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
Anaesthetic complication 162.99 33.24 36 3674 1781 46680571
Monoplegia 145.87 33.24 35 3675 2501 46679851
Peripheral nerve injury 123.27 33.24 22 3688 355 46681997
Cauda equina syndrome 116.94 33.24 23 3687 640 46681712
Cardiac arrest 92.53 33.24 68 3642 90331 46592021
Generalised tonic-clonic seizure 91.11 33.24 44 3666 27078 46655274
Anaphylactic shock 90.29 33.24 40 3670 20234 46662118
Maternal exposure during pregnancy 89.21 33.24 70 3640 102479 46579873
Toxicity to various agents 87.09 33.24 95 3615 211671 46470681
Exposure during pregnancy 81.69 33.24 68 3642 108144 46574208
Myoclonus 79.32 33.24 33 3677 14319 46668033
Seizure 78.05 33.24 70 3640 122984 46559368
Maternal exposure during delivery 77.78 33.24 17 3693 799 46681553
Paraplegia 68.71 33.24 19 3691 2375 46679977
Hypotension 63.78 33.24 85 3625 232504 46449848
Neurotoxicity 57.64 33.24 26 3684 13691 46668661
Respiratory depression 55.22 33.24 24 3686 11576 46670776
Oliguria 54.73 33.24 22 3688 8737 46673615
Spinal epidural haemorrhage 53.45 33.24 9 3701 101 46682251
Vitamin K deficiency 51.73 33.24 11 3699 453 46681899
Incorrect route of product administration 50.25 33.24 25 3685 16358 46665994
Circulatory collapse 49.18 33.24 27 3683 21597 46660755
Hypoaesthesia 44.68 33.24 51 3659 118818 46563534
Delayed recovery from anaesthesia 39.93 33.24 10 3700 851 46681501
Foetal heart rate abnormal 38.95 33.24 9 3701 544 46681808
Epidural haemorrhage 38.81 33.24 7 3703 120 46682232
Caesarean section 38.49 33.24 21 3689 16582 46665770
Diaphragmatic paralysis 38.47 33.24 9 3701 575 46681777
Fatigue 37.31 33.24 3 3707 608694 46073658
Bradycardia 36.66 33.24 35 3675 66263 46616089
Anterior spinal artery syndrome 36.45 33.24 6 3704 58 46682294
Motor dysfunction 34.43 33.24 15 3695 7267 46675085
Haematuria 33.87 33.24 23 3687 26835 46655517

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
Anaesthetic complication 106.93 29.27 23 2265 1046 29949144
Cardiac arrest 91.34 29.27 67 2221 92783 29857407
Delayed recovery from anaesthesia 86.59 29.27 18 2270 693 29949497
Negative pressure pulmonary oedema 80.09 29.27 14 2274 208 29949982
Anaphylactic shock 67.96 29.27 29 2259 13964 29936226
Spinal cord infarction 66.47 29.27 12 2276 216 29949974
Local anaesthetic systemic toxicity 56.33 29.27 10 2278 163 29950027
Generalised tonic-clonic seizure 55.72 29.27 28 2260 19523 29930667
Phrenic nerve paralysis 54.49 29.27 9 2279 93 29950097
Ventricular fibrillation 50.06 29.27 24 2264 15114 29935076
Patent ductus arteriosus 43.09 29.27 14 2274 3155 29947035
Cauda equina syndrome 42.26 29.27 9 2279 389 29949801
Respiratory depression 40.35 29.27 19 2269 11484 29938706
Stress cardiomyopathy 39.00 29.27 11 2277 1538 29948652
Bradycardia 38.27 29.27 35 2253 65491 29884699
Arteriospasm coronary 37.36 29.27 12 2276 2606 29947584
Infantile apnoea 35.07 29.27 9 2279 880 29949310
Foetal exposure during pregnancy 34.72 29.27 26 2262 36845 29913345
Incorrect route of product administration 34.57 29.27 17 2271 11298 29938892
Seizure 32.92 29.27 39 2249 98436 29851754
Hyperthermia malignant 32.84 29.27 10 2278 1824 29948366
Recurrence of neuromuscular blockade 32.68 29.27 6 2282 119 29950071
Post procedural complication 31.07 29.27 16 2272 11710 29938480
Respiratory arrest 30.63 29.27 22 2266 29236 29920954
Neonatal respiratory distress 29.99 29.27 7 2281 461 29949729

Pharmacologic Action:

SourceCodeDescription
ATC N01BB09 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
FDA CS M0000897 Amides
FDA EPC N0000175682 Amide Local Anesthetic
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 PE N0000175976 Local Anesthesia

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
4024055 VUID
N0000022060 NUI
D08490 KEGG_DRUG
132112-35-7 SECONDARY_CAS_RN
4021017 VANDF
4024055 VANDF
C4704727 UMLSCUI
CHEBI:8890 CHEBI
CHEMBL1077896 ChEMBL_ID
CHEMBL1889140 ChEMBL_ID
D000077212 MESH_DESCRIPTOR_UI
7602 IUPHAR_LIGAND_ID
5376 INN_ID
DB00296 DRUGBANK_ID
7IO5LYA57N UNII
175805 PUBCHEM_CID
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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
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
NULLROPIN 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 21 sections
Ropivacaine Hydrochloride Human Prescription Drug Label 1 55150-196 INJECTION, SOLUTION 2 mg INFILTRATION ANDA 21 sections
Ropivacaine Hydrochloride Human Prescription Drug Label 1 55150-197 INJECTION, SOLUTION 5 mg INFILTRATION ANDA 21 sections
Ropivacaine Hydrochloride Human Prescription Drug Label 1 55150-198 INJECTION, SOLUTION 5 mg INFILTRATION ANDA 21 sections
Ropivacaine Hydrochloride Human Prescription Drug Label 1 55150-199 INJECTION, SOLUTION 7.50 mg PERINEURAL ANDA 21 sections
Ropivacaine Hydrochloride Human Prescription Drug Label 1 55150-200 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 21 sections
Ropivacaine Hydrochloride Human Prescription Drug Label 1 55150-201 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 21 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
Naropin HUMAN PRESCRIPTION DRUG LABEL 1 63323-285 INJECTION, SOLUTION 2 mg EPIDURAL NDA 17 sections