TERIFLUNOMIDE

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

National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H9F3N2O2
Molecular Weight	270.2073
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0
Stereo Comments	Teriflunomide then can interconvert between the E and Z enolic forms (and the corresponding keto-amide), with the Z-enol being the most stable and therefore most predominant form (https://en.wikipedia.org/wiki/Leflunomide)

SHOW SMILES / InChI

Structure of TERIFLUNOMIDE

Structure Search

SMILES

C\C(O)=C(/C#N)C(=O)NC1=CC=C(C=C1)C(F)(F)F

InChI

InChIKey=UTNUDOFZCWSZMS-YFHOEESVSA-N

InChI=1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-

HIDE SMILES / InChI

Molecular Formula	C12H9F3N2O2
Molecular Weight	270.2073
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:43:19 UTC 2023` Edited by `admin` on `Fri Dec 15 15:43:19 UTC 2023`
Record UNII	1C058IKG3B
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TERIFLUNOMIDE

Official Name

English

TERIFLUNOMIDE [MI]

Common Name

English

teriflunomide [INN]

Common Name

English

AUBAGIO

Brand Name

English

HMR-1726

Code

English

LEFLUNOMIDE RELATED COMPOUND B

Common Name

English

TERIFLUNOMIDE [USAN]

Common Name

English

HMR1726

Code

English

LEFLUNOMIDE RELATED COMPOUND B [USP IMPURITY]

Common Name

English

2-BUTENAMIDE, 2-CYANO-3-HYDROXY-N-(4-(TRIFLUOROMETHYL)PHENYL)-, (2Z)-

Systematic Name

English

LEFLUNOMIDE IMPURITY B [EP IMPURITY]

Common Name

English

TERIFLUNOMIDE [ORANGE BOOK]

Common Name

English

A77 1726

Code

English

TERIFLUNOMIDE [VANDF]

Common Name

English

Teriflunomide [WHO-DD]

Common Name

English

TERIFLUNOMIDE [EP MONOGRAPH]

Common Name

English

LEFLUNOMIDE RELATED COMPOUND B [USP-RS]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548525

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

WHO-VATC

QL04AA31

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

NCI_THESAURUS

C471

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

EMA ASSESSMENT REPORTS

AUBAGIO (AUTHORIZED: MULTIPLE SCLEROSIS)

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

NDF-RT

N0000185502

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

WHO-ATC

L04AA31

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

Code System Code Type Description

DRUG BANK

DB08880

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

CHEBI

68540

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

PUBCHEM

54684141

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

EVMPD

SUB25218

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

RS_ITEM_NUM

1357056

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

MESH

C527525

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

WIKIPEDIA

TERIFLUNOMIDE

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

USAN

YY-88

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

FDA UNII

1C058IKG3B

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

LACTMED

Teriflunomide

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

INN

7761

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

SMS_ID

100000089234

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

NDF-RT

N0000185501

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

Dihydroorotate Dehydrogenase Inhibitors [MoA]

MERCK INDEX

m10578

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

Merck Index

ChEMBL

CHEMBL973

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

CAS

108605-62-5

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

NON-SPECIFIC STEREOCHEMISTRY

NCI_THESAURUS

C76662

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

DAILYMED

1C058IKG3B

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

DRUG CENTRAL

4634

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

IUPHAR

6844

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

RXCUI

1310520

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

RxNorm

CAS

163451-81-8

Created by admin on Fri Dec 15 15:43:19 UTC 2023 , Edited by admin on Fri Dec 15 15:43:19 UTC 2023

PRIMARY

Related Record Type Details


					805SU96HKF

CYTOCHROME P450 3A5

METABOLIC ENZYME -> NON-SUBSTRATE


					L0423Z5LDW

CYTOCHROME P450 2C8

METABOLIC ENZYME -> NON-SUBSTRATE


					1C058IKG3B

EXCRETED UNCHANGED

Qualification:

FECAL

Amount:


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> INHIBITOR

Comments:

Terifluniomide is an inhibitor of BCRP, OAT3, OATP1B1, OCT2 in vitro


					ZWJ2Y6JZWY

OAT-3

TRANSPORTER -> INHIBITOR

Comments:

Terifluniomide is an inhibitor of BCRP, OAT3, OATP1B1, OCT2 in vitro


					1C058IKG3B

EXCRETED UNCHANGED

Qualification:

URINE

Amount:


					AIN96D6SGL

OATP1B1

TRANSPORTER -> INHIBITOR

Comments:

Terifluniomide is an inhibitor of BCRP, OAT3, OATP1B1, OCT2 in vitro


					Z1GD6Y2I9Q

DIHYDROOROTATE DEHYDROGENASE (QUINONE), MITOCHONDRIAL

TARGET -> INHIBITOR

Interaction Type:

INHIBITOR

Qualification:

IC50

Amount:


					081I12ZA58

CYTOCHROME P450 2C19

METABOLIC ENZYME -> NON-SUBSTRATE


					0UY97CSG1T

CYTOCHROME P450 2B6

METABOLIC ENZYME -> NON-SUBSTRATE


					L9DP834D1P

CYTOCHROME P450 2C9

METABOLIC ENZYME -> NON-SUBSTRATE


					6ZJT0Z4FA9

DIMETHYLANILINE MONOOXYGENASE (N-OXIDE-FORMING) 5

METABOLIC ENZYME -> NON-SUBSTRATE


					482M00274D

OCT-2

TRANSPORTER -> INHIBITOR

Comments:

Terifluniomide is an inhibitor of BCRP, OAT3, OATP1B1, OCT2 in vitro


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> SUBSTRATE

Comments:

Teriflunomide is a substrate of BCRP in vitro


					9971WH3C6O

FETAL HEPATIC FLAVIN-CONTAINING MONOOXYGENASE 3 (HUMAN)

METABOLIC ENZYME -> NON-SUBSTRATE


					8E4LAA4357

CYTOCHROME P450 2D6

METABOLIC ENZYME -> NON-SUBSTRATE


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> NON-SUBSTRATE


					VK4SQL11C0

CYTOCHROME P450 1A2

METABOLIC ENZYME -> NON-SUBSTRATE

Related Record Type Details


					T4N584WTC2

2-CYANO-N-(4-(TRIFLUOROMETHYL)PHENYL)ACETAMIDE

METABOLITE -> PARENT


					ENX2MR5ALD

2-AMINO-5-(TRIFLUOROMETHYL)PHENOL

METABOLITE -> PARENT


					7E7G2PTL6J

(2-HYDROXY-4-(TRIFLUOROMETHYL)PHENYL)SULFAMIC ACID

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE

Amount:


					SG8LF6NJ4W

2-HYDROXY-3-OXO-3-(4-(TRIFLUOROMETHYL)ANILINO)PROPANOIC ACID

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE

Amount:


					FZB8EA8KMZ

2-HYDROXY-N-(4-(TRIFLUOROMETHYL)PHENYL)ACETAMIDE

METABOLITE -> PARENT


					NRC7BA9FEK

(2Z)-2-CYANO-3,4-DIHYDROXY-N-(4-(TRIFLUOROMETHYL)PHENYL)-2-BUTENAMIDE

METABOLITE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE

Amount:


					RQJ623MB8G

4-(TRIFLUOROMETHYL)ANILINE

METABOLITE -> PARENT

Comments:

4-TFMA was not detected in the single dose metabolism study, but was detected in very small amount after repeated dosing in clinical trials 4-TFMA plasma concentrations were measurable at relatively low concentrations after repeated teriflunomide doses of 7 mg (≤1.7 ng/mL) and 14 mg (≤5.31 ng/mL) for 468 weeks.

Interaction Type:

MINOR


					G162GK9U4W

PRODRUG -> METABOLITE ACTIVE

Related Record Type Details


					G162GK9U4W

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

Related Record Type Details


					1C058IKG3B

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC				DOSE

Tmax	PHARMACOKINETIC				ORAL ADMINISTRATION