bupivacaine indications/contra

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

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
Oct. 3, 1972 FDA HOSPIRA

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
Drug ineffective 2001.15 44.48 700 2603 115390 3267166
Anaesthetic complication 1054.62 44.48 167 3136 618 3381938
Hypotension 715.56 44.48 267 3036 49247 3333309
Chondrolysis 617.90 44.48 90 3213 151 3382405
Exposure during pregnancy 560.45 44.48 192 3111 27371 3355185
Pain 477.99 44.48 223 3080 71334 3311222
Hypoaesthesia 316.31 44.48 123 3180 24816 3357740
Drug withdrawal syndrome 277.45 44.48 92 3211 11693 3370863
Cauda equina syndrome 247.30 44.48 41 3262 210 3382346
Cardiac arrest 199.14 44.48 91 3212 27228 3355328
Muscular weakness 194.38 44.48 82 3221 20259 3362297
Bradycardia 189.13 44.48 76 3227 16593 3365963
Lagophthalmos 183.45 44.48 29 3274 103 3382453
Maternal exposure during pregnancy 178.61 44.48 64 3239 10207 3372349
Drug effect decreased 176.35 44.48 66 3237 11903 3370653
Medical device site pain 171.75 44.48 25 3278 41 3382515
Musculoskeletal pain 170.12 44.48 65 3238 12401 3370155
Horner's syndrome 167.67 44.48 27 3276 111 3382445
Product quality issue 163.71 44.48 79 3224 26656 3355900
Maternal exposure during delivery 163.04 44.48 26 3277 99 3382457
Paraplegia 157.18 44.48 34 3269 819 3381737
Incorrect route of drug administration 154.69 44.48 56 3247 9187 3373369
Post procedural complication 149.86 44.48 47 3256 4970 3377586
Therapy non-responder 146.15 44.48 56 3247 10753 3371803
Unresponsive to stimuli 143.32 44.48 51 3252 7957 3374599
Seizure 138.30 44.48 81 3222 40319 3342237
Implant site extravasation 135.72 44.48 26 3277 332 3382224
Loss of consciousness 130.68 44.48 69 3234 28078 3354478
Myopathy toxic 129.12 44.48 22 3281 136 3382420
Drug effect delayed 128.87 44.48 27 3276 555 3382001

Pharmacologic Action:

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SourceCodeDescription
ATC N01BB01 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Amides
ATC N01BB51 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:37887 adrenergic antagonist
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 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 DOID:13548
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:2527
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 DOID:1826
Bleeding contraindication 131148009
Drug-induced psychosis contraindication 191483003 DOID:1742
Angina pectoris contraindication 194828000
Primary dilated cardiomyopathy contraindication 195021004 DOID:12930
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 DOID:2883
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 DOID:13774
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

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

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
133MG/10ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION 8182835 Sept. 18, 2018 SINGLE DOSE ADMINISTRATION INTO THE SURGICAL SITE TO PRODUCE POSTSURGICAL ANALGESIA
133MG/10ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION 8834921 Sept. 18, 2018 SINGLE-DOSE INFILTRATION INTO THE SURGICAL SITE TO PRODUCE POSTSURGICAL ANALGESIA.
266MG/20ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION 8182835 Sept. 18, 2018 SINGLE DOSE ADMINISTRATION INTO THE SURGICAL SITE TO PRODUCE POSTSURGICAL ANALGESIA
266MG/20ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION 8834921 Sept. 18, 2018 SINGLE-DOSE INFILTRATION INTO THE SURGICAL SITE TO PRODUCE POSTSURGICAL ANALGESIA.
266MG/20ML (13.3MG/ML) EXPAREL PACIRA PHARMS INC N022496 Oct. 28, 2011 RX INJECTABLE, LIPOSOMAL INJECTION 9205052 Sept. 18, 2018 SINGLE DOSE ADMINISTRATION INTO THE SURGICAL SITE TO PRODUCE POSTSURGICAL ANALGESIA

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 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:

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IDSource
DB00297 DRUGBANK_ID
2397 IUPHAR_LIGAND_ID
4019643 VUID
N0000147736 NUI
C0006400 UMLSCUI
D07552 KEGG_DRUG
7TQO7W3VT8 UNII
73360-54-0 SECONDARY_CAS_RN
2474 PUBCHEM_CID
4019643 VANDF
N0000007415 NDFRT
N0000147736 NDFRT
005054 NDDF
1815 RXNORM
27196008 SNOMEDCT_US
387150008 SNOMEDCT_US
d00180 MMSL
CHEMBL1098 ChEMBL_ID
CHEBI:3215 CHEBI
CHEMBL1200396 ChEMBL_ID
C472824 MESH_SUPPLEMENTAL_RECORD_UI
D002045 MESH_DESCRIPTOR_UI
2279 INN_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Vivacaine HUMAN PRESCRIPTION DRUG LABEL 2 0362-9011 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 11 sections
Gapeam Budibac HUMAN PRESCRIPTION DRUG LABEL 7 15455-0717 KIT 1 g TOPICAL unapproved drug other 5 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 2 31382-557 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 11 sections
Sensorcaine HUMAN PRESCRIPTION DRUG LABEL 1 52584-465 INJECTION, SOLUTION 2.50 mg INFILTRATION ANDA 9 sections
Sensorcaine HUMAN PRESCRIPTION DRUG LABEL 1 52584-467 INJECTION, SOLUTION 5 mg PERINEURAL ANDA 10 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 1 52584-560 INJECTION, SOLUTION 5 mg EPIDURAL NDA 11 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 1 54868-3134 INJECTION, SOLUTION 5 mg INFILTRATION NDA 11 sections
Marcaine HUMAN PRESCRIPTION DRUG LABEL 1 54868-3437 INJECTION, SOLUTION 2.50 mg INFILTRATION NDA 11 sections
Marcaine with Epinephrine HUMAN PRESCRIPTION DRUG LABEL 2 54868-3438 INJECTION, SOLUTION 2.50 mg INFILTRATION NDA 11 sections
Marcaine with Epinephrine HUMAN PRESCRIPTION DRUG LABEL 2 54868-3439 INJECTION, SOLUTION 5 mg INFILTRATION NDA 11 sections
EXPAREL HUMAN PRESCRIPTION DRUG LABEL 1 65250-133 INJECTION, SUSPENSION, LIPOSOMAL 13.30 mg INFILTRATION NDA 17 sections
EXPAREL HUMAN PRESCRIPTION DRUG LABEL 1 65250-266 INJECTION, SUSPENSION, LIPOSOMAL 13.30 mg INFILTRATION NDA 17 sections