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Tedizolid phosphate

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Identification

Summary

Tedizolid phosphate is an oxazolidinone class antibiotic that inhibits bacterial protein synthesis and is proven to be effective in the treatment of certain Gram-positive bacterial infections.

Brand Names
Sivextro
Generic Name
Tedizolid phosphate
DrugBank Accession Number
DB09042
Background

Drug-resistant bacteria, such as methicillin-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus faecium, and penicillin-resistant Streptococcus penumoniae, represent a massive public health threat.7,10 Tedizolid is a member of the oxazolidinone class of antibiotics, which includes the previously approved linezolid and is generally effective against multidrug-resistant Gram-positive bacteria. Tedizolid is indicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) and is generally more effective and more tolerable than linezolid.15,7,3

Tedizolid was approved by the FDA on June 20, 2014, for sale by Cubist Pharmaceuticals as tedizolid phosphate (SIVEXTRO®). This product is currently available as both an oral tablet and as a powder for intravenous injection.15

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 450.323
Monoisotopic: 450.08529742
Chemical Formula
C17H16FN6O6P
Synonyms
  • [(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl dihydrogen phosphate
  • Tedizolid phosphate
  • Torezolid phosphate
External IDs
  • TR 701
  • TR-701
  • TR-701 FA
  • TR-701FA
  • TR701
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Pharmacology

Indication

Tedizolid is indicated for the treatment of acute bacterial infections of the skin and skin structure (ABSSSI). To prevent drug resistance, tedizolid should only be used for infections that are caused by susceptible bacteria.15

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute bacterial skin and skin structure infections••••••••••••••••••••• •• •••••••• •••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tedizolid is an oxazolidinone antibiotic that works by inhibiting protein synthesis by bacterial ribosomes.15,4,7 However, oxazolidinone antibiotics can also bind to human mitochondrial, but not cytoplasmic, ribosomes.5,9 Mitochondrial protein synthesis inhibition is associated with adverse patient effects such as neurological, hematological, and gastrointestinal toxicity, although tedizolid is tolerated better than the related linezolid.3 Alternative therapies should be considered when treating neutropenic patients with ABSSSI. Clostridium difficile-associated diarrhea has been reported in patients treated with tedizolid.15

Mechanism of action

Despite renewed efforts to combat the spread of antimicrobial resistance, multidrug-resistant organisms, including gram-positive bacteria such as methicillin-resistant Staphylococcus aureus, remain a threat.10,7 Oxazolidinones represent a relatively new class of antibacterials inhibiting protein synthesis that is generally capable of overcoming resistance to other bacterial protein synthesis inhibitors.15,7,8

Protein synthesis involves the action of ribosomes, multi-subunit complexes composed of both protein and ribosomal RNA (rRNA) substituents. Translocation along the length of a messenger RNA and concomitant protein synthesis involves the action of the A, P, and E sites of the peptidyltransferase centre (PTC), which accepts charged aminoacyl-tRNAs and catalyzes the formation of peptide bonds between them. The bacterial 70S ribosome comprises a small (30S) and a large (50S) subunit.11

Early studies into the mechanism of action of oxazolidinone antibiotics suggested that they inhibit a step in the initiation of protein synthesis.6 However, this mechanism was inconsistent with mapped resistance mutations, and later studies involving cross-linking and direct structural determination of the binding site revealed that oxazolidinones, including both linezolid and tedizolid, bind in the A site of the PTC by interacting with the 23S rRNA component.5,4 The structural studies also revealed that oxazolidinone binding alters the conformation of a conserved nucleotide in the 23S rRNA (U2585 in Escherichia coli), which renders the PTC non-productive for peptide bond formation.4 Hence, tedizolid exerts its effect through inhibiting bacterial protein synthesis.15

TargetActionsOrganism
A23S ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
Absorption

Tedizolid reaches peak plasma concentrations within three hours for oral administration and within one hour following intravenous administration; the absolute oral bioavailability is approximately 91%. Food has no effect on absorption. When given once daily, either orally or intravenously, tedizolid reaches steady-state concentrations in approximately three days.15,2,12

The Cmax for tedizolid after a single dose/at steady-state is 2.0 ± 0.7/2.2 ± 0.6 mcg/mL for oral administration, and 2.3 ± 0.6/3.0 ± 0.7 mcg/mL for intravenous administration, respectively. Similarly, the Tmax has a median (range) of 2.5 (1.0 - 8.0)/3.5 (1.0 - 6.0) hrs for the oral route and 1.1 (0.9 - 1.5)/1.2 (0.9 - 1.5) hrs when given intravenous. The AUC is 23.8 ± 6.8/25.6 ± 8.4 mcg*hr/mL for oral and 26.6 ± 5.2/29.2 ± 6.2 mcg*hr/mL for intravenous.15,2,12

Volume of distribution

The volume of distribution for tedizolid following a single intravenous dose of 200 mg is between 67 and 80 L.15 In a study involving oral administration of 200 mg tedizolid to steady-state, the volume of distribution was 108 ± 21 L, while a single 600 mg oral dose resulted in an apparent volume of distribution of 113.3 ± 19.3 L.13,14 Tedizolid has been observed to penetrate the interstitial space of both adipose and skeletal muscle tissue and is also found in the epithelial lining fluid as well as in alveolar macrophages.1,15,13,14

Protein binding

Approximately 70 to 90% of tedizolid is bound to human plasma proteins.15,3,13,14

Metabolism

Tedizolid is administered as a phosphate prodrug that is converted to tedizolid (the circulating active moiety). Prior to excretion, the majority of tedizolid is converted to an inactive sulphate conjugate in the liver, though this is unlikely to involve the action of cytochrome P450-family enzymes.1,15,3

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Route of elimination

When given as a single oral dose, approximately 82% of tedizolid is excreted via the feces and 18% in urine. The majority is found as the inactive sulphate conjugate, with only 3% recovered unchanged. Over 85% of the elimination occurs within 96 hours.1,15,3

Half-life

Tedizolid has a half-life of approximately 12 hours.1,15,12,2

Clearance

Tedizolid has an apparent oral clearance of 6.9 ± 1.7 L/hr for a single dose and 8.4 ± 2.1 L/hr at steady-state. The systemic clearance is 6.4 ± 1.2 L/hr for a single dose and 5.9 ± 1.4 L/hr at steady-state.15,12,2

Adverse Effects
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Toxicity

Toxicity information regarding tedizolid is not readily available. Patients experiencing an overdose are at an increased risk of severe adverse effects such as nausea, headache, dizziness, diarrhea, and vomiting. Symptomatic and supportive measures are recommended.15

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
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interactions in your software
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Tedizolid phosphate.
AcebutololTedizolid phosphate may increase the hypertensive activities of Acebutolol.
AcenocoumarolThe risk or severity of bleeding can be increased when Tedizolid phosphate is combined with Acenocoumarol.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Tedizolid phosphate.
AldesleukinThe risk or severity of myelosuppression can be increased when Aldesleukin is combined with Tedizolid phosphate.
Food Interactions
  • Take at the same time every day.
  • Take with or without food.

Products

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Active Moieties
NameKindUNIICASInChI Key
Tedizolidprodrug97HLQ82NGL856866-72-3XFALPSLJIHVRKE-GFCCVEGCSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SivextroTablet200 mgOralMerck Ltd.Not applicableNot applicableCanada flag
SivextroInjection, powder, lyophilized, for solution200 mg/4mLIntravenousMerck Sharp & Dohme Llc2014-06-20Not applicableUS flag
SivextroTablet, film coated200 mgOralMerck Sharp & Dohme B.V.2016-09-08Not applicableEU flag
SivextroInjection, powder, lyophilized, for solution200 mg/4mLIntravenousNabriva Therapeutics US, Inc.2014-06-20Not applicableUS flag
SivextroTablet, film coated200 mg/1OralMerck Sharp & Dohme Llc2014-06-20Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Phenylpyridines
Direct Parent
Phenylpyridines
Alternative Parents
Fluorobenzenes / Monoalkyl phosphates / Oxazolidinones / Aryl fluorides / Tetrazoles / Carbamate esters / Heteroaromatic compounds / Organic carbonic acids and derivatives / Azacyclic compounds / Oxacyclic compounds
show 6 more
Substituents
3-phenylpyridine / Alkyl phosphate / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Carbamic acid ester / Carbonic acid derivative
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, carbamate ester, tetrazoles, pyridines, ring assembly, oxazolidinone (CHEBI:83326)
Affected organisms
  • Staphylococcus
  • Enterococcus
  • Streptococcus

Chemical Identifiers

UNII
O7DRJ6R4DW
CAS number
856867-55-5
InChI Key
QCGUSIANLFXSGE-GFCCVEGCSA-N
InChI
InChI=1S/C17H16FN6O6P/c1-23-21-16(20-22-23)15-5-2-10(7-19-15)13-4-3-11(6-14(13)18)24-8-12(30-17(24)25)9-29-31(26,27)28/h2-7,12H,8-9H2,1H3,(H2,26,27,28)/t12-/m1/s1
IUPAC Name
{[(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-1,2,3,4-tetrazol-5-yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methoxy}phosphonic acid
SMILES
CN1N=NC(=N1)C1=CC=C(C=N1)C1=CC=C(C=C1F)N1C[C@H](COP(O)(O)=O)OC1=O

References

Synthesis Reference

Katharina Reichenbacher, Robert J. Duguid, Jacqueline A. Ware, Douglas Phillipson. "Forms of R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate." U.S. Patent US9624250B2, issued April 18, 2017.

General References
  1. Ong V, Flanagan S, Fang E, Dreskin HJ, Locke JB, Bartizal K, Prokocimer P: Absorption, distribution, metabolism, and excretion of the novel antibacterial prodrug tedizolid phosphate. Drug Metab Dispos. 2014 Aug;42(8):1275-84. doi: 10.1124/dmd.113.056697. Epub 2014 May 29. [Article]
  2. Flanagan S, Fang E, Munoz KA, Minassian SL, Prokocimer PG: Single- and multiple-dose pharmacokinetics and absolute bioavailability of tedizolid. Pharmacotherapy. 2014 Sep;34(9):891-900. doi: 10.1002/phar.1458. Epub 2014 Jul 3. [Article]
  3. Roger C, Roberts JA, Muller L: Clinical Pharmacokinetics and Pharmacodynamics of Oxazolidinones. Clin Pharmacokinet. 2018 May;57(5):559-575. doi: 10.1007/s40262-017-0601-x. [Article]
  4. Wilson DN, Schluenzen F, Harms JM, Starosta AL, Connell SR, Fucini P: The oxazolidinone antibiotics perturb the ribosomal peptidyl-transferase center and effect tRNA positioning. Proc Natl Acad Sci U S A. 2008 Sep 9;105(36):13339-44. doi: 10.1073/pnas.0804276105. Epub 2008 Aug 29. [Article]
  5. Leach KL, Swaney SM, Colca JR, McDonald WG, Blinn JR, Thomasco LM, Gadwood RC, Shinabarger D, Xiong L, Mankin AS: The site of action of oxazolidinone antibiotics in living bacteria and in human mitochondria. Mol Cell. 2007 May 11;26(3):393-402. doi: 10.1016/j.molcel.2007.04.005. [Article]
  6. Shinabarger DL, Marotti KR, Murray RW, Lin AH, Melchior EP, Swaney SM, Dunyak DS, Demyan WF, Buysse JM: Mechanism of action of oxazolidinones: effects of linezolid and eperezolid on translation reactions. Antimicrob Agents Chemother. 1997 Oct;41(10):2132-6. [Article]
  7. Koulenti D, Xu E, Mok IYS, Song A, Karageorgopoulos DE, Armaganidis A, Lipman J, Tsiodras S: Novel Antibiotics for Multidrug-Resistant Gram-Positive Microorganisms. Microorganisms. 2019 Aug 18;7(8). pii: microorganisms7080270. doi: 10.3390/microorganisms7080270. [Article]
  8. McCusker KP, Fujimori DG: The chemistry of peptidyltransferase center-targeted antibiotics: enzymatic resistance and approaches to countering resistance. ACS Chem Biol. 2012 Jan 20;7(1):64-72. doi: 10.1021/cb200418f. Epub 2011 Dec 30. [Article]
  9. McKee EE, Ferguson M, Bentley AT, Marks TA: Inhibition of mammalian mitochondrial protein synthesis by oxazolidinones. Antimicrob Agents Chemother. 2006 Jun;50(6):2042-9. doi: 10.1128/AAC.01411-05. [Article]
  10. Laxminarayan R, Van Boeckel T, Frost I, Kariuki S, Khan EA, Limmathurotsakul D, Larsson DGJ, Levy-Hara G, Mendelson M, Outterson K, Peacock SJ, Zhu YG: The Lancet Infectious Diseases Commission on antimicrobial resistance: 6 years later. Lancet Infect Dis. 2020 Apr;20(4):e51-e60. doi: 10.1016/S1473-3099(20)30003-7. Epub 2020 Feb 11. [Article]
  11. Ling C, Ermolenko DN: Structural insights into ribosome translocation. Wiley Interdiscip Rev RNA. 2016 Sep;7(5):620-36. doi: 10.1002/wrna.1354. Epub 2016 Apr 27. [Article]
  12. Flanagan SD, Bien PA, Munoz KA, Minassian SL, Prokocimer PG: Pharmacokinetics of tedizolid following oral administration: single and multiple dose, effect of food, and comparison of two solid forms of the prodrug. Pharmacotherapy. 2014 Mar;34(3):240-50. doi: 10.1002/phar.1337. Epub 2013 Aug 7. [Article]
  13. Housman ST, Pope JS, Russomanno J, Salerno E, Shore E, Kuti JL, Nicolau DP: Pulmonary disposition of tedizolid following administration of once-daily oral 200-milligram tedizolid phosphate in healthy adult volunteers. Antimicrob Agents Chemother. 2012 May;56(5):2627-34. doi: 10.1128/AAC.05354-11. Epub 2012 Feb 13. [Article]
  14. Sahre M, Sabarinath S, Grant M, Seubert C, Deanda C, Prokocimer P, Derendorf H: Skin and soft tissue concentrations of tedizolid (formerly torezolid), a novel oxazolidinone, following a single oral dose in healthy volunteers. Int J Antimicrob Agents. 2012 Jul;40(1):51-4. doi: 10.1016/j.ijantimicag.2012.03.006. Epub 2012 May 13. [Article]
  15. FDA Approved Products: Sivextro (tedizolid phosphate) tablet and injection [Link]
KEGG Drug
D09686
PubChem Compound
11476460
PubChem Substance
310264990
ChemSpider
9651289
BindingDB
50017198
RxNav
1540824
ChEBI
83326
ChEMBL
CHEMBL2105669
ZINC
ZINC000043100953
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tedizolid
FDA label
Download (378 KB)

Clinical Trials

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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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4CompletedHealth Services ResearchObesity1somestatusstop reasonjust information to hide
4Unknown StatusTreatmentProstheses Infection1somestatusstop reasonjust information to hide
3CompletedTreatmentAcute Bacterial Skin and Skin Structure Infection (ABSSSI)1somestatusstop reasonjust information to hide
3CompletedTreatmentBacterial skin infections / Skin Diseases, Infectious1somestatusstop reasonjust information to hide
3CompletedTreatmentPneumonia1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous200 mg/4mL
Powder, for solutionIntravenous200 mg / vial
TabletOral200 mg
Tablet, film coatedOral200 mg/1
Injection, solution200 mg
Tablet, film coatedOral200 mg
Injection, powder, for solutionIntravenous200 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7816379No2010-10-192028-02-23US flag
US8420676No2013-04-162028-02-23US flag
US8426389No2013-04-232030-12-31US flag
US9624250No2017-04-182030-02-03US flag
US9988406No2018-06-052030-02-03US flag
US10065947No2018-09-042030-02-03US flag
US10442829No2019-10-152030-02-03US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP4.89ChEMBL
Predicted Properties
PropertyValueSource
Water Solubility0.608 mg/mLALOGPS
logP0.82ALOGPS
logP1.97Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)1.35Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area152.79 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity125.93 m3·mol-1Chemaxon
Polarizability41.46 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0006900000-bcd86f3fd18988482e3d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000800000-8f2db82b3b9b021d8bc9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6x-0009300000-e3b02a72b5adfa37384b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-1797e5412a18fd959058
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9010000000-9acd84e2ec55d154fb62
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06ur-0059200000-e22a30c19d590adb70ef
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]-188.25896
predicted
DeepCCS 1.0 (2019)
[M+H]+190.65451
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.67125
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 23S ribosomal RNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Binding of tedizolid to 23S rRNA in the A pocket of the bacterial 70S ribosome inhibits bacterial protein synthesis.
In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.
References
  1. Wilson DN, Schluenzen F, Harms JM, Starosta AL, Connell SR, Fucini P: The oxazolidinone antibiotics perturb the ribosomal peptidyl-transferase center and effect tRNA positioning. Proc Natl Acad Sci U S A. 2008 Sep 9;105(36):13339-44. doi: 10.1073/pnas.0804276105. Epub 2008 Aug 29. [Article]
  2. Leach KL, Swaney SM, Colca JR, McDonald WG, Blinn JR, Thomasco LM, Gadwood RC, Shinabarger D, Xiong L, Mankin AS: The site of action of oxazolidinone antibiotics in living bacteria and in human mitochondria. Mol Cell. 2007 May 11;26(3):393-402. doi: 10.1016/j.molcel.2007.04.005. [Article]
  3. Shinabarger DL, Marotti KR, Murray RW, Lin AH, Melchior EP, Swaney SM, Dunyak DS, Demyan WF, Buysse JM: Mechanism of action of oxazolidinones: effects of linezolid and eperezolid on translation reactions. Antimicrob Agents Chemother. 1997 Oct;41(10):2132-6. [Article]
  4. FDA Approved Products: Sivextro (tedizolid phosphate) tablet and injection [Link]

Enzymes

Details1. Amine oxidase [flavin-containing] A
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Tedizolid displays weak reversible inhibition of both MAO-A and MAO-B in vitro.
General Function
Catalyzes the oxidative deamination of primary and some secondary amine such as neurotransmitters, with concomitant reduction of oxygen to hydrogen peroxide and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:18391214, PubMed:20493079, PubMed:24169519, PubMed:8316221). Preferentially oxidizes serotonin (PubMed:20493079, PubMed:24169519). Also catalyzes the oxidative deamination of kynuramine to 3-(2-aminophenyl)-3-oxopropanal that can spontaneously condense to 4-hydroxyquinoline (By similarity)
Specific Function
Aliphatic amine oxidase activity
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Flanagan S, Bartizal K, Minassian SL, Fang E, Prokocimer P: In vitro, in vivo, and clinical studies of tedizolid to assess the potential for peripheral or central monoamine oxidase interactions. Antimicrob Agents Chemother. 2013 Jul;57(7):3060-6. doi: 10.1128/AAC.00431-13. Epub 2013 Apr 22. [Article]
  2. FDA Approved Products: Sivextro (tedizolid phosphate) tablet and injection [Link]
Details2. Amine oxidase [flavin-containing] B
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Tedizolid displays weak reversible inhibition of both MAO-A and MAO-B in vitro.
General Function
Catalyzes the oxidative deamination of primary and some secondary amines such as neurotransmitters, and exogenous amines including the tertiary amine, neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), with concomitant reduction of oxygen to hydrogen peroxide and participates in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924). Preferentially degrades benzylamine and phenylethylamine (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924)
Specific Function
Aliphatic amine oxidase activity
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Flanagan S, Bartizal K, Minassian SL, Fang E, Prokocimer P: In vitro, in vivo, and clinical studies of tedizolid to assess the potential for peripheral or central monoamine oxidase interactions. Antimicrob Agents Chemother. 2013 Jul;57(7):3060-6. doi: 10.1128/AAC.00431-13. Epub 2013 Apr 22. [Article]
  2. FDA Approved Products: Sivextro (tedizolid phosphate) tablet and injection [Link]

Drug created at April 27, 2015 22:15 / Updated at September 12, 2024 23:21