TEDIZOLID

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

HIDE SMILES / InChI

Molecular Formula	C17H15FN6O3
Molecular Weight	370.3378
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 180	Antagonist 2,849
Bacterial 70S ribosome 180	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Skin infections 59	Curative	Approved 8,583	SIVEXTRO
Staphylococcal skin infections 4	Curative	Approved 8,583	SIVEXTRO
Skin bacterial infections 4	Curative	Approved 8,583	SIVEXTRO
Unknown 2,596

C_max

Value	Dose	Analyte	Population
2.2 μg/mL	200 mg 1 times / day steady-state, oral	[NO STEREO] TEDIZOLID plasma	Homo sapiens
3 μg/mL	200 mg 1 times / day steady-state, intravenous	[NO STEREO] TEDIZOLID plasma	Homo sapiens
2 μg/mL	200 mg single, oral	[NO STEREO] TEDIZOLID plasma	Homo sapiens
2.3 μg/mL	200 mg single, intravenous	[NO STEREO] TEDIZOLID plasma	Homo sapiens
2 μg/mL	200 mg single, oral	TEDIZOLID plasma	Homo sapiens
2.2 μg/mL	200 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
2.3 μg/mL	200 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
3 μg/mL	200 mg 1 times / day steady-state, intravenous	TEDIZOLID plasma	Homo sapiens
1.99 μg/mL	200 mg single, oral	TEDIZOLID plasma	Homo sapiens
3.77 μg/mL	400 mg single, oral	TEDIZOLID plasma	Homo sapiens
5.21 μg/mL	800 mg single, oral	TEDIZOLID plasma	Homo sapiens
5.52 μg/mL	800 mg single, oral	TEDIZOLID plasma	Homo sapiens
9.49 μg/mL	1200 mg single, oral	TEDIZOLID plasma	Homo sapiens
1.8 μg/mL	200 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
1.8 μg/mL	200 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
2.1 μg/mL	300 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
2.7 μg/mL	300 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
4.2 μg/mL	400 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
4.7 μg/mL	400 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
1.16 μg/mL	100 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
2.62 μg/mL	200 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
4.53 μg/mL	300 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
5.13 μg/mL	400 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
2.34 μg/mL	200 mg 1 times / day multiple, intravenous	TEDIZOLID plasma	Homo sapiens
3.01 μg/mL	200 mg 1 times / day steady-state, intravenous	TEDIZOLID plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
25.6 μg × h/mL	200 mg 1 times / day steady-state, oral	[NO STEREO] TEDIZOLID plasma	Homo sapiens
29.2 μg × h/mL	200 mg 1 times / day steady-state, intravenous	[NO STEREO] TEDIZOLID plasma	Homo sapiens
23.8 μg × h/mL	200 mg single, oral	[NO STEREO] TEDIZOLID plasma	Homo sapiens
26.6 μg × h/mL	200 mg single, intravenous	[NO STEREO] TEDIZOLID plasma	Homo sapiens
23.8 μg × h/mL	200 mg single, oral	TEDIZOLID plasma	Homo sapiens
25.6 μg × h/mL	200 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
26.6 μg × h/mL	200 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
29.2 μg × h/mL	200 mg 1 times / day steady-state, intravenous	TEDIZOLID plasma	Homo sapiens
25.35 μg × h/mL	200 mg single, oral	TEDIZOLID plasma	Homo sapiens
56.1 μg × h/mL	400 mg single, oral	TEDIZOLID plasma	Homo sapiens
79.26 μg × h/mL	800 mg single, oral	TEDIZOLID plasma	Homo sapiens
91.8 μg × h/mL	800 mg single, oral	TEDIZOLID plasma	Homo sapiens
123.1 μg × h/mL	1200 mg single, oral	TEDIZOLID plasma	Homo sapiens
16.7 μg × h/mL	200 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
22.5 μg × h/mL	200 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
24.1 μg × h/mL	300 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
31.2 μg × h/mL	300 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
46 μg × h/mL	400 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
52 μg × h/mL	400 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
17.36 μg × h/mL	100 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
32.58 μg × h/mL	200 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
51.9 μg × h/mL	300 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
58.7 μg × h/mL	400 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
22.29 μg × h/mL	200 mg 1 times / day multiple, intravenous	TEDIZOLID plasma	Homo sapiens
29.18 μg × h/mL	200 mg 1 times / day steady-state, intravenous	TEDIZOLID plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
12 h	200 mg 1 times / day steady-state, oral	[NO STEREO] TEDIZOLID plasma	Homo sapiens
12 h	200 mg 1 times / day steady-state, intravenous	[NO STEREO] TEDIZOLID plasma	Homo sapiens
12 h	200 mg single, oral	[NO STEREO] TEDIZOLID plasma	Homo sapiens
12 h	200 mg single, intravenous	[NO STEREO] TEDIZOLID plasma	Homo sapiens
11.2 h	200 mg single, oral	TEDIZOLID plasma	Homo sapiens
10.8 h	400 mg single, oral	TEDIZOLID plasma	Homo sapiens
11.4 h	800 mg single, oral	TEDIZOLID plasma	Homo sapiens
10.6 h	800 mg single, oral	TEDIZOLID plasma	Homo sapiens
10.4 h	1200 mg single, oral	TEDIZOLID plasma	Homo sapiens
11.1 h	200 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
10.2 h	200 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
10.1 h	300 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
11.9 h	300 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
8.01 h	400 mg 1 times / day multiple, oral	TEDIZOLID plasma	Homo sapiens
12.8 h	400 mg 1 times / day steady-state, oral	TEDIZOLID plasma	Homo sapiens
13.4 h	100 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
11 h	200 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
9.3 h	300 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
11.3 h	400 mg single, intravenous	TEDIZOLID plasma	Homo sapiens
9.33 h	200 mg 1 times / day multiple, intravenous	TEDIZOLID plasma	Homo sapiens
12.4 h	200 mg 1 times / day steady-state, intravenous	TEDIZOLID plasma	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
20%	200 mg 1 times / day steady-state, oral	[NO STEREO] TEDIZOLID plasma	Homo sapiens
20%	200 mg 1 times / day steady-state, intravenous	[NO STEREO] TEDIZOLID plasma	Homo sapiens
20%	200 mg single, oral	[NO STEREO] TEDIZOLID plasma	Homo sapiens
20%	200 mg single, intravenous	[NO STEREO] TEDIZOLID plasma	Homo sapiens
15.4%		TEDIZOLID plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1200 mg single, oral Highest studied dose	healthy, ADULT	Disc. AE: Vomiting... Other AEs: Diarrhea, Nausea...
400 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT	Other AEs: Platelets decreased, Neutrophil Count...
200 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT	Disc. AE: Hypertension...
200 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT	Disc. AE: Nausea... Other AEs: Cytopenia...
1200 mg single, oral Studied dose	healthy, 18-45 years	Disc. AE: Vomiting... Other AEs: Diarrhea, Headache...

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AEs

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AE	Significance	Dose	Population
Headache	10.9%	1200 mg single, oral Highest studied dose	healthy, ADULT
Diarrhea	13%	1200 mg single, oral Highest studied dose	healthy, ADULT
Vomiting	2.2% Disc. AE	1200 mg single, oral Highest studied dose	healthy, ADULT
Nausea	6.5%	1200 mg single, oral Highest studied dose	healthy, ADULT
Platelets decreased	100%	400 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inhibitor 2,252 inducer 1,087	substrate 1,193 inhibitor 2,438 inducer 440	substrate 1,388 inhibitor 2,507 inducer 109	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2B6 926 CYP2C8 1,057 CYP2C19 2,057 OAT1 725 OAT3 747 OATP1B1 1,079 OATP1B3 961 OCT1 620 OCT2 779 P-gp 1,741 BCRP 910	CYP1A2 1,197 CYP2B6 776 CYP2C8 810 CYP2C19 1,119 OAT1 395 OAT3 391 OATP1B1 503 OATP1B3 435 OCT1 393 OCT2 434 P-gp 2,052 SULT1A1 37 SULT2A1 28	CYP1A2 832 CYP2B6 669 CYP2C8 198 CYP2C19 329

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 2,333	inducer 1,966	no
CYP1A2 2,333	inhibitor 4,027	no
CYP2B6 1,160	inducer 1,966	no
CYP2B6 1,160	inhibitor 4,027	no
CYP2C19 2,141	inducer 1,966	no

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Drug as victim

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Target	Modality	Activity
CYP1A2 1,197	substrate 4,014	no
CYP2B6 776	substrate 4,014	no
CYP2C19 1,119	substrate 4,014	no
CYP2C8 810	substrate 4,014	no
CYP2C9 1,193	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:82717	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:82717
ChemicalBook	CB02484972	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB02484972
MolPort	MolPort-042-624-220	https://www.molport.com/shop/molecule-link/MolPort-042-624-220
ZINC	ZINC000043100956	http://zinc15.docking.org/substances/ZINC000043100956

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PubMed

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Title	Date	PubMed
Prolonged use of tedizolid in a pulmonary non-tuberculous mycobacterial infection after linezolid-induced toxicity.	2017 Feb	27999019
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	28061827

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Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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
Record UNII	97HLQ82NGL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEDIZOLID

Official Name

English

tedizolid [INN]

Preferred 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

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175495

Other antibacterials

WHO-ATC

J01XX11

Anti-Infective Agent

NCI_THESAURUS

C258

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Code System

Code

Type

Description

RXCUI

1540825

PRIMARY

RxNorm

USAN

UU-155

PRIMARY

NDF-RT

N0000190113

PRIMARY

Breast Cancer Resistance Protein Inhibitors [MoA]

PUBCHEM

11234049

PRIMARY

CHEBI

82717

PRIMARY

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Related Record

Type

Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

[70 to 90] % (average)


					3OV8HVI592

AMINE OXIDASE (FLAVIN-CONTAINING) B

METABOLIC ENZYME -> INHIBITOR

Comments:

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

Qualification:

IC50

Amount:

5.7 MICROMOLAR (average)


					65P5WPF3BJ

METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS

TARGET ORGANISM->INHIBITOR

Amount:


					TYR9KD6MVB

Tedizolid, (S)-

ENANTIOMER -> ENANTIOMER

Amount:

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Related Record

Type

Details


					G5ADH118ED

CARBOXY TEDIZOLID

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

FECAL; URINE

Amount:


					2LN88S7R9P

TEDIZOLID O-SULFATE

METABOLITE -> PARENT

Interaction Type:

MAJOR

Qualification:

PLASMA; URINE

Amount:


					RXX49NX4AW

DESMETHYL TEDIZOLID SULFATE

METABOLITE -> PARENT

Amount:


					Z11QI50Q37

DESMETHYL TEDIZOLID

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE

Amount:


					6MM3KJ999B

(3-FLUORO-4-(6-(2-METHYLTETRAZOL-5-YL)-3-PYRIDYL)PHENYL)-METHYL-CARBAMIC ACID

METABOLITE -> PARENT

Amount:

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Related Record

Type

Details


					97HLQ82NGL

TEDIZOLID

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	[0.95 to 1.14] Liters/Kilogram (average)

Tmax	PHARMACOKINETIC	2.5 hours [1 to 8] (average)	SINGLE DOSE 200 mg (average) ORAL ADMINISTRATION

Biological Half-life	PHARMACOKINETIC	12 hours (average)

Tmax	PHARMACOKINETIC	1.1 hours [0.9 to 1.5] (average)	SINGLE DOSE 200 mg (average) INTRAVENOUS ADMINISTRATION

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator