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

Molecular Formula	C8H10N2O3S
Molecular Weight	214.242
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
[The effective antibacterial spectrum of sulfacetamide].	1992 Mar	1578876
Topical bactrim versus trimethoprim and sulfonamide against nocardia keratitis.	2001 Mar	11248825
Ocular nocardia infections with special emphasis on the cornea.	2001 Mar-Apr	11274691
Studies on the influence of auxiliary substances on the physico-chemical characteristics of ophthalmic drugs. Part I. Studies on the influence of auxiliary substances on the critical micellar concentration of surfactants solutions in eye drops containing sulphacetamidum natricum.	2002 Jul-Aug	12403298
A new, sensitive, and rapid spectrophotometric method for the determination of sulfa drugs.	2002 Jul-Aug	12180680
Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.	2002 Mar	11880002
Mycobacterium chelonae keratitis associated with soft contact lens wear.	2002 Oct	12394553
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.	2003 Jun	12739095
Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection.	2004 Aug 20	15481463
Rosacea. An overview of diagnosis and management.	2004 Dec	15615217
The use of sulfur in dermatology.	2004 Jul-Aug	15303787
Rosacea: where are we now?	2004 May-Jun	15176158
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
Diagnosing and managing the patient with rosacea.	2005 Apr	15916227
Topical metronidazole combination therapy in the clinical management of rosacea.	2005 Jul-Aug	16004021
Combination sodium sulfacetamide 10% and sulfur 5% cream with sunscreens versus metronidazole 0.75% cream for rosacea.	2005 Jun	16047874
Adjunctive skin care in the management of rosacea: cleansers, moisturizers, and photoprotectants.	2005 Mar	15810806
Seborrheic dermatitis. The link between facial rash and neurologic disease.	2005 Mar	15782673
Resistant scalp folliculitis secondary to Demodex infestation.	2005 Nov	16422467
Demodex mites as a cause of human disease.	2005 Nov	16422462
Monitoring of five sulfonamide antibacterial residues in milk by in-tube solid-phase microextraction coupled to high-performance liquid chromatography.	2005 Nov 2	16248539
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.	2005 Sep-Oct	16385979
Refractory Demodex folliculitis in five children with acute lymphoblastic leukemia.	2005 Sep-Oct	16190988
Epidermal growth factor receptor (EGFR) inhibitor associated skin eruption.	2006 Apr	16673807
Topical therapies for rosacea.	2006 Jan	16468288
Copper complexes with heterocyclic sulfonamides: synthesis, spectroscopic characterization, microbiological and SOD-like activities: crystal structure of [Cu(sulfisoxazole)2(H2O)4] . 2H2O.	2006 Jul	16584779
Broad-specificity immunoassays for sulfonamide detection: immunochemical strategy for generic antibodies and competitors.	2006 Mar 1	16503608
Determination of sulfonamide antibiotics in wastewater: a comparison of solid phase microextraction and solid phase extraction methods.	2006 Oct 27	16879830
Clinical development of 1% azithromycin in DuraSite, a topical azalide anti-infective for ocular surface therapy.	2007 Mar	19668461
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
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
An alternative purification method for human serum paraoxonase 1 and its interactions with sulfonamides.	2010 Dec	21040495
Synthesis of novel selenium-containing sulfa drugs and their antibacterial activities.	2010 May-Jun	20644596
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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:23:04 GMT 2023` Edited by `admin` on `Fri Dec 15 17:23:04 GMT 2023`
Record UNII	4965G3J0F5
Record Status	`Validated (UNII)`
Record Version

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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