SULFACETAMIDE

First approved in 1941

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H10N2O3S
Molecular Weight	214.242
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1

InChI

InChIKey=SKIVFJLNDNKQPD-UHFFFAOYSA-N

InChI=1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c68ebddc-dcb5-4695-a66b-d03a65a110f6

Sulfacetamide is a synthetic sulfonamide antibiotic, which exerts its effect through inhibition of bacterial dihydrofolate synthetase, an enzyme responsible for the conversion of p-aminobenzoic acid into folic acid in bacterias. The topical formulation of the drug is prescribed for the treatment of acne vulgaris and the ophtalmic formulation is used in patients with eye infections.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Eye infections 13 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c68ebddc-dcb5-4695-a66b-d03a65a110f6	Curative		Approved 8429	BLEPHAMIDE Approved Use Blephamide ophthalmic ointment is indicated for steroid-responsive inflammatory ocular conditions for which a corticosteroid is indicated and where superficial bacterial ocular infection or a risk of bacterial ocular infection exists. Ocular corticosteroids are indicated in inflammatory conditions of the palpebral and bulbar conjunctiva, cornea, and anterior segment of the globe where the inherent risk of corticosteroid use in certain infective conjunctivitides is accepted to obtain diminution in edema and inflammation. They are also indicated in chronic anterior uveitis and corneal injury from chemical, radiation or thermal burns or penetration of foreign bodies. Launch Date 1961
Acne vulgaris 34 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	Curative		Approved 8429	KLARON Approved Use Klaron Lotion is indicated in the topical treatment of acne vulgaris. Launch Date 1996

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63845	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63845
ChemicalBook	CB4264350	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4264350
MolPort	MolPort-000-900-614	https://www.molport.com/shop/molecule-link/MolPort-000-900-614
ZINC	ZINC000005179119	http://zinc15.docking.org/substances/ZINC000005179119
eMolecules	511811	https://www.emolecules.com/cgi-bin/more?vid=511811

PubMed

Title	Date	PubMed
Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase.	1990 Feb	2298911
Acute infectious conjunctivitis in childhood.	2001 Jul	20084257
Determination of prednisolone acetate, sulfacetamide and phenylefrine in local pharmaceutical preparations by micellar electrokinetic chromatography.	2003 Apr 1	12684100
3-Aminophenol as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.	2003 Dec	14630242
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.	2003 Jun	12739095
Actinomyces canaliculitis: diagnosis of a masquerading disease.	2004 Aug	15221305
Rosacea. An overview of diagnosis and management.	2004 Dec	15615217
The treatment of rosacea.	2004 Jan	14959944
Medical treatment of rosacea with emphasis on topical therapies.	2004 Jan	14680431
Sulfur/sodium sulfacetamide preparations.	2004 Mar-Apr	15010636
Nocardia keratitis in a human immunodeficiency virus patient.	2004 May-Jun	15175921
Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection.	2004 Sep 8	18969572
Combination sodium sulfacetamide 10% and sulfur 5% cream with sunscreens versus metronidazole 0.75% cream for rosacea.	2005 Jun	16047874
Seborrheic dermatitis. The link between facial rash and neurologic disease.	2005 Mar	15782673
Monitoring of five sulfonamide antibacterial residues in milk by in-tube solid-phase microextraction coupled to high-performance liquid chromatography.	2005 Nov 2	16248539
Refractory Demodex folliculitis in five children with acute lymphoblastic leukemia.	2005 Sep-Oct	16190988
Researches concerning the synthesis and antituberculosis action of some new sulphacetamide derivatives.	2006 Apr-Jun	17802961
Combination topical therapy in the treatment of acne.	2006 Aug	17966494
Broad-specificity immunoassays for sulfonamide detection: immunochemical strategy for generic antibodies and competitors.	2006 Mar 1	16503608
Toxicity and biodegradability of sulfonamides and products of their photocatalytic degradation in aqueous solutions.	2006 Nov	16750553
Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods.	2006 Oct 27	16879830
Demodex folliculorum and Demodex brevis as a cause of chronic marginal blepharitis.	2007	18561612
Pilot investigation of the hydrating effects of topical acne medications.	2007 Aug	17763612
Clinical development of 1% azithromycin in DuraSite, a topical azalide anti-infective for ocular surface therapy.	2007 Mar	19668461
[Determination of 12 sulfonamides in cosmetics by ultra performance liquid chromatography].	2007 Mar	17580695
[Simultaneous determination of seven sulfonamides and metronidazole and chloramphenicol in cosmetics by high performance liquid chromatography].	2007 Sep	18161331
A sensitive spectrophotometric method for the determination of sulfonamides in pharmaceutical preparations.	2007 Sep	17878112
Prescription refills and healthcare costs associated with topical metronidazole in Medicaid enrolled patients with rosacea.	2008	19160531
Ocular myasis and associated mucopurulent conjuctivitis acquired occupationally: A case study.	2008 Apr	20040993
Emerging topical antimicrobial options for mild-to-moderate acne: a review of the clinical evidence.	2008 Feb	18404864
N-(2,6-Dimethyl-phen-yl)-2-methyl-acetamide.	2008 Jan 9	21201410
Comparative study of robustness between micellar electrokinetic capillary chromatography and high-performance liquid chromatography using one-variable-at-a-time and a new multi-variable-at-a-time approach.	2008 Jul 14	18558136
Application of liquid-liquid-liquid microextraction and high-performance liquid-chromatography for the determination of sulfonamides in water.	2008 Mar 31	18331856
Expression profile of CREB knockdown in myeloid leukemia cells.	2008 Sep 18	18801183
Bioadhesive sulfacetamide sodium microspheres: evaluation of their effectiveness in the treatment of bacterial keratitis caused by Staphylococcus aureus and Pseudomonas aeruginosa in a rabbit model.	2009 Aug	19223014
Rosacea and its topical management.	2009 Feb	19330270
Treatment of papulopustular rosacea with sodium sulfacetamide 10%/sulfur 5% emollient foam.	2009 Mar	19271381
Analytical method for simultaneous determination of pesticide and veterinary drug residues in milk by CE-MS.	2009 May	19384986
A new and simple method to determine trace levels of sulfonamides in honey by high performance liquid chromatography with fluorescence detection.	2009 Oct 23	19505691
Updates on the pathophysiology and management of acne rosacea.	2009 Sep	19820288
Interaction of topical sulfacetamide and topical dapsone with benzoyl peroxide.	2009 Sep	19770443
Sulfacetamide loaded Eudragit® RL100 nanosuspension with potential for ocular delivery.	2010	21486528
Synthesis and biological activities of some novel triazoloquinazolines and triazinoquinazolines containing benzenesulfonamide moieties.	2010	20329657
An alternative purification method for human serum paraoxonase 1 and its interactions with sulfonamides.	2010 Dec	21040495
[Rosacea: pathogenesis, clinical forms and therapy].	2010 Jul 25	20650811
Curvularia keratomycosis in a dog.	2010 Mar	20447033
The multifunctionality of 10% sodium sulfacetamide, 5% sulfur emollient foam in the treatment of inflammatory facial dermatoses.	2010 Mar	20232584
Pharmacokinetic study on the mechanism of interaction of sulfacetamide sodium with bovine serum albumin: a spectroscopic method.	2010 Mar	20073032
Effectiveness and safety of doxycycline 40 mg (30-mg immediate-release and 10-mg delayed-release beads) once daily as add-on therapy to existing topical regimens for the treatment of papulopustular rosacea: results from a community-based trial.	2010 Nov	21229827
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

Patents

Sample Use Guides

In Vivo Use Guide

Topical: apply a thin film to affected areas twice daily. Ophtalmic suspension/ointment: two drops of suspension should be instilled into the conjunctival sac every four hours during the day and at bedtime. A small amount, approximately 1/2 inch ribbon of ointment, should be applied in the conjunctival sac three or four times daily and once or twice at night.

Route of Administration: Other

In Vitro Use Guide

P. aeruginosa, S. marcescens, St. epidermidis, C. albicans, and A. fumigatus (spores) were exposed to two ophthalmic solutions each formulated with 10% sodium sulfacetamide and a preservative. Sulfacetamide solutions preserved with thimerosal have MIC values ranging from 0.2 to 2.8 for the five test microorganisms. The solutions preserved with parabens exhibit slightly higher MIC values for Pseudomonas, Serratia, and spores of Aspergillus (1.5-6.5) and significantly higher MIC values for Staphylococcus and Candida (19.6 and 5.0, respectively).

Name

Type

Language

SULFACETAMIDE

Official Name

English

SULFACETAMIDE [ORANGE BOOK]

Common Name

English

TRYSUL COMPONENT SULFACETAMIDE

Common Name

English

GYNE-SULF COMPONENT SULFACETAMIDE

Common Name

English

SULFACETAMIDE [USP IMPURITY]

Common Name

English

SULTRIN COMPONENT SULFACETAMIDE

Common Name

English

SULFACETAMIDE [MART.]

Common Name

English

SULFACETAMIDUM [WHO-IP LATIN]

Common Name

English

Sulfacetamide [WHO-DD]

Common Name

English

NSC-63871

Code

English

UROSULFON

Common Name

English

SULFACETAMIDE COMPONENT OF VAGILIA

Common Name

English

TRIPLE SULFA (SULFACETAMIDE)

Common Name

English

sulfacetamide [INN]

Common Name

English

SULFACETAMIDE COMPONENT OF SULTRIN

Common Name

English

SULFACETAMIDE COMPONENT OF GYNE-SULF

Common Name

English

N-((4-AMINOPHENYL)SULFONYL)ACETAMIDE [WHO-IP]

Systematic Name

English

TRIPLE SULFA (SULFACETAMIDE) [ORANGE BOOK]

Common Name

English

SULFADIMIDINE IMPURITY E [EP IMPURITY]

Common Name

English

VAGILIA COMPONENT SULFACETAMIDE

Common Name

English

SULFACETAMIDE [VANDF]

Common Name

English

SULFACETAMIDE [MI]

Common Name

English

SULFACETAMIDE COMPONENT OF TRYSUL

Common Name

English

SULFACETAMIDE [WHO-IP]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01EQ21