ropivacaine ๐Ÿถ Veterinary Use | 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 ยตM/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
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
Myoclonus 84.55 36.06 33 3841 15835 63469313
Local anaesthetic systemic toxicity 80.61 36.06 17 3857 882 63484266
Neurotoxicity 75.49 36.06 31 3843 16959 63468189
Toxicity to various agents 70.78 36.06 81 3793 247169 63237979
Phrenic nerve paralysis 64.09 36.06 11 3863 185 63484963
Tracheal deviation 59.22 36.06 10 3864 152 63484996
Seizure 58.78 36.06 55 3819 132579 63352569
Motor dysfunction 55.97 36.06 22 3852 10739 63474409
Spinal epidural haemorrhage 55.83 36.06 9 3865 101 63485047
Monoplegia 54.72 36.06 16 3858 3185 63481963
Respiratory depression 54.11 36.06 23 3851 13692 63471456
Vitamin K deficiency 49.24 36.06 10 3864 430 63484718
Nerve block 48.91 36.06 11 3863 771 63484377
Oliguria 48.72 36.06 19 3855 9082 63476066
Paraplegia 48.53 36.06 14 3860 2658 63482490
Premature delivery 47.34 36.06 27 3847 30254 63454894
Caesarean section 43.22 36.06 21 3853 17011 63468137
Hypoaesthesia 42.82 36.06 52 3822 168341 63316807
Anaesthetic complication neurological 41.69 36.06 8 3866 256 63484892
Epidural haemorrhage 40.66 36.06 7 3867 120 63485028
Anaphylactic reaction 40.51 36.06 33 3841 66067 63419081
Myelitis transverse 38.77 36.06 10 3864 1250 63483898
Brain stem syndrome 37.79 36.06 8 3866 422 63484726
Apnoea 36.85 36.06 15 3859 8007 63477141

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
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
Bradycardia 46.12 34.94 39 2295 75379 34879218
Spinal cord infarction 45.92 34.94 9 2325 294 34954303
Hyperthermia malignant 45.60 34.94 13 2321 2164 34952433
Stress cardiomyopathy 41.80 34.94 12 2322 2047 34952550
Neuromuscular block prolonged 41.41 34.94 9 2325 492 34954105
Recurrence of neuromuscular blockade 36.03 34.94 7 2327 218 34954379

FDA Adverse Event Reporting System (Geriatric)

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 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
Respiratory depression 88.88 27.28 43 6045 27587 79710713
Exposure during pregnancy 87.96 27.28 68 6020 101064 79637236
Neurotoxicity 79.40 27.28 42 6046 32476 79705824
Negative pressure pulmonary oedema 79.09 27.28 14 6074 224 79738076
Myoclonus 76.95 27.28 39 6049 27621 79710679
Monoplegia 76.91 27.28 23 6065 3948 79734352
Incorrect route of product administration 76.58 27.28 42 6046 34887 79703413
Peripheral nerve injury 74.99 27.28 16 6072 698 79737602
Anaphylactic reaction 74.31 27.28 57 6031 83686 79654614
Seizure 73.60 27.28 81 6007 188753 79549547
Bradycardia 68.76 27.28 67 6021 135490 79602810
Paraplegia 67.38 27.28 22 6066 5031 79733269
Ventricular fibrillation 66.18 27.28 37 6051 31889 79706411
Stress cardiomyopathy 63.77 27.28 26 6062 11140 79727160
Delayed recovery from anaesthesia 61.44 27.28 16 6072 1657 79736643
Motor dysfunction 59.99 27.28 27 6061 14706 79723594
Spinal cord paralysis 58.01 27.28 10 6078 136 79738164
Toxicity to various agents 56.65 27.28 109 5979 421431 79316869
Tracheal deviation 55.87 27.28 10 6078 171 79738129
Tachycardia 55.40 27.28 68 6020 177700 79560600
Circulatory collapse 48.05 27.28 32 6056 37636 79700664
Tonic clonic movements 47.71 27.28 14 6074 2250 79736050
Nerve block 47.46 27.28 11 6077 702 79737598
Diarrhoea 47.03 27.28 6 6082 880483 78857817
Product packaging confusion 46.18 27.28 9 6079 248 79738052
Hyperaesthesia 45.36 27.28 21 6067 12201 79726099
Paraparesis 44.48 27.28 15 6073 3788 79734512
Spinal epidural haemorrhage 44.20 27.28 8 6080 146 79738154
Respiratory arrest 44.20 27.28 36 6052 57514 79680786
Premature delivery 42.73 27.28 25 6063 23442 79714858
Hypoaesthesia 42.52 27.28 60 6028 179292 79559008
Vitamin K deficiency 41.99 27.28 10 6078 718 79737582
Caesarean section 41.78 27.28 20 6068 12515 79725785
Epidural haemorrhage 41.14 27.28 8 6080 218 79738082
Paralysis 40.83 27.28 20 6068 13157 79725143
Hyperthermia malignant 40.11 27.28 13 6075 2904 79735396
Fatigue 39.77 27.28 11 6077 929716 78808584
Type I hypersensitivity 38.58 27.28 14 6074 4384 79733916
Neuromuscular block prolonged 38.54 27.28 10 6078 1020 79737280
Spinal cord infarction 38.24 27.28 9 6079 614 79737686
Wrong product administered 38.23 27.28 17 6071 8995 79729305
Diplegia 37.34 27.28 11 6077 1792 79736508
Apnoea 36.97 27.28 18 6070 11686 79726614
Foetal heart rate abnormal 36.91 27.28 8 6080 376 79737924
Spinal anaesthesia 35.90 27.28 6 6082 67 79738233
Altered state of consciousness 34.88 27.28 28 6060 43794 79694506
Uterine hypotonus 34.64 27.28 6 6082 84 79738216
Diaphragmatic paralysis 33.06 27.28 9 6079 1103 79737197
Anaesthetic complication neurological 32.79 27.28 8 6080 636 79737664
Loss of consciousness 32.36 27.28 51 6037 167892 79570408
Myelitis transverse 32.25 27.28 10 6078 1937 79736363
Post procedural complication 32.22 27.28 21 6067 23808 79714492
Anterior spinal artery syndrome 31.91 27.28 6 6082 136 79738164
Oliguria 31.35 27.28 18 6070 16291 79722009
Epidural analgesia 30.42 27.28 5 6083 50 79738250
Oxygen saturation decreased 30.30 27.28 43 6045 129004 79609296
Product administration error 28.92 27.28 22 6066 31824 79706476
Tachypnoea 28.79 27.28 22 6066 32041 79706259
Arthralgia 27.94 27.28 5 6083 571798 79166502
Nervous system disorder 27.63 27.28 20 6068 26836 79711464

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
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|

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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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 5 subunit alpha Ion channel BLOCKER IC50 4.56 IUPHAR CHEMBL
Sodium channel protein type 1 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 3 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 8 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 10 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Potassium channel subfamily K member 3 Ion channel IC50 4.28 CHEMBL

External reference:

IDSource
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9265 INJECTION 7.50 mg EPIDURAL ANDA 30 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9266 INJECTION 10 mg EPIDURAL ANDA 30 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9266 INJECTION 10 mg EPIDURAL ANDA 30 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9266 INJECTION 10 mg EPIDURAL ANDA 30 sections
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 0409-9300 INJECTION, SOLUTION 2 mg INFILTRATION ANDA 28 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-9300 INJECTION, SOLUTION 2 mg INFILTRATION ANDA 28 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-9301 INJECTION, SOLUTION 5 mg EPIDURAL ANDA 28 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-9301 INJECTION, SOLUTION 5 mg EPIDURAL ANDA 28 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-9302 INJECTION, SOLUTION 7.50 mg EPIDURAL ANDA 28 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-9302 INJECTION, SOLUTION 7.50 mg EPIDURAL ANDA 28 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-9303 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 28 sections
Ropivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-9303 INJECTION, SOLUTION 10 mg EPIDURAL ANDA 28 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 17478-081 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 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 34 sections
ropivacaine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-652 INJECTION, SOLUTION 5 mg EPIDURAL ANDA 34 sections