PRETOMANID

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H12F3N3O5
Molecular Weight	359.2574
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of PRETOMANID

Structure Search

SMILES

[O-][N+](=O)C1=CN2C[C@@H](COC2=N1)OCC3=CC=C(OC(F)(F)F)C=C3

InChI

InChIKey=ZLHZLMOSPGACSZ-NSHDSACASA-N

InChI=1S/C14H12F3N3O5/c15-14(16,17)25-10-3-1-9(2-4-10)7-23-11-5-19-6-12(20(21)22)18-13(19)24-8-11/h1-4,6,11H,5,7-8H2/t11-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C14H12F3N3O5
Molecular Weight	359.2574
Charge	0
Count

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

Approval Year

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:15:52 UTC 2023` Edited by `admin` on `Sat Dec 16 02:15:52 UTC 2023`
Record UNII	2XOI31YC4N
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PRETOMANID

Official Name

English

(S)-2-NITRO-6-(4-(TRIFLUOROMETHOXY)BENZYLOXY)-6,7-DIHYDRO-5H-IMIDAZO(2,1-B)(1,3)OXAZINE

Systematic Name

English

PA-824

Code

English

Pretomanid [WHO-DD]

Common Name

English

pretomanid [INN]

Common Name

English

PA 824

Code

English

PRETOMANID [ORANGE BOOK]

Common Name

English

(3S)-3-(4-TRIFLUOROMETHOXYBENZYLOXY)-6-NITRO-2H-3,4-DIHYDROIMIDAZO(2,1-B)OXAZINE

Common Name

English

PRETOMANID [MI]

Common Name

English

PRETOMANID [USAN]

Common Name

English

PA824

Code

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/07/513

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

FDA ORPHAN DRUG

243107

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

Code System Code Type Description

DRUG BANK

DB05154

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

DAILYMED

2XOI31YC4N

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

DRUG CENTRAL

5344

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

WIKIPEDIA

Pretomanid

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

CAS

187235-37-6

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

EPA CompTox

DTXSID8041163

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

ChEMBL

CHEMBL227875

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

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MERCK INDEX

m12157

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

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FDA UNII

2XOI31YC4N

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

INN

9871

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

PUBCHEM

456199

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

SMS_ID

100000141666

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

LACTMED

Pretomanid

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

RXCUI

2198359

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

NCI_THESAURUS

C166606

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

USAN

BC-53

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

EVMPD

SUB96086

Created by admin on Sat Dec 16 02:15:53 UTC 2023 , Edited by admin on Sat Dec 16 02:15:53 UTC 2023

PRIMARY

Related Record Type Details


					ZWJ2Y6JZWY

OAT-3

TRANSPORTER -> INHIBITOR

Comments:

In vitro studies indicate that pretomanid significantly inhibits the OAT3 drug transporter which could result in increased concentrations of OAT3 substrates at clinically relevant concentrations of pretomanid. No clinical DDI studies have been conducted with OAT3 substrates.


					L0423Z5LDW

CYTOCHROME P450 2C8

METABOLIC ENZYME -> INHIBITOR

Comments:

Pretomanid is a weak time-dependent inhibitor of CYP2C8 and CYP2C19.

Interaction Type:

TIME-DEPENDENT INHIBITION


					081I12ZA58

CYTOCHROME P450 2C19

METABOLIC ENZYME -> INHIBITOR

Comments:

Pretomanid is a weak time-dependent inhibitor of CYP2C8 and CYP2C19.

Interaction Type:

TIME-DEPENDENT INHIBITION


					R0EM8D5HFD

MYCOBACTERIUM TUBERCULOSIS

TARGET ORGANISM->INHIBITOR


					2XOI31YC4N

EXCRETED UNCHANGED

Interaction Type:

AMOUNT EXCRETED

Qualification:

FECAL; URINE

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Comments:

Human plasma protein binding of pretomanid is approximately 86.4% and is independent of drug concentration.

Interaction Type:

BINDING

Amount:

Related Record Type Details


					C658O375NL

2-HYDROXYIMIDAZOLE

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:


					KPJ4EW9JVT

2-AMINO-1,3-OXAZINAN-5-OL

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:

Related Record Type Details


					2XOI31YC4N

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Tmax	PHYSICAL				FASTED CONDITION SINGLE DOSE ADMINISTRATION

Biological Half-life	PHARMACOKINETIC				FASTED CONDITION SINGLE DOSE ADMINISTRATION

Tmax	PHARMACOKINETIC				SINGLE DOSE ADMINISTRATION FED CONDITION

Volume of Distribution	PHARMACOKINETIC				SINGLE DOSE ADMINISTRATION FED CONDITION

Volume of Distribution	PHARMACOKINETIC				FASTED CONDITION SINGLE DOSE ADMINISTRATION

Biological Half-life	PHARMACOKINETIC				FED CONDITION SINGLE DOSE ADMINISTRATION