A77 1726

ChemicalBook > CAS DataBase List > A77 1726

Product Name: A77 1726
CAS No.: 163451-81-8
Chemical Name: A77 1726
Synonyms: Flucyamide;A77 1726 (Teriflunomide);2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-, (2Z)-;A 1726;HMR 1726;A77 1726;Teriflunomide(b);Teriflunomide (cGMP);Leflunomide Impurity B;LeflunoMide EP IMpurity B
CBNumber: CB02486749
Molecular Formula: C12H9F3N2O2
Formula Weight: 270.21
MOL File: 163451-81-8.mol

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A77 1726 Property

Melting point:: 229-232°C
Boiling point:: 410.8±45.0 °C(Predicted)
Density: 1.424±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: DMSO: soluble5mg/mL, clear (warmed)
pka: 5.20±0.50(Predicted)
form: powder
color: white to beige
λmax: 203nm(MeOH)(lit.)
Merck: 14,9165
Stability:: Hygroscopic
InChIKey: UTNUDOFZCWSZMS-YFHOEESVSA-N

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Safety

Hazard Codes: Xn
Risk Statements: 22
WGK Germany: 3
HS Code: 2926.90.4801

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0936
Product name: Teriflunomide
Purity: ≥98% (HPLC)
Packaging: 10mg
Price: $73.6
Updated: 2024/03/01

Sigma-Aldrich

Product number: T-122
Product name: Teriflunomidesolution
Purity: 1?mg/mLinacetonitrile,certifiedreferencematerial,ampuleof1?mL
Packaging: 1mL
Price: $130
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0936
Product name: Teriflunomide
Purity: ≥98% (HPLC)
Packaging: 50mg
Price: $313
Updated: 2024/03/01

TCI Chemical

Product number: T3287
Product name: Teriflunomide
Purity: >98.0%(GC)
Packaging: 100mg
Price: $79
Updated: 2024/03/01

TCI Chemical

Product number: T3287
Product name: Teriflunomide
Purity: >98.0%(GC)
Packaging: 1g
Price: $475
Updated: 2024/03/01

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A77 1726 Chemical Properties,Usage,Production

Description

In September 2012, the US FDA approved teriflunomide (also referred to as HMR-1726) as a therapy for patients with relapsing forms of multiple sclerosis (MS). Teriflunomide is the second approved oral treatment option for MS, after Gilenya? which was approved in 2010. Teriflunomide, which is the active metabolite of leflunomide (a marketed drug for the treatment of rheumatoid and psoriatic arthritis), is a non?competitive and selective inhibitor of dihydroorotate dehydrogenase (DHODH), the rate-limiting enzyme in the de novo synthesis of pyrimidines. Although the net effect of inhibition of DHODH by teriflunomide and its therapeutic effect in MS are not clear, it is hypothesized that by inhibiting de novo pyrimidine synthesis, the effector functions of activated lymphocytes are suppressed, thus dampening the effect of an overactive immune system.

Description

A-771726 is an active metabolite of the prodrug leflunomide that inhibits dihydroorotate dehydrogenase (DHODH; IC₅₀ = 0.23 μM). A-771726 inhibits the production of prostaglandin E₂ (PGE₂; ) in TNF-α- or IL-1α-stimulated isolated human synoviocytes (IC₅₀s = 7 and 3 μM, respectively). It inhibits the proliferation of isolated human peripheral blood mononuclear cells (PBMCs) when used at concentrations of 25 and 100 μM. A-771726 (3 and 10 mg/kg) delays disease onset and decreases neurological deficits in a rat model of experimental autoimmune encephalomyelitis (EAE) induced by complete Freund’s adjuvant (CFA) and M. tuberculosis. Formulations containing teriflunomide have been used in the treatment of multiple sclerosis.

Chemical Properties

White Solid

Originator

Genzyme (United States)

Uses

Teriflunomide has been used as a dihydroorotate dehydrogenase (DHODH) inhibitor.

Uses

The active metabolite of Leflunomide, a potent disease-modifying antirheumatic drug used in the treatment of rheumatoid arthritis. LEF-M interferes with dendritic cell function.

Uses

A-771726 is the active metabolite of leflunomide, a prodrug approved by the FDA for treatment of rheumatoid arthritis. A-771726 reversibly inhibits dihydroorotate dehydrogenase, the rate-limiting step in the de novo synthesis of pyrimidines. It prevents activated lymphocytes from accumulating sufficient pyrimidines to support DNA synthesis (IC50s = 0.09, 3.5, and 12.5 μM for rat, mouse, and human, respectively). At higher doses, A-771726 inhibits tyrosine kinases responsible for early T cell and B cell signaling in the G0/G1 phase of the cell cycle. A-771726 has also been shown to inhibit the production of prostaglandin E2 in synoviocytes activated by TNF-α and IL-1α (IC50s = 7 and 3 μM, respectively) as well as inhibit MMP-1 and IL-6 production at concentrations >10 μM.[Cayman Chemical]

Definition

ChEBI: An enamide obtained by formal condensation of the carboxy group of (2Z)-2-cyano-3-hydroxybut-2-enoic acid with the anilino group of 4-(trifluoromethyl)aniline. Used for the treatment of relapsing forms of multiple sclerosis and rheumatoid arthritis.

brand name

Aubagio

General Description

Teriflunomide, marketed under the trade name Aubagio, is the active metabolite of leflunomide, an immunosuppressive disease-modifying antirheumatic drug, used in active moderate-to-severe rheumatoid arthritis and psoriatic arthritis. An analytical reference standard for use in LC/MS or GC/MS applications including clinical and diagnostic testing such as therapeutic drug monitoring assays.

Biochem/physiol Actions

Teriflunomide is an orally available anti-inflammatory immunomodulator. It blocks the activity of dihydroorotate dehydrogenase, preventing pyrimidine synthesis and T and B cell proliferation and function. Teriflunomide has been used to treat rheumatoid arthritis and was recently approved for multiple sclerosis.

References

[1] yao h w, li j, chen j q, et al. a 771726, the active metabolite of leflunomide, inhibits tnf-α and il-1 from kupffer cells[j]. inflammation, 2004, 28(2): 97-103.
[2] breedveld f c, dayer j m. leflunomide: mode of action in the treatment of rheumatoid arthritis[j]. annals of the rheumatic diseases, 2000, 59(11): 841-849.
[3] burger d, begué‐pastor n, benavent s, et al. the active metabolite of leflunomide, a77 1726, inhibits the production of prostaglandin e2, matrix metalloproteinase 1 and interleukin 6 in human fibroblast‐like synoviocytes[j]. rheumatology, 2003, 42(1): 89-96.
[4] davis j p, cain g a, pitts w j, et al. the immunosuppressive metabolite of leflunomide is a potent inhibitor of human dihydroorotate dehydrogenase[j]. biochemistry, 1996, 35(4): 1270-1273.

A77 1726 Preparation Products And Raw materials

Raw materials

Preparation Products

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A77 1726 Suppliers

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View Lastest Price from A77 1726 manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Teriflunomide 163451-81-8
Price: US $0.00-0.00/Kg/Drum
Min. Order: 1KG
Purity: 98%min
Supply Ability: 1000KGS
Release date: 2021-11-08

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.

Product: Teriflunomide 163451-81-8
Price: US $0.00/g
Min. Order: 1g
Purity: More Than 99%
Supply Ability: 100kg/Month
Release date: 2024-10-11

Wuhan Nutra Biotechnology Co.,Ltd

Product: Teriflunomide;A77 1726 163451-81-8
Price: US $285.00-0.00/g
Min. Order: 1g
Purity: 98%+
Supply Ability: 100kgs
Release date: 2021-05-23

163451-81-8, A77 1726Related Search:

Teriflunomide-d4 5-DesMethyl-3-Methyl LeflunoMide Pregabalin Sofosbuvir LeflunoMide EP IMpurity G 2-cyano-N-[4-(trifluoromethyl)phenyl]acetamide 5-Methyl-4-isoxazolecarboxylic acid LeflunoMide EP IMpurity F Leflunomide 3-Isomer LeflunoMide EP IMpurity E 4-Aminobenzotrifluoride Leflunomide

A77 1726 (Teriflunomide)

A 1726

Flucyamide

HMR 1726

(Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-butenamide

LeflunoMide EP IMpurity B

Leflunomide Impurity 2(Leflunomide EP Impurity B)

A-771726;A 771726;A771726

A-771726;A 77-1726;A771726;HMR-1726

(2Z)-2-Cyano-3-hydroxy-N-[4-(triflu

Teriflunomide(b)

Leflunomide EP Impurity B (Teriflunomide)

2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-, (2Z)-

Leflunomide Impurity B

Leflunomide EP Impurity B/ Leflunomide Related Compound B

Teriflunomide (cGMP)

Leflunomide impurities1341

TeriflunomideQ: What is Teriflunomide Q: What is the CAS Number of Teriflunomide Q: What is the storage condition of Teriflunomide Q: What are the applications of Teriflunomide

LeflunomideEPImpurityB-d4

A77 1726

Leflunomide EP Impurity B Leflunomide USP RC B

(2Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide (Teriflunomide)

Teriflunomide, 10 mM in DMSO

163451-81-8

204395-49-4

Metabolites & Impurities

Tyrosine Kinase Inhibitors