Bufexamac

Names

[ Name ]:
Bufexamac

[Synonym ]:
Feximac
Bufexamaco
Flogicid
Bufexamacum
Bufexamic acid
MFCD00078936
2-(4-Butoxyphenyl)-N-hydroxyacetamide
4-butoxy-N-hydroxybenzeneacetamide
Droxaryl
2-(4-butoxyphenyl)acetohydroxamic acid
2-(p-Butoxyphenyl)acetohydroxamic acid
Benzeneacetamide, 4-butoxy-N-hydroxy-
2-(4-butoxyphenyl)acethydroxamic acid
EINECS 219-451-1
Bufexamac
Malipuran
Parfenac

Biological Activity

[Description]:

Bufexamac is a class IIB histone deacetylases (HDAC6 and HDAC10) inhibitor used as an anti-inflammatory agent.

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

HDAC6:10.7 μM (Kd app)

HDAC10:12.3 μM (Kd app)

HDAC8:235 μM (Kd app)

HDAC3:341 μM (Kd app)

[References]

[1]. Bantscheff, M., et al., Chemoproteomics profiling of HDAC inhibitors reveals selective targeting of HDAC complexes. Nat Biotechnol, 2011. 29(3): p. 255-65.

[2]. Kranke, B., et al., Epidemiological significance of bufexamac as a frequent and relevant contact sensitizer. Contact Dermatitis, 1997. 36(4): p. 212-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Melting Point ]:
161 - 162ºC

[ Molecular Formula ]:
C₁₂H₁₇NO₃

[ Molecular Weight ]:
223.268

[ Exact Mass ]:
223.120850

[ PSA ]:
58.56000

[ LogP ]:
1.70

[ Index of Refraction ]:
1.530

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AK8280000

CHEMICAL NAME :: Acetohydroxamic acid, 2-(p-butoxyphenyl)-

CAS REGISTRY NUMBER :: 2438-72-4

LAST UPDATED :: 199612

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C12-H17-N-O3

MOLECULAR WEIGHT :: 223.30

WISWESSER LINE NOTATION :: QMV1R DO4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3370 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - alteration in gastric secretion Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 805 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - ulceration or bleeding from stomach Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - alteration in gastric secretion Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - alteration in gastric secretion Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1195 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - ulceration or bleeding from stomach Skin and Appendages - hair

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - alteration in gastric secretion Skin and Appendages - hair

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 32760 mg/kg/26W-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from stomach

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12 gm/kg/30D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from stomach

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3250 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 400 umol/L/3H

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 88,81,1981

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
AK8280000

[ HS Code ]:
2924299090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Erythema-multiforme-like, urticarial papular and plaque eruptions from bufexamac: report of 4 cases.

Contact Dermatitis 31(2) , 97-101, (1994)

4 patients developed an erythema-multiforme-like reaction following acute contact dermatitis from 2 different bufexamac-containing topical preparations. Histologically, the lesions did not show change...

[A severe epicutaneous test reaction to the bufexamac in a hemorrhoidal therapeutic preparation].

Dtsch. Med. Wochenschr. 124(40) , 1168-70, (1999)

A 49-year-old woman presented with acute perianal vesicular/bullous contact dermatitis. Other areas were over the trunk, face, neck and wrists. She reported occasional application of an ointment (Mast...

[A common and insidious side-effect: allergic contact dermatitis caused by bufexamac used in the treatment of dermatitis. Results from the Information Network of Departments of Dermatology (IDVK)].

Dtsch. Med. Wochenschr. 130(50) , 2881-6, (2005)

Bufexamac is a non-steroidal, anti-inflammatory drug used in the topical treatment of atopic dermatitis, stasis dermatitis and perianal eczema. The substance is known to cause severe allergic contact ...