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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:

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

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Approvals:

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

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
Maternal exposure during delivery	179.35	36.06	36	3838	1464	63483684
Anaesthetic complication	158.37	36.06	34	3840	1926	63483222
Anaphylactic shock	129.05	36.06	50	3824	23583	63461565
Peripheral nerve injury	118.47	36.06	21	3853	430	63484718
Generalised tonic-clonic seizure	115.77	36.06	49	3825	28967	63456181
Cauda equina syndrome	113.52	36.06	23	3851	979	63484169
Exposure during pregnancy	100.67	36.06	80	3794	155467	63329681
Cardiac arrest	92.61	36.06	62	3812	92483	63392665
Hypotension	89.74	36.06	96	3778	272508	63212640
Maternal exposure during pregnancy	87.82	36.06	86	3788	219976	63265172

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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
Anaphylactic shock	113.79	34.94	42	2292	15899	34938698
Anaesthetic complication	103.23	34.94	22	2312	1098	34953499
Negative pressure pulmonary oedema	81.29	34.94	14	2320	219	34954378
Cardiac arrest	78.89	34.94	59	2275	96100	34858497
Local anaesthetic systemic toxicity	64.40	34.94	12	2322	298	34954299
Urethral valves	58.96	34.94	11	2323	275	34954322
Delayed recovery from anaesthesia	58.50	34.94	13	2321	788	34953809
Respiratory depression	51.52	34.94	24	2310	16221	34938376
Incorrect route of product administration	47.28	34.94	22	2312	14823	34939774
Phrenic nerve paralysis	47.01	34.94	8	2326	116	34954481

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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
Anaesthetic complication	227.58	27.28	51	6037	2808	79735492
Anaphylactic shock	223.88	27.28	89	5999	35907	79702393
Maternal exposure during delivery	169.28	27.28	35	6053	1311	79736989
Cardiac arrest	157.29	27.28	119	5969	171977	79566323
Local anaesthetic systemic toxicity	136.00	27.28	28	6060	1026	79737274
Generalised tonic-clonic seizure	131.37	27.28	65	6023	43845	79694455
Cauda equina syndrome	122.47	27.28	27	6061	1376	79736924
Phrenic nerve paralysis	106.32	27.28	19	6069	322	79737978
Maternal exposure during pregnancy	93.86	27.28	80	6008	136458	79601842
Hypotension	89.99	27.28	137	5951	440180	79298120

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N01BB09	NERVOUS SYSTEM ANESTHETICS ANESTHETICS, LOCAL Amides
CHEBI has role	CHEBI:36333	local anesthetics
FDA CS	M0000897	Amides
FDA EPC	N0000175682	Amide Local Anesthetic
FDA PE	N0000175976	Local Anesthesia
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

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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
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

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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	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:

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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

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External reference:

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ID	Source
006248	NDDF
006249	NDDF
109094008	SNOMEDCT_US
1298851	RXNORM
132112-35-7	SECONDARY_CAS_RN
175805	PUBCHEM_CID
19197	MMSL
334196006	SNOMEDCT_US
386969005	SNOMEDCT_US
4021017	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
NAROPIN	HUMAN PRESCRIPTION DRUG LABEL	1	0404-9924	INJECTION, SOLUTION	5 mg	INFILTRATION	NDA	12 sections
NAROPIN	HUMAN PRESCRIPTION DRUG LABEL	1	0404-9924	INJECTION, SOLUTION	5 mg	INFILTRATION	NDA	12 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9263	INJECTION	2 mg	EPIDURAL	ANDA	30 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9263	INJECTION	2 mg	EPIDURAL	ANDA	30 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9263	INJECTION	2 mg	EPIDURAL	ANDA	30 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9264	INJECTION	5 mg	EPIDURAL	ANDA	30 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9264	INJECTION	5 mg	EPIDURAL	ANDA	30 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9264	INJECTION	5 mg	EPIDURAL	ANDA	30 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9265	INJECTION	7.50 mg	EPIDURAL	ANDA	30 sections
Ropivacaine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9265	INJECTION	7.50 mg	EPIDURAL	ANDA	30 sections

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