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Details

Stereochemistry ACHIRAL
Molecular Formula C12H17NO3
Molecular Weight 223.2683
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUFEXAMAC

SMILES

CCCCOC1=CC=C(CC(=O)NO)C=C1

InChI

InChIKey=MXJWRABVEGLYDG-UHFFFAOYSA-N
InChI=1S/C12H17NO3/c1-2-3-8-16-11-6-4-10(5-7-11)9-12(14)13-15/h4-7,15H,2-3,8-9H2,1H3,(H,13,14)

HIDE SMILES / InChI
Molecular Formula C12H17NO3
Molecular Weight 223.2683
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/referrals/Bufexamac/human_referral_000209.jsp&mid=WC0b01ac05805c516f | https://www.ncbi.nlm.nih.gov/pubmed/14607020 | https://www.ncbi.nlm.nih.gov/pubmed/25751058 | https://www.ncbi.nlm.nih.gov/pubmed/21258344 | https://www.ncbi.nlm.nih.gov/pubmed/27126280

Bufexamac is a nonsteroidal antiinflammatory drug (NSAID) used in topical formulations to treat dermatological diseases (eczema and dermatitis) and proctological conditions (haemorrhoids and anal fissure). Bufexamac-containing medicines have been available in EU Member States since the 1970s. In 2010 European Medicines Agency recommends revocation of marketing authorisations for bufexamac due to high risk of contact allergies. The phenolic bufexamac decomposition products could be the reason for its eczema-provoking properties frequently described in the literature. Bufexamac is a class IIb histone deacetylase (HDAC6, HDAC10) inhibitor. Bufexamac also triggered an HDAC6-independent, hypoxia-like response by stabilizing Hypoxia-inducible factor 1-alpha, providing a possible mechanistic explanation of its adverse, pro-inflammatory effects. Bufexamac was capable of specifically inhibiting leukotriene A4 hydrolase and attenuating lung inflammation in acute lung injury mouse model.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
 10.7 µM [Kd]
Inhibitor
8504
 12.3 µM [Kd]
Activator
1447
Inhibitor
8504
 15.86 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
BUFEXAMAC

Approved Use

Bufexamac are used for the treatment of subacute and chronic eczema of the skin, including atopic eczema, as well as sunburn and other minor burns, and itching. Suppositories containing bufexamac in combination with local anaesthetics are used against haemorrhoids.
Primary
Withdrawn
BUFEXAMAC

Approved Use

Bufexamac are used for the treatment of subacute and chronic eczema of the skin, including atopic eczema, as well as sunburn and other minor burns, and itching. Suppositories containing bufexamac in combination with local anaesthetics are used against haemorrhoids.
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Chemoproteomics profiling of HDAC inhibitors reveals selective targeting of HDAC complexes.
2011-03
Contact dermatitis due to topical drugs.
2009-10
Prevalence and risk factors for allergic contact dermatitis to topical treatment in atopic dermatitis: a study in 641 children.
2009-05
[Bufexamac-induced pigmented purpuric eruption].
2009-05
[Facial allergic contact dermatitis. Data from the IVDK and review of literature].
2009-01
A systematic review of randomized controlled trials of treatments for inherited forms of epidermolysis bullosa.
2009-01
Allergic contact dermatitis to topical drugs--epidemiological risk assessment.
2008-08
Acute generalized exanthematous pustulosis induced by bufexamac in an atopic girl.
2008-04
Non-steroidal anti-inflammatory drugs selectively inhibit cytokine production by NK cells and gamma delta T cells.
2006-12
Changes in MMP-2 and -9 activity and MMP-8 reactivity after amphotericin B induced synovitis and treatment with bufexamac.
2006-08
Chronic urticaria due to Blastocystis hominis.
2006-05
Type-IV sensitization profile of individuals with atopic eczema: results from the Information Network of Departments of Dermatology (IVDK) and the German Contact Dermatitis Research Group (DKG).
2006-05
[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)].
2005-12-16
[Anogenital dermatoses--allergic and irritative causative factors. Analysis of IVDK data and review of the literature].
2005-12
Screening for new antioxidative compounds for topical administration using skin lipid model systems.
2005-09-15
Frequency of contact allergy in German children and adolescents patch tested between 1995 and 2002: results from the Information Network of Departments of Dermatology and the German Contact Dermatitis Research Group.
2004-09
Allergic contact dermatitis with spreading over extensive regions due to topical use of 5% bufexamac ointment.
2004-02
Examinations of the antioxidative properties of the topically administered drug bufexamac reveal new insights into its mechanism of action.
2003-10
[Epidemiologic surveillance of contact allergens. The "monitoring series" of IVDK (Information Network ofDermatologic Clinics for Detection and Scientific Evaluation of Contact Allergy].
2003-08
[Severe allergic contact dermatitis with generalized spread due to bufexamac presenting as the "baboon" syndrome].
2003-03-14
An integrative approach to eczema (atopic dermatitis).
2003-02-25
[Retrospective of national pharmacovigilance surveys on drug-induced bullous, vesicular eruptions: methods and results ].
2002-11-09
[Mastu S - a new antihemorrhoidal cream for pregnant women].
2002
Effects of intra-articular injections of bufexamac suspension in healthy horses.
2001-10
[Dermatological local therapy. How to control eczema].
2001-06-14
Skin sensitizing properties of arylalcanoic acids and their analogues.
1979-09
Patents

Patents

08829079
1
JPH0217115A
2
JPH11302198A
1
JPS62418A
1

Sample Use Guides

In Vivo Use Guide
Apply 5% cream to affected areas.
Route of Administration: Topical
In Vitro Use Guide
Treatment of peripheral blood mononuclear cells with bufexamac inhibits the secretion of IFN-α (EC50 = 8.9 uM)
Substance Class Chemical
Created
by admin
on Wed Apr 02 07:05:07 GMT 2025
Edited
by admin
on Wed Apr 02 07:05:07 GMT 2025
Record UNII
4T3C38J78L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUFEXAMAC
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
CP 1044 J3
Preferred Name English
PARADERM
Common Name English
BUFEXAMAC [JAN]
Common Name English
ANDERM
Common Name English
CP-1044-J3
Code English
Bufexamac [WHO-DD]
Common Name English
BUFEXAMAC [EP MONOGRAPH]
Common Name English
bufexamac [INN]
Common Name English
BUFEXAMAC [MART.]
Common Name English
NSC-758153
Code English
PARFENAC
Common Name English
2-(P-BUTOXYPHENYL)-ACETOHYDROXAMIC ACID
Common Name English
BUFEXAMAC [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QM02AA09
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
WHO-ATC M02AA09
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
WHO-ATC M01AB17
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
WHO-VATC QM01AB17
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
219-451-1
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
MERCK INDEX
m2749
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C166783
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
DRUG BANK
DB13346
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
PUBCHEM
2466
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
CAS
2438-72-4
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
WIKIPEDIA
Bufexamac
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
DRUG CENTRAL
3047
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
FDA UNII
4T3C38J78L
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
INN
2557
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
RXCUI
1796
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY RxNorm
CHEBI
31317
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
IUPHAR
7498
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
NSC
758153
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
MESH
D002019
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
EVMPD
SUB05961MIG
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
SMS_ID
100000091974
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
EPA CompTox
DTXSID7045368
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
ChEMBL
CHEMBL94394
Created by admin on Wed Apr 02 07:05:07 GMT 2025 , Edited by admin on Wed Apr 02 07:05:07 GMT 2025
PRIMARY
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Structure of BUFEXAMAC
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