Identification

Name
Chloramphenicol
Accession Number
DB00446  (APRD00862, EXPT00942)
Type
Small Molecule
Groups
Approved, Vet approved
Description

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)

Structure
Thumb
Synonyms
  • Chloramphénicol
  • Chloramphenicolum
  • Chlornitromycin
  • Cloramfenicol
  • 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
Product Ingredients
IngredientUNIICASInChI Key
Chloramphenicol sodium succinate872109HX6B982-57-0RPLOPBHEZLFENN-HTMVYDOJSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cebenicol Oph Liq 0.4%Liquid.4 %OphthalmicChauvin Pharma Inc.1992-12-311997-07-15Canada
ChloramphenicolOintment1 %Ophthalmic; TopicalEberth Pharmaceuticals Inc1994-12-31Not applicableCanada
ChloramphenicolSolution0.5 %OphthalmicEberth Pharmaceuticals Inc1994-12-31Not applicableCanada
ChloromycetinOintment10 mg/1gOphthalmicPARKE-DAVIS2006-10-08Not applicableUs
Chloromycetin Oph Ont 1%Ointment1 %OphthalmicParke Davis Division, Warner Lambert Canada Inc.1951-12-311999-04-08Canada
Chloromycetin Oph Soln 0.5%Liquid.5 %OphthalmicParke Davis Division, Warner Lambert Canada Inc.1971-12-311997-08-25Canada
Chloromycetin OticSolution / drops5 mg/1mLAuricular (otic)Monarch Pharmaceuticals, Inc.1953-03-302002-02-12Us
Chloromycetin Sodium SuccinateInjection100 mg/1mLIntravenousMonarch Pharmaceuticals, Inc.1959-02-202007-10-05Us
Chloromycetin Succinate Injection 1gmPowder, for solution1 gIntramuscular; IntravenousErfa Canada 2012 Inc1959-12-31Not applicableCanada
Chloroptic Dps 0.5%Solution / drops.5 %OphthalmicAllergan1963-12-312011-08-04Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chloramphenicol Sodium SuccinateInjection, powder, lyophilized, for solution1 g/10mLIntravenousFresenius Kabi2001-01-12Not applicableUs
Chloramphenicol Sodium SuccinateInjection, powder, lyophilized, for solution1 g/10mLIntravenousGeneral Injectables & Vaccines2010-09-012017-01-18Us
Novo-chlorocap Cap 250mgCapsule250 mgOralNovopharm Limited1966-12-312005-08-10Canada
Odan-chloramphenicolOintment10 mgOphthalmicOdan Laboratories Ltd1992-12-31Not applicableCanada
Odan-chloramphenicolLiquid0.5 mgOphthalmicOdan Laboratories Ltd1985-12-31Not applicableCanada
PMS-chloramphenicol Ophthalmic OintmentOintment10 mgOphthalmicPharmascience IncNot applicableNot applicableCanada
PMS-chloramphenicol Ophthalmic Soln 0.5%Solution / drops.5 %OphthalmicPharmascience Inc1992-12-312016-10-28Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Actinac PwrChloramphenicol (40 mg) + Allantoin (24 mg) + Hydrocortisone acetate (40 mg) + Nicoboxil (24 mg) + Octasulfur (320 mg)PowderTopicalRoussel Canada Inc.1978-12-311996-09-09Canada
Actinac PwsChloramphenicol (40 mg) + Allantoin (24 mg) + Hydrocortisone acetate (40 mg) + Nicoboxil (24 mg) + Octasulfur (320 mg)Powder, for solutionTopicalHoechst Roussel Canada Inc.1994-12-312001-07-20Canada
Ophthocort OntChloramphenicol (10 mg) + Hydrocortisone acetate (5 mg) + Polymyxin B Sulfate (5000 unit)OintmentOphthalmicParke Davis Division, Warner Lambert Canada Inc.1958-12-311998-04-07Canada
Pentamycetin/hcChloramphenicol (10 mg) + Hydrocortisone acetate (10 mg)OintmentAuricular (otic); OphthalmicSandoz Canada Incorporated1992-12-31Not applicableCanada
Pentamycetin/hcChloramphenicol (2 mg) + Hydrocortisone acetate (10 mg)SuspensionAuricular (otic); OphthalmicSandoz Canada Incorporated1992-12-31Not applicableCanada
Sopamycetin/hc OintmentChloramphenicol (10 mg) + Hydrocortisone acetate (10 mg)OintmentAuricular (otic); OphthalmicLaboratoires Charton Laboratories1992-12-311999-01-16Canada
Sopamycetin/hc OntChloramphenicol (.2 %) + Hydrocortisone acetate (1 %)OintmentAuricular (otic); OphthalmicLaboratoires Charton Laboratories1988-12-311999-01-16Canada
Sopamycetin/hc SuspChloramphenicol (.2 %) + Hydrocortisone acetate (1 %)Solution / dropsOphthalmicLaboratoires Charton Laboratories1988-12-311999-01-16Canada
International/Other Brands
Brochlor (Sanofi-Aventis) / Chloramex (Actavis) / Chlorocid (Egyt) / Chlorocol / Chloromycetin (Pfizer) / Chlorsig (Sigma) / Fenicol (Alcon) / Globenicol / Halomycetin (Wabosan) / Oleomycetin / Sificetina (SIFI)
Categories
UNII
66974FR9Q1
CAS number
56-75-7
Weight
Average: 323.129
Monoisotopic: 322.012326918
Chemical Formula
C11H12Cl2N2O5
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

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.

Associated Conditions
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.

TargetActionsOrganism
U50S ribosomal protein L16
inhibitor
Escherichia coli (strain K12)
UDr hemagglutinin structural subunit
antagonist
Escherichia coli
UComplement decay-accelerating factor
other
Human
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
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.

Affected organisms
  • Enteric bacteria and other eubacteria
  • Gram negative and gram positive bacteria
  • Streptococcus pneumoniae
  • Neisseria meningitidis
  • Haemophilus influenzae
  • Enterococcus faecium
Pathways
PathwayCategory
Chloramphenicol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Chloramphenicol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Chloramphenicol.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be decreased when combined with Chloramphenicol.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Chloramphenicol.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Chloramphenicol.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Chloramphenicol.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Chloramphenicol.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Chloramphenicol.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when 9-(N-methyl-L-isoleucine)-cyclosporin A is combined with Chloramphenicol.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Chloramphenicol.
Food Interactions
  • Take on an empty stomach.

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
  1. Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(2):213-9. [PubMed:1398851]
  2. 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. [PubMed:538813]
  3. 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. [PubMed:6464136]
  4. 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. [PubMed:1681224]
  5. 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. [PubMed:16039333]
External Links
Human Metabolome Database
HMDB0014589
KEGG Drug
D00104
KEGG Compound
C00918
PubChem Compound
5959
PubChem Substance
46505318
ChemSpider
5744
BindingDB
50028502
ChEBI
17698
ChEMBL
CHEMBL130
Therapeutic Targets Database
DAP001356
PharmGKB
PA448927
HET
CLM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Chloramphenicol
ATC Codes
J01BA01 — ChloramphenicolG01AA05 — ChloramphenicolS01AA01 — ChloramphenicolD10AF03 — ChloramphenicolS02AA01 — ChloramphenicolS03AA08 — ChloramphenicolD06AX02 — Chloramphenicol
AHFS Codes
  • 52:04.04 — Antibacterials
  • 08:12.08 — Chloramphenicol
PDB Entries
1cla / 1k01 / 1nji / 1qhs / 1qhy / 1usq / 2jkj / 2jkl / 2uxp / 2xat
show 10 more
FDA label
Download (191 KB)
MSDS
Download (74.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1

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
FormRouteStrength
PowderTopical
Powder, for solutionTopical
LiquidOphthalmic.4 %
OintmentOphthalmic; Topical1 %
SolutionOphthalmic0.5 %
Injection, powder, lyophilized, for solutionIntravenous1 g/10mL
OintmentOphthalmic10 mg/1g
OintmentOphthalmic1 %
LiquidOphthalmic.5 %
Solution / dropsAuricular (otic)5 mg/1mL
InjectionIntravenous100 mg/1mL
Powder, for solutionIntramuscular; Intravenous1 g
Solution / dropsOphthalmic.5 %
OintmentOphthalmic10 mg
SolutionOphthalmic5 mg/1mL
Solution / dropsOphthalmic; Topical.5 %
CapsuleOral250 mg
LiquidOphthalmic0.5 mg
OintmentOphthalmic
SolutionOphthalmic2.5 mg
SolutionOphthalmic5 mg
SuspensionAuricular (otic); Ophthalmic
OintmentOphthalmic.2 %
Solution / dropsAuricular (otic)5 %
Solution / dropsOphthalmic.2 %
OintmentAuricular (otic); Ophthalmic
Solution / dropsOphthalmic
Prices
Unit descriptionCostUnit
Chloramphen na succ 1 gm vial28.74USD vial
Chloramphenicol palm powder2.52USD g
Chloramphenicol crystals1.32USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)171Bartz, 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 solubility2500 mg/L (at 25 °C)MERCK INDEX (2001)
logP1.14HANSCH,C ET AL. (1995)
logS-2.11ADME Research, USCD
Caco2 permeability-4.69ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.461 mg/mLALOGPS
logP1.15ALOGPS
logP0.88ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)7.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area115.38 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity73.2 m3·mol-1ChemAxon
Polarizability28.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9157
Blood Brain Barrier+0.9366
Caco-2 permeable+0.7367
P-glycoprotein substrateNon-substrate0.7305
P-glycoprotein inhibitor INon-inhibitor0.9216
P-glycoprotein inhibitor IINon-inhibitor0.8822
Renal organic cation transporterNon-inhibitor0.9477
CYP450 2C9 substrateNon-substrate0.7775
CYP450 2D6 substrateNon-substrate0.8934
CYP450 3A4 substrateNon-substrate0.5936
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.5483
BiodegradationReady biodegradable0.5053
Rat acute toxicity2.2247 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9658
hERG inhibition (predictor II)Non-inhibitor0.8764
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.9 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0kmi-0945000000-40a09f3f9528bd669823
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-64dbb16119292f4410e2
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-5c8fbcad8e93fa9f2906
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0uk9-1900000000-4c6518583a7488591aa3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-1900000000-00574ed667d64b4a45e9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-1900000000-d4ac63e9260ab31ac6b1
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zml-0933000000-4ae209b29cb52d4e3844
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-056r-0933000000-74ff5ec451e56526d425
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4l-0590000000-90d108018a0f99815fb7
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4l-0690000000-161f2afa43298fd3437a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0uk9-0923000000-86308db0ec59b40b1533
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05fr-0094000000-ad8da59124745b38a76f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0390000000-06fcf307f2fdb79741ad
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-1940000000-be07d702045f4d3e05ac
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-1910000000-55a74a828c3c9750ee1c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0159-2900000000-bf685c17ab79583133ee
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0159-4900000000-e6f6ccbfffe89c345365
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0191000000-41f70006e2b4e5f8d8aa
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0960000000-d64346c38bebc079f066
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0f89-0491000000-c7e13efc8c7ed0e68cff
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0f89-0492000000-4b6f8c10f6acc0f02196
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0920000000-96bfb1c31d89e3f10caf
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0600-0592000000-129db104bb506af06de0

Taxonomy

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
Nitrobenzene / Nitroaromatic compound / C-nitro compound / Secondary alcohol / Organic nitro compound / Carboximidic acid / Carboximidic acid derivative / Organic oxoazanium / Allyl-type 1,3-dipolar organic compound / Propargyl-type 1,3-dipolar organic compound
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organochlorine compound (CHEBI:17698) / Aromatic compounds (C00918)

Targets

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
  1. 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. [PubMed:7500366]
  2. 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. [PubMed:4365366]
  3. 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. [PubMed:3549294]
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
  1. 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. [PubMed:1670929]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:15331605]
  2. 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. [PubMed:17376081]

Enzymes

Kind
Protein
Organism
Human
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:14576103]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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
  1. 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. [PubMed:7500366]
  2. 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. [PubMed:1525158]
  3. 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. [PubMed:2050670]
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
  1. 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. [PubMed:12363006]
  2. Potrykus J, Wegrzyn G: Chloramphenicol-sensitive Escherichia coli strain expressing the chloramphenicol acetyltransferase (cat) gene. Antimicrob Agents Chemother. 2001 Dec;45(12):3610-2. [PubMed:11709351]
  3. 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. [PubMed:10488163]
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
  1. 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. [PubMed:10216290]
  2. Izard T, Ellis J: The crystal structures of chloramphenicol phosphotransferase reveal a novel inactivation mechanism. EMBO J. 2000 Jun 1;19(11):2690-700. [PubMed:10835366]
  3. 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. [PubMed:7592948]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:14576103]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10411577]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:26