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Revision as of 18:11, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456713022 of page Sulfacetamide for the Chem/Drugbox validation project (updated: 'DrugBank').		Latest revision as of 07:58, 24 November 2024 edit Boghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,800 edits →References: + cat
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			{{Short description|Sulfonamide antibiotic}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
			{{cs1 config|name-list-style=vanc|display-authors=6}}
	{{Drugbox		{{Drugbox
			| Watchedfields = changed
	| verifiedrevid = 408575719		| verifiedrevid = 470472833
	| IUPAC_name = ''N''-acetamide		| IUPAC_name = ''N''-acetamide
	| image = Sulfacetamide.svg		| image = Sulfacetamide.svg
	|image2= Sulfacetamid molecule.png		| image2= Sulfacetamide molecule ball.png
	<!--Clinical data-->		<!--Clinical data-->
	| tradename = Bleph-10		| tradename = Bleph-10
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	| legal_US = <!-- OTC / Rx-only -->		| legal_US = <!-- OTC / Rx-only -->
	| legal_status =		| legal_status =
	| routes_of_administration =		| routes_of_administration =
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	| bioavailability =		| bioavailability =
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	| metabolism =		| metabolism =
	| elimination_half-life = 7 to 12.8 hours		| elimination_half-life = 7 to 12.8 hours
	| excretion =		| excretion =
	<!--Identifiers-->		<!--Identifiers-->
	| CASNo_Ref = {{cascite|correct|CAS}}
	| CAS_number_Ref = {{cascite|correct|??}}		| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 144-80-9		| CAS_number = 144-80-9
	| ATC_prefix = S01		| ATC_prefix = D10
	| ATC_suffix = AB04		| ATC_suffix = AF06
	| ATC_supplemental =		| ATC_supplemental = {{ATC|S01|AB04}}, {{ATCvet|J01|EQ21}}
	| PubChem = 5320		| PubChem = 5320
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 455		| ChEMBL = 455
	<!--Chemical data-->		<!--Chemical data-->
	| C=8 | H=10 | N=2 | O=3 | S=1		| C=8 | H=10 | N=2 | O=3 | S=1
	| molecular_weight = 214.243 g/mol
	| smiles = O=S(=O)(c1ccc(N)cc1)NC(=O)C		| smiles = O=S(=O)(c1ccc(N)cc1)NC(=O)C
	| InChI = 1/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)
	| InChIKey = SKIVFJLNDNKQPD-UHFFFAOYAW
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)		| StdInChI = 1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = SKIVFJLNDNKQPD-UHFFFAOYSA-N		| StdInChIKey = SKIVFJLNDNKQPD-UHFFFAOYSA-N
			| melting_point = 182
			| melting_high = 184
	}}		}}
			]
			'''Sulfacetamide''' is a ] ] commonly used in the treatment of bacterial infections, particularly those affecting the eyes and skin. It functions by inhibiting the synthesis of ] in bacteria, which is essential for their growth and reproduction, thereby exerting a ] effect. Available in various forms, including eye drops, topical solutions, and creams, sulfacetamide is often prescribed for conditions such as ], ], and ]. Its efficacy, coupled with a relatively low risk of side effects, makes it a widely utilized agent in both ophthalmic and dermatologic care.
			== Medical uses ==
			Sulfacetamide is a sulfonamide antibiotic, that is used as a cream to treat skin infections and as eye drops to treat eye infections. On the skin it is used to treat acne and ].<ref name=":4" /> In cream form it is used to treat bacterial infections on the skin. It can also be used orally to treat ]s.<ref name="DrugBank_2013" /> It kills the bacteria by restricting the production of folic acid, which is essential for bacterial growth.<ref name="www.drugs.com">{{Cite web|url=https://www.drugs.com/cdi/sulfacetamide-cream.html|title=Sulfacetamide cream: Indications, Side Effects, Warnings - Drugs.com|website=www.drugs.com|access-date=2016-03-09}}</ref> It mainly inhibits the multiplication of bacteria as it acts in a competitive inhibitor.
			Sulfacetamide 10% topical lotion, sold under the brand name Klaron or Ovace, is approved for the treatment of ] and ].<ref>{{cite web|url=https://www.drugs.com/mtm/klaron.html|title=Klaron medical facts | work = Drugs.com}}</ref> When combined with ], it is sold under the brand names ], Clenia, Prascion, and Avar, which contain 10% sulfacetamide and 5% sulfur.<ref>{{cite web |url= https://www.drugs.com/cdi/avar-cream.html|title=Avar cream: Indications, Side Effects, Warnings | work = Drugs.com }}</ref><ref>{{cite web|url=https://www.drugs.com/mtm/plexion.html|title=Plexion medical facts | work = Drugs.com}}</ref><ref>{{cite web |url= http://www.walgreens.com/marketing/library/finddrug/druginfo1.html;jsessionid=PbrFt7xeQx07A7CTF6HcFA**.p_dotcom34?particularDrug=Prascion&id=645494 |title=&#124; Drug Information &#124; Pharmacy | work = Walgreens |access-date=2013-01-31 |url-status=dead |archive-url=https://web.archive.org/web/20130516204356/http://www.walgreens.com/marketing/library/finddrug/druginfo1.html;jsessionid=PbrFt7xeQx07A7CTF6HcFA**.p_dotcom34?particularDrug=Prascion&id=645494 |archive-date=2013-05-16 }}</ref><ref>{{cite web|url=https://www.drugs.com/pro/clenia-cream.html|title=Clenia Cream - FDA prescribing information, side effects and uses}}</ref>
			=== Available forms ===
			Sulfacetamide as a medicine is available as solution, eye drops, lotion, and powder.<ref>{{Cite web|url=http://www.medicatione.com/?c=drug&s=sulfacetamide&ingredient=sulfacetamide%2520sodium|title=Sulfacetamide (sulfacetamide sodium) drug & pharmaceuticals. Sulfacetamide available forms, doses, prices|website=www.medicatione.com|access-date=2016-03-09}}</ref> It can also be found in the form of the sodium ], sulfacetamide sodium.<ref>{{cite web | title=Bleph-10- sulfacetamide sodium solution/ drops | website=DailyMed | date=16 July 2014 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=27c8bd30-89ec-464c-b7ac-ca2dbe27e861 | access-date=10 June 2020}}</ref>
			It is available in fixed-dose combinations with prednisolone.<ref>{{cite web | title=Blephamide- sulfacetamide sodium and prednisolone acetate ointment | website=DailyMed | date=29 June 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c68ebddc-dcb5-4695-a66b-d03a65a110f6 | access-date=10 June 2020}}</ref><ref>{{cite web | title=Blephamide- sulfacetamide sodium and prednisolone acetate suspension/ drops | website=DailyMed | date=10 November 2016 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0e5644af-2a3c-493a-bc24-174e5f36235b | access-date=10 June 2020}}</ref>
			== Side effects ==
			The most common side effects are irritation, stinging or burning of the skin. Other side effects include nausea, vomiting, dizziness, tiredness and headache.<ref name="DrugBank_2013" /> There are however also severe side effects including severe allergic reactions, like (nettle) rash, itch, tightness in chest, difficult breathing and swelling in either the face, mouth, lips or tongue. Other severe side effects include bloody or severe diarrhea, fever, joint pain, red, blistered or swollen skin and stomach pain.<ref name="www.drugs.com" /> In the eye, it can cause ]. There are also life-threatening conditions which can be produced by the antibiotic, like ] and ].<ref name="www.druginfosys.com" /> Higher exposure can also cause unconsciousness.<ref name="DrugBank_2013" /> One case showed that sulfacetamide eyedrops can very rarely cause life-threatening skin condition ] (TEN).<ref>{{cite journal | vauthors = Byrom L, Zappala T, Muir J | title = Toxic epidermal necrolysis caused by over the counter eyedrops | journal = The Australasian Journal of Dermatology | volume = 54 | issue = 2 | pages = 144–6 | date = May 2013 | pmid = 22897159 | doi = 10.1111/j.1440-0960.2012.00936.x | s2cid = 37140124 }}</ref> These are however not all side effects. For more information the health care provider can be contacted.
			Sulfacetamide should not be used by individuals who have a sensitivity to sulfur or ].
			=== Toxicity ===
			The acute oral toxicity (LD<sub>50</sub>) in a mouse is 16.5 g/kg.<ref name="DrugBank_2013" /><ref>{{cite web|publisher=ScienceLab.com|year=2013|title=Material Safety Data Sheet Sulfacetamide MSDS|url=http://www.sciencelab.com/msds.php?msdsId=9925121|access-date=2016-03-09|archive-date=2016-04-04|archive-url=https://web.archive.org/web/20160404062612/http://www.sciencelab.com/msds.php?msdsId=9925121|url-status=dead}}</ref> As this falls within Toxicity Category IV of the ] for oral administration, it is practically non-toxic and also not an irritant when taken in orally. However, it is very hazardous in case of skin contact (irritant), ingestion and inhalation.
			Research proved that it is more toxic in the presence of light than in the dark. Sulfacetamide is slightly irritant when UV-A light is present. In the presence of light sulfacetamide gets sensitized and degraded which might cause irritation which will lead to toxicity when it is used continuously. In the dark only slight irritation has been shown. Therefore it should be stored in the dark.<ref>{{cite journal | vauthors = Sahu RK, Singh B, Saraf SA, Kaithwas G, Kishor K | title = Photochemical toxicity of drugs intended for ocular use | journal = Arhiv Za Higijenu Rada I Toksikologiju | volume = 65 | issue = 2 | pages = 157–67 | date = June 2014 | pmid = 24846953 | doi = 10.2478/10004-1254-65-2014-2461 | doi-access = free | url = http://hrcak.srce.hr/file/181590 }}</ref>
			There are no known carcinogenic and mutagenic effects. It has a moderate toxicity according to the Chemwatch hazard ratings.<ref name="CHEMWATCH_2011">{{cite web|publisher=CHEMWATCH|year=2011|title=Sulfacetamide|url=http://datasheets.scbt.com/sds/AGHS/EN/sc-251080.pdf}}</ref>
			== Pharmacology ==
			=== Mechanisms of action ===
			Sulfacetamide is a sulfonamide ].<ref name=":4">{{Cite web|url=http://www.sigmaaldrich.com/catalog/product/sigma/s8627?lang=en&region=NL|title=Sulfacetamide ≥98.0% {{!}} Sigma-Aldrich|website=www.sigmaaldrich.com|access-date=2016-03-09}}</ref> Sulfonamides are synthetic bacteriostatic antibiotics, that are active against ] and ]. It blocks the synthesis of dihydrofolic acid by inhibiting the enzyme ]. It is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA). PABA is required for bacterial synthesis of ] and it is an essential component for bacterial growth.<ref name="DrugBank_2013" /> The multiplication of bacteria is therefore inhibited by the action of sulfacetamide.
			Sulfonamides are generally effective against most gram-positive and many gram-negative organisms.<ref name="PubChem" /> Specifically enteric bacteria and other eubacteria are affected by the antibiotic as it kills the bacteria by restricting the production of folic acid, which is essential for their growth.<ref name="www.druginfosys.com" /> However strains of bacteria can be resistant to the antibiotic. If a bacterium is resistant to a sulfonamide, it is resistant to all the forms. Furthermore, sulfacetamide is toxic to soil organisms.<ref name="CHEMWATCH_2011" />
			=== Pharmacokinetics ===
			Sulfacetamide is absorbed orally. The oral absorption of sulfacetamide is found to be 100%<ref name="www.druginfosys.com">{{Cite web|url=http://www.druginfosys.com/Drug.aspx?drugCode=687&drugName=Sulphacetamide&type=3|title=Sulphacetamide|website=www.druginfosys.com|access-date=2016-03-09}}</ref> and the plasma protein binding is 80–85%. In the liver it is metabolized to inactive metabolites.<ref name="www.robholland.com">{{Cite web|url=http://www.robholland.com/Nursing/Drug_Guide/data/monographframes/S039.html|title=SULFACETAMIDE SODIUM|website=www.robholland.com|access-date=2016-03-09}}</ref> Plasma half-life is 7 – 12.8 hours.<ref name="PubChem" />
			Sulfonamides are usually metabolized by several oxidative pathways, acetylation, and conjugation with ] or ].<ref name="www.merckvetmanual.com">{{Cite web|url=http://www.merckvetmanual.com/mvm/pharmacology/antibacterial_agents/sulfonamides_and_sulfonamide_combinations.html|title=Sulfonamides and Sulfonamide Combinations: Antibacterial Agents: Merck Veterinary Manual|website=www.merckvetmanual.com|access-date=2016-03-09}}</ref> However, there are some differences in ] between certain species. Acetylation, which reduces the solubility of sulfonamides, is for example poor developed in dogs. The acetylated, hydroxylated, and conjugated forms have little antibacterial activity. Furthermore, the hydroxylated and conjugated forms are less likely to precipitate in urine. The hydrolysis takes place by the action of amidases.<ref>HSU, W.H. (2008). Handbook Of Veterinary Pharmacology. Ames, Iowa: John Wiley & Sons.</ref>
			It is excreted primarily in the urine.<ref name="www.robholland.com" /> Secretory routes of less significance are bile, feces, milk and sweat.<ref name="www.merckvetmanual.com" /> Glomerular filtration, active tubular secretion, and tubular reabsorption are the main processes involved.
			== Chemistry ==
			=== Structure and chemical properties ===
			These are organic compounds containing an benzenesulfonamide moiety with an ] group attached to the ] ring.<ref name="DrugBank_2013">{{Cite journal |date=2013-09-16 |title=Sulfacetamide|url=http://www.drugbank.ca/drugs/DB00634|journal=DrugBank}}</ref> The molecular formula is C<sub>8</sub>H<sub>10</sub>N<sub>2</sub>O<sub>3</sub>S. Its scientific name is N-(4-aminophenyl)sulfonylacetamide. At room temperature, it appears as a white powder.<ref name="PubChem">{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/sulfacetamide#section=MS-MS|title=sulfacetamide {{!}} C8H10N2O3S | work = PubChem | publisher = U.S. National Library of Medicine |access-date=2016-03-09}}</ref>
			=== Degradation reactions and stability ===
			Sulfacetamide is stable under normal temperatures and pressures. No dangerous reactions occur under known conditions of normal use.<ref>Bausch and Lomb. (2015). ''Sulfacetamide Sodium 10% and Prednisolone Sodium Phosphate 0.25% Ophthalmic Solution.''</ref> It is an important ] that is commonly used in human and veterinary medicine. Therefore it can accumulate in the environment (mostly surface water).<ref name="Naik_2008">{{cite journal | vauthors = Naik PN, Kulkarni SD, Chimatadar SA, Nandibewoor ST |date=November 2008 |title=Mechanistic study of oxidation of sulfacetamide by diperiodatocuparate(III) in aqueous alkaline medium |journal=Indian Journal of Chemistry |volume=47A |issue=11 |pages=1666–1670 |doi= |url=https://nopr.niscpr.res.in/bitstream/123456789/2472/1/IJCA%2047A(11)%201666-1670.pdf}}</ref>
			It has a long lifetime in the environment so different degradation reactions are researched:
			The photocatalytic degradation of sulfacetamide in water solutions during illumination of UV radiation with TiO<sub>2</sub> was examined. It was found that sulfacetamide is resistant to ] and that it is toxic to the green alga '']''. It undergoes photocatalytic degradation and the toxicity of the intermediate products is significantly lower than the initial toxicity. The intermediates can be mineralized in contrast to sulfacetamide.<ref name="Baran_2006">{{cite journal | vauthors = Baran W, Sochacka J, Wardas W | title = Toxicity and biodegradability of sulfonamides and products of their photocatalytic degradation in aqueous solutions | journal = Chemosphere | volume = 65 | issue = 8 | pages = 1295–9 | date = November 2006 | pmid = 16750553 | doi = 10.1016/j.chemosphere.2006.04.040 | bibcode = 2006Chmsp..65.1295B }}</ref>
			] → organic intermediate products (degradation) (in presence of OH<sup>−</sup>).<ref name="Baran_2006" />
			]
			At higher temperatures sulfacetamide solutions degrade to its hydrolysed product, ] with a first-order rate constant.<ref>{{cite journal|vauthors=Ahmad T|title=Stability of Suiphacetamide Eye drops at Higher Temperature|journal=Journal of Pakistan Medical Association|url=http://www.jpma.org.pk/full_article_text.php?article_id=6422|date=July 1983|access-date=2016-03-09|archive-date=2016-03-09|archive-url=https://web.archive.org/web/20160309193208/http://www.jpma.org.pk/full_article_text.php?article_id=6422|url-status=dead}}</ref>
			Also oxidation of sulfacetamide by {{chem name|diperiodatocuperate(III)}} in an aqueous alkaline medium can occur. Copper(III) is used, as it is involved in many biological electron transfer reactions.<ref name="Naik_2008" />
			The sulphanilamide can oxidise to a blue product with a first order reaction and it can form ] with a ].<ref>{{cite journal | vauthors = Ahmad T | title = Degradation studies on sulphacetamide eye-drops. Part 2: Spectrophotometric evaluation of decomposition products of UV-irradiated solutions of sulphacetamide | journal = Die Pharmazie | volume = 37 | issue = 8 | pages = 559–61 | date = August 1982 | pmid = 7146062 }}</ref>
			=== Synthesis ===
			Sulfacetamide is synthesized either by direct alkylation of ] with 4-aminobenzenesulfonyl chloride, or by reacting 4-aminobenzenesulfonamide with ] and subsequent selective, reductive deacylation of the resultant acetamide using a system of zinc-sodium hydroxide.<ref>{{US patent|2411495}}</ref><ref>{{Cite journal | doi = 10.1021/ja01265a107| title = Sulfanilamide Derivatives. IV. N1,N4-Diacylsulfanilamides and N1-Acylsulfanilamides| journal = Journal of the American Chemical Society| volume = 61| issue = 10| pages = 2950–2955| year = 1939| vauthors = Crossley ML, Northey EH, Hultquist ME }}</ref>
			== Research ==
			Sulfacetamide has been investigated for use in the treatment of ]<ref name="pmid15224788">{{cite journal | vauthors = Hull CA, Johnson SM | title = A double-blind comparative study of sodium sulfacetamide lotion 10% versus selenium sulfide lotion 2.5% in the treatment of pityriasis (tinea) versicolor | journal = Cutis | volume = 73 | issue = 6 | pages = 425–9 | date = June 2004 | pmid = 15224788 }}</ref> and ].<ref name="pmid14959943">{{cite journal | vauthors = Del Rosso JQ | title = Evaluating the role of topical therapies in the management of rosacea: focus on combination sodium sulfacetamide and sulfur formulations | journal = Cutis | volume = 73 | issue = 1 Suppl | pages = 29–33 | date = January 2004 | pmid = 14959943 }}</ref> It also has ] properties when used to treat ] or ] (in eye-drop solution). It is believed to work by limiting the presence of folic acid which bacteria need to survive. It has been suggested that sulfacetamide may also serve as a treatment for mild forms of ].{{citation needed|date=August 2009}} Sulfacetamide has antibacterial activity and is used to control acne. Products containing sulfacetamide and sulfur (a ]) are commonly promoted for the treatment of acne rosacea (rosacea with papules, pustules, or both). There are several prescription topical products containing sulfacetamide, such as ]s, ]s, ] and ].
			Some research indicates that sulfacetamide derivatives may act as antifungals by an ]-independent mechanism.<ref name="pmid18475922">{{cite journal | vauthors = Mastrolorenzo A, Supuran CT | title = Antifungal Activity of Ag(I) and Zn(II) Complexes of Sulfacetamide Derivatives | journal = Metal-Based Drugs | volume = 7 | issue = 1 | pages = 49–54 | year = 2000 | pmid = 18475922 | pmc = 2365193 | doi = 10.1155/MBD.2000.49 | doi-access = free }}</ref>
			== References ==
			{{Reflist}}
			{{Acne Agents}}
			{{SulfonamideAntiBiotics}}
			{{Ophthalmological anti-infectives}}
			]
			]
			]
			]
			]