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
Drug abuse 274.43 70.45 73 861 11953 2345198
Dilatation intrahepatic duct acquired 268.02 70.45 34 900 54 2357097
Hydronephrosis 241.14 70.45 44 890 1223 2355928
Anaphylactic shock 230.67 70.45 52 882 4234 2352917
Haematuria 187.35 70.45 44 890 4274 2352877
Hypercapnia 163.80 70.45 28 906 524 2356627
Hepatotoxicity 148.39 70.45 35 899 3446 2353705
Bronchospasm 147.91 70.45 34 900 2990 2354161
Hypotension 147.85 70.45 58 876 32378 2324773
Cardiac arrest 121.32 70.45 41 893 14889 2342262
Venoocclusive liver disease 121.21 70.45 22 912 586 2356565
Biliary dilatation 118.96 70.45 20 914 336 2356815
Drug ineffective 117.88 70.45 71 863 101553 2255598
Acute kidney injury 106.14 70.45 44 890 28078 2329073
Sterile pyuria 103.18 70.45 12 922 3 2357148
Respiratory acidosis 102.27 70.45 20 914 801 2356350
Lung hyperinflation 100.67 70.45 15 919 109 2357042
Respiratory depression 98.57 70.45 23 911 2147 2355004
Blood lactic acid increased 95.49 70.45 19 915 832 2356319
Blood pH decreased 92.87 70.45 17 917 474 2356677
Reduced bladder capacity 92.25 70.45 11 923 6 2357145
Airway peak pressure increased 90.55 70.45 12 922 31 2357120
Bladder disorder 90.27 70.45 19 915 1102 2356049
Foetal growth restriction 89.95 70.45 19 915 1121 2356030
PCO2 increased 87.32 70.45 14 920 172 2356979
Oliguria 86.65 70.45 19 915 1338 2355813
Hepatocellular injury 84.29 70.45 23 911 4032 2353119
Bladder hypertrophy 83.99 70.45 11 923 25 2357126
Cardio-respiratory arrest 81.61 70.45 27 907 9119 2348032
PO2 decreased 79.73 70.45 14 920 306 2356845
Blood bicarbonate decreased 79.69 70.45 15 919 488 2356663
Intra-abdominal pressure increased 76.89 70.45 10 924 21 2357130
Pollakiuria 76.64 70.45 21 913 3735 2353416
Off label use 76.12 70.45 48 886 73550 2283601
Venoocclusive disease 75.37 70.45 13 921 255 2356896
Liver function test abnormal 74.44 70.45 24 910 7466 2349685
Pneumatosis 74.29 70.45 11 923 76 2357075
Respiratory rate increased 73.71 70.45 17 917 1503 2355648
Lower urinary tract symptoms 72.66 70.45 9 925 10 2357141
Cystitis 72.46 70.45 22 912 5620 2351531
Propofol infusion syndrome 71.32 70.45 11 923 103 2357048
Unwanted awareness during anaesthesia 70.63 70.45 10 924 48 2357103

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
Drug abuse 442.65 64.05 121 815 13568 1732277
Hydronephrosis 234.26 64.05 47 889 1298 1744547
Toxicity to various agents 185.04 64.05 76 860 29065 1716780
Anaphylactic shock 182.68 64.05 44 892 2855 1742990
Cystitis 176.33 64.05 37 899 1274 1744571
Hypotension 140.51 64.05 63 873 29591 1716254
Drug screen positive 131.54 64.05 28 908 1029 1744816
Cholestasis 124.37 64.05 34 902 3631 1742214
Cystitis ulcerative 113.73 64.05 14 922 3 1745842
Cystitis interstitial 94.89 64.05 13 923 23 1745822
Bladder disorder 93.85 64.05 19 917 541 1745304
Cardiac arrest 91.82 64.05 39 897 15891 1729954
Biliary dilatation 91.26 64.05 16 920 203 1745642
Bradycardia 89.07 64.05 34 902 10500 1735345
Drug ineffective 83.08 64.05 58 878 63743 1682102
Biopsy bladder abnormal 81.33 64.05 10 926 2 1745843
Contracted bladder 79.40 64.05 11 925 22 1745823
Bronchospasm 78.41 64.05 21 915 2061 1743784
Delirium 77.85 64.05 27 909 6335 1739510
Accidental death 74.83 64.05 15 921 405 1745440
Intentional product misuse 74.01 64.05 27 909 7331 1738514
Respiratory depression 72.19 64.05 20 916 2227 1743618
Anaphylactic reaction 71.15 64.05 25 911 6088 1739757
Hepatocellular injury 69.28 64.05 21 915 3210 1742635
Reduced bladder capacity 69.11 64.05 9 927 8 1745837
Drug interaction 65.44 64.05 37 899 27921 1717924

Pharmacologic Action:

SourceCodeDescription
ATC N01AX03 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, GENERAL
Other general anesthetics
FDA PE N0000175975 General Anesthesia
FDA EPC N0000175681 General Anesthetic
MeSH PA D000700 Analgesics
MeSH PA D000777 Anesthetics
MeSH PA D000778 Anesthetics, Dissociative
MeSH PA D018686 Anesthetics, Intravenous
CHEBI has role CHEBI:38877 intravenous anaesthetic
CHEBI has role CHEBI:35480 analgesic
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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
General anesthesia indication 50697003
Local anesthesia indication 386761002
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
Cardiac Decompensation contraindication
Psychiatric Disturbance 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
C0022614 UMLSCUI
D00711 KEGG_DRUG
690G0D6V8H UNII
2156 INN_ID
333847008 SNOMEDCT_US
6130 RXNORM
373464007 SNOMEDCT_US
d00272 MMSL
4019796 VANDF
004581 NDDF
3821 PUBCHEM_CID
CHEBI:6121 CHEBI
CHEMBL742 ChEMBL_ID
CHEMBL1714 ChEMBL_ID
1867-66-9 SECONDARY_CAS_RN
DB01221 DRUGBANK_ID
D007649 MESH_DESCRIPTOR_UI
4233 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9508 INJECTION 50 mg INTRAMUSCULAR ANDA 14 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9509 INJECTION 100 mg INTRAMUSCULAR ANDA 14 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-2051 INJECTION, SOLUTION, CONCENTRATE 100 mg INTRAMUSCULAR ANDA 14 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-2053 INJECTION, SOLUTION, CONCENTRATE 50 mg INTRAMUSCULAR ANDA 14 sections
Ketalar HUMAN PRESCRIPTION DRUG LABEL 1 42023-113 INJECTION 10 mg INTRAMUSCULAR NDA 14 sections
Ketalar HUMAN PRESCRIPTION DRUG LABEL 1 42023-114 INJECTION 50 mg INTRAMUSCULAR NDA 14 sections
Ketalar HUMAN PRESCRIPTION DRUG LABEL 1 42023-115 INJECTION 100 mg INTRAMUSCULAR NDA 14 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 13 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-001 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 14 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-108 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 14 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-181 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 14 sections
MKO Melt Dose Pack HUMAN PRESCRIPTION DRUG LABEL 2 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 14 sections
Ketamine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 72572-321 INJECTION 100 mg INTRAMUSCULAR ANDA 14 sections