Cloxacillin

Identification

Summary

Cloxacillin is an antibiotic agent used for the treatment of beta-hemolytic streptococcal and pneumococcal infections as well as staphylococcal infections.

Generic Name
Cloxacillin
DrugBank Accession Number
DB01147
Background

A semi-synthetic penicillin antibiotic which is a chlorinated derivative of oxacillin.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 435.881
Monoisotopic: 435.065569098
Chemical Formula
C19H18ClN3O5S
Synonyms
  • (2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (3-(o-chlorophenyl)-5-methyl-4-isoxazolyl)penicillin
  • 6-(3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid
  • Cloxacilina
  • Cloxacillin
  • Cloxacilline
  • Cloxacillinum

Pharmacology

Indication

Cloxacillin is indicated for the treatment of beta-hemolytic streptococcal, pneumococcal, and staphylococcal infections (including beta-lactamase producing organisms).6

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofInfection caused by staphylococci••••••••••••
Treatment ofInfections caused by penicillinase-producing staphylococci••••••••••••
Treatment ofPneumococcal infection••••••••••••
Treatment ofStreptococcal infections••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin is for use against staphylococci that produce beta-lactamase.

Mechanism of action

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, cloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cloxacillin interferes with an autolysin inhibitor.

TargetActionsOrganism
AD-alanyl-D-alanine carboxypeptidase DacA
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 2X
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Absorption

Well absorbed from the gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

Cloxacillin is approximately 94% protein-bound in plasma,5 primarily to albumin.3

Metabolism

Cloxacillin, like other penicillins, appears to be metabolized via breakage of the beta-lactam ring to form an inactive penicilloic acid metabolite.2

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Oral LD50 in rat and mouse is 5000 mg/kg. Intravenous LD50 in rat is 1660 mg/kg. Symptoms of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, and swelling of face, lips, tongue, or throat.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Cloxacillin which could result in a higher serum level.
AcenocoumarolCloxacillin may increase the anticoagulant activities of Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Cloxacillin is combined with Ambroxol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Cloxacillin.
ArticaineThe risk or severity of methemoglobinemia can be increased when Cloxacillin is combined with Articaine.
Food Interactions
  • Take on an empty stomach. Orally administered cloxacillin should be taken 1-2 hours prior to meals as the presence of food in the stomach and intestine reduces drug absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cloxacillin benzathineAC79L7PV2G23736-58-5COCFKSXGORCFOW-VZHMHXRYSA-N
Cloxacillin sodiumMWQ645MKMF642-78-4SCLZRKVZRBKZCR-SLINCCQESA-M
Cloxacillin sodium hydrate65LCB00B4Y7081-44-9KCUWTKOTPIUBRI-VICXVTCVSA-M
International/Other Brands
Aclox (Southshourne) / Apo-Cloxi (Apotex) / Auropen Inj. (Cirin) / Cloxacil (Saiph) / Cloxam (MacroPhar) / Orbenin (GlaxoSmithKline) / Vaclox (Atlantic) / Vamcloxil (Vamsler)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CloxacillinCapsule500 mgOralPro Doc Limitee1994-12-312013-07-15Canada flag
Cloxacillin for InjectionPowder, for solution1 g / vialIntravenousSterimax Inc2011-07-28Not applicableCanada flag
Cloxacillin for InjectionPowder, for solution10 g / vialIntravenousSterimax Inc2013-04-03Not applicableCanada flag
Cloxacillin for InjectionPowder, for solution500 mg / vialIntramuscular; IntravenousSterimax Inc2011-09-14Not applicableCanada flag
Cloxacillin for InjectionPowder, for solution2 g / vialIntravenousSterimax Inc2011-07-28Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo Cloxi Cap 250mgCapsule250 mgOralApotex Corporation1984-12-31Not applicableCanada flag
Apo Cloxi Cap 500mgCapsule500 mgOralApotex Corporation1984-12-31Not applicableCanada flag
Apo Cloxi for Oral Soln 125mg/5mlPowder, for solution125 mg / 5 mLOralApotex Corporation1985-12-312019-12-03Canada flag
Jamp CloxacillinCapsule500 mgOralJamp Pharma Corporation2022-02-17Not applicableCanada flag
Jamp CloxacillinCapsule250 mgOralJamp Pharma Corporation2022-02-17Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
คล็อกซาติน ดรายไซรับPowder, for suspension125 mg/5mlOralห้างหุ้นส่วนจำกัด โรงงานเลิศสิงห์เภสัชกรรม1998-02-09Not applicableThailand flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CF02 — Cloxacillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Penicillins / N-acyl-alpha amino acids and derivatives / Chlorobenzenes / Aryl chlorides / Thiazolidines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Isoxazoles / Secondary carboxylic acid amides / Azetidines
show 12 more
Substituents
Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azetidine / Azole / Benzenoid / Beta-lactam
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:49566)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
O6X5QGC2VB
CAS number
61-72-3
InChI Key
LQOLIRLGBULYKD-JKIFEVAISA-N
InChI
InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
IUPAC Name
(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O

References

Synthesis Reference

Doyle, F.P. and Nayler, J.H.C.; British Patent 905,778; September 12, 1962; assigned to Beecham Research Laboratories, Ltd. Doyle, F.P. and Nayler, J.H.C.; US. Patent 2,996,501; August 15, 1961.

General References
  1. Lalanne S, Le Vee M, Lemaitre F, Le Corre P, Verdier MC, Fardel O: Differential interactions of the beta-lactam cloxacillin with human renal organic anion transporters (OATs). Fundam Clin Pharmacol. 2020 Aug;34(4):476-483. doi: 10.1111/fcp.12541. Epub 2020 Feb 25. [Article]
  2. Thijssen HH, Mattie H: Active metabolites of isoxazolylpencillins in humans. Antimicrob Agents Chemother. 1976 Sep;10(3):441-6. doi: 10.1128/aac.10.3.441. [Article]
  3. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
  4. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
  5. Health Canada Product Monograph: Cloxacillin sodium for oral use [Link]
  6. Health Canada Product Monograph: Cloxacillin sodium powder for solution for injection [Link]
Human Metabolome Database
HMDB0015278
KEGG Compound
C06923
PubChem Compound
6098
PubChem Substance
46507109
ChemSpider
5873
BindingDB
50022788
RxNav
2625
ChEBI
49566
ChEMBL
CHEMBL891
ZINC
ZINC000003875417
Therapeutic Targets Database
DAP001161
PharmGKB
PA449059
PDBe Ligand
CXN
Drugs.com
Drugs.com Drug Page
Wikipedia
Cloxacillin
MSDS
Download (38 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Apothecon
  • Dispensing Solutions
  • H.J. Harkins Co. Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
Powder, for suspensionOral250 mg/5ml
Powder, for solutionIntravenous10 g / vial
Powder, for solutionIntravenous2 g / vial
Injection, powder, for solutionIntramuscular; Intravenous500 mg
Powder, for solutionIntramuscular; Intravenous500 mg / vial
Powder, for solutionIntravenous1 g / vial
LiquidIntramuscular; Intravenous250 mg / vial
Syrup
Powder, for suspensionOral
CapsuleOral
Injection, powder, for solutionIntramuscular; Intravenous1 g
Injection250 mg
Injection500 mg
CapsuleOral250 mg / cap
CapsuleOral500 mg / cap
Powder, for solutionIntramuscular; Intravenous2 g / vial
Powder, for solutionOral125 mg / 5 mL
Granule, for suspensionOral
Granule, for suspensionOral125 mg/5ml
Powder, for solutionIntramuscular; Intravenous250 mg / vial
Granule, for solutionOral125 mg
Tablet, film coated500 mg
Powder, for suspensionOral125 mg/5ml
CapsuleOral250 mg
Powder250 mg/1vial
CapsuleOral500 mg
CapsuleOral125 mg/5ml
Prices
Unit descriptionCostUnit
Cloxacillin Sodium 2 g/vial7.69USD vial
Cloxacillin Sodium 1 g/vial5.89USD vial
Cloxacillin Sodium 500 mg/vial4.79USD vial
Apo-Cloxi 500 mg Capsule0.38USD capsule
Novo-Cloxin 500 mg Capsule0.38USD capsule
Nu-Cloxi 500 mg Capsule0.38USD capsule
Apo-Cloxi 250 mg Capsule0.19USD capsule
Novo-Cloxin 250 mg Capsule0.19USD capsule
Nu-Cloxi 250 mg Capsule0.19USD capsule
Apo-Cloxi 25 mg/ml Liquid0.05USD ml
Novo-Cloxin 25 mg/ml Liquid0.05USD ml
Nu-Cloxi 25 mg/ml Liquid0.05USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP2.48SANGSTER (1994)
pKa2.78SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0532 mg/mLALOGPS
logP2.61ALOGPS
logP2.3Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.75Chemaxon
pKa (Strongest Basic)-0.41Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area112.74 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity106.64 m3·mol-1Chemaxon
Polarizability41.64 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8368
Blood Brain Barrier-0.9903
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.6204
P-glycoprotein inhibitor INon-inhibitor0.8951
P-glycoprotein inhibitor IINon-inhibitor0.9204
Renal organic cation transporterNon-inhibitor0.9629
CYP450 2C9 substrateNon-substrate0.8262
CYP450 2D6 substrateNon-substrate0.905
CYP450 3A4 substrateSubstrate0.5977
CYP450 1A2 substrateInhibitor0.8592
CYP450 2C9 inhibitorNon-inhibitor0.891
CYP450 2D6 inhibitorNon-inhibitor0.918
CYP450 2C19 inhibitorNon-inhibitor0.8832
CYP450 3A4 inhibitorNon-inhibitor0.819
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9186
Ames testNon AMES toxic0.6979
CarcinogenicityCarcinogens 0.5672
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.9946 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9996
hERG inhibition (predictor II)Non-inhibitor0.8486
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-006x-9442300000-e216b172b6089bc0b628
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03fr-0980100000-1acb1c4e617b9afd066c
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03fr-0980100000-1acb1c4e617b9afd066c
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03fr-0980100000-1acb1c4e617b9afd066c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a5a-0560910000-05dcf2cead0bc1f49482
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01q9-1900000000-a2a9637ec3640b22d439
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0190100000-3caf5358ad67203391c9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090100000-61a99585fb3563494cb2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ka-0890100000-ba68898544189a86f34b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6090300000-ed42ba2fa4226e50c8d0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-9352200000-2b2b6d8ff98c07851901
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0229-0891000000-bf4415e1ae7da7b6e889
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-198.0747355
predicted
DarkChem Lite v0.1.0
[M-H]-191.87189
predicted
DeepCCS 1.0 (2019)
[M+H]+199.8869355
predicted
DarkChem Lite v0.1.0
[M+H]+194.26746
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.4923355
predicted
DarkChem Lite v0.1.0
[M+Na]+200.17998
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name
dacA
Uniprot ID
P0AEB2
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacA
Molecular Weight
44443.62 Da
References
  1. Nicola G, Tomberg J, Pratt RF, Nicholas RA, Davies C: Crystal structures of covalent complexes of beta-lactam antibiotics with Escherichia coli penicillin-binding protein 5: toward an understanding of antibiotic specificity. Biochemistry. 2010 Sep 21;49(37):8094-104. doi: 10.1021/bi100879m. [Article]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Penicillin-binding proteins (PBPs) function in the late steps of murein biosynthesis. Beta-lactams inactivate the PBPs by acylating an essential serine residue in the active site of these proteins.
Gene Name
pbpX
Uniprot ID
P59676
Uniprot Name
Penicillin-binding protein 2X
Molecular Weight
82342.565 Da
References
  1. Chittock RS, Ward S, Wilkinson AS, Caspers P, Mensch B, Page MG, Wharton CW: Hydrogen bonding and protein perturbation in beta-lactam acyl-enzymes of Streptococcus pneumoniae penicillin-binding protein PBP2x. Biochem J. 1999 Feb 15;338 ( Pt 1):153-9. [Article]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Cell wall formation.
Gene Name
pbpA
Uniprot ID
Q8DR59
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
79700.9 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
  2. Friedman LA, Lewis PJ: The effect of semisynthetic penicillins on the binding of bilirubin by neonatal serum. Br J Clin Pharmacol. 1980 Jan;9(1):61-5. [Article]
  3. Okore VC: Effect of ascorbic acid on the binding of cloxacillin sodium to bovine serum albumin. Arzneimittelforschung. 1994 May;44(5):671-3. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Wolman AT, Gionfriddo MR, Heindel GA, Mukhija P, Witkowski S, Bommareddy A, Vanwert AL: Organic anion transporter 3 interacts selectively with lipophilic beta-lactam antibiotics. Drug Metab Dispos. 2013 Apr;41(4):791-800. doi: 10.1124/dmd.112.049569. Epub 2013 Jan 23. [Article]
  2. Lalanne S, Le Vee M, Lemaitre F, Le Corre P, Verdier MC, Fardel O: Differential interactions of the beta-lactam cloxacillin with human renal organic anion transporters (OATs). Fundam Clin Pharmacol. 2020 Aug;34(4):476-483. doi: 10.1111/fcp.12541. Epub 2020 Feb 25. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48