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
Show more names
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
- Formal charge
- 0
- Complexity
- 200
Experimental & physicochemical properties
Solubility
Immiscible
>33.5 [ug/mL] (The mean of the results at pH 7.4)
Collision Cross Section
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.
- pka
- 9.24 · 9.24±0.20(Predicted)
- form
- Solid
- color
- White to Off-White
- Merck
- 14 · 14,1474
- CAS DataBase Reference
- 2438 · 2438-72-4(CAS DataBase Reference)
- FDA UNII
- 4 T3C38J78L · 4T3C38J78L
- ATC code
- 1 AB17,M02AA09 · M01AB17,M02AA09
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317
- Precautionary statements
- 261 · P261-P272-P280-P302+P352+P333+P313+P363-P501
- WGK Germany
- 2 · 2
- RTECS
- 8280000 · AK8280000
- HS Code
- 2928 · 2928.00.2500
- Toxicity
- 50 orally · LD50 orally in mice, rats: >8, >4 g/kg (Lambelin)
Safety & regulation
GHS classification
GHS Classification
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
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
- Hazard statements
- H317
- Precautionary statements
- P261-P272-P280-P302+P352+P333+P313+P363-P501
Chemistry & industry
Pharmacology
ATC Code
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
Pharmacodynamics
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
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.
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Absorption, Distribution and Excretion
Method of application affects the extent of cutaneous absorption. Following rectal administration as suppositories, the systemic absorption was reported to be low.
Following topical administration of 5% bufexamac, the recovery in the urine was 3.5% of the applied dose within 144 hours. Studies in healthy volunteers receiving an oral dose of 125 to 500 mg indicate that an average of 80% of the total dose is excreted in the urine within 48 hours.
No data available.
No data available.
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
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
Compound notes
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