ChemicalBook > CAS DataBase List > Tavaborole

Tavaborole

Product Name
Tavaborole
CAS No.
174671-46-6
Chemical Name
Tavaborole
Synonyms
Kerydin;AN-269;AN 2690;CS-1054;avaborole;Tavaborole;Tavalborole;Tavaborole (USAN);Tavaborole (>90%);Kerydin|||AN-2690
CBNumber
CB42454906
Molecular Formula
C7H6BFO2
Formula Weight
151.93
MOL File
174671-46-6.mol
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Tavaborole Property

Melting point:
120-122℃
Boiling point:
230.8±50.0 °C(Predicted)
Density 
1.28±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
powder
pka
6.81±0.20(Predicted)
color 
white to beige
Stability:
Hygroscopic
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Safety

HS Code 
2934999090
Hazardous Substances Data
174671-46-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H318Causes serious eye damage

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P271Use only outdoors or in a well-ventilated area.

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

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P310Immediately call a POISON CENTER or doctor/physician.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1227
Product name
Tavaborole
Purity
≥95% (HPLC)
Packaging
10MG
Price
$115
Updated
2023/06/20
Sigma-Aldrich
Product number
SML1227
Product name
Tavaborole
Purity
≥95% (HPLC)
Packaging
50MG
Price
$451
Updated
2023/06/20
TCI Chemical
Product number
T3775
Product name
Tavaborole
Packaging
250MG
Price
$257
Updated
2024/03/01
Cayman Chemical
Product number
23101
Product name
AN-2690
Purity
≥98%
Packaging
1g
Price
$97
Updated
2024/03/01
Cayman Chemical
Product number
23101
Product name
AN-2690
Purity
≥98%
Packaging
5g
Price
$360
Updated
2024/03/01
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Tavaborole Chemical Properties,Usage,Production

Description

Tavaborole (Kerydin®), discovered and developed by Anacor, was approved by the US FDA in July 2014. Tavaborole, topical solution, 5% is an oxaborole antifungal indicated for the treatment of onychomycosis of the toenails due to Trichophyton rubrum or Trichophyton mentagrophytes. The mechanism of action of tavaborole is inhibition of fungal protein synthesis, which inhibits an aminoacyl-transfer ribonucleic acid synthetase.

Uses

Tavaborole is a topical treatment of toenail onychomycosis.

Definition

ChEBI: A member of the class of benzoxaboroles that is 1,3-dihydro-1-hydroxy-2,1-benzoxaborole substituted at position 5 by a fluoro group. A topical antifungal agent used for the treatment of onychomycosis (fungal infection of the toenails and fingernails).

General Description

Tavaborole is a boron-based pharmaceutical agent. It has broad-spectrum oxaborole antifungal activity. Due to its low molecular weight, it facilitates maximal nail plate penetration than its predecessors.

Biochem/physiol Actions

Tavaborole (AN2690) is a potent antifungal that targets the post-transfer editing site of leucyl-tRNA synthetase (LeuRS). Tavaborole forms a covalent adduct with the 3′ adenosine of tRNA(leu) at the editing site of fungal, but not bacterial LeuRS, locking the enzyme in an inactive conformation. Tavaborole was recently approved for the treatment of onychomycosis of the toenail in adults.

Synthesis

Three syntheses of tavaborole (XXXII) have been reported. The 26.9 g scale approach started with 2-bromo-5-fluorophenyl methanol (257), which was treated with ethyl vinyl ether (258) to produce o-bromobenzyl alcohol derivative 259 in 82% yield. 259 was then converted into the corresponding phenylboronic acid, followed by the one-pot deprotection and spontaneous cyclization upon treatment with 6 M hydrochloric acid, delivering tavaborole (XXXII) in 43% yield.

in vitro

an2690 showed the most active against fungi and especially against the dermatophytes t. rubrum and t. mentagrophytes, the primary fungal pathogens causing onychomycosis. in addition, an2690 was identified as having a unique profile of in vitro antidermatophyte activity, maintenance of this activity in the presence of keratin, and exceedingly good penetration of human nails [1].

target

Trichophyton species

References

[1] baker sj, zhang yk, akama t, lau a, zhou h, hernandez v, mao w, alley mr, sanders v, plattner jj. discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1- benzoxaborole (an2690), for the potential treatment of onychomycosis. j med chem. 2006;49(15):4447-50.
[2] hui x, baker sj, wester rc, barbadillo s, cashmore ak, sanders v, hold km, akama t, zhang yk, plattner jj, maibach hi. in vitro penetration of a novel oxaborole antifungal (an2690) into the human nail plate. j pharm sci. 2007;96(10):2622-31.
[3] markham a. tavaborole: first global approval. drugs. 2014;74(13):1555-8.

Tavaborole Preparation Products And Raw materials

Raw materials

Preparation Products

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Tavaborole Suppliers

China 179 India 19 Israel 2 Japan 1 United Kingdom 2 United States 15 Global 218
Tianjin Yao Technology Development Co., Ltd.
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View Lastest Price from Tavaborole manufacturers

Zhuhai Hairuide Bioscience and Technology Co., Ltd
Product
Tavaborole 174671-46-6
Price
US $0.00/KG Ton
Min. Order
1KG Ton
Purity
99%+
Supply Ability
2 tons/month
Release date
2022-10-09
Zhuozhou Wenxi import and Export Co., Ltd
Product
Tavaborole 174671-46-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Tavaborole 174671-46-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-08

174671-46-6, TavaboroleRelated Search:

6-aMinobenzo[c][1,2]oxaborol-1(3H)-ol Vaniprevir 2-(Hydroxymethyl)-6-methoxyphenylboronic acid dehydrate (2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE 2,1-Benzoxaborole,1,3-dihydro-1-hydroxy-6-Methoxy benzo[c][1,2]oxaborole-1,6(3H)-diol 6-chlorobenzo[c][1,2]oxaborol-1(3H)-ol 7-fluorobenzo[c][1,2]oxaborol-1(3H)-ol 5-(TRIFLUOROMETHYL)BENZO[C][1,2]OXABOROL-1(3H)-OL 6-FLUOROBENZO[C][1,2]OXABOROL-1(3H)-OL 4-aminobenzo[c][1,2]oxaborol-1(3H)-ol 5-aminobenzo[c][1,2]oxaborol-1(3H)-ol ISOINDOLIN-4-OL HYDROCHLORIDE 7-aminobenzo[c][1,2]oxaborol-1-(3H)-ol 1-Hydroxy-2,1-benzoxaborolane 4-Fluoro-2-methylphenylboronic acid Tavaborole

  • 5-FLUOROBENZO[C][1,2]OXABOROL-1(3H)-OL
  • AN 2690
  • AN-2690;TAVABOROLE;AN2690
  • Tavaborole
  • 5-Fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
  • 5-Fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol
  • AN-2690(Tavaborole)
  • Tavaborole(AN-2690)
  • AN-269
  • 5-Fluoro-1-hydroxyl-1,3-dihydrobenzo[c][1,2]oxaborole
  • AN-2690;AN2690;AN 2690
  • 5-Fluoro-1-hydroxy-2,1-benzoxaborolane
  • TAVABOROLE; AN2690; AN 2690
  • avaborole
  • CS-1054
  • Tavaborole (USAN)
  • 1,3-Dihydro-5-fluoro-1-hydroxy-2,1-benzoxaborole
  • Kerydin
  • 2,1-Benzoxaborole, 5-fluoro-1,3-dihydro-1-hydroxy-
  • Tavaborole (>90%)
  • 5-Fluoro-2,1-benzoxaborol-1(3H)-ol
  • 5-fluoro-1-hydroxy-3H-2,1-benzoxaborole
  • Tavalborole
  • 5-Fluorobenzo[c][1,2]oxaboro-1(3H)-ol
  • 5-FLUOROBENZO[C][1,2]OXABOROL-1(3H)-OL 174671-46-6
  • 5-Fluorobenzo[c][1,2]oxaborole-1(3H)-ol
  • Tavaborole In-House
  • Kerydin|||AN-2690
  • 174671-46-6
  • 174461-46-6