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Identification
NameChloramphenicol
Accession NumberDB00446  (APRD00862, EXPT00942)
TypeSmall Molecule
GroupsApproved, 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
Chloramex
Chloramphenicol
Chloramphenicolum
Chlornitromycin
Chlorocid
Chlorocol
Chloromycetin
Cloramfenicol
D-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-P-nitrophenylethyl)acetamide
D-(-)-threo-1-P-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol
Fenicol
Globenicol
Halomycetin
Laevomycetinum
Levomicetina
Levomycetin
Oleomycetin
Sificetina
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cebenicol Oph Liq 0.4%liquid.4 %ophthalmicChauvin Pharma Inc.1992-12-311997-07-15Canada
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 Succinate Injection 1gmpowder for solution1 gintramuscular; intravenousErfa Canada 2012 Inc1959-12-31Not applicableCanada
Chloroptic Dps 0.5%drops.5 %ophthalmicAllergan Inc1963-12-312011-08-04Canada
Chloroptic Oph Ont 1%ointment10 mgophthalmicAllergan Inc1988-12-312011-08-04Canada
Diochloram Ointment 1%ointment1 %ophthalmic; topicalDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Diochloram Solution 0.5%liquid.5 %ophthalmicDioptic Pharmaceuticals Inc1994-12-31Not applicableCanada
Minims Chloramphenicol 0.5%drops.5 %ophthalmic; topicalChauvin Pharmaceuticals Limited1995-12-311999-12-31Canada
Novo-chlorocap Cap 250mgcapsule250 mgoralNovopharm Limited1966-12-312005-08-10Canada
Odan-chloramphenicolliquid0.5 mgophthalmicOdan Laboratories Ltd1985-12-31Not applicableCanada
Odan-chloramphenicolointment10 mgophthalmicOdan Laboratories Ltd1992-12-31Not applicableCanada
Ophtho-chloram Liq 0.5%liquid.5 %ophthalmicAltimed Pharma Inc.1987-12-311999-09-17Canada
Pentamycetin Liq 2.5mg/mlsolution2.5 mgophthalmicSandoz Canada Incorporated1992-12-31Not applicableCanada
Pentamycetin Ont 10mg/gmointment10 mgophthalmicSandoz Canada Incorporated1992-12-31Not applicableCanada
Pentamycetin Ophthalmic Solution 0.5% - Liqsolution5 mgophthalmicSandoz Canada Incorporated1995-12-31Not applicableCanada
PMS-chloramphenicol Ophthalmic Ointmentointment10 mgophthalmicPharmascience IncNot applicableNot applicableCanada
PMS-chloramphenicol Ophthalmic Soln 0.5%drops.5 %ophthalmicPharmascience Inc1992-12-31Not applicableCanada
Sopamycetin Oph Ont 0.2%ointment.2 %ophthalmicLaboratoires Charton Laboratories1988-12-311999-01-16Canada
Sopamycetin Soln Otique 5%drops5 %oticLaboratoires Charton Laboratories1988-12-311999-01-16Canada
Sopamycetin Solution Ophthalmique 0.2%drops.2 %ophthalmicLaboratoires Charton Laboratories1988-12-311999-01-16Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chloramphenicol Sodium Succinateinjection, powder, lyophilized, for solution133.27 mg/133.27mgintravenousGeneral Injectables and Vaccines, Inc2010-09-01Not applicableUs
Chloramphenicol Sodium Succinateinjection, powder, lyophilized, for solution1 g/10mLintravenousFresenius Kabi USA, LLC2001-01-12Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BrochlorSanofi-Aventis
ChloramexActavis
ChlorocidEgyt
ChlorocolNot Available
ChloromycetinPfizer
ChlorsigSigma
FenicolAlcon
GlobenicolNot Available
HalomycetinWabosan
OleomycetinNot Available
SificetinaSIFI
Brand mixtures
NameLabellerIngredients
Ophthocort OntParke Davis Division, Warner Lambert Canada Inc.
Pentamycetin/hcSandoz Canada Incorporated
Sopamycetin/hc OintmentLaboratoires Charton Laboratories
Sopamycetin/hc OntLaboratoires Charton Laboratories
Sopamycetin/hc SuspLaboratoires Charton Laboratories
Salts
Name/CASStructureProperties
Chloramphenicol palmitate
ThumbNot applicableDBSALT001468
Chloramphenicol sodium succinate
ThumbNot applicableDBSALT001357
Categories
UNII66974FR9Q1
CAS number56-75-7
WeightAverage: 323.129
Monoisotopic: 322.012326918
Chemical FormulaC11H12Cl2N2O5
InChI KeyInChIKey=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)[[email protected]](O)C1=CC=C(C=C1)[N+]([O-])=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as secondary carboxylic acid amides. These are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentSecondary carboxylic acid amides
Alternative Parents
Substituents
  • Organic nitro compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organic nitrite
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organic salt
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed 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.
PharmacodynamicsChloramphenicol 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 actionChloramphenicol 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.
Related Articles
AbsorptionRapidly 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 distributionNot Available
Protein bindingPlasma protein binding is 50-60% in adults and 32% is premature neonates.
Metabolism

Hepatic, with 90% conjugated to inactive glucuronide.

Route of eliminationNot Available
Half lifeHalf-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.
ClearanceNot Available
ToxicityOral, 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
PathwayCategorySMPDB ID
Chloramphenicol Action PathwayDrug actionSMP00729
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Liquidophthalmic.4 %
Injection, powder, lyophilized, for solutionintravenous1 g/10mL
Injection, powder, lyophilized, for solutionintravenous133.27 mg/133.27mg
Ointmentophthalmic1 %
Powder for solutionintramuscular; intravenous1 g
Ointmentophthalmic; topical1 %
Liquidophthalmic.5 %
Dropsophthalmic; topical.5 %
Capsuleoral250 mg
Liquidophthalmic0.5 mg
Ointmentophthalmic
Solutionophthalmic2.5 mg
Ointmentophthalmic10 mg
Solutionophthalmic5 mg
Ointmentophthalmic; otic
Suspensionophthalmic; otic
Dropsophthalmic.5 %
Ointmentophthalmic.2 %
Dropsotic5 %
Dropsophthalmic.2 %
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point171Bartz, 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-2.9ALOGPS
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (10.9 KB)
SpectraNot Available
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
ATC CodesD06AX02D10AF03G01AA05J01BA01S01AA01S02AA01S03AA08
AHFS Codes
  • 08:12.08
  • 52:04.04
PDB Entries
FDA labelDownload (191 KB)
MSDSDownload (74.1 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolChloramphenicol may increase the anticoagulant activities of Acenocoumarol.
AmobarbitalThe metabolism of Amobarbital can be decreased when combined with Chloramphenicol.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Chloramphenicol.
ButabarbitalThe metabolism of Butabarbital can be decreased when combined with Chloramphenicol.
ButethalThe metabolism of Butethal can be decreased when combined with Chloramphenicol.
CarbocisteineThe risk or severity of adverse effects can be increased when Chloramphenicol is combined with Carbocisteine.
CeftazidimeThe therapeutic efficacy of Ceftazidime can be decreased when used in combination with Chloramphenicol.
ChlorpropamideThe metabolism of Chlorpropamide can be decreased when combined with Chloramphenicol.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Chloramphenicol.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Chloramphenicol.
ClopidogrelThe serum concentration of the active metabolites of Clopidogrel can be reduced when Clopidogrel is used in combination with Chloramphenicol resulting in a loss in efficacy.
ClozapineThe risk or severity of adverse effects can be increased when Chloramphenicol is combined with Clozapine.
CyanocobalaminThe therapeutic efficacy of Cyanocobalamin can be decreased when used in combination with Chloramphenicol.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Chloramphenicol.
DicoumarolChloramphenicol may increase the anticoagulant activities of Dicoumarol.
EthanolThe risk or severity of adverse effects can be increased when Chloramphenicol is combined with Ethanol.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Chloramphenicol.
GliclazideThe metabolism of Gliclazide can be decreased when combined with Chloramphenicol.
GlimepirideThe metabolism of Glimepiride can be decreased when combined with Chloramphenicol.
GlipizideThe metabolism of Glipizide can be decreased when combined with Chloramphenicol.
GlyburideThe metabolism of Glyburide can be decreased when combined with Chloramphenicol.
HeptabarbitalThe metabolism of Heptabarbital can be decreased when combined with Chloramphenicol.
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Chloramphenicol.
HydroxocobalaminThe therapeutic efficacy of Hydroxocobalamin can be decreased when used in combination with Chloramphenicol.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Chloramphenicol.
MethohexitalThe metabolism of Methohexital can be decreased when combined with Chloramphenicol.
PantoprazoleThe metabolism of Pantoprazole can be decreased when combined with Chloramphenicol.
PentobarbitalThe metabolism of Pentobarbital can be decreased when combined with Chloramphenicol.
PhenobarbitalThe metabolism of Phenobarbital can be decreased when combined with Chloramphenicol.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Chloramphenicol.
PrimidoneThe metabolism of Primidone can be decreased when combined with Chloramphenicol.
RifampicinThe metabolism of Chloramphenicol can be increased when combined with Rifampicin.
SecobarbitalThe metabolism of Secobarbital can be decreased when combined with Chloramphenicol.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Chloramphenicol.
TolazamideThe metabolism of Tolazamide can be decreased when combined with Chloramphenicol.
TolbutamideThe metabolism of Tolbutamide can be decreased when combined with Chloramphenicol.
VoriconazoleThe serum concentration of Voriconazole can be increased when it is combined with Chloramphenicol.
WarfarinChloramphenicol may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Take on an empty stomach.

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, which is not well understood.
Gene Name:
rplP
Uniprot ID:
P0ADY7
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-mannose (mannose-resistant hemagglutination (MRHA)).
Gene Name:
draA
Uniprot ID:
P24093
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 with cell-associated C4b and C3b polypeptides interferes with their ability to catalyze the conversion of C2 and factor B to enzymatically active C2a and Bb and thereby prevents the formation of C4b2...
Gene Name:
CD55
Uniprot ID:
P08174
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
substrateinhibitor
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. 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
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
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
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 ]

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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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 ]
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Drug created on June 13, 2005 07:24 / Updated on November 30, 2015 12:10