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

Stem definitionDrug idCAS RN
local anaesthetics 432 38396-39-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • bupivacaine hydrochloride anhydrous
  • bupivacaine
  • (+/-)-Bupivacaine
  • bucain
  • bupivan
  • carbostesin
  • DL-Bupivacaine
  • bupivacaine hydrochloride
  • bupivacaine HCl
A widely used local anesthetic agent.
  • Molecular weight: 288.44
  • Formula: C18H28N2O
  • CLOGP: 3.69
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 32.34
  • ALOGS: -3.47
  • ROTB: 5

  • 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) 0.17 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 13.00 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.84 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 4.30 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) 3.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 3, 1972 FDA HOSPIRA

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 1342.87 19.34 258 13285 1559 46670960
Exposure during pregnancy 558.61 19.34 362 13181 107850 46564669
Maternal exposure during delivery 517.34 19.34 102 13441 714 46671805
Drug ineffective 437.69 19.34 732 12811 677106 45995413
Hypotension 362.05 19.34 388 13155 232201 46440318
Chondrolysis 243.92 19.34 44 13499 175 46672344
Maternal exposure during pregnancy 237.29 19.34 213 13330 102336 46570183
Cauda equina syndrome 195.30 19.34 44 13499 619 46671900
Incorrect route of product administration 165.13 19.34 85 13458 16298 46656221
Bradycardia 147.80 19.34 135 13408 66163 46606356
Local anaesthetic systemic toxicity 138.49 19.34 30 13513 348 46672171
Drug withdrawal syndrome 127.02 19.34 86 13457 27298 46645221
Procedural hypotension 122.11 19.34 34 13509 1168 46671351
Wrong product administered 112.61 19.34 47 13496 5583 46666936
Unresponsive to stimuli 101.39 19.34 80 13463 32094 46640425
Respiratory depression 99.34 19.34 54 13489 11546 46660973
Extradural haematoma 99.03 19.34 30 13513 1393 46671126
Caesarean section 98.80 19.34 61 13482 16542 46655977
Implant site extravasation 97.84 19.34 24 13519 496 46672023
Lagophthalmos 94.66 19.34 21 13522 274 46672245
Paralysis 81.41 19.34 43 13500 8678 46663841
Diarrhoea 80.65 19.34 31 13512 559571 46112948
Paraplegia 79.95 19.34 29 13514 2365 46670154
Fatigue 77.88 19.34 40 13503 608657 46063862
Hyperaesthesia 76.94 19.34 40 13503 7816 46664703
Hypoaesthesia 76.01 19.34 129 13414 118740 46553779
Sedation 72.24 19.34 57 13486 22853 46649666
Normal newborn 68.83 19.34 34 13509 5967 46666552
Cardiac arrest 68.52 19.34 106 13437 90293 46582226
Medical device site pain 66.37 19.34 15 13528 214 46672305
Myoclonus 66.34 19.34 45 13498 14307 46658212
Inadequate analgesia 64.74 19.34 26 13517 2798 46669721
Sensory loss 61.51 19.34 33 13510 6869 46665650
Arachnoiditis 60.47 19.34 15 13528 325 46672194
Parophthalmia 59.27 19.34 14 13529 245 46672274
Generalised tonic-clonic seizure 57.96 19.34 54 13489 27068 46645451
Blood pressure decreased 57.95 19.34 77 13466 57082 46615437
Meningitis chemical 57.01 19.34 12 13531 120 46672399
Conjunctival oedema 56.92 19.34 16 13527 569 46671950
Procedural complication 56.74 19.34 28 13515 4902 46667617
Spinal anaesthesia 56.00 19.34 10 13533 37 46672482
Anaphylactic reaction 53.00 19.34 71 13472 53041 46619478
Anaphylactic shock 52.51 19.34 45 13498 20229 46652290
Spinal cord infarction 52.35 19.34 13 13530 283 46672236
Post lumbar puncture syndrome 52.25 19.34 15 13528 576 46671943
Rheumatoid arthritis 51.67 19.34 5 13538 240210 46432309
Therapeutic product effect prolonged 50.45 19.34 13 13530 330 46672189
Hypertensive encephalopathy 50.37 19.34 15 13528 656 46671863
Post procedural complication 49.29 19.34 39 13504 15690 46656829
Pneumonia 49.08 19.34 24 13519 376296 46296223
Hypothermia 48.82 19.34 35 13508 12148 46660371
Procedural pain 48.59 19.34 36 13507 13143 46659376
Vascular resistance systemic decreased 47.24 19.34 10 13533 103 46672416
Anterior spinal artery syndrome 46.68 19.34 9 13534 55 46672464
Platelet aggregation inhibition 46.32 19.34 10 13533 114 46672405
Apnoea 46.30 19.34 28 13515 7311 46665208
Mental status changes postoperative 45.97 19.34 11 13532 204 46672315
Horner's syndrome 45.84 19.34 8 13535 25 46672494
Therapy non-responder 45.70 19.34 58 13485 41094 46631425
Seizure 45.25 19.34 106 13437 122948 46549571
Neurotoxicity 45.12 19.34 35 13508 13682 46658837
Spinal cord injury 44.19 19.34 13 13530 545 46671974
Postpartum haemorrhage 42.77 19.34 17 13526 1780 46670739
Delayed recovery from anaesthesia 42.63 19.34 14 13529 847 46671672
Exophthalmos 42.49 19.34 15 13528 1130 46671389
Pulseless electrical activity 41.78 19.34 26 13517 7141 46665378
Therapeutic product effect delayed 41.72 19.34 17 13526 1898 46670621
Neuromuscular blockade 41.49 19.34 11 13532 313 46672206
Intracranial hypotension 41.32 19.34 11 13532 318 46672201
Spinal cord oedema 40.32 19.34 9 13534 121 46672398
Diplegia 39.82 19.34 14 13529 1042 46671477
Cerebrospinal fluid leakage 38.61 19.34 13 13530 850 46671669
Ophthalmoplegia 38.27 19.34 13 13530 873 46671646
Uterine atony 38.18 19.34 9 13534 156 46672363
Depressed level of consciousness 37.72 19.34 57 13486 47512 46625007
Product quality issue 37.63 19.34 49 13494 35599 46636920
Muscular weakness 36.94 19.34 82 13461 91762 46580757
Motor dysfunction 36.46 19.34 24 13519 7258 46665261
Device infusion issue 35.53 19.34 13 13530 1086 46671433
Overdose 35.48 19.34 86 13457 101893 46570626
Confusion postoperative 35.17 19.34 9 13534 222 46672297
Peripartum cardiomyopathy 35.08 19.34 8 13535 119 46672400
Pain 34.36 19.34 246 13297 476702 46195817
Rash 34.07 19.34 32 13511 356480 46316039
Spinal cord compression 33.91 19.34 18 13525 3666 46668853
Live birth 33.19 19.34 26 13517 10304 46662215
Haemodynamic instability 32.82 19.34 23 13520 7702 46664817
Premature delivery 32.60 19.34 36 13507 22033 46650486
Loss of consciousness 32.16 19.34 86 13457 108152 46564367
Labelled drug-drug interaction medication error 31.73 19.34 24 13519 9037 46663482
Neuromuscular block prolonged 31.62 19.34 10 13533 536 46671983
Complication associated with device 31.56 19.34 30 13513 15411 46657108
Nasopharyngitis 31.08 19.34 4 13539 153994 46518525
Death 31.03 19.34 31 13512 335517 46337002
Bradycardia foetal 30.83 19.34 9 13534 367 46672152
Acute kidney injury 30.76 19.34 15 13528 235840 46436679
Nerve block 29.51 19.34 9 13534 427 46672092
Product measured potency issue 29.45 19.34 7 13536 126 46672393
Product closure issue 29.33 19.34 5 13538 13 46672506
Urinary tract infection 28.73 19.34 14 13529 220252 46452267
Arteriospasm coronary 28.63 19.34 16 13527 3605 46668914
No adverse event 28.54 19.34 42 13501 34189 46638330
Cancer pain 28.45 19.34 14 13529 2436 46670083
Product dose omission issue 28.35 19.34 7 13536 168513 46504006
Cough 28.02 19.34 16 13527 230233 46442286
Stridor 27.91 19.34 15 13528 3132 46669387
Uterine hypertonus 27.91 19.34 7 13536 159 46672360
Rhythm idioventricular 27.86 19.34 7 13536 160 46672359
Ventricular tachycardia 27.38 19.34 29 13514 16938 46655581
Kounis syndrome 27.32 19.34 11 13532 1191 46671328
Pyrexia 27.11 19.34 37 13506 348765 46323754
Infusion site mass 26.53 19.34 10 13533 908 46671611
Implant site infection 26.39 19.34 10 13533 921 46671598
Radiculopathy 26.35 19.34 17 13526 4968 46667551
Neutropenia 26.01 19.34 5 13538 143199 46529320
Device alarm issue 25.78 19.34 11 13532 1379 46671140
Product formulation issue 25.64 19.34 9 13534 667 46671852
Sensorimotor disorder 25.56 19.34 8 13535 414 46672105
Tachycardia 25.50 19.34 75 13468 99547 46572972
Medical device site erythema 25.47 19.34 5 13538 34 46672485
Blood pressure systolic decreased 25.35 19.34 17 13526 5301 46667218
Myelitis transverse 25.23 19.34 10 13533 1039 46671480
Alopecia 24.99 19.34 8 13535 162406 46510113
Anaemia 24.36 19.34 23 13520 255756 46416763
Myopathy toxic 24.28 19.34 7 13536 273 46672246
Obstetric procedure complication 24.19 19.34 4 13539 8 46672511
Abdominal discomfort 24.06 19.34 7 13536 151158 46521361
Cardiac output increased 23.89 19.34 6 13537 137 46672382
Device failure 23.60 19.34 17 13526 5942 46666577
Allodynia 23.41 19.34 8 13535 547 46671972
Chondromalacia 23.36 19.34 7 13536 313 46672206
Arthralgia 23.32 19.34 44 13499 364559 46307960
Mean arterial pressure decreased 23.22 19.34 6 13537 154 46672365
Joint swelling 22.51 19.34 10 13533 166063 46506456
Anaesthetic complication cardiac 21.96 19.34 4 13539 17 46672502
Anaesthetic complication neurological 21.89 19.34 6 13537 194 46672325
Device malfunction 21.83 19.34 23 13520 13351 46659168
Circulatory collapse 21.69 19.34 29 13514 21595 46650924
Incision site pain 21.64 19.34 9 13534 1058 46671461
Trigeminal palsy 21.42 19.34 4 13539 20 46672499
General physical health deterioration 21.10 19.34 4 13539 115765 46556754
Muscle spasticity 21.08 19.34 21 13522 11419 46661100
Vocal cord paralysis 20.89 19.34 10 13533 1638 46670881
Arthrofibrosis 20.53 19.34 4 13539 26 46672493
Blood pressure immeasurable 20.43 19.34 9 13534 1218 46671301
Neurogenic shock 20.43 19.34 6 13537 250 46672269
Maternal drugs affecting foetus 20.17 19.34 15 13528 5503 46667016
Phrenic nerve paralysis 20.15 19.34 4 13539 29 46672490
Respiratory rate decreased 19.96 19.34 12 13531 3098 46669421
Fall 19.92 19.34 41 13502 329056 46343463
Atrioventricular block complete 19.89 19.34 17 13526 7610 46664909
Sensory disturbance 19.85 19.34 21 13522 12246 46660273
Heart rate decreased 19.66 19.34 34 13509 31689 46640830
Hypoxia 19.40 19.34 45 13498 51793 46620726
Respiratory arrest 19.35 19.34 35 13508 33781 46638738

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 589.99 21.41 115 6969 954 29944440
Chondrolysis 251.88 21.41 40 7044 75 29945319
Local anaesthetic systemic toxicity 168.03 21.41 30 7054 143 29945251
Pain 136.84 21.41 185 6899 172456 29772938
Drug withdrawal syndrome 127.00 21.41 71 7013 19738 29925656
Drug ineffective 114.70 21.41 249 6835 340138 29605256
Cauda equina syndrome 103.60 21.41 23 7061 375 29945019
Hypoaesthesia 81.44 21.41 81 7003 54149 29891245
Lagophthalmos 69.86 21.41 13 7071 81 29945313
Incorrect route of product administration 62.94 21.41 37 7047 11278 29934116
Paralysis 54.43 21.41 27 7057 5874 29939520
Hyperaesthesia 53.87 21.41 23 7061 3550 29941844
Cardiotoxicity 52.32 21.41 24 7060 4390 29941004
Medical device site pain 51.44 21.41 10 7074 81 29945313
Bradycardia 51.26 21.41 70 7014 65456 29879938
Paraplegia 49.83 21.41 20 7064 2641 29942753
Autonomic nervous system imbalance 48.14 21.41 19 7065 2402 29942992
Spinal cord infarction 47.56 21.41 11 7073 217 29945177
Device failure 46.75 21.41 18 7066 2130 29943264
Corneal reflex decreased 45.04 21.41 10 7074 163 29945231
Spinal shock 44.84 21.41 7 7077 11 29945383
Generalised tonic-clonic seizure 44.65 21.41 37 7047 19514 29925880
Arachnoiditis 43.10 21.41 11 7073 332 29945062
Device infusion issue 42.35 21.41 12 7072 542 29944852
Anal sphincter atony 41.35 21.41 8 7076 63 29945331
Oculocardiac reflex 41.35 21.41 8 7076 63 29945331
Implant site extravasation 40.16 21.41 11 7073 438 29944956
Anal incontinence 39.45 21.41 23 7061 6899 29938495
Areflexia 39.33 21.41 17 7067 2702 29942692
Therapeutic product effect delayed 38.02 21.41 13 7071 1096 29944298
Respiratory depression 37.73 21.41 27 7057 11476 29933918
Acute kidney injury 36.30 21.41 10 7074 273832 29671562
Apnoea 36.21 21.41 21 7063 6237 29939157
Myopathy toxic 36.13 21.41 10 7074 414 29944980
Loss of consciousness 35.91 21.41 66 7018 79309 29866085
Therapy non-responder 35.22 21.41 39 7045 29414 29915980
Delayed recovery from anaesthesia 35.17 21.41 11 7073 700 29944694
Sensory loss 35.12 21.41 18 7066 4192 29941202
Device power source issue 34.78 21.41 9 7075 287 29945107
Arthrofibrosis 34.50 21.41 7 7077 72 29945322
Sinus arrest 34.02 21.41 13 7071 1507 29943887
Anaesthetic complication neurological 33.68 21.41 9 7075 326 29945068
Sedation 33.31 21.41 29 7055 16344 29929050
Cardiac arrest 33.27 21.41 70 7014 92780 29852614
Muscular weakness 32.74 21.41 56 7028 63589 29881805
Neurotoxicity 32.30 21.41 26 7058 13156 29932238
Pneumonia 31.82 21.41 20 7064 334286 29611108
Infusion site mass 31.82 21.41 8 7076 227 29945167
Paraparesis 31.67 21.41 13 7071 1818 29943576
Electrocardiogram T wave amplitude increased 31.51 21.41 6 7078 43 29945351
Amaurosis 31.51 21.41 10 7074 667 29944727
Device malfunction 31.20 21.41 21 7063 8090 29937304
Muscle rigidity 31.18 21.41 23 7061 10238 29935156
Hypotension 28.56 21.41 108 6976 200457 29744937
Procedural complication 28.46 21.41 16 7068 4481 29940913
Jaundice cholestatic 28.28 21.41 16 7068 4535 29940859
Sinus tachycardia 26.69 21.41 25 7059 15479 29929915
Urinary incontinence 26.67 21.41 26 7058 16914 29928480
Unresponsive to stimuli 26.57 21.41 32 7052 26387 29919007
Post procedural complication 26.36 21.41 22 7062 11704 29933690
Apgar score low 25.07 21.41 9 7075 876 29944518
Complication associated with device 24.89 21.41 16 7068 5704 29939690
Device issue 24.83 21.41 18 7066 7798 29937596
Procedural pain 24.00 21.41 15 7069 5094 29940300
Inadequate analgesia 23.82 21.41 12 7072 2696 29942698
Neuromuscular block prolonged 23.78 21.41 7 7077 362 29945032
Meningitis chemical 23.23 21.41 5 7079 70 29945324
Implant site erythema 22.91 21.41 5 7079 75 29945319
Myoclonus 22.02 21.41 21 7063 13291 29932103
Anaphylactic reaction 22.00 21.41 30 7054 27952 29917442
Catheter site mass 21.77 21.41 4 7080 23 29945371

Pharmacologic Action:

SourceCodeDescription
ATC N01BB01 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
ATC N01BB51 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
ATC N01BB59 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
FDA CS M0000897 Amides
FDA EPC N0000175682 Amide Local Anesthetic
CHEBI has role CHEBI:36333 local anesthetics
CHEBI has role CHEBI:37733 bche inhibitor
CHEBI has role CHEBI:37887 adrenergic receptor blockaders
CHEBI has role CHEBI:59941 amphiphiles
CHEBI has role CHEBI:60186 ca(2+)-pumping atpase inhibitors
CHEBI has role CHEBI:88188 allergenic drug
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
FDA PE N0000175976 Local Anesthesia

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Anesthesia for cesarean section indication 4847005
Local anesthetic intrathecal block indication 231249005
Skin irritation indication 367466007
Local anesthesia indication 386761002
Itching of skin indication 418363000
Minor Skin Wound Pain indication
Major Nerve Block for Surgery indication
Regional Anesthesia for Surgery indication
Regional Anesthesia for Labor Pain indication
Regional Anesthesia for Ophthalmologic Surgery indication
Regional Anesthesia for Postoperative Pain indication
Local Anesthesia for Ophthalmologic Procedure indication
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
Alcoholism contraindication 7200002
Alcohol withdrawal delirium contraindication 8635005
Sinus tachycardia contraindication 11092001
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Asthenia contraindication 13791008
Constipation contraindication 14760008 DOID:2089
Chronic disease of respiratory system contraindication 17097001
Mood swings contraindication 18963009
Myocardial infarction contraindication 22298006 DOID:5844
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Alcohol intoxication contraindication 25702006
Complete atrioventricular block contraindication 27885002
Shock contraindication 27942005
Hypovolemia contraindication 28560003
Hypercapnia contraindication 29596007
Parkinsonism contraindication 32798002
Dehydration contraindication 34095006
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Hypokalemia contraindication 43339004
Decreased cardiac function contraindication 43650005
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Stokes-Adams syndrome contraindication 46935006
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Atrial fibrillation contraindication 49436004 DOID:0060224
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Sinus bradycardia contraindication 49710005
Bleeding hemorrhoids contraindication 51551000
Paralytic ileus contraindication 55525008 DOID:8442
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Cerebral arteriosclerosis contraindication 65312002
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Diabetes mellitus contraindication 73211009 DOID:9351
Wolff-Parkinson-White pattern contraindication 74390002 DOID:384
Urethral stricture contraindication 76618002
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Cor pulmonale contraindication 83291003 DOID:8515
Pulmonary emphysema contraindication 87433001
Cardiogenic shock contraindication 89138009
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Disorder of mucous membrane contraindication 95351003
Disorder of biliary tract contraindication 105997008 DOID:9741
Acute abdominal pain contraindication 116290004
Procedure on urinary system contraindication 118677009
Open wound contraindication 125643001
Neoplasm of brain contraindication 126952004 DOID:1319
Seizure disorder contraindication 128613002
Bleeding contraindication 131148009
Drug-induced psychosis contraindication 191483003 DOID:1742
Angina pectoris contraindication 194828000
Primary dilated cardiomyopathy contraindication 195021004
Partial atrioventricular block contraindication 195039008
Disease of liver contraindication 235856003 DOID:409
Morbid obesity contraindication 238136002 DOID:11981
Sepsis syndrome contraindication 238150007
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Exacerbation of asthma contraindication 281239006
Lesion of brain contraindication 301766008
Deficiency of cholinesterase contraindication 360607009
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Disorder of coronary artery contraindication 414024009
Central nervous system depression contraindication 418072004
Denuded skin contraindication 418242004
Dysfunction of sphincter of Oddi contraindication 430887001
Acute exacerbation of asthma contraindication 708038006
Reduced Hepatic Blood Flow contraindication
Lidocaine Toxicity contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.24 acidic
pKa2 7.92 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
133MG/10ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION April 6, 2021 REVISION OF THE INDICATION SECTION OF THE PACKAGE INSERT REGARDING AN INTERSCALENE BRACHIAL PLEXUS NERVE BLOCK TO PRODUCE POSTSURGICAL REGIONULLL ANULLLGESIA
266MG/20ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION April 6, 2021 REVISION OF THE INDICATION SECTION OF THE PACKAGE INSERT REGARDING AN INTERSCALENE BRACHIAL PLEXUS NERVE BLOCK TO PRODUCE POSTSURGICAL REGIONULLL ANULLLGESIA
100MG XARACOLL INNOCOLL PHARMS N209511 Aug. 28, 2020 RX IMPLANT IMPLANTATION Aug. 28, 2023 NEW PRODUCT
660MG/5ML (132MG/ML) POSIMIR DURECT N204803 Feb. 1, 2021 DISCN SOLUTION, EXTENDED RELEASE INFILTRATION Feb. 1, 2024 NEW PRODUCT
133MG/10ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION March 22, 2024 NEW PATIENT POPULATION
266MG/20ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION March 22, 2024 NEW PATIENT POPULATION

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 4 subunit alpha Ion channel BLOCKER IC50 6 WOMBAT-PK CHEMBL
Potassium voltage-gated channel subfamily A member 5 Ion channel BLOCKER Kd 5.40 IUPHAR
Cytochrome P450 2D6 Enzyme IC50 6.40 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 4.66 CHEMBL
Potassium voltage-gated channel subfamily D member 3 Ion channel IC50 4.50 WOMBAT-PK
Prostaglandin E2 receptor EP1 subtype GPCR IC50 5.51 WOMBAT-PK
5-hydroxytryptamine receptor 3A Ion channel IC50 4.23 WOMBAT-PK
Sodium channel protein type 1 subunit alpha Ion channel IC50 5.29 WOMBAT-PK
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER IC50 5.66 IUPHAR
Potassium voltage-gated channel subfamily D member 3 Unclassified BLOCKER IC50 4.50 IUPHAR

External reference:

IDSource
4019643 VUID
N0000147736 NUI
D07552 KEGG_DRUG
73360-54-0 SECONDARY_CAS_RN
4018244 VANDF
4019643 VANDF
C1175496 UMLSCUI
CHEBI:3215 CHEBI
2474 PUBCHEM_CID
CHEMBL1098 ChEMBL_ID
CHEMBL1200396 ChEMBL_ID
DB00297 DRUGBANK_ID
D002045 MESH_DESCRIPTOR_UI
2279 INN_ID
C472824 MESH_SUPPLEMENTAL_RECORD_UI
2397 IUPHAR_LIGAND_ID
Y8335394RO UNII
1375412 RXNORM
3621 MMSL
4305 MMSL
d00180 MMSL
001341 NDDF
005054 NDDF
24022008 SNOMEDCT_US
27196008 SNOMEDCT_US
387150008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9328 INJECTION, SOLUTION 2.50 mg INFILTRATION ANDA 25 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9329 INJECTION, SOLUTION 5 mg PERINEURAL ANDA 25 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9330 INJECTION, SOLUTION 2.50 mg EPIDURAL ANDA 24 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9331 INJECTION, SOLUTION 5 mg EPIDURAL ANDA 24 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9332 INJECTION, SOLUTION 7.50 mg EPIDURAL ANDA 24 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9333 INJECTION, SOLUTION 2.50 mg EPIDURAL ANDA 24 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9334 INJECTION, SOLUTION 5 mg EPIDURAL ANDA 24 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9335 INJECTION, SOLUTION 7.50 mg EPIDURAL ANDA 24 sections
Bupivacaine Hydrochloride with Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0264-9379 INJECTION 7.50 mg SUBARACHNOID ANDA 22 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 2 0362-0557 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 19 sections
Vivacaine HUMAN PRESCRIPTION DRUG LABEL 2 0362-9011 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 19 sections
Vivacaine HUMAN PRESCRIPTION DRUG LABEL 2 0362-9011 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 19 sections
BUPIVACAINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0409-1159 INJECTION, SOLUTION 2.50 mg INFILTRATION ANDA 12 sections
BUPIVACAINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0409-1159 INJECTION, SOLUTION 2.50 mg INFILTRATION ANDA 12 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-1160 INJECTION, SOLUTION 2.50 mg INFILTRATION ANDA 28 sections
BUPIVACAINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0409-1162 INJECTION, SOLUTION 5 mg INTRACAUDAL ANDA 12 sections
BUPIVACAINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0409-1162 INJECTION, SOLUTION 5 mg INTRACAUDAL ANDA 12 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-1163 INJECTION, SOLUTION 5 mg PERINEURAL ANDA 28 sections
Bupivacaine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-1165 INJECTION, SOLUTION 7.50 mg EPIDURAL ANDA 28 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1559 INJECTION, SOLUTION 2.50 mg EPIDURAL NDA 28 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1560 INJECTION, SOLUTION 5 mg EPIDURAL NDA 28 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1582 INJECTION, SOLUTION 7.50 mg EPIDURAL NDA 28 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1587 INJECTION, SOLUTION 2.50 mg INFILTRATION NDA 28 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1610 INJECTION, SOLUTION 5 mg PERINEURAL NDA 28 sections
Marcaine with Epinephrine HUMAN PRESCRIPTION DRUG LABEL 2 0409-1746 INJECTION, SOLUTION 2.50 mg INFILTRATION NDA 28 sections
Marcaine with Epinephrine HUMAN PRESCRIPTION DRUG LABEL 2 0409-1749 INJECTION, SOLUTION 5 mg EPIDURAL NDA 28 sections
Marcaine with Epinephrine HUMAN PRESCRIPTION DRUG LABEL 2 0409-1752 INJECTION, SOLUTION 2.50 mg INFILTRATION NDA 28 sections
Marcaine with Epinephrine HUMAN PRESCRIPTION DRUG LABEL 2 0409-1755 INJECTION, SOLUTION 5 mg PERINEURAL NDA 28 sections
Marcaine Spinal HUMAN PRESCRIPTION DRUG LABEL 1 0409-1761 INJECTION, SOLUTION 7.50 mg SUBARACHNOID NDA 21 sections
Bupivacaine Spinal HUMAN PRESCRIPTION DRUG LABEL 1 0409-3613 INJECTION, SOLUTION 7.50 mg SUBARACHNOID ANDA 12 sections