Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H15FN6O3 |
Molecular Weight | 370.3378 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1N=NC(=N1)C2=NC=C(C=C2)C3=CC=C(C=C3F)N4C[C@H](CO)OC4=O
InChI
InChIKey=XFALPSLJIHVRKE-GFCCVEGCSA-N
InChI=1S/C17H15FN6O3/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(9-25)27-17(24)26/h2-7,12,25H,8-9H2,1H3/t12-/m1/s1
Molecular Formula | C17H15FN6O3 |
Molecular Weight | 370.3378 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24688035http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205435s000lbl.pdfCurator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/?term=25136252
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24688035http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205435s000lbl.pdf
Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/?term=25136252
Tedizolid phosphate is an oxazolidinone prodrug which in the body is dephosphorylated to the active compound tedizolid. The antibacterial activity of tedizolid is mediated by binding to the 50S subunit of the bacterial ribosome resulting in inhibition of protein synthesis. Tedizolid inhibits bacterial protein synthesis through a mechanism of action different from that of other non-oxazolidinone class antibacterial drugs; therefore, cross-resistance between tedizolid and other classes of antibacterial drugs is unlikely. Tedizolid is bacteriostatic against Gram Positive bacteria such as enterococci, staphylococci, and streptococci. No drug-drug interactions were identified with tedizolid.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16940121http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:83326
Curator's Comment: It was developed by Cubist Pharmaceuticals, following acquisition of Trius Therapeutics (originator: Dong-A Pharmaceuticals)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363135 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=25136252 |
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Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24688035 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | SIVEXTRO Approved UseIndicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by designated susceptible bacteria in adults. To reduce the development of drug-resistant bacteria and maintain the effectiveness of SIVEXTRO and other antibacterial drugs,
SIVEXTRO should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria. Launch Date1.40322236E12 |
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Curative | SIVEXTRO Approved UseIndicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by designated susceptible bacteria in adults. To reduce the development of drug-resistant bacteria and maintain the effectiveness of SIVEXTRO and other antibacterial drugs,
SIVEXTRO should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria. Launch Date1.40322236E12 |
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Curative | SIVEXTRO Approved UseIndicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by designated susceptible bacteria in adults. To reduce the development of drug-resistant bacteria and maintain the effectiveness of SIVEXTRO and other antibacterial drugs,
SIVEXTRO should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria. Launch Date1.40322236E12 |
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Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 μg/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.2 μg/mL |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.3 μg/mL |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3 μg/mL |
200 mg 1 times / day steady-state, intravenous dose: 200 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.8 μg × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
25.6 μg × h/mL |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
26.6 μg × h/mL |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
29.2 μg × h/mL |
200 mg 1 times / day steady-state, intravenous dose: 200 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12 h |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12 h |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12 h |
200 mg 1 times / day steady-state, intravenous dose: 200 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20% |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
20% |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
20% |
200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
20% |
200 mg 1 times / day steady-state, intravenous dose: 200 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
[NO STEREO] TEDIZOLID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg single, oral Studied dose |
healthy, 18-45 years n = 6 Health Status: healthy Age Group: 18-45 years Sex: M+F Population Size: 6 Sources: |
Disc. AE: Vomiting... Other AEs: Diarrhea, Headache... AEs leading to discontinuation/dose reduction: Vomiting (3 patients) Other AEs:Diarrhea (13%) Sources: Headache (10.9%) Nausea (6.5%) Abdominal pain (4.3%) Vomiting (4.3%) |
400 mg single, intravenous Highest studied dose Dose: 400 mg Route: intravenous Route: single Dose: 400 mg Sources: |
healthy, 29 years n = 9 Health Status: healthy Age Group: 29 years Sex: M+F Population Size: 9 Sources: |
|
400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
healthy, 31.0 years (range: 18–41) n = 8 Health Status: healthy Age Group: 31.0 years (range: 18–41) Sex: M+F Population Size: 8 Sources: |
Disc. AE: Reticulocyte count, White blood cell decreased... AEs leading to discontinuation/dose reduction: Reticulocyte count (1 patient) Sources: White blood cell decreased (1 patient) |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p. 117 |
unhealthy, 42 years (range: 17 - 86 years) n = 662 Health Status: unhealthy Age Group: 42 years (range: 17 - 86 years) Population Size: 662 Sources: Page: p. 117 |
Disc. AE: Abdominal discomfort, Diarrhea... AEs leading to discontinuation/dose reduction: Abdominal discomfort (0.2%) Sources: Page: p. 117Diarrhea (0.2%) Vomiting (0.2%) Osteomyelitis (0.2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Headache | 10.9% | 1200 mg single, oral Studied dose |
healthy, 18-45 years n = 6 Health Status: healthy Age Group: 18-45 years Sex: M+F Population Size: 6 Sources: |
Diarrhea | 13% | 1200 mg single, oral Studied dose |
healthy, 18-45 years n = 6 Health Status: healthy Age Group: 18-45 years Sex: M+F Population Size: 6 Sources: |
Vomiting | 3 patients Disc. AE |
1200 mg single, oral Studied dose |
healthy, 18-45 years n = 6 Health Status: healthy Age Group: 18-45 years Sex: M+F Population Size: 6 Sources: |
Abdominal pain | 4.3% | 1200 mg single, oral Studied dose |
healthy, 18-45 years n = 6 Health Status: healthy Age Group: 18-45 years Sex: M+F Population Size: 6 Sources: |
Vomiting | 4.3% | 1200 mg single, oral Studied dose |
healthy, 18-45 years n = 6 Health Status: healthy Age Group: 18-45 years Sex: M+F Population Size: 6 Sources: |
Nausea | 6.5% | 1200 mg single, oral Studied dose |
healthy, 18-45 years n = 6 Health Status: healthy Age Group: 18-45 years Sex: M+F Population Size: 6 Sources: |
Reticulocyte count | 1 patient Disc. AE |
400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
healthy, 31.0 years (range: 18–41) n = 8 Health Status: healthy Age Group: 31.0 years (range: 18–41) Sex: M+F Population Size: 8 Sources: |
White blood cell decreased | 1 patient Disc. AE |
400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
healthy, 31.0 years (range: 18–41) n = 8 Health Status: healthy Age Group: 31.0 years (range: 18–41) Sex: M+F Population Size: 8 Sources: |
Abdominal discomfort | 0.2% Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p. 117 |
unhealthy, 42 years (range: 17 - 86 years) n = 662 Health Status: unhealthy Age Group: 42 years (range: 17 - 86 years) Population Size: 662 Sources: Page: p. 117 |
Diarrhea | 0.2% Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p. 117 |
unhealthy, 42 years (range: 17 - 86 years) n = 662 Health Status: unhealthy Age Group: 42 years (range: 17 - 86 years) Population Size: 662 Sources: Page: p. 117 |
Osteomyelitis | 0.2% Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p. 117 |
unhealthy, 42 years (range: 17 - 86 years) n = 662 Health Status: unhealthy Age Group: 42 years (range: 17 - 86 years) Population Size: 662 Sources: Page: p. 117 |
Vomiting | 0.2% Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p. 117 |
unhealthy, 42 years (range: 17 - 86 years) n = 662 Health Status: unhealthy Age Group: 42 years (range: 17 - 86 years) Population Size: 662 Sources: Page: p. 117 |
Overview
OverviewOther
Drug as perpetrator
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205436Orig1s000PharmR.pdf#page=31 Page: 31.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Recent development of potent analogues of oxazolidinone antibacterial agents. | 2013 Feb 1 |
|
Absorption, distribution, metabolism, and excretion of the novel antibacterial prodrug tedizolid phosphate. | 2014 Aug |
|
Tedizolid phosphate for the treatment of acute bacterial skin and skin structure infections. | 2014 Nov |
|
Single- and multiple-dose pharmacokinetics and absolute bioavailability of tedizolid. | 2014 Sep |
|
Tedizolid Phosphate: a Next-Generation Oxazolidinone. | 2015 Feb 24 |
|
Critical role of tedizolid in the treatment of acute bacterial skin and skin structure infections. | 2017 |
|
Prolonged use of tedizolid in a pulmonary non-tuberculous mycobacterial infection after linezolid-induced toxicity. | 2017 Feb |
|
Systematic review and network meta-analysis of tedizolid for the treatment of acute bacterial skin and skin structure infections caused by MRSA. | 2017 Jan 7 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: SIVEXTRO (tedizolid phosphate) tablet, for oral use or SIVEXTRO (tedizolid phosphate) for injection, for
intravenous use.
Unknown
Route of Administration:
Unknown
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16940121
In vitro activities of DA-7157 against clinical isolates of Nocardia brasiliensis and Mycobacterium tuberculosis were determined. Equal MIC50s and MIC90s (0.25 and 0.5 μg/ml, respectively) were found for susceptible and multidrug-resistant isolates of M. tuberculosis. The N. brasiliensis isolates showed an MIC90 of 1 μg/ml and an MIC50 of 1 μg/ml.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:45:42 UTC 2023
by
admin
on
Thu Jul 06 22:45:42 UTC 2023
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Record UNII |
97HLQ82NGL
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Record Status |
Validated (UNII)
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NDF-RT |
N0000175495
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WHO-ATC |
J01XX11
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NCI_THESAURUS |
C258
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1540825
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UU-155
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N0000190113
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PRIMARY | Breast Cancer Resistance Protein Inhibitors [MoA] | ||
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11234049
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82717
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Tedizolid
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M10517
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97HLQ82NGL
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Tedizolid
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97HLQ82NGL
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100000168846
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CHEMBL1257051
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DB14569
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856866-72-3
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9136
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C84222
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SUB182420
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DTXSID10234975
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Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> INHIBITOR |
MAO inhibition can lead to peripheral or central neurotransmitter accumulation, with potentially serious consequences. MAO inhibitors, when taken in combination with vasoconstrictors, such as pseudoephedrine, or high dietary tyramine can cause sudden blood pressure elevations that may lead to hypertensive crises. Combination with serotonergic agents may lead to rare, but potentially life-threatening, serotonin syndrome
IC50
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TARGET ORGANISM->INHIBITOR |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MINOR
FECAL; URINE
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METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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SINGLE DOSE |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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SINGLE DOSE |
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