Identification
- Summary
Chloramphenicol succinate is a broad-spectrum antibiotic agent used for the treatment of acute and severe infections caused by susceptible bacterial strains.
- Generic Name
- Chloramphenicol succinate
- DrugBank Accession Number
- DB07565
- Background
Chloramphenicol succinate is an ester prodrug of chloramphenicol.2 Chloramphenicol is a bacteriostatic antibiotic.5 Use of chloramphenicol succinate and chloramphenicol has decreased due to the risk of potentially fatal blood dyscrasias.10
Chloramphenicol succinate was granted FDA approval on 20 February 1959.9
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Chloramphenicol succinate (DB07565)
- Weight
- Average: 423.202
Monoisotopic: 422.028370912 - Chemical Formula
- C15H16Cl2N2O8
- Synonyms
- Chloramphenicol hemisuccinate
Pharmacology
- Indication
Chloramphenicol succinate is indicated to treat serious and susceptible bacterial infections where less dangerous drugs are ineffective or contraindicated.9
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute infection caused by salmonella typhi •••••••••••• ••••••••• Treatment of Salmonella typhi infection •••••••••••• ••••••••• Treatment of Serious bacterial infection •••••••••••• ••••••••• - Contraindications & Blackbox Warnings
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Chloramphenicol succinate is a prodrug of chloramphenicol, which binds to bacterial ribosomes and prevents translation.1,6,7 It has a narrow therapeutic index8 and a moderate duration of action.10 Patients should be counselled regarding the risk of serious fatal blood dyscrasias.10
- Mechanism of action
Chloramphenicol succinate is hydrolyzed into the active chloramphenicol.1 Chloramphenicol resembles uridine-5'-phosphate.6 It binds to the residues A2451 and A2452 in the 23S rRNA of the 50S ribosomal subunit of E. coli, which prevents translation.7
Target Actions Organism UDr hemagglutinin structural subunit inhibitorEscherichia coli - Absorption
Chloramphenicol succinate has a high degree of interpatient variability, with a Tmax of 18 minutes to 3 hours.2 A 1g oral chloramphenicol succinate dose every 6-8 hours reaches a mean Cmax of 11.2µg/mL with a Tmax of 1 hour.10
- Volume of distribution
Chloramphenicol succinate has a volume of distribution of 0.2-3.1L/kg.2
- Protein binding
Chloramphenicol succinate is 57-92% protein bound in plasma.2
- Metabolism
Chloramphenicol succinate is hydrolyzed to chloramphenicol.1 The propane-diol moiety of chloramphenicol can be metabolised through a number of pathways including glucuronidation, sulfate conjugation, phosphorylation, acetylation, and oxidation.4 The dichloroacetate moiety can be metabolised through hydrolysis of the amide group and dechlorination.4 The nitro functional group can also be metabolised to an aryl amine and aryl amide metabolite.4
Hover over products below to view reaction partners
- Route of elimination
6-80% of chloramphenicol succinate is eliminated unchanged in the urine, though this is highly variable between patients.2 On average, 30% of chloramphenicol succinate is eliminated unchanged in the urine and 10% is eliminated as the active chloramphenicol in the urine.2
- Half-life
The half life of chloramphenicol succinate in patients with normal renal and hepatic function is 0.6-2.7h.2
- Clearance
Chloramphenicol succinate's total clearance is 530-540mL/min in patients with normal renal and hepatic function, and 354mL/min in patients with renal or hepatic dysfunction.2 Chloramphenicol succinate's renal clearance is 222-260mL/min in patients with normal renal and hepatic function, and 66mL/min in patients with renal or hepatic dysfunction.2
- Adverse Effects
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Patients experiencing an overdose may present with shock, cyanosis, and coma.3 Treat patients with symptomatic and supportive measures which may include administration of fluids, exchange transfusions, and administration of dopamine.3
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 softwareAcenocoumarol The risk or severity of bleeding can be increased when Chloramphenicol succinate is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Chloramphenicol succinate is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Chloramphenicol succinate is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Chloramphenicol succinate. Benzocaine The risk or severity of methemoglobinemia can be increased when Chloramphenicol succinate is combined with Benzocaine. - Food Interactions
- No interactions found.
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 Chloramphenicol sodium succinate 872109HX6B 982-57-0 RPLOPBHEZLFENN-HTMVYDOJSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Chloromycetin Sodium Succinate Injection 100 mg/1mL Intravenous Monarch Pharmaceuticals, Inc. 1959-02-20 2007-10-05 US 
Chloromycetin Succinate Injection Powder, for solution 1 g / vial Intravenous Searchlight Pharma Inc 1959-12-31 Not applicable Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Chloramphenicol Sodium Succinate Injection, powder, lyophilized, for solution 1 g/10mL Intravenous Fresenius Kabi USA, LLC 2001-01-12 Not applicable US Chloramphenicol Sodium Succinate Injection, powder, lyophilized, for solution 1 g/10mL Intravenous General Injectables & Vaccines 2010-09-01 2017-01-18 US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Nitrobenzenes
- Direct Parent
- Nitrobenzenes
- Alternative Parents
- Nitroaromatic compounds / Fatty acid esters / Dicarboxylic acids and derivatives / Secondary carboxylic acid amides / Secondary alcohols / Carboxylic acid esters / Propargyl-type 1,3-dipolar organic compounds / Carboxylic acids / Organic oxoazanium compounds / Organic oxides show 8 more
- Substituents
- Alcohol / Alkyl chloride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Aromatic alcohol / Aromatic homomonocyclic compound / C-nitro compound / Carbonyl group / Carboxamide group / Carboxylic acid show 23 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Gram negative and gram positive bacteria
Chemical Identifiers
- UNII
- ZCX619U9A1
- CAS number
- 3544-94-3
- InChI Key
- LIRCDOVJWUGTMW-ZWNOBZJWSA-N
- InChI
- InChI=1S/C15H16Cl2N2O8/c16-14(17)15(24)18-10(7-27-12(22)6-5-11(20)21)13(23)8-1-3-9(4-2-8)19(25)26/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21)/t10-,13-/m1/s1
- IUPAC Name
- 4-[(2R,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid
- SMILES
- O[C@@H]([C@@H](COC(=O)CCC(O)=O)NC(=O)C(Cl)Cl)C1=CC=C(C=C1)[N+]([O-])=O
References
- General References
- Borde AS, Karlsson EM, Andersson K, Bjorhall K, Lennernas H, Abrahamsson B: Assessment of enzymatic prodrug stability in human, dog and simulated intestinal fluids. Eur J Pharm Biopharm. 2012 Apr;80(3):630-7. doi: 10.1016/j.ejpb.2011.11.011. Epub 2011 Dec 4. [Article]
- Ambrose PJ: Clinical pharmacokinetics of chloramphenicol and chloramphenicol succinate. Clin Pharmacokinet. 1984 May-Jun;9(3):222-38. doi: 10.2165/00003088-198409030-00004. [Article]
- Thompson WL, Anderson SE, Lipsky JJ, Lietman PS: Letter: Overdoses of chloramphenicol. JAMA. 1975 Oct 13;234(2):149-50. [Article]
- Bories GF, Cravedi JP: Metabolism of chloramphenicol: a story of nearly 50 years. Drug Metab Rev. 1994;26(4):767-83. doi: 10.3109/03602539408998326. [Article]
- Loree J, Lappin SL: Bacteriostatic Antibiotics . [Article]
- Jardetzky O: Studies on the Mechanism of Action of Chloramphenicol The Journal of Biological Chemistry. 1963 July;238(7):2498-2508. [Article]
- Schifano JM, Edifor R, Sharp JD, Ouyang M, Konkimalla A, Husson RN, Woychik NA: Mycobacterial toxin MazF-mt6 inhibits translation through cleavage of 23S rRNA at the ribosomal A site. Proc Natl Acad Sci U S A. 2013 May 21;110(21):8501-6. doi: 10.1073/pnas.1222031110. Epub 2013 May 6. [Article]
- Wiest DB, Cochran JB, Tecklenburg FW: Chloramphenicol toxicity revisited: a 12-year-old patient with a brain abscess. J Pediatr Pharmacol Ther. 2012 Apr;17(2):182-8. doi: 10.5863/1551-6776-17.2.182. [Article]
- FDA Approved Drug Products: Chloramphenicol Sodium Succinate Intravenous Injection [Link]
- DailyMed: Chloramphenicol Succinate Powder for Injection [Link]
- External Links
- KEGG Compound
- C11727
- PubChem Compound
- 656580
- PubChem Substance
- 99444036
- ChemSpider
- 570947
- 20769
- ChEBI
- 3606
- ChEMBL
- CHEMBL1201281
- ZINC
- ZINC000001532336
- PDBe Ligand
- CL8
- Wikipedia
- Chloramphenicol
- PDB Entries
- 2jkn / 2w5p
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, lyophilized, for solution Intravenous 1 g/10mL Powder 1000 mg/1vial Injection Intravenous 100 mg/1mL Powder, for solution Intravenous 1 g / vial Capsule Injection, powder, for solution Intravenous 1 G Injection, powder, lyophilized, for solution Intravenous 1.377 g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.112 mg/mL ALOGPS logP 1.34 ALOGPS logP 1.14 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 3.65 Chemaxon pKa (Strongest Basic) -3.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 156.07 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 92.24 m3·mol-1 Chemaxon Polarizability 37.74 Å3 Chemaxon Number of Rings 1 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 + 0.6818 Blood Brain Barrier + 0.9097 Caco-2 permeable - 0.5067 P-glycoprotein substrate Non-substrate 0.6633 P-glycoprotein inhibitor I Non-inhibitor 0.7924 P-glycoprotein inhibitor II Non-inhibitor 0.8358 Renal organic cation transporter Non-inhibitor 0.923 CYP450 2C9 substrate Non-substrate 0.8336 CYP450 2D6 substrate Non-substrate 0.8552 CYP450 3A4 substrate Non-substrate 0.5375 CYP450 1A2 substrate Non-inhibitor 0.6683 CYP450 2C9 inhibitor Inhibitor 0.5155 CYP450 2D6 inhibitor Non-inhibitor 0.8638 CYP450 2C19 inhibitor Inhibitor 0.797 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6768 Ames test Non AMES toxic 0.9159 Carcinogenicity Non-carcinogens 0.7575 Biodegradation Not ready biodegradable 0.6038 Rat acute toxicity 1.9742 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9022 hERG inhibition (predictor II) Non-inhibitor 0.781
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0udi-2900000000-dffb4890eac313691b97 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]- 180.69968 predictedDeepCCS 1.0 (2019) [M+H]+ 183.09525 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.0334 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Hemagglutinins of uropathogenic E.coli mediate adherence to the upper urinary tract. These adhesins bind to the Dr blood group antigen and also agglutinate human erythrocytes in the presence of D-m...
- Gene Name
- draA
- Uniprot ID
- P24093
- Uniprot Name
- Dr hemagglutinin structural subunit
- Molecular Weight
- 17058.095 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Enzymes
- Kind
- Protein
- Organism
- Escherichia coli
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Chloramphenicol o-acetyltransferase activity
- Specific Function
- This enzyme is an effector of chloramphenicol resistance in bacteria.
- Gene Name
- cat3
- Uniprot ID
- P00484
- Uniprot Name
- Chloramphenicol acetyltransferase 3
- Molecular Weight
- 24993.32 Da
References
- Shaw WV: Chloramphenicol acetyltransferase: enzymology and molecular biology. CRC Crit Rev Biochem. 1983;14(1):1-46. doi: 10.3109/10409238309102789. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Vodrazka Z, Jandova D, Grafnetterova J, Schuck O, Kalousek I, Tomaasek R, Lachmanova J: The binding of chloramphenicol to albumin of normal and uremic sera. Biochem Pharmacol. 1978;27(13):1717-20. doi: 10.1016/0006-2952(78)90545-2. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Nurbaeti SN, Olivier JC, Adier C, Marchand S, Couet W, Brillault J: Active Mediated Transport of Chloramphenicol and Thiamphenicol in a Calu-3 Lung Epithelial Cell Model. J Pharm Sci. 2018 Apr;107(4):1178-1184. doi: 10.1016/j.xphs.2017.11.021. Epub 2017 Dec 5. [Article]
Drug created at September 15, 2010 21:23 / Updated at February 02, 2024 22:53