ropivacaine indications/contra

Stem definitionDrug idCAS RN
local anaesthetics 2403 84057-95-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ropivacaine
  • (-)-Ropivacaine
  • anapeine
  • naropeine
  • naropine
  • S-Ropivacaine
  • ropivacaine hydrochloride monohydrate
  • ropivacaine hydrochloride
  • ropivacaine HCl
amide local anesthetic with characteristics similar to bupivacaine; from Apothekernes Laboratorium, Oslo, Norway; RN given refers to (S)-isomer; RN for parent cpd without isomeric designation not available 2/89
  • Molecular weight: 274.41
  • Formula: C17H26N2O
  • CLOGP: 3.16
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 32.34
  • ALOGS: -3.04
  • ROTB: 4

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
Sept. 24, 1996 FDA FRESENIUS KABI USA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 265.96 67.19 99 1179 46955 3337626
Anaesthetic complication 260.61 67.19 44 1234 741 3383840
Seizure 257.79 67.19 93 1185 40307 3344274
Cardiac arrest 248.27 67.19 82 1196 27237 3357344
Generalised tonic-clonic seizure 230.21 67.19 59 1219 7983 3376598
Monoplegia 227.98 67.19 40 1238 851 3383730
Horner's syndrome 161.08 67.19 23 1255 115 3384466
Cauda equina syndrome 154.77 67.19 24 1254 227 3384354
Hypotension 150.53 67.19 67 1211 49447 3335134
Post procedural complication 134.48 67.19 35 1243 4982 3379599
Anaphylactic shock 129.82 67.19 35 1243 5704 3378877
Bradycardia 123.15 67.19 43 1235 16626 3367955
Delayed recovery from anaesthesia 113.74 67.19 19 1259 296 3384285
Spinal cord infarction 110.95 67.19 17 1261 147 3384434
Respiratory depression 108.78 67.19 28 1250 3806 3380775
Oliguria 103.32 67.19 24 1254 2126 3382455
Loss of consciousness 94.63 67.19 41 1237 28106 3356475
Hypoaesthesia 89.31 67.19 38 1240 24901 3359680
Drug ineffective 87.62 67.19 63 1215 116027 3268554
Peripheral nerve injury 87.01 67.19 13 1265 93 3384488
Depressed level of consciousness 78.53 67.19 28 1250 11437 3373144
Neurotoxicity 73.23 67.19 20 1258 3401 3381180
Exposure during pregnancy 72.96 67.19 34 1244 27529 3357052
Incorrect route of drug administration 72.59 67.19 25 1253 9218 3375363
Paraplegia 71.31 67.19 15 1263 838 3383743

Pharmacologic Action:

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SourceCodeDescription
ATC N01BB09 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
FDA EPC N0000175682 Amide Local Anesthetic
FDA Chemical/Ingredient N0000007681 Amides
FDA PE N0000175976 Local Anesthesia
MeSH PA D000777 Anesthetics
MeSH PA D000779 Anesthetics, Local
CHEBI has role CHEBI:36333 local anaesthetic
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

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
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:2527
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 DOID:2883
Lesion of brain contraindication 301766008
Deficiency of cholinesterase contraindication 360607009
Acute exacerbation of asthma contraindication 708038006

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (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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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 10 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 9 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 8 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 4 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 3 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 2 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 1 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER IC50 4.56 IUPHAR CHEMBL

External reference:

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IDSource
DB00296 DRUGBANK_ID
4024055 VUID
N0000022060 NUI
C0073571 UMLSCUI
7602 IUPHAR_LIGAND_ID
D08490 KEGG_DRUG
7IO5LYA57N UNII
5376 INN_ID
175805 PUBCHEM_CID
4024055 VANDF
N0000006648 NDFRT
N0000022060 NDFRT
d04051 MMSL
5435 MMSL
35780 RXNORM
109094008 SNOMEDCT_US
386969005 SNOMEDCT_US
006248 NDDF
CHEBI:60803 CHEBI
CHEMBL1077896 ChEMBL_ID
CHEMBL1889140 ChEMBL_ID
132112-35-7 SECONDARY_CAS_RN
C037663 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
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 0781-3142 INJECTION, SOLUTION 10 mg PARENTERAL ANDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 17478-081 INJECTION, SOLUTION 5 mg EPIDURAL ANDA 14 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-652 INJECTION, SOLUTION 5 mg INFILTRATION ANDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-653 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-654 INJECTION, SOLUTION 7.50 mg EPIDURAL ANDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-671 INJECTION, SOLUTION 2 mg INFILTRATION ANDA 13 sections
NAROPIN HUMAN PRESCRIPTION DRUG LABEL 1 52584-286 INJECTION, SOLUTION 5 mg INFILTRATION NDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-195 INJECTION, SOLUTION 2 mg INFILTRATION ANDA 12 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-196 INJECTION, SOLUTION 2 mg INFILTRATION ANDA 12 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-197 INJECTION, SOLUTION 5 mg INFILTRATION ANDA 12 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-198 INJECTION, SOLUTION 5 mg INFILTRATION ANDA 12 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-199 INJECTION, SOLUTION 7.50 mg PERINEURAL ANDA 12 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-200 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 12 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-201 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 12 sections
Naropin HUMAN PRESCRIPTION DRUG LABEL 1 63323-285 INJECTION, SOLUTION 2 mg INFILTRATION NDA 13 sections
NAROPIN HUMAN PRESCRIPTION DRUG LABEL 1 63323-286 INJECTION, SOLUTION 5 mg EPIDURAL NDA 13 sections
Naropin HUMAN PRESCRIPTION DRUG LABEL 1 63323-287 INJECTION, SOLUTION 7.50 mg PERINEURAL NDA 13 sections
Naropin HUMAN PRESCRIPTION DRUG LABEL 1 63323-288 INJECTION, SOLUTION 10 mg EPIDURAL NDA 13 sections