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Identification
Name Chloramphenicol
Accession Number DB00446 (APRD00862, EXPT00942)
Type small molecule
Groups 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
CAF
CAP
Chloramfenikol
Chloramphenicole
Chloroamphenicol
Cloroamfenicolo
D-Chloramphenicol
Salts Not Available
Brand names
Name Company
Ak-chlor
Ak-Chlor Ophthalmic Ointment
Ak-Chlor Ophthalmic Solution
Alficetyn
Ambofen
Amphenicol
Amphicol
Amseclor
Anacetin
Aquamycetin
Austracil
Austracol
Biocetin
Biophenicol
Catilan
Chemicetin
Chemicetina
Chlomin
Chlomycol
Chlora-Tabs
Chloracol Ophthalmic Solution
Chloramex
Chloramficin
Chloramfilin
Chloramsaar
Chlorasol
Chloricol
Chlornitromycin
Chloro-25 vetag
Chlorocaps
Chlorocid
Chlorocid S
Chlorocide
Chlorocidin C
Chlorocidin C tetran
Chlorocol
Chlorofair
Chlorofair Ophthalmic Ointment
Chlorofair Ophthalmic Solution
Chloroject L
Chloromax
Chloromycetin for Ophthalmic Solution
Chloromycetin Hydrocortisone
Chloromycetin Ophthalmic Ointment
Chloromycetin Palmitate
Chloromycetny
Chloromyxin
Chloronitrin
Chloroptic
Chloroptic Ophthalmic Solution
Chloroptic S.O.P.
Chloroptic-P S.O.P.
Chlorovules
Cidocetine
Ciplamycetin
Cloramfen
Cloramficin
Cloramicol
Cloramidina
Clorocyn
Cloromisan
Clorosintex
Comycetin
Cylphenicol
Desphen
Detreomycin
Detreomycine
Dextromycetin
Doctamicina
Econochlor
Econochlor Ophthalmic Ointment
Econochlor Ophthalmic Solution
Elase-Chloromycetin
Embacetin
Emetren
Enicol
Enteromycetin
Erbaplast
Ertilen
Farmicetina
Farmitcetina
Fenicol
Fenicol Ophthalmic Ointment
Globenicol
Glorous
Halomycetin
Hortfenicol
I-Chlor Ophthalmic Solution
Intramycetin
Isicetin
Ismicetina
Isophenicol
Isopto fenicol
Juvamycetin
Kamaver
Kemicetina
Kemicetine
Klorita
Klorocid S
Leukamycin
Leukomyan
Leukomycin
Levomicetina
Levomitsetin
Levomycetin
Loromisan
Loromisin
Mastiphen
Mediamycetine
Medichol
Micloretin
Micochlorine
Micoclorina
Microcetina
Mychel
Mychel-Vet
Mycinol
Normimycin V
Novochlorocap
Novomycetin
Novophenicol
Ocu-Chlor Ophthalmic Ointment
Ocu-Chlor Ophthalmic Solution
Oftalent
Oleomycetin
Opclor
Opelor
Ophtho-Chloram Ophthalmic Solution
Ophthochlor
Ophthochlor Ophthalmic Solution
Ophthoclor
Ophthocort
Ophtochlor
Optomycin
Otachron
Otophen
Pantovernil
Paraxin
Pentamycetin
Pentamycetin Ophthalmic Ointment
Pentamycetin Ophthalmic Solution
Quemicetina
Rivomycin
Romphenil
Ronphenil
Septicol
Sificetina
Sintomicetina
Sintomicetine R
Sno-Phenicol
Sopamycetin Ophthalmic Ointment
Sopamycetin Ophthalmic Solution
Spectro-Chlor Ophthalmic Ointment
Spectro-Chlor Ophthalmic Solution
Stanomycetin
Synthomycetin
Synthomycetine
Synthomycine
Tega-Cetin
Tevcocin
Tevcosin
Tifomycin
Tifomycine
Tiromycetin
Treomicetina
Tyfomycine
Unimycetin
Veticol
Viceton
First Prev Next Last
Brand mixtures
Brand Name Ingredients
Actinac Pwr Allantoin + Butoxyethyl Nicotinate + Chloramphenicol + Hydrocortisone Acetate + Sulfur
Actinac Pws Allantoin + Butoxyethyl Nicotinate + Chloramphenicol + Hydrocortisone Acetate + Sulfur
Chlorasone Chloramphenicol + Prednisolone Acetate
Elase Chloromycetin Ont Chloramphenicol + Deoxyribonuclease Pancreatic + Fibrinolysin
Liquichlor Chloramphenicol + Prednisolone + Squalane + Tetracaine
Ophthocort Ont Chloramphenicol + Hydrocortisone Acetate + Polymyxin B
Sopamycetin/Hc Ointment Chloramphenicol + Hydrocortisone Acetate
Sopamycetin/Hc Ont Chloramphenicol + Hydrocortisone Acetate
Sopamycetin/Hc Susp Chloramphenicol + Hydrocortisone Acetate
Zoomycetine Spray Chloramphenicol + Isopropyl Alcohol + Methyl Violet
Categories
  • Anti-Bacterial Agents
  • Protein Synthesis Inhibitors
CAS number 56-75-7
Weight Average: 323.129
Monoisotopic: 322.012326918
Chemical Formula C11H12Cl2N2O5
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec show (10.9 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
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.
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.
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
Pathways Not Available
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
Form Route Strength
Liquid Ophthalmic
Ointment Ophthalmic
Powder, for solution Intramuscular
Solution Ophthalmic
Solution / drops Ophthalmic
Prices
Unit description Cost Unit
Chloramphen na succ 1 gm vial 28.74 USD vial
Chloramphenicol palm powder 2.52 USD g
Chloramphenicol crystals 1.32 USD 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 150.5 °C PhysProp
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 4.61e-01 g/l ALOGPS
logP 1.15 ALOGPS
logP 0.88 ChemAxon
logS -2.9 ALOGPS
pKa (strongest acidic) 7.49 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 115.38 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 73.2 ChemAxon
polarizability 28.08 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
  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
  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
  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
  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
External Links
Resource Link
KEGG Drug D00104 Link_out
KEGG Compound C00918 Link_out
BindingDB 50028502 Link_out
ChEBI 17698 Link_out
ChEMBL 17698 Link_out
Therapeutic Targets Database DAP001356 Link_out
PharmGKB PA448927 Link_out
HET CLM Link_out
Drug Product Database 798398 Link_out
RxList http://www.rxlist.com/cgi/generic3/chloramphenicol.htm Link_out
Drugs.com http://www.drugs.com/mtm/chloramphenicol-ophthalmic.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Chloramphenicol Link_out
ATC Codes
  • D06AX02
  • D10AF03
  • G01AA05
  • J01BA01
  • S01AA01
  • S02AA01
  • S03AA08
AHFS Codes
  • 08:12.08
  • 52:04.04
PDB Entries
FDA label show (191 KB)
MSDS show (74.1 KB)
Interactions
Drug Interactions
Drug Interaction
Acetohexamide Chloramphenicol may increase the effect of sulfonylurea, acetohexamide.
Butalbital Barbiturates such as butalbital may increase the metabolism of Chloramphenicol. Chloramphenicol may decrease the metabolism of Barbiturates. Monitor for decreased serum concentrations/therapeutic effects of chloramphenicol if a barbiturate is initiated/dose increased, or increased effects if a barbiturate is discontinued/dose decreased. In addition, monitor for increased effects of barbiturates if chloramphenicol is initiated/dose increased, or decreased effects if chloramphenicol is discontinued/dose decreased.
Chlorpropamide Chloramphenicol may increase the effect of sulfonylurea, chlorpropamide.
Cyclosporine Chloramphenicol may increase the effect of cyclosporine.
Ethotoin Increases phenytoin, modifies chloramphenicol
Fosphenytoin Increases phenytoin, modifies chloramphenicol
Gliclazide Chloramphenicol may increase the effect of sulfonylurea, gliclazide.
Glipizide Chloramphenicol may increase the effect of sulfonylurea, glipizide.
Glisoxepide Chloramphenicol may increase the effect of sulfonylurea, glisoxepide.
Glyburide Chloramphenicol may increase the effect of sulfonylurea, glibenclamide.
Glycodiazine Chloramphenicol may increase the effect of sulfonylurea, glycodiazine.
Lurasidone Concomitant therapy with a strong CYP3A4 inhibitor will increase level or effect of lurasidone. Coadministration with lurasidone is contraindicated.
Mephenytoin Increases phenytoin, modifies chloramphenicol
Phenytoin Increases phenytoin, modifies chloramphenicol
Rifampin Rifampin decreases the effect of chloramphenicol
Silodosin Chloramphenicol is a strong inhibitor of CYP3A4 may increase the serum concentration of silodosin by decreasing its metabolism thus increases the potential for adverse side effects. Combination therapy is contraindicated.
Tacrolimus Chloramphenicol may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Chloramphenicol therapy is initiated, discontinued or altered.
Thiopental Chloramphenicol may increase the serum concentration of Thiopental by decreasing Thiopental metabolism. Thiopental may decrease the serum concentration of Chloramphenicol by increasing Chloramphenicol metabolism. Monitor for changes in therapeutic effects of both agents if concomitant therapy is initiated, discontinued or doses are adjusted.
Tolazamide Chloramphenicol may increase the effect of sulfonylurea, tolazamide.
Tolbutamide Chloramphenicol may increase the effect of sulfonylurea, tolbutamide.
Food Interactions
  • Take on an empty stomach.
Targets

1. 50S ribosomal protein L16

Pharmacological action: unknown
Actions: inhibitor
UniProt ID: P0ADY7 Link_out
Gene: rplP
SNPs: SNPJam Report Link_out

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
  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
  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

2. Dr hemagglutinin structural subunit

Pharmacological action: unknown
Actions: antagonist

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))

Organism class: bacterial
UniProt ID: P24093 Link_out
Gene: draA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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

3. Complement decay-accelerating factor

Pharmacological action: unknown
Actions: other

Also acts as the receptor for echovirus 7 and related viruses (echoviruses 13, 21, 29 and 33)

Organism class: human
UniProt ID: P08174 Link_out
Gene: CD55 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
Enzymes

1. Cytochrome P450 3A4

Actions: inhibitor

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 xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. 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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A5

Actions: inhibitor

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

UniProt ID: P20815 Link_out
Gene: CYP3A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

3. Cytochrome P450 3A7

Actions: inhibitor

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

UniProt ID: P24462 Link_out
Gene: CYP3A7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

4. Cytochrome P450 2C19

Actions: substrate, inhibitor

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

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. 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. Epub 2009 Nov 24. Pubmed

5. Chloramphenicol acetyltransferase 3

Actions: substrate

This enzyme is an effector of chloramphenicol resistance in bacteria

UniProt ID: P00484 Link_out
Gene: cat3
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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
  4. 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
  5. 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

6. Chloramphenicol acetyltransferase

Actions: substrate

This enzyme is an effector of chloramphenicol (Cm) resistance in bacteria. Acetylates Cm but not 1-acetoxy-Cm

UniProt ID: P26841 Link_out
Gene: cat
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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
  4. 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
  5. 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

7. Chloramphenicol 3-O phosphotransferase

Actions: substrate

Inactivates chloramphenicol by catalyzing the transfer of the gamma-phosphate of ATP to the antibiotic's C-3' hydroxyl group

UniProt ID: Q56148 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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
  4. 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
  5. 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

8. Cytochrome P450 2C8

Actions: inhibitor

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 responsible for the metabolism the anti- cancer drug paclitaxel (taxol)

UniProt ID: P10632 Link_out
Gene: CYP2C8
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed

9. Cytochrome P450 2C9

Actions: inhibitor

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, phenytoin, tolbutamide and losartan

UniProt ID: P11712 Link_out
Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19