Bufexamac

HCID 2466

Basic information

CAS
2438-72-4
Standard SMILES
CCCCOc1ccc(CC(=O)NO)cc1
InChIKey
MXJWRABVEGLYDG-UHFFFAOYSA-N
Molecular formula
C12H17NO3
Average molar mass
223.27 g/mol
Monoisotopic mass
223.1208434

Names & identifiers

Preferred name
Bufexamac
IUPAC
2-(4-butoxyphenyl)-N-hydroxyacetamide
English name
Bufexamac
Molecular formula
C12H17NO3
Molecular weight
223.27

Names & synonyms

bufexamac2438-72-42-(4-Butoxyphenyl)-N-hydroxyacetamideBufexamic acidParfenacAndermParadermBufexamacop-Butoxyphenylacetohydroxamic acid4-Butoxy-N-hydroxybenzeneacetamideBufexamacum4-Butoxyphenylacetohydroxamic acid
Show more names
j3cp1044feximacmofenardroxaryldroxarolcp1044j3flogicidnorfemac
2-(p-Butoxyphenyl)-acetohydroxamic acidCP 1044 J3Acide p-butoxyphenylacethydroxamiqueDTXSID7045368CP-1044-J3NSC-758153CHEBI:313174T3C38J78L

Database identifiers

CAS
2438-72-4
PubChem CID
2466
DTXSID
DTXSID7045368
ChEMBL
CHEMBL94394
ChEBI
CHEBI:31317
UNII
4T3C38J78L
EC Number
219-451-1
Nikkaji
J3.390A

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
58.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
16

Experimental & physicochemical properties

Solubility · 2 items

Immiscible

>33.5 [ug/mL] (The mean of the results at pH 7.4)

Melting Point153
Collision Cross Section · 2 items

161.48 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];158.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

161 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
153 · 153-155°
Boiling point
364.56 °C · 364.56°C (rough estimate)
Density
1.1223 · 1.1223 (rough estimate)
refractive index
1.53 · 1.5300 (estimate)
storage temp.
-20 °C · Inert atmosphere,Store in freezer, under -20°C
solubility
Practically insoluble in water, soluble in dimethylformamide, slightly soluble in ethyl acetate and in methanol.

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral];H317 (33.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.;There are 2 notifications provided by 2 of 3 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Other Safety InformationIMAP assessments - Benzeneacetamide, 4-butoxy-N-hydroxy-: Environment tier I assessment;IMAP assessments - Benzeneacetamide, 4-butoxy-N-hydroxy-: Human health tier I assessment
Hazard Classes and CategoriesSkin Sens. 1B (33.3%)

Safety data

wgk
2
rtecs
AK8280000
hs_code
2928.00.2500
Toxicity
LD50 orally in mice, rats: >8, >4 g/kg (Lambelin)
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

ATC Code · 4 items

M - Musculo-skeletal system;M02 - Topical products for joint and muscular pain;M02A - Topical products for joint and muscular pain;M02AA - Antiinflammatory preparations, non-steroids for topical use;M02AA09 - Bufexamac

M - Musculo-skeletal system;M01 - Antiinflammatory and antirheumatic products;M01A - Antiinflammatory and antirheumatic products, non-steroids;M01AB - Acetic acid derivatives and related substances;M01AB17 - Bufexamac

QM - Musculo-skeletal system;QM02 - Topical products for joint and muscular pain;QM02A - Topical products for joint and muscular pain;QM02AA - Antiinflammatory preparations, non-steroids for topical use;QM02AA09 - Bufexamac

QM - Musculo-skeletal system;QM01 - Antiinflammatory and antirheumatic products;QM01A - Antiinflammatory and antirheumatic products, non-steroids;QM01AB - Acetic acid derivatives and related substances;QM01AB17 - Bufexamac

Protein BindingNo data available.
Pharmacodynamics · 1 item

Bufexamac is a topically-active anti-inflammatory agent that inhibits the cyclooxygenase enzyme. In cutaneous and deep experimental inflammation, topical administration of bufexamac exerted a dose-related anti-inflammatory effect. In guinea pigs, bufexamax was shown to be more active than topical acetylsalicylic acid 5% or phenylbutazone 5% in delaying the local increase in temperature resulting from UV exposure. Bufexamac is unlikely to have any effect on wound healing.

Mechanism of Action · 1 item

The full mechanism of action is unclear. It is proposed that bufexamac acts similarly to other non-steroidal anti-inflammatory drugs to inhibit prostaglandin biosynthesis _in vitro_, via inhibiting cyclo-oxygenase (COX) enzymes. Systematically administered bufexamac may accumulate preferentially in the adrenal cortex of rats and may play a role in adrenal stimulation; however its topical anti-inflammatory action is likely to be independent of this effect.

Biological Half-LifeNo data available.
Metabolism/MetabolitesNo data available.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >5000;Consumption (g per capita; approx.) in Germany (2009): 0.0611;Excretion rate: 0.845;Calculated removal (%): 76
Use ClassificationPharmaceuticals
Applications · 3 items

Usesantiinflammatory, analgesic, antipyretic

UsesBufexamac is a specific inhibitor of class IIB histone deacetylases (HDAC6 and HDAC10). Bufexamac is a non-steroidal anti-inflammatory drug used topically as well as rectally. Formulations containing Bufexamac is used by many patients with eczematous disorders as an alternative to topical corticosteroids.

UsesBufexamac is a non-steroidal topical medication used for treatment of a variety of problems in which the skin is inflamed. These vary widely from insect bites to bums, plant stings and a wide variety of medical conditions induding psoriasis, hemorrhoidal symptoms, eczema and inflammation of the skin following radiotherapy. In this last case, it can be used before radiotherapy to help prevent inflammation of the skin caused by radiation therapy.

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]

Additional notes

DefinitionChEBI: A hydroxamic acid derived from phenylacetamide in which the benzene moiety is substituted at C-4 by a butoxy group. It has anti-inflammatory, analgesic, and antipyretic properties.

Related reactions

1 records

Compound notes

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