U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of TEDIZOLID

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

HIDE SMILES / InChI

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

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=25136252

Tedizolid (also known as TR-700, DA-7157) as is an active compound, which is produced by plasma or intestinal phosphatases, after administration of the drug, tedizolid phosphate either orally or intravenously. The mechanism of action of tedizolid occurs through inhibition of bacterial protein synthesis by binding to the 23S ribosomal RNA of the 50S subunit, thereby preventing the formation of the 70S initiation complex and inhibiting protein synthesis.

Originator

Curator's Comment: It was developed by Cubist Pharmaceuticals, following acquisition of Trius Therapeutics (originator: Dong-A Pharmaceuticals)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SIVEXTRO

Approved Use

Indicated 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 Date

1.40322236E12
Curative
SIVEXTRO

Approved Use

Indicated 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 Date

1.40322236E12
Curative
SIVEXTRO

Approved Use

Indicated 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 Date

1.40322236E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
1200 mg single, oral
Studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
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%)
Headache (10.9%)
Nausea (6.5%)
Abdominal pain (4.3%)
Vomiting (4.3%)
Sources:
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)
White blood cell decreased (1 patient)
Sources:
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%)
Diarrhea (0.2%)
Vomiting (0.2%)
Osteomyelitis (0.2%)
Sources: Page: p. 117
AEs

AEs

AESignificanceDosePopulation
Headache 10.9%
1200 mg single, oral
Studied dose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
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
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
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
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
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
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
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
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
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
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
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
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 51.1 uM]
yes (co-administration study)
Comment: Coadministration of multiple oral doses of SIVEXTRO (200 mg once daily) increased the Cmax and AUC of rosuvastatin (10 mg single oral dose), a known BCRP substrate, by approximately 55% and 70%, respectively, in healthy adult subjects
Page: 10.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Patents

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.
The recommended dosage of SIVEXTRO is 200 mg administered once daily for six (6) days either orally (with or without food) or as an intravenous (IV) infusion in patients 18 years of age or older.
Route of Administration: Oral
At least 90% of the microorganisms (Staphylococcus aureus (including methicillin-resistant [MRSA] and methicillinsusceptible [MSSA] isolates); Streptococcus pyogenes; Streptococcus agalactiae; Streptococcus anginosus Group (including S. anginosus, S. intermedius, and S. constellatus); Enterococcus faecalis; Staphylococcus epidermidis (including methicillin-susceptible and methicillin-resistant isolates); Staphylococcus haemolyticus; Staphylococcus lugdunensis; Enterococcus faecium) exhibit an in vitro minimum inhibitory concentration (MIC) less than or equal to 0.5 mcg/mL for tedizolid.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:22:20 UTC 2023
Edited
by admin
on Sat Dec 16 17:22:20 UTC 2023
Record UNII
97HLQ82NGL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEDIZOLID
INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
Tedizolid [WHO-DD]
Common Name English
(5R)-3-{3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl]phenyl}-5-(hydroxymethyl)oxazolidin-2-one
Systematic Name English
TOREZOLID
Common Name English
tedizolid [INN]
Common Name English
TEDIZOLID [USAN]
Common Name English
TEDIZOLID [MI]
Common Name English
TR-700
Code English
2-OXAZOLIDINONE, 3-(3-FLUORO-4-(6-(2-METHYL-2H-TETRAZOL-5-YL)-3-PYRIDINYL)PHENYL)-5-(HYDROXYMETHYL)-, (5R)-
Systematic Name English
TEDIZOLID [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175495
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
WHO-ATC J01XX11
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
NCI_THESAURUS C258
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
Code System Code Type Description
RXCUI
1540825
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY RxNorm
USAN
UU-155
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
NDF-RT
N0000190113
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
PUBCHEM
11234049
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
CHEBI
82717
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
LACTMED
Tedizolid
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
MERCK INDEX
m10517
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY Merck Index
FDA UNII
97HLQ82NGL
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
WIKIPEDIA
Tedizolid
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
DAILYMED
97HLQ82NGL
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
SMS_ID
100000168846
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL1257051
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
DRUG BANK
DB14569
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
CAS
856866-72-3
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
INN
9136
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
NCI_THESAURUS
C84222
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
EVMPD
SUB182420
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID10234975
Created by admin on Sat Dec 16 17:22:21 UTC 2023 , Edited by admin on Sat Dec 16 17:22:21 UTC 2023
PRIMARY
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Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
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Biological Half-life PHARMACOKINETIC
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INTRAVENOUS ADMINISTRATION