BUPIVACAINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1972)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N01BB01
UNII: Y8335394RO

Structure
InChI Key LEBVLXFERQHONN-UHFFFAOYSA-N
Smile CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C
InChI
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H28N2O
Molecular Weight 288.44
AlogP 3.9
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 32.34
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 21.0

Pharmacology

Action Mechanism of Action Reference
BLOCKER Sodium channel protein type IV alpha subunit blocker PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Two-pore domain potassium channel
- 100000 - - 50
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 5400 - - 63

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hernia 4 D006547 ClinicalTrials
Pain 4 D010146 ClinicalTrials
Liver Diseases 3 D008107 ClinicalTrials
Ileus 3 D045823 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Pancreatic Neoplasms 3 D010190 ClinicalTrials
Hemorrhoids 3 D006484 ClinicalTrials
Ankle Fractures 3 D064386 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Fractures, Bone 3 D050723 ClinicalTrials
Chronic Pain 3 D059350 ClinicalTrials
Cough 3 D003371 ClinicalTrials
Wounds and Injuries 3 D014947 ClinicalTrials
Genital Neoplasms, Female 3 D005833 ClinicalTrials
Toothache 3 D014098 ClinicalTrials
Breech Presentation 3 D001946 ClinicalTrials
Hallux Valgus 3 D006215 ClinicalTrials
Postoperative Complications 3 D011183 ClinicalTrials
Migraine Disorders 3 D008881 ClinicalTrials
Urethral Stricture 3 D014525 ClinicalTrials
Peritoneal Neoplasms 3 D010534 ClinicalTrials
Radiculopathy 3 D011843 ClinicalTrials
Postoperative Nausea and Vomiting 3 D020250 ClinicalTrials
Hernia, Inguinal 3 D006552 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Pancreatitis, Chronic 3 D050500 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Blepharoptosis 2 D001763 ClinicalTrials
Hip Fractures 2 D006620 ClinicalTrials
Osteoarthritis, Hip 2 D015207 ClinicalTrials
Hypospadias 2 D007021 ClinicalTrials
Dupuytren Contracture 2 D004387 ClinicalTrials
Appendicitis 2 D001064 ClinicalTrials
Rotator Cuff Injuries 2 D000070636 ClinicalTrials
Femoral Neck Fractures 2 D005265 ClinicalTrials
Mucositis 2 D052016 ClinicalTrials
Fasciitis, Plantar 2 D036981 ClinicalTrials
Cleft Palate 2 D002972 ClinicalTrials
Headache 2 D006261 ClinicalTrials
Hemorrhage 2 D006470 ClinicalTrials
Pulpitis 2 D011671 ClinicalTrials
Pregnancy 2 D011247 ClinicalTrials
Spinal Stenosis 2 D013130 ClinicalTrials
Blood Coagulation Disorders 2 D001778 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Hernia, Umbilical 2 D006554 ClinicalTrials
Shoulder Pain 2 D020069 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Osteoarthritis, Knee 2 D020370 ClinicalTrials
Rib Fractures 2 D012253 ClinicalTrials
Low Back Pain 2 D017116 ClinicalTrials
Lacrimal Apparatus Diseases 2 D007766 ClinicalTrials
Lung Neoplasms 2 D008175 ClinicalTrials
Abdominal Pain 2 D015746 ClinicalTrials
Hypotension 2 D007022 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials
Aortic Coarctation 1 D001017 ClinicalTrials
Vasospasm, Intracranial 1 D020301 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Sinusitis 1 D012852 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials
Neuralgia 0 D009437 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Gastrointestinal disorder 42.3
Gastrointestinal disorders Nausea 40.2
Gastrointestinal disorders Gastrointestinal disorder
Gastrointestinal disorders Nausea
Nervous system disorders Nervous system disorder
Vascular disorders Hypotension 31.0
Gastrointestinal disorders Vomiting 27.8
Cardiac disorders Dizziness
Gastrointestinal disorders Nausea 21.0
Nervous system disorders Nervous system disorder 20.6
Vascular disorders Hypotension 20.5
Vascular disorders Hypotension 19.6
General disorders and administration site conditions Procedural pain 18.0
Gastrointestinal disorders Vomiting
Investigations Body temperature increased 17.0
Gastrointestinal disorders Nausea 14.6
Gastrointestinal disorders Vomiting 14.0
Gastrointestinal disorders Gastrointestinal disorder
Blood and lymphatic system disorders Anaemia 12.0
Gastrointestinal disorders Nausea 11.6
Cardiac disorders Dizziness 11.3
Blood and lymphatic system disorders Anaemia 9.63
Pregnancy, puerperium and perinatal conditions Foetal distress syndrome 9.63
Pregnancy, puerperium and perinatal conditions Foetal distress syndrome 9.05
Skin and subcutaneous tissue disorders Pruritus 9.0
Nervous system disorders Headache
Skin and subcutaneous tissue disorders Skin disorder 8.25
Gastrointestinal disorders Vomiting 8.25
Blood and lymphatic system disorders Anaemia 8.17
General disorders and administration site conditions Procedural pain 8.17
General disorders and administration site conditions Pain 8.0
Investigations Body temperature increased 7.73
Gastrointestinal disorders Gastrointestinal disorder 7.37
Skin and subcutaneous tissue disorders Skin disorder
General disorders and administration site conditions Procedural pain 7.27
Gastrointestinal disorders Constipation 7.0
Nervous system disorders Headache 7.0
Pregnancy, puerperium and perinatal conditions Delayed delivery 6.84
Gastrointestinal disorders Vomiting 6.62
Investigations Body temperature increased 6.48
Pregnancy, puerperium and perinatal conditions Delayed delivery 6.29
Pruritus generalised
Cardiac disorders Dizziness 6.2
Cardiac disorders Dizziness 6.0
Skin and subcutaneous tissue disorders Pruritus 5.74
Musculoskeletal and connective tissue disorders Back pain 5.7
Gastrointestinal disorders Dyschezia
Nervous system disorders Headache 5.15
Pruritus generalised 5.15
Nervous system disorders Somnolence 5.15
Cardiac disorders Dizziness 5.11
Pregnancy, puerperium and perinatal conditions Foetal distress syndrome 5.0
Cardiac disorders Dizziness 4.86
Nervous system disorders Headache 4.52
Gastrointestinal disorders Constipation 4.42
Gastrointestinal disorders Anal haemorrhage
Gastrointestinal disorders Vomiting
Musculoskeletal and connective tissue disorders Back pain 4.19
Nervous system disorders Headache 3.97
Cardiac disorders Tachycardia 3.9
Nervous system disorders Headache 3.8
Investigations Electrocardiogram abnormal 3.75
General disorders and administration site conditions Pain 3.75
Skin and subcutaneous tissue disorders Pruritus 3.73
General disorders and administration site conditions Pain 3.54
Nervous system disorders Hypoaesthesia 3.31
Investigations Body temperature increased
Gastrointestinal disorders Rectal discharge
Gastrointestinal disorders Anal haemorrhage 3.16
Investigations Body temperature increased 3.16
Investigations Electrocardiogram abnormal 3.14
Investigations Alanine aminotransferase increased
Investigations Alanine aminotransferase increased 3.09
Investigations Aspartate aminotransferase increased 3.09
Eye disorders Diplopia 3.09
Skin and subcutaneous tissue disorders Pruritus 3.09
Gastrointestinal disorders Abdominal distension 2.95
General disorders and administration site conditions Chills 2.95
General disorders and administration site conditions Wound secretion 2.87
Gastrointestinal disorders Constipation 2.75
Gastrointestinal disorders Abdominal distension 2.65
General disorders and administration site conditions Chills 2.65
Pregnancy, puerperium and perinatal conditions Haemorrhage in pregnancy 2.65
Eye disorders Diplopia 2.55
Nervous system disorders Hypoaesthesia 2.55
Gastrointestinal disorders Dyspepsia 2.43
Gastrointestinal disorders Flatulence 2.43
Gastrointestinal disorders Flatulence 2.36
Cardiac disorders Bradycardia 2.21
Gastrointestinal disorders Abdominal pain 2.16
Investigations Body temperature decreased 2.16
Cardiac disorders Bradycardia 2.16
Gastrointestinal disorders Gastrointestinal pain 2.16
General disorders and administration site conditions Hypothermia 2.16
Gastrointestinal disorders Constipation
Gastrointestinal disorders Constipation 2.11
Gastrointestinal disorders Dyschezia 2.11
Gastrointestinal disorders Nausea 2.11
Gastrointestinal disorders Vomiting 2.11
Nervous system disorders Somnolence 2.1
Investigations Aspartate aminotransferase increased
General disorders and administration site conditions Decreased appetite
Metabolism and nutrition disorders Malnutrition
Investigations Blood creatinine increased 2.06
Investigations Body temperature increased 2.06
Gastrointestinal disorders Constipation 2.06
General disorders and administration site conditions Decreased appetite 2.06
Cardiac disorders Dizziness 2.06
General disorders and administration site conditions Feeling hot 2.06
Infections and infestations Fungal infection 2.06
Infections and infestations Infection 2.06
Infections and infestations Infestation 2.06
Nervous system disorders Loss of consciousness 2.06
Metabolism and nutrition disorders Malnutrition 2.06
Injury, poisoning and procedural complications Post procedural swelling 2.06
Vascular disorders Shock 2.06
Cardiac disorders Syncope 2.06
Gastrointestinal disorders Dyspepsia 1.96
Renal and urinary disorders Haematuria 1.96
Pregnancy, puerperium and perinatal conditions Haemorrhage in pregnancy 1.77
Vascular disorders Hypertension 1.77
Nervous system disorders Paraesthesia 1.77
Cardiac disorders Tachycardia 1.77
Renal and urinary disorders Urine abnormality 1.77
Investigations Urine analysis abnormal 1.77
Cardiac disorders Bradycardia 1.6
Cardiac disorders Tachycardia 1.55
Nervous system disorders Hypoaesthesia 1.5
Blood and lymphatic system disorders Purpura 1.38
Blood and lymphatic system disorders Vascular purpura 1.38
General disorders and administration site conditions Wound secretion 1.38
Gastrointestinal disorders Abdominal pain 1.32
Psychiatric disorders Anxiety 1.32
Investigations Body temperature decreased 1.32
Gastrointestinal disorders Diarrhoea 1.32
Gastrointestinal disorders Gastrointestinal pain 1.32
General disorders and administration site conditions Hypothermia 1.32
Renal and urinary disorders Urine abnormality 1.32
Investigations Urine analysis abnormal 1.32
General disorders and administration site conditions Lethargy 1.3
Respiratory, thoracic and mediastinal disorders Cough 1.18
Blood and lymphatic system disorders Leukocytosis 1.18
Nervous system disorders Somnolence 1.18
Nervous system disorders Urinary incontinence 1.18
Renal and urinary disorders Haematuria 1.1
Investigations Body temperature increased
Gastrointestinal disorders Nausea
Investigations Alanine aminotransferase increased 1.05
Investigations Body temperature increased 1.05
Gastrointestinal disorders Rectal discharge 1.05
Gastrointestinal disorders Constipation
Infections and infestations Fungal infection
Infections and infestations Infection
Infections and infestations Infestation
Skin and subcutaneous tissue disorders Pruritus
Nervous system disorders Somnolence
Psychiatric disorders Anxiety 0.982
Reproductive system and breast disorders Breast pain 0.982
Gastrointestinal disorders Diarrhoea 0.982
Vascular disorders Hypertension 0.982
Infections and infestations Urinary tract infection 0.982
Renal and urinary disorders Urine flow decreased 0.982
Reproductive system and breast disorders Breast pain 0.883
Blood and lymphatic system disorders Purpura 0.883
Nervous system disorders Somnolence 0.883
Blood and lymphatic system disorders Vascular purpura 0.883
Respiratory, thoracic and mediastinal disorders Cough 0.662
Blood and lymphatic system disorders Leukocytosis 0.662
Infections and infestations Urinary tract infection 0.662
Renal and urinary disorders Urine flow decreased 0.662
Nervous system disorders Paraesthesia 0.442
Nervous system disorders Urinary incontinence 0.221

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
13.36
Injury, poisoning and procedural complications
11.07
Vascular disorders
10.54
Cardiac disorders
9.14
General disorders and administration site conditions
8.79
Skin and subcutaneous tissue disorders
6.33
Respiratory, thoracic and mediastinal disorders
5.8
Gastrointestinal disorders
5.45
Infections and infestations
4.57
Surgical and medical procedures
4.22
Musculoskeletal and connective tissue disorders
4.04
Investigations
3.69
Psychiatric disorders
2.99
Renal and urinary disorders
2.81

Cross References

Resources Reference
CAS NUMBER 38396-39-3
ChEBI 77431
ChEMBL CHEMBL1098
DrugBank DB00297
DrugCentral 432
EPA CompTox DTXSID2022703
FDA SRS Y8335394RO
Human Metabolome Database HMDB0014442
Guide to Pharmacology 2397
KEGG C07529
PharmGKB PA135057240
PubChem 2474
SureChEMBL SCHEMBL25438
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