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

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
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:

PropertyValueReference
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 ┬ÁM/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:

DateAgencyCompanyOrphan
Sept. 24, 1996 FDA FRESENIUS KABI USA

FDA Adverse Event Reporting System (Female)

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
Monoplegia 208.40 73.38 34 755 570 2356726
Toxicity to various agents 207.01 73.38 71 718 32683 2324613
Anaesthetic complication 203.22 73.38 32 757 423 2356873
Seizure 189.92 73.38 62 727 24404 2332892
Cardiac arrest 170.87 73.38 51 738 14879 2342417
Generalised tonic-clonic seizure 144.30 73.38 36 753 5336 2351960
Peripheral nerve injury 116.28 73.38 16 773 74 2357222
Oliguria 113.25 73.38 23 766 1334 2355962
Cauda equina syndrome 108.87 73.38 16 773 127 2357169
Hypoaesthesia 100.96 73.38 37 752 20178 2337118
Hypotension 97.23 73.38 41 748 32395 2324901
Anaphylactic shock 82.16 73.38 22 767 4264 2353032
Haematuria 82.00 73.38 22 767 4296 2353000
Exposure during pregnancy 75.83 73.38 32 757 25187 2332109
Acute kidney injury 75.74 73.38 33 756 28089 2329207
Paraplegia 75.43 73.38 14 775 502 2356794
Horner's syndrome 74.96 73.38 11 778 86 2357210
Loss of consciousness 74.20 73.38 29 760 18738 2338558

FDA Adverse Event Reporting System (Male)

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
Cardiac arrest 108.82 69.54 36 408 15894 1730443
Anaesthetic complication 107.41 69.54 17 427 251 1746086
Generalised tonic-clonic seizure 90.15 69.54 23 421 4023 1742314
Spinal cord infarction 85.35 69.54 12 432 73 1746264
Bradycardia 80.55 69.54 26 418 10508 1735829

Pharmacologic Action:

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
CHEBI has role CHEBI:36333 local anaesthetic
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

Drug Use (View source of the data)

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: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

Acid dissociation constants calculated using MoKa v3.0.0

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:

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:

IDSource
D000077212 MESH_DESCRIPTOR_UI
4024055 VUID
N0000022060 NUI
C0073571 UMLSCUI
D08490 KEGG_DRUG
7IO5LYA57N UNII
5376 INN_ID
109094008 SNOMEDCT_US
4024055 VANDF
d04051 MMSL
5435 MMSL
35780 RXNORM
386969005 SNOMEDCT_US
006248 NDDF
CHEBI:60803 CHEBI
DB00296 DRUGBANK_ID
CHEMBL1077896 ChEMBL_ID
132112-35-7 SECONDARY_CAS_RN
175805 PUBCHEM_CID
CHEMBL1889140 ChEMBL_ID
7602 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 17478-082 INJECTION, SOLUTION 2 mg INFILTRATION ANDA 14 sections
ropivacaine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-652 INJECTION, SOLUTION 5 mg EPIDURAL ANDA 13 sections
ropivacaine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-671 INJECTION, SOLUTION 2 mg EPIDURAL 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 EPIDURAL 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 12 sections
Naropin HUMAN PRESCRIPTION DRUG LABEL 1 63323-288 INJECTION, SOLUTION 10 mg EPIDURAL NDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65145-107 INJECTION 2 mg EPIDURAL ANDA 11 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65145-108 INJECTION 5 mg EPIDURAL ANDA 11 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65145-109 INJECTION 5 mg EPIDURAL ANDA 11 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65145-110 INJECTION 10 mg EPIDURAL ANDA 11 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-875 INJECTION, SOLUTION 40 mg INFILTRATION ANDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-876 INJECTION, SOLUTION 150 mg INFILTRATION ANDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-877 INJECTION, SOLUTION 200 mg EPIDURAL ANDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-878 INJECTION, SOLUTION 150 mg EPIDURAL ANDA 13 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70069-061 INJECTION 2 mg EPIDURAL ANDA 12 sections