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The FDA has withdrawn all oral drug products containing chloramphenicol, due to the high risk of fatal aplastic anemia associated with this specific route of administration.^6,7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Approved, Vet approved, Withdrawn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

Similar Structures

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

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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.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	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

Skin disinfection

Contraindications & Blackbox Warnings

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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	inhibitor	Escherichia coli (strain K12)
UDr hemagglutinin structural subunit	antagonist	Escherichia coli
UComplement decay-accelerating factor	other	Humans

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

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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
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Abatacept	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

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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
Cebenicol Oph Liq 0.4%	Liquid	.4 %	Ophthalmic	Chauvin Pharma Inc.	1992-12-31	1997-07-15
Chloramphenicol	Ointment	1 % w/w	Ophthalmic; Topical	Pharma Stulln Inc.	1994-12-31	2019-11-23
Chloramphenicol	Solution	0.5 %	Ophthalmic	Pharma Stulln Inc.	1994-12-31	Not applicable
Chloromycetin	Ointment	10 mg/1g	Ophthalmic	PARKE-DAVIS	2006-10-08	Not applicable
Chloromycetin Oph Ont 1%	Ointment	1 %	Ophthalmic	Parke Davis Division, Warner Lambert Canada Inc.	1951-12-31	1999-04-08

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Novo-chlorocap Cap 250mg	Capsule	250 mg / cap	Oral	Novopharm Limited	1966-12-31	2005-08-10
Odan-chloramphenicol	Liquid	0.5 mg / mL	Ophthalmic	Odan Laboratories Ltd	1985-12-31	Not applicable
Odan-chloramphenicol	Ointment	10 mg / g	Ophthalmic	Odan Laboratories Ltd	1992-12-31	Not applicable
PMS-chloramphenicol Ophthalmic Soln 0.5%	Solution / drops	.5 %	Ophthalmic	Pharmascience Inc	1992-12-31	2016-10-28

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
OPTIVIS OPHTHALMIC OINTMENT	Ointment	1 %w/w	Ophthalmic	บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด	2004-04-04	Not applicable
VANAFEN OPTHALMIC OINTMENT	Ointment	1 %w/w	Ophthalmic	บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด	1986-06-08	Not applicable
VENAFEN-S EYE DROP	Liquid	5 mg/1ml	Ophthalmic	บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด	1985-02-06	Not applicable
ขี้ผึ้ง ยูนีซัน	Ointment	1 %w/w	Topical	บริษัท ยูนีซัน จำกัด	1985-06-18	Not applicable
ขี้ผึ้งโคลฟามีน ใส่แผล	Ointment	1 %w/w	Topical	บริษัท แลชแมน จำกัด จำกัด	1987-03-17	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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
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
CLORADEX	Chloramphenicol (0.5 %) + Dexamethasone (0.2 %)	Suspension / drops	Ophthalmic	Bausch & Lomb Iom S.P.A.	2014-07-08	Not applicable
CLORADEX	Chloramphenicol (0.5 %) + Dexamethasone (0.2 %)	Suspension / drops	Ophthalmic	Bausch & Lomb Iom S.P.A.	2014-07-08	Not applicable
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

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
RxNav: 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 …

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FDA label

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MSDS

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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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

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Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0udi-3900000000-2ba6754ba027027454d1
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-014i-0920000000-96bfb1c31d89e3f10caf
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0kmi-0945000000-40a09f3f9528bd669823
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0udi-0900000000-64dbb16119292f4410e2
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0udi-0900000000-5c8fbcad8e93fa9f2906
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0uk9-1900000000-4c6518583a7488591aa3
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00di-1900000000-00574ed667d64b4a45e9
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00di-1900000000-d4ac63e9260ab31ac6b1
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-0zml-0933000000-4ae209b29cb52d4e3844
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-056r-0933000000-74ff5ec451e56526d425
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-0a4l-0590000000-90d108018a0f99815fb7
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-0a4l-0690000000-161f2afa43298fd3437a
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0uk9-0923000000-86308db0ec59b40b1533
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-05fr-0094000000-ad8da59124745b38a76f
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00di-0390000000-06fcf307f2fdb79741ad
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-014i-1940000000-be07d702045f4d3e05ac
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-014i-1910000000-55a74a828c3c9750ee1c
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0159-2900000000-bf685c17ab79583133ee
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0159-4900000000-e6f6ccbfffe89c345365
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00di-0191000000-41f70006e2b4e5f8d8aa
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-0960000000-d64346c38bebc079f066
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0f89-0491000000-c7e13efc8c7ed0e68cff
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0f89-0492000000-4b6f8c10f6acc0f02196
MS/MS Spectrum - , positive	LC-MS/MS	splash10-014i-0920000000-96bfb1c31d89e3f10caf
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0600-0592000000-129db104bb506af06de0
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]-	170.2835324	predicted	DarkChem Lite v0.1.0
[M-H]-	161.1189213	predicted	DarkChem Lite v0.1.0
[M-H]-	170.4010324	predicted	DarkChem Lite v0.1.0
[M-H]-	162.07011	predicted	DeepCCS 1.0 (2019)
[M+H]+	170.8240324	predicted	DarkChem Lite v0.1.0
[M+H]+	170.29197	predicted	DarkChem Lite v0.1.0
[M+H]+	170.7960324	predicted	DarkChem Lite v0.1.0
[M+H]+	164.42812	predicted	DeepCCS 1.0 (2019)
[M+Na]+	170.9343324	predicted	DarkChem Lite v0.1.0
[M+Na]+	180.2667776	predicted	DarkChem Lite v0.1.0
[M+Na]+	170.3030324	predicted	DarkChem Lite v0.1.0
[M+Na]+	170.52127	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. 50S ribosomal protein L16

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]

Details2. Dr hemagglutinin structural subunit

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]

Details3. Complement decay-accelerating factor

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

Details1. Chloramphenicol acetyltransferase 3

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]

Details2. Chloramphenicol acetyltransferase

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]

Details3. Chloramphenicol 3-O phosphotransferase

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]

Details4. Cytochrome P450 2C19

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

Park JY, Kim KA, Kim SL: Chloramphenicol is a potent inhibitor of cytochrome P450 isoforms CYP2C19 and CYP3A4 in human liver microsomes. Antimicrob Agents Chemother. 2003 Nov;47(11):3464-9. [Article]
Flockhart Table of Drug Interactions [Link]

Details5. Cytochrome P450 3A4

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

Park JY, Kim KA, Kim SL: Chloramphenicol is a potent inhibitor of cytochrome P450 isoforms CYP2C19 and CYP3A4 in human liver microsomes. Antimicrob Agents Chemother. 2003 Nov;47(11):3464-9. [Article]
Flockhart Table of Drug Interactions [Link]

Details6. Cytochrome P450 3A5

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]

Details7. Cytochrome P450 3A7

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

Details1. Solute carrier family 22 member 6

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

Chloramphenicol

Identification

Structure for Chloramphenicol (DB00446)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

Enzymes

References

References

References

References

References

References

References

Transporters

References