ChemicalBook > CAS DataBase List > Febuxostat

Febuxostat

Product Name
Febuxostat
CAS No.
144060-53-7
Chemical Name
Febuxostat
Synonyms
FBX;Uloric;Febuxostat Impurity;2-(3-cyano-4-isobutoxyphenyl);TMX 67;CS-1598;Tei-6720;NSC63871;Febrista;Adenuric
CBNumber
CB4841564
Molecular Formula
C16H16N2O3S
Formula Weight
316.37
MOL File
144060-53-7.mol
More
Less

Febuxostat Property

Melting point:
238-239°(dec.)
Boiling point:
536.6±60.0 °C(Predicted)
Density 
1.31±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
2.48±0.10(Predicted)
form 
powder
color 
White to Off-White
Merck 
14,3948
InChI
InChI=1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)
InChIKey
BQSJTQLCZDPROO-UHFFFAOYSA-N
SMILES
S1C(C(O)=O)=C(C)N=C1C1=CC=C(OCC(C)C)C(C#N)=C1
CAS DataBase Reference
144060-53-7(CAS DataBase Reference)
More
Less

Safety

RTECS 
XJ3675310
HS Code 
2934.10.2000
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P330Rinse mouth.

P501Dispose of contents/container to..…

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1285
Product name
Febuxostat
Purity
98.5-102.0% (HPLC)
Packaging
1G
Price
$202
Updated
2023/06/20
TCI Chemical
Product number
F0847
Product name
Febuxostat
Purity
>97.0%(HPLC)(T)
Packaging
1g
Price
$98
Updated
2024/03/01
TCI Chemical
Product number
F0847
Product name
Febuxostat
Purity
>97.0%(HPLC)(T)
Packaging
5g
Price
$316
Updated
2024/03/01
Cayman Chemical
Product number
14127
Product name
Febuxostat
Purity
≥98%
Packaging
5mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
14127
Product name
Febuxostat
Purity
≥98%
Packaging
10mg
Price
$107
Updated
2024/03/01
More
Less

Febuxostat Chemical Properties,Usage,Production

Description

Febuxostat, a selective xanthine oxidase inhibitor, was launched for the chronic management of hyperuricemia in patients with gout. Hyperuricemia is defined as a serum uric acid concentration exceeding the limit of solubility. It predisposes affected persons to gout, a disease characterized by the formation of crystals of monosodium urate or uric acid from supersaturated fluids in joints and other tissues. Crystal deposition is asymptomatic, but it is revealed by bouts of joint inflammation. If left untreated, further crystals accumulate in joints and can form deposits known as tophi. A major aim in gout management is the long-term reduction of serum uric acid concentrations below saturation levels, as this results in crystal dissolution and eventual disappearance.
Febuxostat is a nonpurine derivative with higher potency and selectivity than allopurinol for inhibiting xanthine oxidase. It completely inhibits human xanthine oxidase activity in the lung cancer cell line A549, whereas the activities of other enzymes involved in purine or pyrimidine metabolism (e.g., purine nucleoside phosphorylase, adenosine deaminase, and pyrimidine nucleoside phosphorylase) are affected by<4%.

Chemical Properties

Crystalline Solid

Physical properties

Febuxostat has low solubility. It is almost insoluble in acidic conditions, slightly soluble in neutral conditions, and slightly more soluble in alkaline conditions. It is not suitable for making injections, but it can be taken orally because of its high oil-water partition coefficient and strong ability to cross cell membranes.

Originator

Teijin (Japan)

Uses

Febuxostat is a new generation xanthine oxidase inhibitor developed by Tejin Co. (Japan,) used clinically for for long-term treatment of hyperuicemia (gout,) a new and highly effective non-purine selective inhibitor of xanthine oxidase. 40-120 mg/day febuxostat was proven effective in lowering serum urate levels when administered to manage hyperuricemia in patients with gout. It is not recommended for gout patients without hyperuricemia.

Preparation

Febuxostat can be synthesized in a multistep sequence from 2,4-dicyanophenol, starting with the alkylation of the phenolic hydroxyl group with isobutyl bromide and potassium carbonate, followed by treatment with thioacetamide in hot dimethyl formamide to yield 3-cyano-4-isobutoxythiobenzamide. Cyclization of the thioamide group with 2-chloroacetoacetic acid ethyl ester in refluxing ethanol affords 2-(3-cyano-4-isoutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester, which is hydrolyzed with sodium hydroxide to produce febuxostat.

Definition

ChEBI: Febuxostat is a 1,3-thiazolemonocarboxylic acid that is 4-methyl-1,3-thiazole-5-carboxylic acid which is substituted by a 3-cyano-4-(2-methylpropoxy)phenyl group at position 2. It is an orally-active, potent, and selective xanthine oxidase inhibitor used for the treatment of chronic hyperuricaemia in patients with gout. It has a role as an EC 1.17.3.2 (xanthine oxidase) inhibitor. It is an aromatic ether, a nitrile and a 1,3-thiazolemonocarboxylic acid.

brand name

Uloric, Adenuric

General Description

Febuxostat is a potent, non-purine compound, which inhibits the expression of cytokines/chemokines. It has also been reported to inhibit LPS-induced TNF-α, VCAM-1, MMP9 and MCP-1 expression.

Biological Activity

Febuxostat is an antihyperuricemic nonpurine inhibitor of both the oxidized and reduced forms of xanthine oxidase. It inhibits bovine milk xanthine oxidase as well as mouse and rat liver xanthine oxidase/xanthine dehydrogenase (IC50s = 1.4, 1.8, and 2.2 nM, respectively). It is 10-30 times more potent than the hypoxanthine analog allopurinol (; Kis = 0.7 nM and 0.7 μM, respectively). Febuxostat decreases the serum level of urate in a potassium oxonate rat model of hyperuricemia (ED50 = 1.5 mg/kg). It reduces hepatic macrovesicular steatosis in mice fed a high-fat diet containing trans fatty acids when administered at a dose of 1 mg/kg per day. Febuxostat (0.75 mg/kg) also increases CNS expression of glutamate oxaloacetate transaminase 2 (GOT2) and improves neurological symptoms in a mouse model of secondary progressive experimental autoimmune encephalomyelitis (EAE). Formulations containing febuxostat have been used in the treatment of symptomatic hyperuricemia in patients with gout.

Biochem/physiol Actions

Febuxostat is a potent non-purine xanithine oxidase inhibitor. Febuxostat is used in urate lowering therapies (ULTs) for the treatment of gout.

Clinical Use

Fabuxostat was discovered by Teijin Pharmaceuticals and licensed to TAP Pharmaceuticals (which is currently part of Takeda Pharmaceuticals) and was approved in the U.S. for the treatment of hyperuricemia in patients with gout. It is a once-daily non-purine based agent with potent inhibitory activity against xanthine oxidase. The safety profile of the drug also does not require dose adjustment for patients with mild to moderate renal or hepatic impairment. Febuxostat is the first new agent cleared for this indication in 40 years.

Side effects

The incidence of adverse events such as dizziness, diarrhea, headache, and nausea with febuxostat was similar to allopurinol. Febuxostat is contraindicated in patients being treated with the xanthine oxidase substrates such as azathioprine, mercaptopurine, and theophylline.

Synthesis

There are a number of routes available to prepare this agent as discussed in recent publications. The synthesis shown in Scheme 10 is a short and concise route and does not require the use of toxic reagents. Thus the commercially available and easily prepared 4-hydroxythiobenzamide (52) was reacted with ethyl bromoacetoacetate (53) in refluxing ethanol to provide the thiazole ester 54 in ??60% yield after crystallization. The phenolic ester 54 was then treated with hexamethylenetetramine (HMTA) in polyphosphoric acid at 80 ??C to provide the crude aldehyde 55 (74% conversion by HPLC). Reaction of phenol 55 and isobutyl bromide (56) in the presence of potassium carbonate with catalytic potassium iodide in DMF gave isobutyl ether 57 (64%, two steps). This ether was then converted in one pot to nitrile 58 in 93% by reacting the aldehyde with hydroxylamine hydrochloride and sodium formate in refluxing formic acid. Saponification of the ester 58 with aqueous sodium hydroxide provided fabuxostat (X).

Drug interactions

Potentially hazardous interactions with other drugs
Azathioprine: avoid concomitant use, increased risk of neutropenia.
Cytotoxics: avoid concomitant use with mercaptopurine.
Theophylline: use with caution

Metabolism

Extensively metabolised by conjugation via the uridine diphosphate glucuronosyltransferase (UDPGT) enzyme system, and by oxidation via the cytochrome P450 isoenzyme system to form active metabolites. About 49% of a dose is excreted via the urine, and 45% via the faeces (12% as unchanged drug)

storage

Store at RT

Mode of action

Xanthine oxidase is the main enzyme promoting uric acid production. It works by non-competitively blocking the molybdenum pterin center, which is the active site of xanthine oxidase. Through highly selective inhibition of oxidized and reduced xanthine oxidase, Febuxostat can reduce the synthesis of uric acid, decreasing its concentration and effectively treating gout. Through liver metabolism, Xanthine oxidase does not rely on renal excretion, so patients with moderate to severe liver and kidney dysfunction do not need to reduce dosages. Febuxostat is a non-purine XOR inhibitor, so it is very safe.

Febuxostat Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Febuxostat Suppliers

Americas 1 Argentina 2 Brazil 1 Canada 4 China 601 Cyprus 1 Europe 1 France 1 Germany 5 Greece 1 India 179 Indonesia 1 Israel 2 Italy 1 Japan 3 Mexico 1 Nepal 1 Philippines 1 South Korea 5 Spain 2 Switzerland 1 The Netherlands 2 United Arab Emirates 1 United Kingdom 12 United States 51 Global 881
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
HBCChem, Inc.
Tel
+1-510-219-6317
Fax
+1-650-486-1361
Email
sales@hbcchem.com
Country
United States
ProdList
10648
Advantage
60
Alfa Chemistry
Tel
1-516-6625404
Fax
1-516-927-0118
Email
support@alfa-chemistry.com
Country
United States
ProdList
9171
Advantage
60
EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8447
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32159
Advantage
58
RR Scientific LLC
Tel
+86-13917743231
Email
sales@rrscientific.com
Country
United States
ProdList
878
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
Cckinase, Inc.
Tel
+1 (732)236-3202
Email
sales@cckinase.com
Country
United States
ProdList
2738
Advantage
58
Cato Research Chemicals Inc.
Tel
020-81215950 4000-868-328
Email
customer@uwalab.com
Country
United States
ProdList
10404
Advantage
58
TargetMol Chemicals Inc.
Tel
+8613564774135
Email
zijue.cai@tsbiochem.com
Country
United States
ProdList
19881
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38630
Advantage
58
Aladdin Scientific
Tel
Email
tp@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
Protheragen-ING
Tel
+16313385890
Email
info@protheragen-ing.com
Country
United States
ProdList
3868
Advantage
58
ApexBio Technology
Tel
--
Fax
--
Email
sales@apexbt.com
Country
United States
ProdList
6251
Advantage
58
CarboMer, Inc.
Tel
--
Fax
--
Email
sales@carbomer.com
Country
United States
ProdList
4026
Advantage
67
SynFine Research
Tel
--
Fax
--
Email
research@synfine.com
Country
United States
ProdList
1024
Advantage
68
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
Byron Chemical Company, Inc
Tel
--
Fax
--
Email
bcc@byronchemical.com
Country
United States
ProdList
88
Advantage
58
Aozeal Certified Standards (AOCS), Inc.
Tel
--
Fax
--
Email
info@aozeal.com
Country
United States
ProdList
504
Advantage
58
Amarantine Pharmaceuticals LLC
Tel
--
Fax
--
Email
info@amarantinepharma.com
Country
United States
ProdList
16
Advantage
58
Cpl Inc.
Tel
--
Fax
--
Email
info@cplinc.net
Country
United States
ProdList
25
Advantage
58
Interchem Corporation USA
Tel
--
Fax
--
Email
esa@interchem.com
Country
United States
ProdList
469
Advantage
58
Selleck Chemicals LLC
Tel
--
Fax
--
Email
sales@selleckchem.com
Country
United States
ProdList
1848
Advantage
58
Jubilant Pharma Holdings Inc.
Tel
--
Fax
--
Email
bd.api@jubl.com
Country
United States
ProdList
39
Advantage
58
SST Corporation
Tel
--
Fax
--
Email
info@sst-corp.com
Country
United States
ProdList
237
Advantage
38
ACIC Fine Chemicals Inc.
Tel
--
Fax
--
Email
sales@acic.com
Country
United States
ProdList
492
Advantage
48
Genegobio Inc.
Tel
--
Fax
--
Email
mark@genegobio.com
Country
United States
ProdList
195
Advantage
0
TOPCHEM PHARMACEUTICALS LTD
Tel
--
Fax
--
Email
Vinchem@vinchem.com
Country
United States
ProdList
140
Advantage
58
OChem Incorporation
Tel
--
Fax
--
Email
sales@ocheminc.com
Country
United States
ProdList
6501
Advantage
60
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
HBCChem Inc.
Tel
--
Fax
--
Email
sales@hbcchem-inc.com
Country
United States
ProdList
4569
Advantage
30
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
Creative Enzymes
Tel
--
Fax
--
Email
info@creative-enzymes.com
Country
United States
ProdList
6057
Advantage
58
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
MYLAN LABORATORIES LTD
Tel
--
Fax
--
Email
info@amstock.com
Country
United States
ProdList
179
Advantage
58
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
Axon Medchem LLC
Tel
--
Fax
--
Email
info@axonmedchem.com
Country
United States
ProdList
763
Advantage
58
TCI America
Tel
--
Fax
--
Email
sales@tciamerica.com
Country
United States
ProdList
6909
Advantage
75
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
Tecoland Corporation
Tel
--
Fax
--
Email
info@tecoland.com
Country
United States
ProdList
275
Advantage
50
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
APAC Pharmaceutical, LLC
Tel
--
Fax
--
Email
sales@apacpharma.com
Country
United States
ProdList
6322
Advantage
38
More
Less

View Lastest Price from Febuxostat manufacturers

Sinoway Industrial co., ltd.
Product
Febuxostat 144060-53-7
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
99% up, High Density
Supply Ability
20 tons
Release date
2022-08-08
Hebei Mujin Biotechnology Co.,Ltd
Product
Febuxostat 144060-53-7
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-09-19
Jinan Jianfeng Chemical Co., Ltd
Product
Febuxostat 144060-53-7
Price
US $0.00/kg
Min. Order
1kg
Purity
99%min
Supply Ability
20ton
Release date
2024-08-09

144060-53-7, FebuxostatRelated Search:

Methylchloroisothiazolinone/methylisothiazolinone mixture (MCIT/MIT) Methyl salicylate Lithium tri-tert-butoxyaluminum hydride Ethyl cyanoformate Methyl 4-cyanobenzoate Tribenuron methyl 4-Biphenylcarboxylic acid Thiazole Methylene dithiocyanate Benzothiazole ethyl 2-(4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate 2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL MONO-DESACETYL FAMCICLOVIR 4-HYDROXYTHIOBENZAMIDE Thiophanate-methyl THIAZOLE ORANGE

  • Febuxostat (Uloric)
  • FBX
  • Uloric
  • Febuxostat (TEI-6720)
  • Febuxostat Tablets
  • FEBUXOSTAT API
  • Febuxostat (This product is unavailable in the U.S.)
  • Febuxostat Tabletshehe
  • Febuxostat 2-[3-Cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid
  • Febuxostat, >=99%
  • Febuxostat Impurity
  • CS-1598
  • TEI 6720 - Febuxostat
  • 2-(3-cyano-4-isobutoxyphenyl)
  • Febuxostat IMP
  • Tei-6720
  • 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
  • 2-[3-Cyano-4-isobutoxyphenyl]-4-methylthiazole-5-carboxylic acid
  • 2-(3-Cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylic Acid
  • 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic Acid
  • TMX 67
  • FEBUXOSTAT
  • Febuxosta
  • Febuxostat Impurity V
  • Febuxostat(ThisproductisunavailableintheU.S.)&gt
  • 5-Thiazolecarboxylic acid, 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-
  • Febuxostat A
  • Fubuxostat
  • 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylicaci
  • Febuxostat USP/EP/BP
  • Febuxostat Working std
  • Febuxostat (A/C crystal)
  • FebuxostatQ: What is Febuxostat Q: What is the CAS Number of Febuxostat Q: What is the storage condition of Febuxostat Q: What are the applications of Febuxostat
  • NSC 63871
  • NSC63871
  • NSC-63871
  • The cloth sutent
  • Febrista
  • Fesotan *
  • Febuxostat（ China GMP ）
  • 2-(3-Cyano-4-isobutoxyphenyl)-4-methylthiazol-5-carboxylic acid
  • Febuxostat CRS
  • Febuxostat 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5- carboxylic acid
  • Febuxostat Form-A, C & G
  • Adenuric
  • Febuxostat Reference Standard
  • Febuxostat, 10 mM in DMSO
  • FEBUXOSTAT NON-STERILE BULK DRUG SUBSTANCE
  • 144060-53-7
  • Heterocycles
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • eterocycles
  • TRILIPIX
  • Other APIs
  • Febuxostat
  • API