Chloramphenicol
Identification
- Summary
Chloramphenicol is a broad spectrum antibiotic that is effective against a variety of susceptible and serious bacterial infections but is not frequently used because of its high risk of bone marrow toxicity.
- Brand Names
- Chloromycetin
- Generic Name
- Chloramphenicol
- DrugBank Accession Number
- DB00446
- Background
An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106)
The FDA has withdrawn all oral drug products containing chloramphenicol, due to the high risk of fatal aplastic anemia associated with this specific route of administration.6,7
- Type
- Small Molecule
- Groups
- Approved, Vet approved, Withdrawn
- Structure
- Weight
- Average: 323.129
Monoisotopic: 322.012326918 - Chemical Formula
- C11H12Cl2N2O5
- Synonyms
- Chloramphénicol
- Chloramphenicol
- Chloramphenicolum
- Chlornitromycin
- Cloramfenicol
- Cloranfenicol
- D-(−)-2,2-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenylethyl)acetamide
- D-(−)-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propanediol
- Laevomycetinum
- Levomicetina
- Levomycetin
- External IDs
- NSC-3069
Pharmacology
- Indication
Used in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against tetracycline-resistant vibrios. It is also used in eye drops or ointment to treat bacterial conjunctivitis.
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 Used in combination to treat Acne Combination Product in combination with: Allantoin (DB11100), Hydrocortisone acetate (DB14539), Nicoboxil (DB12911), Octasulfur (DB09353) •••••••••••• Used in combination to treat Bacterial conjunctivitis Combination Product in combination with: Tetracycline (DB00759), Colistimethate (DB01111) •••••••••••• ••••• ••••••••• •••••••• • ••••• Used in combination to treat Bacterial conjunctivitis caused by susceptible bacteria Combination Product in combination with: Dexamethasone (DB01234) •••••••••••• •••••••••• • ••••• Treatment of Bacterial infections •••••••••••• Used in combination to treat Bacterial dacryocystitis Combination Product in combination with: Colistimethate (DB01111), Tetracycline (DB00759) •••••••••••• ••••• ••••••••• •••••••• • ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Chloramphenicol is a broad-spectrum antibiotic that was derived from the bacterium Streptomyces venezuelae and is now produced synthetically. Chloramphenicol is effective against a wide variety of microorganisms, but due to serious side-effects (e.g., damage to the bone marrow, including aplastic anemia) in humans, it is usually reserved for the treatment of serious and life-threatening infections (e.g., typhoid fever). Chloramphenicol is bacteriostatic but may be bactericidal in high concentrations or when used against highly susceptible organisms. Chloramphenicol stops bacterial growth by binding to the bacterial ribosome (blocking peptidyl transferase) and inhibiting protein synthesis.
- Mechanism of action
Chloramphenicol is lipid-soluble, allowing it to diffuse through the bacterial cell membrane. It then reversibly binds to the L16 protein of the 50S subunit of bacterial ribosomes, where transfer of amino acids to growing peptide chains is prevented (perhaps by suppression of peptidyl transferase activity), thus inhibiting peptide bond formation and subsequent protein synthesis.
Target Actions Organism U50S ribosomal protein L16 inhibitorEscherichia coli (strain K12) UDr hemagglutinin structural subunit antagonistEscherichia coli UComplement decay-accelerating factor otherHumans - Absorption
Rapidly and completely absorbed from gastrointestinal tract following oral administration (bioavailability 80%). Well absorbed following intramuscular administration (bioavailability 70%). Intraocular and some systemic absorption also occurs after topical application to the eye.
- Volume of distribution
Not Available
- Protein binding
Plasma protein binding is 50-60% in adults and 32% is premature neonates.
- Metabolism
Hepatic, with 90% conjugated to inactive glucuronide.
- Route of elimination
Not Available
- Half-life
Half-life in adults with normal hepatic and renal function is 1.5 - 3.5 hours. In patients with impaired renal function half-life is 3 - 4 hours. In patients with severely impaired hepatic function half-life is 4.6 - 11.6 hours. Half-life in children 1 month to 16 years old is 3 - 6.5 hours, while half-life in infants 1 to 2 days old is 24 hours or longer and is highly variable, especially in low birth-weight infants.
- 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
Oral, mouse: LD50 = 1500 mg/kg; Oral, rat: LD50 = 2500 mg/kg. Toxic reactions including fatalities have occurred in the premature and newborn; the signs and symptoms associated with these reactions have been referred to as the gray syndrome. Symptoms include (in order of appearance) abdominal distension with or without emesis, progressive pallid cyanosis, vasomotor collapse frequently accompanied by irregular respiration, and death within a few hours of onset of these symptoms.
- Pathways
Pathway Category Chloramphenicol 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 softwareAbatacept The risk or severity of adverse effects can be increased when Chloramphenicol is combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Chloramphenicol. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Chloramphenicol. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Chloramphenicol. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is combined with Chloramphenicol. - Food Interactions
- Take on an empty stomach.
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.
- International/Other Brands
- Brochlor (Sanofi-Aventis) / Chloramex (Actavis) / Chlorocid (Egyt) / Chlorocol / Chlorsig (Sigma) / Fenicol (Alcon) / Globenicol / Halomycetin (Wabosan) / Oleomycetin / Sificetina (SIFI)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cebenicol Oph Liq 0.4% Liquid .4 % Ophthalmic Chauvin Pharma Inc. 1992-12-31 1997-07-15 Canada Chloramphenicol Ointment 1 % w/w Ophthalmic; Topical Pharma Stulln Inc. 1994-12-31 2019-11-23 Canada Chloramphenicol Solution 0.5 % Ophthalmic Pharma Stulln Inc. 1994-12-31 Not applicable Canada Chloromycetin Ointment 10 mg/1g Ophthalmic PARKE-DAVIS 2006-10-08 Not applicable US Chloromycetin Oph Ont 1% Ointment 1 % Ophthalmic Parke Davis Division, Warner Lambert Canada Inc. 1951-12-31 1999-04-08 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Novo-chlorocap Cap 250mg Capsule 250 mg / cap Oral Novopharm Limited 1966-12-31 2005-08-10 Canada Odan-chloramphenicol Liquid 0.5 mg / mL Ophthalmic Odan Laboratories Ltd 1985-12-31 Not applicable Canada Odan-chloramphenicol Ointment 10 mg / g Ophthalmic Odan Laboratories Ltd 1992-12-31 Not applicable Canada PMS-chloramphenicol Ophthalmic Soln 0.5% Solution / drops .5 % Ophthalmic Pharmascience Inc 1992-12-31 2016-10-28 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image OPTIVIS OPHTHALMIC OINTMENT Ointment 1 %w/w Ophthalmic บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด 2004-04-04 Not applicable Thailand VANAFEN OPTHALMIC OINTMENT Ointment 1 %w/w Ophthalmic บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด 1986-06-08 Not applicable Thailand VENAFEN-S EYE DROP Liquid 5 mg/1ml Ophthalmic บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด 1985-02-06 Not applicable Thailand ขี้ผึ้ง ยูนีซัน Ointment 1 %w/w Topical บริษัท ยูนีซัน จำกัด 1985-06-18 Not applicable Thailand ขี้ผึ้งโคลฟามีน ใส่แผล Ointment 1 %w/w Topical บริษัท แลชแมน จำกัด จำกัด 1987-03-17 Not applicable Thailand - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Actinac Pwr Chloramphenicol (40 mg / g) + Allantoin (24 mg / g) + Hydrocortisone acetate (40 mg / g) + Nicoboxil (24 mg / g) + Octasulfur (320 mg / g) Powder Topical Roussel Canada Inc. 1978-12-31 1996-09-09 Canada Actinac Pws Chloramphenicol (40 mg / g) + Allantoin (24 mg / g) + Hydrocortisone acetate (40 mg / g) + Nicoboxil (24 mg / g) + Octasulfur (320 mg / g) Powder, for solution Topical Hoechst Roussel Canada Inc. 1994-12-31 2001-07-20 Canada CLORADEX Chloramphenicol (0.5 %) + Dexamethasone (0.2 %) Suspension / drops Ophthalmic Bausch & Lomb Iom S.P.A. 2014-07-08 Not applicable Italy CLORADEX Chloramphenicol (0.5 %) + Dexamethasone (0.2 %) Suspension / drops Ophthalmic Bausch & Lomb Iom S.P.A. 2014-07-08 Not applicable Italy COLBIOCIN Chloramphenicol (4 MG/G) + Colistimethate sodium (180000 IU) + Tetracycline (4.2 MG/G) Solution / drops Ophthalmic Sifi S.P.A. 2014-07-08 2022-06-01 Italy
Categories
- ATC Codes
- D06AX02 — Chloramphenicol
- D06AX — Other antibiotics for topical use
- D06A — ANTIBIOTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- D10AF — Antiinfectives for treatment of acne
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- G01AA — Antibiotics
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- J01BA — Amphenicols
- J01B — AMPHENICOLS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Alcohols
- Amphenicols
- Anti-Acne Preparations
- Anti-Acne Preparations for Topical Use
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antibiotics for Topical Use
- Antiinfectives for Systemic Use
- Antiinfectives for Treatment of Acne
- Benzene Derivatives
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (strong)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Glycols
- Gynecological Antiinfectives and Antiseptics
- Immunosuppressive Agents
- Myelosuppressive Agents
- Nitro Compounds
- Nitrobenzenes
- OAT1/SLC22A6 inhibitors
- Ophthalmological and Otological Preparations
- Ophthalmologicals
- Otologicals
- Propylene Glycols
- Protein Synthesis Inhibitors
- Sensory Organs
- 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 / Secondary alcohols / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Carboximidic acids / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic zwitterions show 4 more
- Substituents
- Alcohol / Alkyl chloride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Aromatic alcohol / Aromatic homomonocyclic compound / C-nitro compound / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative show 17 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- organochlorine compound (CHEBI:17698) / Aromatic compounds (C00918)
- Affected organisms
- Enteric bacteria and other eubacteria
- Gram negative and gram positive bacteria
- Streptococcus pneumoniae
- Neisseria meningitidis
- Haemophilus influenzae
- Enterococcus faecium
Chemical Identifiers
- UNII
- 66974FR9Q1
- CAS number
- 56-75-7
- InChI Key
- WIIZWVCIJKGZOK-RKDXNWHRSA-N
- InChI
- InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
- IUPAC Name
- 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
- SMILES
- OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O
References
- Synthesis Reference
Guang-Zhong Wu, Wanda I. Tormos, "Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates." U.S. Patent US5352832, issued May, 1992.
US5352832- General References
- Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(2):213-9. [Article]
- Wali SS, Macfarlane JT, Weir WR, Cleland PG, Ball PA, Hassan-King M, Whittle HC, Greenwood BM: Single injection treatment of meningococcal meningitis. 2. Long-acting chloramphenicol. Trans R Soc Trop Med Hyg. 1979;73(6):698-702. [Article]
- Puddicombe JB, Wali SS, Greenwood BM: A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of meningococcal meningitis. Trans R Soc Trop Med Hyg. 1984;78(3):399-403. [Article]
- Pecoul B, Varaine F, Keita M, Soga G, Djibo A, Soula G, Abdou A, Etienne J, Rey M: Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis. Lancet. 1991 Oct 5;338(8771):862-6. [Article]
- Nathan N, Borel T, Djibo A, Evans D, Djibo S, Corty JF, Guillerm M, Alberti KP, Pinoges L, Guerin PJ, Legros D: Ceftriaxone as effective as long-acting chloramphenicol in short-course treatment of meningococcal meningitis during epidemics: a randomised non-inferiority study. Lancet. 2005 Jul 23-29;366(9482):308-13. [Article]
- Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
- Federal Register: Determination That CHLOROMYCETIN (Chloramphenicol) Capsules, 250 Milligrams, Were Withdrawn From Sale for Reasons of Safety or Effectiveness [Link]
- External Links
- Human Metabolome Database
- HMDB0014589
- KEGG Drug
- D00104
- KEGG Compound
- C00918
- PubChem Compound
- 5959
- PubChem Substance
- 46505318
- ChemSpider
- 5744
- BindingDB
- 23447
- 2348
- ChEBI
- 17698
- ChEMBL
- CHEMBL130
- ZINC
- ZINC000000113382
- Therapeutic Targets Database
- DAP001356
- PharmGKB
- PA448927
- PDBe Ligand
- CLM
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Chloramphenicol
- PDB Entries
- 1cla / 1k01 / 1nji / 1qhs / 1qhy / 1usq / 2jkj / 2jkl / 2uxp / 2xat … show 25 more
- FDA label
- Download (191 KB)
- MSDS
- Download (74.1 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 4 Completed Treatment Ophthalmopathy , Lacrimal System 1 0 Terminated Treatment Osteomyelitis 1 Not Available Completed Not Available Antibiotic Resistant Infection / Bacterial Infections / Surgical Site Infections 1
Pharmacoeconomics
- Manufacturers
- John j ferrante
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Parkedale pharmaceuticals inc
- Armenpharm ltd
- Parke davis pharmaceutical research div warner lambert co
- Altana inc
- Pharmafair inc
- Allergan pharmaceutical
- Alcon laboratories inc
- Akorn inc
- Optopics laboratories corp
- Elkins sinn div ah robins co inc
- App pharmaceuticals llc
- Gruppo lepetit spa sub merrell dow pharmaceuticals inc
- Angus chemical co
- Packagers
- Akorn Inc.
- APP Pharmaceuticals
- Darby Dental Supply Co. Inc.
- General Injectables and Vaccines Inc.
- Gruppo Lepetit SPA
- Ivax Pharmaceuticals
- Medisca Inc.
- Professional Compounding Centers America LLC
- Spectrum Pharmaceuticals
- Dosage Forms
Form Route Strength Powder Topical Powder, for solution Topical Solution Ophthalmic 5.0 mg Capsule Oral 250 mg Syrup Oral 125 mg/5ml Gel Conjunctival Ointment Conjunctival Solution / drops Conjunctival Suspension / drops Conjunctival Suspension / drops Conjunctival 0.5 % Liquid Ophthalmic .4 % Ointment Ophthalmic Insert Vaginal 250 MG Insert Vaginal 500 MG Capsule Oral Cream Ointment Ophthalmic; Topical 1 % w/w Solution Ophthalmic 0.5 % Ointment Ophthalmic Solution Auricular (otic) 5 % Solution Auricular (otic) 5 % w/v Solution Ophthalmic 25 mg/5ml Injection, powder, for solution Intravenous; Parenteral 1 G Suspension Oral Ointment Ophthalmic 10 mg/1g Capsule, liquid filled Oral 250 mg Ointment Ophthalmic 1 % Liquid Ophthalmic .5 % Solution / drops Auricular (otic) 5 mg/1mL Solution / drops Ophthalmic .5 % Ointment Ophthalmic 10 mg / g Suspension / drops Ophthalmic Capsule, coated Oral 250 mg Solution Ophthalmic 5.000 mg Ointment Ophthalmic 5.000 g Injection, powder, for solution Intravenous 1 G/10ML Ointment Solution Conjunctival; Ophthalmic 5 mg Injection, powder, for solution Parenteral 1000 mg Ointment Ophthalmic 0.500 g Solution Ophthalmic Cream Solution / drops Auricular (otic) Ointment Conjunctival; Ophthalmic Solution Ophthalmic 5 mg/1mL Ointment Ophthalmic 5.000 mg Solution Ophthalmic 5.00 mg Suspension Oral 100 ml Suspension Oral 50 ml Solution 5.000 mg Capsule Oral 0.25 g Insert Vaginal 0.25 g Suspension Oral 125 mg Ointment Ophthalmic 10 mg Solution Auricular (otic) 2.5 mg Ointment Topical Injection, solution Intramuscular; Intravenous 1 g Ointment 1 % w/w Ointment 10 mg/g Solution / drops Ophthalmic; Topical .5 % Solution Ophthalmic 0.5 % w/v Solution / drops Ophthalmic 0.5 %W/V Capsule Oral 250 mg / cap Liquid Ophthalmic 0.5 mg / mL Ointment Ophthalmic 10 mg/g Solution Ophthalmic 5.0 mg/ml Solution Ophthalmic 2.5 mg / mL Solution Ophthalmic 5 mg / mL Suspension Auricular (otic); Ophthalmic Solution Auricular (otic) Solution Intravenous 1.000 g Solution / drops Auricular (otic) Solution / drops Ophthalmic Tablet, coated Oral 250 mg Suppository 125 mg Suppository 250 mg Solution / drops Ophthalmic Solution / drops Ophthalmic 0.4 % Ointment Ophthalmic .2 % Solution / drops Auricular (otic) 5 % Solution / drops Ophthalmic .2 % Ointment Auricular (otic); Ophthalmic Solution Conjunctival; Ophthalmic Solution / drops Ophthalmic 0.5 % W/V Cream; ointment Solution / drops Solution Ophthalmic 5 MG/ML Ointment Topical 1 %w/w Ointment Topical 2 %w/w Liquid Ophthalmic 5 mg/1ml Capsule Oral 100 mg Solution Liquid Ophthalmic Liquid Auricular (otic) 10 mg/1ml Tablet, coated Oral 100 mg Liquid Auricular (otic) 50 mg/1ml Liquid Auricular (otic) Tablet 250 mg Ointment Ophthalmic 1 %w/w - Prices
Unit description Cost Unit Chloramphen na succ 1 gm vial 28.74USD vial Chloramphenicol palm powder 2.52USD g Chloramphenicol crystals 1.32USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 171 Bartz, Q.R.; U.S. Patent 2,483,871; October 4, 1949; assigned to Parke, Davis & Company Crooks, H.M., Jr., Rebstock, M.C., Controulis, J. and Bartz, Q.R.; U.S. Patent 2,483,884; October 4, 1949; assigned to Parke, Davis & Company. Ehrlich, J., Smith, R.M. and Penner, M.A.; U.S. Patent 2,483,892; October 4, 1949; assigned to Parke, Davis & Company. Carrara, G.; U.S. Patent 2,776,312; January 1, 1957 Slack, R.; U.S. Patent 2,786,870; March 26, 1957; assigned to Parke, Davis & Company. water solubility 2500 mg/L (at 25 °C) MERCK INDEX (2001) logP 1.14 HANSCH,C ET AL. (1995) logS -2.11 ADME Research, USCD Caco2 permeability -4.69 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.461 mg/mL ALOGPS logP 1.15 ALOGPS logP 0.88 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 8.69 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 112.7 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 72.2 m3·mol-1 Chemaxon Polarizability 28.13 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 + 0.9157 Blood Brain Barrier + 0.9366 Caco-2 permeable + 0.7367 P-glycoprotein substrate Non-substrate 0.7305 P-glycoprotein inhibitor I Non-inhibitor 0.9216 P-glycoprotein inhibitor II Non-inhibitor 0.8822 Renal organic cation transporter Non-inhibitor 0.9477 CYP450 2C9 substrate Non-substrate 0.7775 CYP450 2D6 substrate Non-substrate 0.8934 CYP450 3A4 substrate Non-substrate 0.5936 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.5483 Biodegradation Ready biodegradable 0.5053 Rat acute toxicity 2.2247 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9658 hERG inhibition (predictor II) Non-inhibitor 0.8764
Spectra
- Mass Spec (NIST)
- Download (10.9 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 170.2835324 predictedDarkChem Lite v0.1.0 [M-H]- 161.1189213 predictedDarkChem Lite v0.1.0 [M-H]- 170.4010324 predictedDarkChem Lite v0.1.0 [M-H]- 162.07011 predictedDeepCCS 1.0 (2019) [M+H]+ 170.8240324 predictedDarkChem Lite v0.1.0 [M+H]+ 170.29197 predictedDarkChem Lite v0.1.0 [M+H]+ 170.7960324 predictedDarkChem Lite v0.1.0 [M+H]+ 164.42812 predictedDeepCCS 1.0 (2019) [M+Na]+ 170.9343324 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.2667776 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.3030324 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.52127 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Trna binding
- Specific Function
- This protein binds directly to 23S ribosomal RNA and is located at the A site of the peptidyltransferase center. It contacts the A and P site tRNAs. It has an essential role in subunit assembly, wh...
- Gene Name
- rplP
- Uniprot ID
- P0ADY7
- Uniprot Name
- 50S ribosomal protein L16
- Molecular Weight
- 15281.125 Da
References
- Murray IA, Cann PA, Day PJ, Derrick JP, Sutcliffe MJ, Shaw WV, Leslie AG: Steroid recognition by chloramphenicol acetyltransferase: engineering and structural analysis of a high affinity fusidic acid binding site. J Mol Biol. 1995 Dec 15;254(5):993-1005. [Article]
- Nierhaus D, Nierhaus KH: Identification of the chloramphenicol-binding protein in Escherichia coli ribosomes by partial reconstitution. Proc Natl Acad Sci U S A. 1973 Aug;70(8):2224-8. [Article]
- Baxter RM, Ganoza MC, Zahid N, Chung DG: Reconstruction of peptidyltransferase activity on 50S and 70S ribosomal particles by peptide fragments of protein L16. Eur J Biochem. 1987 Mar 16;163(3):473-9. [Article]
- Kind
- Protein
- Organism
- Escherichia coli
- Pharmacological action
- Unknown
- Actions
- Antagonist
- 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
- Swanson TN, Bilge SS, Nowicki B, Moseley SL: Molecular structure of the Dr adhesin: nucleotide sequence and mapping of receptor-binding domain by use of fusion constructs. Infect Immun. 1991 Jan;59(1):261-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other
- General Function
- Virus receptor activity
- Specific Function
- This protein recognizes C4b and C3b fragments that condense with cell-surface hydroxyl or amino groups when nascent C4b and C3b are locally generated during C4 and c3 activation. Interaction of daf...
- Gene Name
- CD55
- Uniprot ID
- P08174
- Uniprot Name
- Complement decay-accelerating factor
- Molecular Weight
- 41399.79 Da
References
- Pettigrew D, Anderson KL, Billington J, Cota E, Simpson P, Urvil P, Rabuzin F, Roversi P, Nowicki B, du Merle L, Le Bouguenec C, Matthews S, Lea SM: High resolution studies of the Afa/Dr adhesin DraE and its interaction with chloramphenicol. J Biol Chem. 2004 Nov 5;279(45):46851-7. Epub 2004 Aug 24. [Article]
- Korotkova N, Chattopadhyay S, Tabata TA, Beskhlebnaya V, Vigdorovich V, Kaiser BK, Strong RK, Dykhuizen DE, Sokurenko EV, Moseley SL: Selection for functional diversity drives accumulation of point mutations in Dr adhesins of Escherichia coli. Mol Microbiol. 2007 Apr;64(1):180-94. [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
- Murray IA, Cann PA, Day PJ, Derrick JP, Sutcliffe MJ, Shaw WV, Leslie AG: Steroid recognition by chloramphenicol acetyltransferase: engineering and structural analysis of a high affinity fusidic acid binding site. J Mol Biol. 1995 Dec 15;254(5):993-1005. [Article]
- Derrick JP, Lian LY, Roberts GC, Shaw WV: Analysis of the binding of 1,3-diacetylchloramphenicol to chloramphenicol acetyltransferase by isotope-edited 1H NMR and site-directed mutagenesis. Biochemistry. 1992 Sep 8;31(35):8191-5. [Article]
- Murray IA, Lewendon A, Shaw WV: Stabilization of the imidazole ring of His-195 at the active site of chloramphenicol acetyltransferase. J Biol Chem. 1991 Jun 25;266(18):11695-8. [Article]
- Kind
- Protein
- Organism
- Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Chloramphenicol o-acetyltransferase activity
- Specific Function
- This enzyme is an effector of chloramphenicol (Cm) resistance in bacteria. Acetylates Cm but not 1-acetoxy-Cm.
- Gene Name
- cat
- Uniprot ID
- P26841
- Uniprot Name
- Chloramphenicol acetyltransferase
- Molecular Weight
- 23524.385 Da
References
- Potrykus J, Baranska S, Wegrzyn G: Inactivation of the acrA gene is partially responsible for chloramphenicol sensitivity of Escherichia coli CM2555 strain expressing the chloramphenicol acetyltransferase gene. Microb Drug Resist. 2002 Fall;8(3):179-85. [Article]
- Potrykus J, Wegrzyn G: Chloramphenicol-sensitive Escherichia coli strain expressing the chloramphenicol acetyltransferase (cat) gene. Antimicrob Agents Chemother. 2001 Dec;45(12):3610-2. [Article]
- Navia MM, Capitano L, Ruiz J, Vargas M, Urassa H, Schellemberg D, Gascon J, Vila J: Typing and characterization of mechanisms of resistance of Shigella spp. isolated from feces of children under 5 years of age from Ifakara, Tanzania. J Clin Microbiol. 1999 Oct;37(10):3113-7. [Article]
- Kind
- Protein
- Organism
- Streptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745)
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Kinase activity
- Specific Function
- Inactivates chloramphenicol by catalyzing the transfer of the gamma-phosphate of ATP to the antibiotic's C-3' hydroxyl group.
- Gene Name
- Not Available
- Uniprot ID
- Q56148
- Uniprot Name
- Chloramphenicol 3-O phosphotransferase
- Molecular Weight
- 18816.255 Da
References
- Ellis J, Campopiano DJ, Izard T: Cubic crystals of chloramphenicol phosphotransferase from Streptomyces venezuelae in complex with chloramphenicol. Acta Crystallogr D Biol Crystallogr. 1999 May;55(Pt 5):1086-8. [Article]
- Izard T, Ellis J: The crystal structures of chloramphenicol phosphotransferase reveal a novel inactivation mechanism. EMBO J. 2000 Jun 1;19(11):2690-700. [Article]
- Mosher RH, Camp DJ, Yang K, Brown MP, Shaw WV, Vining LC: Inactivation of chloramphenicol by O-phosphorylation. A novel resistance mechanism in Streptomyces venezuelae ISP5230, a chloramphenicol producer. J Biol Chem. 1995 Nov 10;270(45):27000-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- 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
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- 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
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Flockhart Table of Drug Interactions [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54