Ketobemidone
Identification
- Generic Name
- Ketobemidone
- DrugBank Accession Number
- DB06738
- Background
Ketobemidone is a powerful opioid analgesic. It also has some NMDA-antagonist properties. This makes it useful for some types of pain that don't respond well to other opioids. The most commonly cited equalisation ratio for analgesic doses is 25 mg of ketobemidone hydrobromide to 60 mg of morphine hydrochloride or sulfate and circa 8 mg of ketobemidone by injection.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 247.3327
Monoisotopic: 247.157228921 - Chemical Formula
- C15H21NO2
- Synonyms
- Cetobemidona
- Cetobemidone
- Cetobemidonum
- Ketobemidone
- External IDs
- CIBA 7115
- IDS-NK-001
- IDS-NK-001(SECT.3)
- NSC-117863
Pharmacology
- Indication
For the treatment of all types of severe pain, such as postoperative, cancer, kidney stones and fractures.
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- Pharmacodynamics
Not Available
- Mechanism of action
Ketobemidone (Cliradon, Ketogan, Ketodur, Cymidon, Ketorax, &c.) is a powerful opioid analgesic. It also has some NMDA-antagonist properties. This makes it useful for some types of pain that don't respond well to other opioids. The most commonly cited equalisation ratio for analgesic doses is 25 mg of ketobemidone hydrobromide to 60 mg of morphine hydrochloride or sulfate and circa 8 mg of ketobemidone by injection.
Target Actions Organism AMu-type opioid receptor agonistHumans AKappa-type opioid receptor agonistHumans ADelta-type opioid receptor agonistHumans UNMDA receptor antagonistHumans - Absorption
34% (oral), 44% (rectal)
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Ketobemidone is mainly metabolised by conjugation of the phenolic hydroxyl group, and by N-desmethylation. Only about 13-24% is excreted unchanged after iv. administration.
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- Route of elimination
Not Available
- Half-life
Plasma half-life: 2.42 +/- 0.41 h (m +/- SD). Elimination half-life: 3.27 +/- 0.32 h
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Base: Rat Intravenous LD50: 10 mg/kg; Mouse Intravenous LD50: 14 mg/kg. Hydrochloride salt: Rat Oral LD50: 215 mg/kg; Rat Intravenous LD50: 40 mg/kg
- Pathways
Pathway Category Ketobemidone Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Ketobemidone is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Ketobemidone can be increased when it is combined with Abametapir. Abatacept The metabolism of Ketobemidone can be increased when combined with Abatacept. Abiraterone The metabolism of Ketobemidone can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Ketobemidone. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Ketobemidone hydrochloride U9U6LTV80K 5965-49-1 HYDFAZFVKRXNJX-UHFFFAOYSA-N Ketobemidone oxalate Not Available Not Available OPKJKUCDOASCBQ-UHFFFAOYSA-N - International/Other Brands
- Cliradon (Pfizer) / Ketogan (Pfizer) / Ketorax (Pfizer)
Categories
- ATC Codes
- N02AB01 — KetobemidoneN02AG02 — Ketobemidone and antispasmodics
- Drug Categories
- Analgesics
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Excitatory Amino Acid Agents
- Excitatory Amino Acid Antagonists
- Isonipecotic Acids
- Narcotics
- Nervous System
- Neurotransmitter Agents
- Opioids
- Peripheral Nervous System Agents
- Phenylpiperidine opioids
- Piperidines
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- UGT1A9 Substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Piperidines
- Sub Class
- Phenylpiperidines
- Direct Parent
- Phenylpiperidines
- Alternative Parents
- Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Gamma-amino ketones / Benzene and substituted derivatives / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Gamma-aminoketone / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- piperidines (CHEBI:6125)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- PQS1L514CF
- CAS number
- 469-79-4
- InChI Key
- ALFGKMXHOUSVAD-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3
- IUPAC Name
- 1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one
- SMILES
- CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1
References
- General References
- Bondesson U, Hartvig P, Danielsson B: Quantitative determination of the urinary excretion of ketobemidone and four of its metabolites after intravenous and oral administration in man. Drug Metab Dispos. 1981 Jul-Aug;9(4):376-80. [Article]
- Anderson P, Arner S, Bondesson U, Boreus LO, Hartvig P: Clinical pharmacokinetics of ketobemidone. Its bioavailability after rectal administration. Eur J Clin Pharmacol. 1981 Feb;19(3):217-23. [Article]
- External Links
- Human Metabolome Database
- HMDB0041913
- KEGG Drug
- D08100
- KEGG Compound
- C11792
- PubChem Compound
- 10101
- PubChem Substance
- 175427088
- ChemSpider
- 9697
- BindingDB
- 50231237
- ChEBI
- 6125
- ChEMBL
- CHEMBL47072
- ZINC
- ZINC000000001600
- Wikipedia
- Ketobemidone
- MSDS
- Download (83.4 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 156.5 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 3.01 mg/mL ALOGPS logP 2.01 ALOGPS logP 2.49 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 9.44 Chemaxon pKa (Strongest Basic) 8.09 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 40.54 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 73.12 m3·mol-1 Chemaxon Polarizability 28.09 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.996 Blood Brain Barrier + 0.9777 Caco-2 permeable + 0.7753 P-glycoprotein substrate Substrate 0.8263 P-glycoprotein inhibitor I Non-inhibitor 0.6758 P-glycoprotein inhibitor II Non-inhibitor 0.6722 Renal organic cation transporter Inhibitor 0.6578 CYP450 2C9 substrate Non-substrate 0.8324 CYP450 2D6 substrate Substrate 0.6178 CYP450 3A4 substrate Substrate 0.6483 CYP450 1A2 substrate Non-inhibitor 0.8062 CYP450 2C9 inhibitor Non-inhibitor 0.889 CYP450 2D6 inhibitor Inhibitor 0.6678 CYP450 2C19 inhibitor Non-inhibitor 0.9396 CYP450 3A4 inhibitor Non-inhibitor 0.6532 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9154 Ames test Non AMES toxic 0.882 Carcinogenicity Non-carcinogens 0.8277 Biodegradation Not ready biodegradable 0.9801 Rat acute toxicity 2.5982 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6132 hERG inhibition (predictor II) Inhibitor 0.6146
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-3910000000-6decb78c046347ae40f5 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0190000000-1c6104d5b0acf89c9197 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00kb-0090000000-fa69762a10b64a67c514 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0012-3970000000-8be384fa99d96bba1f1f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00kb-1190000000-58eae9a020e98269d767 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-4900000000-964d46c37d129759fd58 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000g-5930000000-a2e38da298e8a8903bf8 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 167.4920066 predictedDarkChem Lite v0.1.0 [M-H]- 168.7886066 predictedDarkChem Lite v0.1.0 [M-H]- 159.04753 predictedDeepCCS 1.0 (2019) [M+H]+ 168.1134066 predictedDarkChem Lite v0.1.0 [M+H]+ 169.1809066 predictedDarkChem Lite v0.1.0 [M+H]+ 161.40552 predictedDeepCCS 1.0 (2019) [M+Na]+ 167.6803066 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.6094066 predictedDarkChem Lite v0.1.0 [M+Na]+ 167.49867 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Kristensen K, Christensen CB, Christrup LL, Nielsen LC: The mu1 and mu2 opioid receptor binding of ketobemidone, norketobemidone and 3-dimethylamino-1,1-diphenylbutene. Pharmacol Toxicol. 1996 Aug;79(2):103-4. [Article]
- Christensen CB: The opioid receptor binding profiles of ketobemidone and morphine. Pharmacol Toxicol. 1993 Dec;73(6):344-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Christensen CB: The opioid receptor binding profiles of ketobemidone and morphine. Pharmacol Toxicol. 1993 Dec;73(6):344-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- Christensen CB: The opioid receptor binding profiles of ketobemidone and morphine. Pharmacol Toxicol. 1993 Dec;73(6):344-5. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Voltage-gated cation channel activity
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Components:
References
- Ebert B, Andersen S, Krogsgaard-Larsen P: Ketobemidone, methadone and pethidine are non-competitive N-methyl-D-aspartate (NMDA) antagonists in the rat cortex and spinal cord. Neurosci Lett. 1995 Mar 10;187(3):165-8. [Article]
- Ebert B, Thorkildsen C, Andersen S, Christrup LL, Hjeds H: Opioid analgesics as noncompetitive N-methyl-D-aspartate (NMDA) antagonists. Biochem Pharmacol. 1998 Sep 1;56(5):553-9. doi: 10.1016/s0006-2952(98)00088-4. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Yasar U, Annas A, Svensson JO, Lazorova L, Artursson P, Al-Shurbaji A: Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. Xenobiotica. 2005 Aug;35(8):785-96. doi: 10.1080/00498250500183181 . [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Yasar U, Annas A, Svensson JO, Lazorova L, Artursson P, Al-Shurbaji A: Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. Xenobiotica. 2005 Aug;35(8):785-96. doi: 10.1080/00498250500183181 . [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Yasar U, Annas A, Svensson JO, Lazorova L, Artursson P, Al-Shurbaji A: Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. Xenobiotica. 2005 Aug;35(8):785-96. doi: 10.1080/00498250500183181 . [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Yasar U, Annas A, Svensson JO, Lazorova L, Artursson P, Al-Shurbaji A: Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. Xenobiotica. 2005 Aug;35(8):785-96. doi: 10.1080/00498250500183181 . [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Yasar U, Annas A, Svensson JO, Lazorova L, Artursson P, Al-Shurbaji A: Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. Xenobiotica. 2005 Aug;35(8):785-96. doi: 10.1080/00498250500183181 . [Article]
Drug created at August 31, 2010 21:02 / Updated at January 02, 2024 23:49