder of cardiovascular system	contraindication	49601007	DOID:1287
Paralytic ileus	contraindication	55525008	DOID:8442
Drug AND/OR toxin-induced diarrhea	contraindication	65979008
Substance abuse	contraindication	66214007
Benign intracranial hypertension	contraindication	68267002	DOID:11459
Urethral stricture	contraindication	76618002
Decreased respiratory function	contraindication	80954004
Injury of head	contraindication	82271004
Cor pulmonale	contraindication	83291003	DOID:8515
Kidney disease	contraindication	90708001	DOID:557
Myasthenia gravis	contraindication	91637004	DOID:437
Disorder of biliary tract	contraindication	105997008	DOID:9741
Procedure on urinary system	contraindication	118677009
Disease of liver	contraindication	235856003	DOID:409
Benign prostatic hyperplasia	contraindication	266569009
Lesion of brain	contraindication	301766008
Deficiency of cholinesterase	contraindication	360607009
Acute exacerbation of asthma	contraindication	708038006

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.24	acidic
pKa2	7.84	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])	Bioact source	MoA source
Sodium channel protein type 5 subunit alpha	Ion channel	Q14524	SCN5A_HUMAN	BLOCKER	IC50	4.56	IUPHAR	CHEMBL
Sodium channel protein type 1 subunit alpha	Ion channel	P35498	SCN1A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Sodium channel protein type 2 subunit alpha	Ion channel	Q99250	SCN2A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Sodium channel protein type 3 subunit alpha	Ion channel	Q9NY46	SCN3A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Sodium channel protein type 4 subunit alpha	Ion channel	P35499	SCN4A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Sodium channel protein type 8 subunit alpha	Ion channel	Q9UQD0	SCN8A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Sodium channel protein type 9 subunit alpha	Ion channel	Q15858	SCN9A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Sodium channel protein type 10 subunit alpha	Ion channel	Q9Y5Y9	SCNAA_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Potassium channel subfamily K member 3	Ion channel	O14649	KCNK3_HUMAN		IC50	4.28	CHEMBL

External reference:

ID	Source
4024055	VUID
N0000022060	NUI
D08490	KEGG_DRUG
132112-35-7	SECONDARY_CAS_RN
4021017	VANDF
4024055	VANDF
C0073571	UMLSCUI
CHEBI:8890	CHEBI
CHEMBL1077896	ChEMBL_ID
DB00296	DRUGBANK_ID
CHEMBL1889140	ChEMBL_ID
D000077212	MESH_DESCRIPTOR_UI
175805	PUBCHEM_CID
7602	IUPHAR_LIGAND_ID
5376	INN_ID
7IO5LYA57N	UNII
1298851	RXNORM
19197	MMSL
43154	MMSL
5435	MMSL
d04051	MMSL
006248	NDDF
006249	NDDF
109094008	SNOMEDCT_US
334196006	SNOMEDCT_US
386969005	SNOMEDCT_US
725651008	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9263	INJECTION	2 mg	EPIDURAL	ANDA	24 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9264	INJECTION	5 mg	EPIDURAL	ANDA	24 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9265	INJECTION	7.50 mg	EPIDURAL	ANDA	24 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9266	INJECTION	10 mg	EPIDURAL	ANDA	24 sections
NAROPIN	HUMAN PRESCRIPTION DRUG LABEL	1	0404-9924	INJECTION, SOLUTION	5 mg	INFILTRATION	NDA	12 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0409-9300	INJECTION, SOLUTION	2 mg	INFILTRATION	ANDA	12 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0409-9301	INJECTION, SOLUTION	5 mg	EPIDURAL	ANDA	12 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0409-9302	INJECTION, SOLUTION	7.50 mg	EPIDURAL	ANDA	12 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0409-9303	INJECTION, SOLUTION	10 mg	EPIDURAL	ANDA	12 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3140	INJECTION, SOLUTION	5 mg	PARENTERAL	ANDA	21 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3142	INJECTION, SOLUTION	10 mg	PARENTERAL	ANDA	21 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	17478-081	INJECTION, SOLUTION	5 mg	EPIDURAL	ANDA	25 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	17478-082	INJECTION, SOLUTION	2 mg	INFILTRATION	ANDA	24 sections
ropivacaine hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	25021-652	INJECTION, SOLUTION	5 mg	EPIDURAL	ANDA	25 sections
ropivacaine hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	25021-671	INJECTION, SOLUTION	2 mg	EPIDURAL	ANDA	26 sections
ropivacaine hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	25021-671	INJECTION, SOLUTION	2 mg	EPIDURAL	ANDA	26 sections
ROPIVACAINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	43066-015	INJECTION	2 mg	EPIDURAL	ANDA	23 sections
ROPIVACAINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	43066-019	INJECTION	5 mg	EPIDURAL	ANDA	23 sections
ROPIVACAINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	43066-023	INJECTION	5 mg	EPIDURAL	ANDA	23 sections
ROPIVACAINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	43066-027	INJECTION	10 mg	EPIDURAL	ANDA	23 sections
NAROPIN	HUMAN PRESCRIPTION DRUG LABEL	1	52584-286	INJECTION, SOLUTION	5 mg	INFILTRATION	NDA	12 sections
Ropivacaine Hydrochloride	Human Prescription Drug Label	1	55150-195	INJECTION, SOLUTION	2 mg	INFILTRATION	ANDA	20 sections
Ropivacaine Hydrochloride	Human Prescription Drug Label	1	55150-196	INJECTION, SOLUTION	2 mg	INFILTRATION	ANDA	20 sections
Ropivacaine Hydrochloride	Human Prescription Drug Label	1	55150-197	INJECTION, SOLUTION	5 mg	INFILTRATION	ANDA	20 sections
Ropivacaine Hydrochloride	Human Prescription Drug Label	1	55150-198	INJECTION, SOLUTION	5 mg	INFILTRATION	ANDA	20 sections
Ropivacaine Hydrochloride	Human Prescription Drug Label	1	55150-199	INJECTION, SOLUTION	7.50 mg	PERINEURAL	ANDA	20 sections
Ropivacaine Hydrochloride	Human Prescription Drug Label	1	55150-200	INJECTION, SOLUTION	10 mg	EPIDURAL	ANDA	20 sections
Ropivacaine Hydrochloride	Human Prescription Drug Label	1	55150-201	INJECTION, SOLUTION	10 mg	EPIDURAL	ANDA	20 sections
Naropin	HUMAN PRESCRIPTION DRUG LABEL	1	63323-285	INJECTION, SOLUTION	2 mg	EPIDURAL	NDA	17 sections
Naropin	HUMAN PRESCRIPTION DRUG LABEL	1	63323-285	INJECTION, SOLUTION	2 mg	EPIDURAL	NDA	17 sections