Bunaprolast

Modify Date: 2024-01-02 17:31:55

Bunaprolast Structure
Bunaprolast structure
Common Name Bunaprolast
CAS Number 99107-52-5 Molecular Weight 272.33900
Density 1.084g/cm3 Boiling Point 413ºC at 760mmHg
Molecular Formula C17H20O3 Melting Point N/A
MSDS N/A Flash Point 175.3ºC

 Use of Bunaprolast


U66858 is a potent inhibitor of LTB4 production in human whole blood. U66858 also exhibits significant inhibition of lipoxygenase and TXB2 release.

 Names

Name 2-Butyl-4-methoxy-1-naphthyl acetate
Synonym More Synonyms

 Bunaprolast Biological Activity

Description U66858 is a potent inhibitor of LTB4 production in human whole blood. U66858 also exhibits significant inhibition of lipoxygenase and TXB2 release.
Related Catalog
Target

LTB4

TXB2

5-Lipoxygenase

In Vitro U66858 (U-66,858) undergoes deacetylation to an initial metabolite with similar pharmacological potency. The inhibitory effects of the semi-quinone U66858 and its metabolite U-68,244 on the ionophore-induced formation of leukotriene B4 (LTB4) are examined in human whole blood (WB). Preincubation of U-66858 and U-68,244 for 1 min prior to challenge of blood with calcium ionophore A23187 results in IC50s of 1080±644 and 820±442 nM, respectively. After 60 min preincubation, IC50s are 250±85 and 270±79 nM. The activity of the lipoxygenase inhibitor AA-861 in this system is similar to that of U-66858, while vitamin K and the sulphate conjugate of U-66858 show significant inhibition of LTB4 release only at micromolar concentrations. U-66858 exhibits significant inhibition of thromboxane A2 release (p<0.02) in a comparative study with the known cyclooxygenase (CO) inhibitor Flurbiprofen[1].
In Vivo The IgE-mediated hypersensitivity to Ascaris antigen in reactor rhesus primates is used to assess the pharmacologic profile of U66858 (U-66,858). When U-66858 is given by the oral route, it shows dose-related inhibition of resistance (RL) and compliance (Cdyn) changes. When U-66858 is given by the aerosol route, it shows dose independent inhibition. In 15 animals, aerosols (52±32 to 53±10% for RL, p=0.05 and 45±19 to 28±19% Cdyn inhibitions, p=0.05) for 5.0-0.1% aerosol. By the oral route, inhibition is seen at 1-4 h following administration. In 5 animals, oral doses of 10 and 5 mg/kg inhibit (RL by 98±2 to 78±1.5%, p=0.01 and Cdyn by 75±17 to 60.9±9.1%, p=0.05) by 10 and 5 mg/kg U-66858, respectively[2].
References

[1]. Summers JA, et al. Lipoxygenase inhibitory activity of U-66,858 and its deacetylated metabolite U-68,244 in human whole blood. Agents Actions. 1994 Mar;41(1-2):32-6.

[2]. Johnson HG, et al. Activity of a novel hydroquinone inhibitor of leukotriene synthesis (U-66,858) in the rhesus monkey Ascaris reactor. Int Arch Allergy Appl Immunol. 1988;87(2):204-7.

 Chemical & Physical Properties

Density 1.084g/cm3
Boiling Point 413ºC at 760mmHg
Molecular Formula C17H20O3
Molecular Weight 272.33900
Flash Point 175.3ºC
Exact Mass 272.14100
PSA 35.53000
LogP 4.11630
Index of Refraction 1.558

 Safety Information

HS Code 2915390090

 Synthetic Route

~81%

Bunaprolast Structure

Bunaprolast

CAS#:99107-52-5

Literature: Yamashita; Schaub; Back; White; Toy; Ghazal; Burdick; Brashler; Holm Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 775 - 781

~63%

Bunaprolast Structure

Bunaprolast

CAS#:99107-52-5

Literature: Yamashita, A.; Timko, J.M.; Watt, W. Tetrahedron Letters, 1988 , vol. 29, # 21 p. 2513 - 2516

~66%

Bunaprolast Structure

Bunaprolast

CAS#:99107-52-5

Literature: Yamashita, A.; Timko, J.M.; Watt, W. Tetrahedron Letters, 1988 , vol. 29, # 21 p. 2513 - 2516

 Customs

HS Code 2915390090
Summary 2915390090. esters of acetic acid. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:5.5%. General tariff:30.0%

 Synonyms

Bunamiodilo
Bunamiodylum
Bunamijodylum
BUNAMIODYL
1-acetoxy-2-butyl-4-methoxynaphthalene
bunaprolast
Bunamiodylsaeure
3-(3-Butylamido-2,4,6-triiodphenyl)-2-ethylacrylsaeure
2-(3-Butyramido-3,4,6-triiodophenylmethylene)butyric acid
Buniodyl
Bunamiodylum [INN-Latin]
2-(3-Butyrylamino-2,4,6-triiod-benzyliden)-buttersaeure
Bunamiodilo [INN-Spanish]
1-acetoxy-2-n-butyl-4-methoxy-naphthalene
U66858