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

Stem definitionDrug idCAS RN
1523 6740-88-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ketamine
  • narketan
  • (+/-)-Ketamine
  • ketamine hydrochloride
  • ketamine HCl
A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.
  • Molecular weight: 237.73
  • Formula: C13H16ClNO
  • CLOGP: 2.93
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 29.10
  • ALOGS: -3.71
  • ROTB: 2

  • 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) 200 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 4 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 8.41 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 20 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 19 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.47 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.80 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 19, 1970 FDA PAR STERILE PRODUCTS

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
Anaphylactic shock 439.12 20.46 159 8634 20115 46657154
Status epilepticus 136.70 20.46 62 8731 13917 46663352
Dilatation intrahepatic duct acquired 136.08 20.46 31 8762 725 46676544
Bronchospasm 129.79 20.46 62 8731 15645 46661624
Propofol infusion syndrome 129.73 20.46 30 8763 751 46676518
Hydronephrosis 103.28 20.46 44 8749 8501 46668768
Mitochondrial DNULL mutation 101.02 20.46 20 8773 231 46677038
Biliary dilatation 95.67 20.46 29 8764 2095 46675174
Drug abuse 94.06 20.46 85 8708 63323 46613946
Respiratory depression 90.40 20.46 44 8749 11556 46665713
Intra-abdominal pressure increased 85.34 20.46 17 8776 203 46677066
Delirium 82.51 20.46 63 8730 37165 46640104
Sterile pyuria 81.21 20.46 12 8781 15 46677254
Hypercapnia 80.65 20.46 31 8762 4595 46672674
Pneumatosis 79.37 20.46 18 8775 412 46676857
Hypotension 77.84 20.46 149 8644 232440 46444829
Reduced bladder capacity 75.78 20.46 10 8783 0 46677269
Blood lactic acid increased 74.61 20.46 31 8762 5626 46671643
Drug ineffective for unapproved indication 73.39 20.46 43 8750 16370 46660899
Body tinea 70.14 20.46 19 8774 916 46676353
Blood pH decreased 69.69 20.46 24 8769 2603 46674666
Unwanted awareness during anaesthesia 68.99 20.46 15 8778 281 46676988
Gene mutation 67.43 20.46 19 8774 1061 46676208
Cardiac arrest 67.35 20.46 84 8709 90315 46586954
Blood gases abnormal 67.32 20.46 17 8776 621 46676648
Haematuria 65.17 20.46 48 8745 26810 46650459
Necrosis ischaemic 62.58 20.46 17 8776 828 46676441
Hyperaesthesia 61.81 20.46 30 8763 7826 46669443
Cystitis ulcerative 60.62 20.46 8 8785 0 46677269
Shock 59.77 20.46 42 8751 21803 46655466
Intestinal ischaemia 59.21 20.46 28 8765 6897 46670372
Cardio-respiratory arrest 56.82 20.46 63 8730 59806 46617463
Inhibitory drug interaction 55.94 20.46 19 8774 1976 46675293
Venoocclusive liver disease 55.06 20.46 23 8770 4228 46673041
Local anaesthetic systemic toxicity 54.78 20.46 13 8780 365 46676904
Infection susceptibility increased 54.30 20.46 19 8774 2160 46675109
Impaired quality of life 53.93 20.46 21 8772 3221 46674048
Airway peak pressure increased 52.53 20.46 12 8781 284 46676985
Lower urinary tract symptoms 51.14 20.46 9 8784 51 46677218
Arthralgia 50.80 20.46 5 8788 364598 46312671
Bladder hypertrophy 50.35 20.46 11 8782 211 46677058
Respiratory acidosis 49.94 20.46 24 8769 6124 46671145
Lung hyperinflation 48.55 20.46 15 8778 1154 46676115
Multiple-drug resistance 47.62 20.46 18 8775 2547 46674722
PCO2 increased 47.52 20.46 15 8778 1239 46676030
Off label use 46.64 20.46 167 8626 379674 46297595
Anaphylactic reaction 45.48 20.46 53 8740 53059 46624210
Drug ineffective 43.83 20.46 246 8547 677592 45999677
Systemic inflammatory response syndrome 43.73 20.46 21 8772 5350 46671919
Anaphylactoid shock 41.66 20.46 10 8783 295 46676974
Hallucination 41.36 20.46 49 8744 49902 46627367
Contracted bladder 41.31 20.46 6 8787 6 46677263
PO2 decreased 40.74 20.46 14 8779 1508 46675761
Tonic clonic movements 40.21 20.46 13 8780 1159 46676110
Hepatotoxicity 39.96 20.46 35 8758 24974 46652295
Glucose tolerance impaired 39.67 20.46 19 8774 4812 46672457
Agitation 38.86 20.46 50 8743 55365 46621904
Ureteral polyp 37.89 20.46 5 8788 0 46677269
Dysphoria 37.53 20.46 18 8775 4571 46672698
Oesophageal spasm 37.08 20.46 14 8779 1975 46675294
Hepatocellular injury 36.86 20.46 36 8757 29486 46647783
Infantile apnoea 36.68 20.46 11 8782 765 46676504
Ultrasound ovary abnormal 35.42 20.46 7 8786 80 46677189
Metabolic acidosis 35.38 20.46 40 8753 38740 46638529
Blood bicarbonate decreased 35.33 20.46 15 8778 2870 46674399
Diastolic hypotension 35.18 20.46 7 8786 83 46677186
Status asthmaticus 34.65 20.46 11 8782 925 46676344
Cystitis interstitial 34.58 20.46 12 8781 1330 46675939
Intensive care unit acquired weakness 34.29 20.46 10 8783 631 46676638
Rheumatoid arthritis 34.20 20.46 3 8790 240212 46437057
Foetal growth restriction 34.16 20.46 19 8774 6548 46670721
Perforation 34.08 20.46 11 8782 976 46676293
Drug tolerance 33.75 20.46 15 8778 3203 46674066
Oesophageal pain 33.74 20.46 14 8779 2529 46674740
Bladder disorder 32.83 20.46 19 8774 7059 46670210
Headache 32.02 20.46 26 8767 478326 46198943
Bladder necrosis 31.77 20.46 5 8788 12 46677257
Mucocutaneous haemorrhage 31.66 20.46 6 8787 54 46677215
Impaired work ability 31.58 20.46 23 8770 12613 46664656
Nausea 31.32 20.46 51 8742 687403 45989866
Post procedural stroke 31.18 20.46 6 8787 59 46677210
Diarrhoea 31.00 20.46 36 8757 559566 46117703
Drug interaction 30.78 20.46 96 8697 202998 46474271
Sedation 30.60 20.46 29 8764 22881 46654388
Ureteric stenosis 30.15 20.46 9 8784 616 46676653
Poor quality sleep 29.85 20.46 24 8769 15229 46662040
Biliary tract disorder 29.20 20.46 9 8784 687 46676582
Oliguria 29.10 20.46 19 8774 8740 46668529
Stress cardiomyopathy 28.62 20.46 18 8775 7766 46669503
Cholestasis 28.47 20.46 30 8763 26863 46650406
Circulatory collapse 28.17 20.46 27 8766 21597 46655672
Reversible cerebral vasoconstriction syndrome 28.13 20.46 11 8782 1706 46675563
Tachyphylaxis 28.12 20.46 7 8786 241 46677028
Cystitis 27.87 20.46 37 8756 42204 46635065
Oxygen saturation decreased 27.70 20.46 48 8745 69116 46608153
Left ventricular hypertrophy 27.58 20.46 15 8778 4948 46672321
Bone density decreased 27.25 20.46 19 8774 9733 46667536
Intensive care unit delirium 26.91 20.46 5 8788 40 46677229
Purpura 26.89 20.46 19 8774 9939 46667330
Cyanosis 26.82 20.46 23 8770 15948 46661321
Blood creatine phosphokinase increased 25.97 20.46 29 8764 27695 46649574
Depersonalisation/derealisation disorder 25.91 20.46 9 8784 1001 46676268
Tachycardia 25.18 20.46 57 8736 99565 46577704
Bradypnoea 25.09 20.46 12 8781 3027 46674242
Apnoea 24.58 20.46 16 8777 7323 46669946
Euthyroid sick syndrome 24.57 20.46 5 8788 67 46677202
Anaesthetic complication neurological 24.46 20.46 6 8787 194 46677075
Ventricular fibrillation 24.45 20.46 19 8774 11477 46665792
Arrhythmia 23.73 20.46 31 8762 34810 46642459
Ureteral disorder 22.83 20.46 6 8787 257 46677012
Bladder neck obstruction 22.73 20.46 3 8790 0 46677269
Respiratory rate increased 22.39 20.46 18 8775 11415 46665854
Platelet disorder 22.08 20.46 9 8784 1554 46675715
Product dose omission issue 21.71 20.46 3 8790 168517 46508752
Selective eating disorder 21.12 20.46 9 8784 1736 46675533
Tidal volume decreased 20.73 20.46 4 8789 40 46677229

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 282.76 20.41 113 7459 13880 29931026
Drug abuse 242.31 20.41 185 7387 81887 29863019
Cystitis ulcerative 131.12 20.41 18 7554 0 29944906
Hydronephrosis 103.93 20.41 49 7523 8934 29935972
Cystitis 82.72 20.41 41 7531 8333 29936573
Anaphylactic reaction 82.05 20.41 63 7509 27919 29916987
Bronchospasm 80.14 20.41 43 7529 10295 29934611
Biliary dilatation 73.07 20.41 20 7552 742 29944164
Biopsy bladder abnormal 72.84 20.41 10 7562 0 29944906
Cystitis interstitial 71.54 20.41 11 7561 13 29944893
Hypotension 70.77 20.41 156 7416 200409 29744497
Reduced bladder capacity 70.22 20.41 10 7562 3 29944903
Drug screen positive 69.96 20.41 30 7542 4377 29940529
Contracted bladder 63.29 20.41 10 7562 16 29944890
Drug ineffective 61.74 20.41 207 7365 340180 29604726
Delirium 59.91 20.41 62 7510 40569 29904337
Hyperaesthesia 58.96 20.41 25 7547 3548 29941358
Toxicity to various agents 55.96 20.41 132 7440 177051 29767855
Bradycardia 55.06 20.41 75 7497 65451 29879455
Respiratory depression 55.05 20.41 35 7537 11468 29933438
Cholestasis 51.81 20.41 46 7526 24904 29920002
Bladder disorder 47.13 20.41 20 7552 2843 29942063
Tachycardia 45.49 20.41 73 7499 73666 29871240
Laryngospasm 42.18 20.41 15 7557 1328 29943578
Accidental death 35.81 20.41 15 7557 2064 29942842
Status epilepticus 34.78 20.41 26 7546 11046 29933860
Lower urinary tract symptoms 34.65 20.41 8 7564 146 29944760
Diarrhoea 34.50 20.41 21 7551 334082 29610824
Delayed recovery from anaesthesia 34.44 20.41 11 7561 700 29944206
Cardiac arrest 33.46 20.41 73 7499 92777 29852129
Serotonin syndrome 33.24 20.41 31 7541 17860 29927046
Biliary tract disorder 32.71 20.41 11 7561 824 29944082
Substance abuse 32.63 20.41 21 7551 7019 29937887
Agitation 31.24 20.41 52 7520 54021 29890885
Anaphylactoid shock 31.11 20.41 9 7563 409 29944497
Hypoxia 30.34 20.41 48 7524 47806 29897100
Apnoea 29.83 20.41 19 7553 6239 29938667
Sedation 29.71 20.41 28 7544 16345 29928561
Bladder hypertrophy 29.54 20.41 8 7564 285 29944621
Hyperammonaemia 29.44 20.41 18 7554 5502 29939404
Ureteral polyp 29.13 20.41 4 7568 0 29944906
Sedation complication 28.81 20.41 10 7562 824 29944082
Drug tolerance 28.76 20.41 13 7559 2149 29942757
Drug dependence 28.70 20.41 31 7541 21264 29923642
Wolff-Parkinson-White syndrome 27.43 20.41 7 7565 197 29944709
Metabolic acidosis 27.16 20.41 40 7532 37421 29907485
Cholangiolitis 26.56 20.41 5 7567 31 29944875
Brain oedema 26.00 20.41 23 7549 12375 29932531
Fatigue 25.70 20.41 26 7546 320647 29624259
Haemodynamic instability 25.57 20.41 19 7553 7996 29936910
Nystagmus 25.35 20.41 15 7557 4323 29940583
Diabetes insipidus 25.22 20.41 12 7560 2227 29942679
Pulseless electrical activity 25.14 20.41 17 7555 6170 29938736
Ureteric stenosis 25.02 20.41 10 7562 1221 29943685
Airway complication of anaesthesia 25.01 20.41 6 7566 130 29944776
Diastolic hypertension 24.72 20.41 5 7567 47 29944859
Propofol infusion syndrome 24.67 20.41 9 7563 857 29944049
Dissociative disorder 24.55 20.41 6 7566 141 29944765
Drug ineffective for unapproved indication 24.46 20.41 21 7551 10859 29934047
Anaesthetic complication neurological 23.99 20.41 7 7565 328 29944578
Haematuria traumatic 23.71 20.41 6 7566 163 29944743
Pneumonia 23.64 20.41 30 7542 334276 29610630
Transcranial electrical motor evoked potential monitoring abnormal 23.59 20.41 4 7568 12 29944894
Urinary tract disorder 23.33 20.41 11 7561 2000 29942906
Conversion disorder 23.21 20.41 7 7565 368 29944538
Off label use 23.20 20.41 124 7448 249166 29695740
Malaise 22.71 20.41 7 7565 166955 29777951
Hepatocellular injury 22.64 20.41 30 7542 25441 29919465
Neonatal hypoxia 21.51 20.41 6 7566 239 29944667
Dyspnoea 21.46 20.41 32 7540 333263 29611643
Circulatory collapse 21.44 20.41 26 7546 20188 29924718
Behaviour disorder 21.44 20.41 11 7561 2401 29942505
Hyperthermia malignant 21.18 20.41 10 7562 1824 29943082
Drug interaction 21.15 20.41 103 7469 199465 29745441

Pharmacologic Action:

SourceCodeDescription
ATC N01AX03 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, GENERAL
Other general anesthetics
FDA EPC N0000175681 General Anesthetic
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:38877 intravenous anesthetics
CHEBI has role CHEBI:50910 agente neurotoxico
CHEBI has role CHEBI:60643 n-methyl-d-aspartate receptor antagonists
CHEBI has role CHEBI:78298 environmental contaminants
MeSH PA D000700 Analgesics
MeSH PA D000777 Anesthetics
MeSH PA D000778 Anesthetics, Dissociative
MeSH PA D018686 Anesthetics, Intravenous
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D018691 Excitatory Amino Acid Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
FDA PE N0000175975 General Anesthesia

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
General anesthesia indication 50697003
Local anesthesia indication 386761002
Pain off-label use 22253000
Inflammatory disease of mucous membrane off-label use 95361005
Major depressive disorder off-label use 370143000
Delirium contraindication 2776000
Ocular hypertension contraindication 4210003 DOID:9282
Alcoholism contraindication 7200002
Myocardial infarction contraindication 22298006 DOID:5844
Alcohol intoxication contraindication 25702006
Hypertensive disorder contraindication 38341003 DOID:10763
Decreased respiratory function contraindication 80954004
Thyrotoxicosis contraindication 90739004 DOID:7997
Acute disease of cardiovascular system contraindication 128487001
Decompensated cardiac failure contraindication 195111005
Cerebrovascular accident contraindication 230690007
Raised intracranial pressure contraindication 271719001 DOID:9428
Cerebral trauma contraindication 275382005
Impaired cognition contraindication 386806002
Myocardial ischemia contraindication 414795007 DOID:3393
Hypertensive urgency contraindication 443482000
Psychiatric Disturbance contraindication
Cardiac Decompensation contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.65 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
Glutamate [NMDA] receptor Ion channel BLOCKER Ki 6.38 CHEMBL CHEMBL
Glutamate receptor ionotropic AMPA Ion channel OPENER SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Glutamate NMDA receptor Ion channel IC50 6.21 CHEMBL
Acetylcholine receptor subunit alpha Ion channel IC50 5.31 CHEMBL

External reference:

IDSource
4019796 VUID
N0000147885 NUI
D00711 KEGG_DRUG
1867-66-9 SECONDARY_CAS_RN
4018154 VANDF
4019796 VANDF
C0022614 UMLSCUI
CHEBI:6121 CHEBI
3821 PUBCHEM_CID
CHEMBL742 ChEMBL_ID
CHEMBL1714 ChEMBL_ID
D007649 MESH_DESCRIPTOR_UI
DB01221 DRUGBANK_ID
4233 IUPHAR_LIGAND_ID
2156 INN_ID
690G0D6V8H UNII
203184 RXNORM
4944 MMSL
9883 MMSL
d00272 MMSL
001403 NDDF
004581 NDDF
31706007 SNOMEDCT_US
333847008 SNOMEDCT_US
373464007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9508 INJECTION 50 mg INTRAMUSCULAR ANDA 27 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9509 INJECTION 100 mg INTRAMUSCULAR ANDA 27 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-2051 INJECTION, SOLUTION, CONCENTRATE 100 mg INTRAMUSCULAR ANDA 31 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-2053 INJECTION, SOLUTION, CONCENTRATE 50 mg INTRAMUSCULAR ANDA 31 sections
Ketalar HUMAN PRESCRIPTION DRUG LABEL 1 42023-113 INJECTION 10 mg INTRAMUSCULAR NDA 27 sections
Ketalar HUMAN PRESCRIPTION DRUG LABEL 1 42023-114 INJECTION 50 mg INTRAMUSCULAR NDA 27 sections
Ketalar HUMAN PRESCRIPTION DRUG LABEL 1 42023-115 INJECTION 100 mg INTRAMUSCULAR NDA 27 sections
KETALAR HUMAN PRESCRIPTION DRUG LABEL 1 52584-037 INJECTION 10 mg INTRAVENOUS NDA 14 sections
KETAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 52584-038 INJECTION, SOLUTION, CONCENTRATE 50 mg INTRAMUSCULAR ANDA 14 sections
KETAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 52584-040 INJECTION, SOLUTION, CONCENTRATE 100 mg INTRAMUSCULAR ANDA 14 sections
KETAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 52584-108 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 14 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-4399 INJECTION, SOLUTION, CONCENTRATE 50 mg INTRAMUSCULAR ANDA 19 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-001 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 22 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-108 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 22 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-181 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 22 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 70518-2787 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 22 sections
MKO Melt Dose Pack HUMAN PRESCRIPTION DRUG LABEL 3 71384-410 TROCHE 25 mg SUBLINGUAL unapproved drug other 2 sections
MKH Dose Pack HUMAN PRESCRIPTION DRUG LABEL 3 71384-420 TROCHE 25 mg SUBLINGUAL unapproved drug other 2 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 72572-320 INJECTION 50 mg INTRAMUSCULAR ANDA 27 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 72572-321 INJECTION 100 mg INTRAMUSCULAR ANDA 27 sections