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Revision as of 12:49, 12 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit		Latest revision as of 02:35, 9 January 2024 edit undoWikiCleanerBot (talk | contribs)Bots928,113 editsm v2.05b - Bot T20 CW#61 - Fix errors for CW project (Reference before punctuation)Tag: WPCleaner
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			{{cs1 config|name-list-style=vanc}}
	{{Drugbox| verifiedrevid = 388076291
			{{Short description|Chemical compound}}
	|
			{{Drugbox
	|IUPAC_name = (6''R'',7''R'')-7-{amino}- 3-chloro-8-oxo-5-thia-1-azabicyclooct-2-ene- 2-carboxylic acid
			| Verifiedfields = changed
	| image=Cefaclor.svg
			| verifiedrevid = 460022281
	| ChemSpiderID = 46259
			| IUPAC_name = (6''R'',7''R'')-7-{amino}- 3-chloro-8-oxo-5-thia-1-azabicyclooct-2-ene- 2-carboxylic acid
			| image = Cefaclor.svg
			<!--Clinical data-->
			| tradename = Biocef, Ceclor, Medacef, Distaclor, Keflor, Raniclor
			| Drugs.com = {{drugs.com|monograph|cefaclor}}
			| MedlinePlus = a682729
			| pregnancy_AU = B1
			| pregnancy_US = B
			| legal_status = Rx-only
			| routes_of_administration = Oral
			<!--Pharmacokinetic data-->
			| bioavailability = Well absorbed, independent of food intake
			| metabolism = 15% to 40%
			| elimination_half-life = 0.6 to 0.9 hours
			| excretion = ]
			<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|??}}
			| CAS_number = 53994-73-3
			| ATC_prefix = J01
			| ATC_suffix = DC04
			| PubChem = 51038
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank = DB00833
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 46260
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 3Z6FS3IK0K		| UNII = 3Z6FS3IK0K
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| InChI = 1/C15H14ClN3O4S.H2O/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7;/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23);1H2/t9-,10-,14-;/m1./s1
			| KEGG = D00256
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 8867
			<!--Chemical data-->
			| C=15 | H=14 | Cl=1 | N=3 | O=4 | S=1
	| smiles = O=C2N1/C(=C(/Cl)CS12NC(=O)(c3ccccc3)N)C(=O)O.O		| smiles = O=C2N1/C(=C(/Cl)CS12NC(=O)(c3ccccc3)N)C(=O)O.O
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| InChIKey = WKJGTOYAEQDNIA-IOOZKYRYBK
	| CASNo_Ref = {{cascite|correct|CAS}}
	| StdInChI = 1S/C15H14ClN3O4S.H2O/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7;/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23);1H2/t9-,10-,14-;/m1./s1		| StdInChI = 1S/C15H14ClN3O4S.H2O/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7;/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23);1H2/t9-,10-,14-;/m1./s1
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = WKJGTOYAEQDNIA-IOOZKYRYSA-N		| StdInChIKey = WKJGTOYAEQDNIA-IOOZKYRYSA-N
	| CAS_number=53994-73-3
	| ATC_prefix=J01
	| ATC_suffix=DC04
	| PubChem = 51038
	| DrugBank=APRD00243
	| C = 15 | H = 14 | Cl = 1 | N = 3 | O = 4 | S = 1
	| molecular_weight = 367.808 g/mol
	| bioavailability= Well absorbed, independent of food intake
	| metabolism = 15% to 40%
	| elimination_half-life= 0.6 to 0.9 hours
	| excretion = ]
	| pregnancy_AU = B1
	| pregnancy_US = B
	| legal_status = Rx-only
	| routes_of_administration= Oral
	}}		}}
	'''Cefaclor''', also known as '''cefachlor''' or '''cefaclorum''' (brand names '''Ceclor''', '''Distaclor''', '''Keflor''', '''Raniclor'''), is a second-generation ] ] used to treat certain ]s caused by ] such as ] and ear, lung, skin, throat, and urinary tract infections.		'''Cefaclor''', sold under the trade name '''Ceclor''' among others, is a second-generation ] ] used to treat certain ]s such as ] and infections of the ear, lung, skin, throat, and urinary tract. It is also available from other manufacturers as a generic.<ref>{{Cite web|url=https://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm|title = Drugs@FDA: FDA-Approved Drugs}}</ref>
			<!-- Society and culture -->
	== Indications==
			It was patented in 1973 and approved for medical use in 1979.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=493 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA493 |language=en}}</ref>
			== Medical uses==
	Cefaclor belongs to the family of antibiotics known as the ] (cefalosporins). The cephalosporins are broad-spectrum ] that are used for the treatment of ], ], ], biliary-tract infections, ], and urinary-tract infections. The pharmacology of the cephalosporins is similar to that of the ], excretion being principally renal. Cephalosporins penetrate the ] poorly unless the meninges are inflamed; ] is a more suitable cephalosporin than cefaclor for infections of the ], e.g. ]. Cefaclor is active against many ], including both ] and ] organisms.
			Cefaclor belongs to the family of antibiotics known as the ] (cefalosporins). The cephalosporins are broad-spectrum ] that are used for the treatment of ], ], ], biliary tract infections, ], and urinary tract infections. The pharmacology of the cephalosporins is similar to that of the ], excretion being principally renal. Cephalosporins penetrate the ] poorly unless the meninges are inflamed; ] is a more suitable cephalosporin than cefaclor for infections of the ], e.g. ]. Cefaclor is active against many ], including both ] and ] organisms.{{cn|date=March 2023}}
			===Spectrum of activity===
			Cefaclor is frequently used against bacteria responsible for causing skin infections, otitis media, urinary tract infections, and others.
			Cefaclor has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Gram positive aerobes - Staphylococci (including coagulase-positive, coagulase-negative, and penicillinase-producing strains), Streptococcus pneumoniae, and Streptococcus pyogenes (group A β-hemolytic streptococci).
			<ref>{{Cite web | vauthors = Salvi R |url=http://www.medicatione.com/?c=ing&s=cefaclor|title = Cefaclor drugs and health products | work = sdrugs.com }}</ref>
			The following represents MIC susceptibility data for a few medically significant microorganisms.
			* ''Haemophilus influenzae'': 0.03 μg/mL - 128 μg/mL
			* ''Staphylcoccus aureus'': 0.6 μg/mL - 128 μg/mL
			* ''Streptococcus pyogenes'': 0.06 μg/mL - 4 μg/mL
			<ref>{{Cite web |url=http://www.toku-e.com/Assets/MIC/Cefaclor.pdf |title=Cefaclor Susceptibilty and Resistance Data | date = 18 August 2014 | work = TOKU-E |access-date=2013-08-13 |archive-date=2016-03-03 |archive-url=https://web.archive.org/web/20160303222841/http://www.toku-e.com/Assets/MIC/Cefaclor.pdf |url-status=dead }}</ref>
	==Cautions and contraindications==		==Cautions and contraindications==
	Cautions include known sensitivity to beta-lactam antibacterials, such as penicillins (Cefaclor should be avoided if there is a history of immediate ] reaction); renal impairment (no dose adjustment required, although manufacturer advises caution); ] and ] (but appropriate to use); false positive urinary glucose (if tested for reducing substances) and false positive ]. Cefaclor has also been reported to cause a ]-like reaction in children.<ref>{{cite journal |author=Hebert A, Sigman E, Levy M |title=Serum sickness-like reactions from cefaclor in children |journal=J Am Acad Dermatol |volume=25 |issue=5 Pt 1 |pages=805–8 |year=1991 |pmid=1802903 |doi=10.1016/S0190-9622(08)80973-5}}</ref><ref>{{cite journal |author=Parra F, Igea J, Martín J, Alonso M, Lezaun A, Sainz T |title=Serum sickness-like syndrome associated with cefaclor therapy |journal=Allergy |volume=47 |issue=4 Pt 2 |pages=439–40 |year=1992 |pmid=1456417 |doi=10.1111/j.1398-9995.1992.tb02086.x}}</ref>		Cautions include known sensitivity to beta-lactam antibacterials, such as penicillins (Cefaclor should be avoided if there is a history of immediate ] reaction); renal impairment (no dose adjustment required, although manufacturer advises caution); ] and ] (but appropriate to use); false positive urinary glucose (if tested for reducing substances) and false positive ]. Cefaclor has also been reported to cause a ] in children.<ref>{{cite journal | vauthors = Hebert AA, Sigman ES, Levy ML | title = Serum sickness-like reactions from cefaclor in children | journal = Journal of the American Academy of Dermatology | volume = 25 | issue = 5 Pt 1 | pages = 805–808 | date = November 1991 | pmid = 1802903 | doi = 10.1016/S0190-9622(08)80973-5 }}</ref><ref>{{cite journal | vauthors = Parra FM, Igea JM, Martín JA, Alonso MD, Lezaun A, Sainz T | title = Serum sickness-like syndrome associated with cefaclor therapy | journal = Allergy | volume = 47 | issue = 4 Pt 2 | pages = 439–440 | date = August 1992 | pmid = 1456417 | doi = 10.1111/j.1398-9995.1992.tb02086.x | s2cid = 46029579 }}</ref>
	Cefaclor is contraindicated in case of hypersensitivity (i.e. allergy) to cephalosporins.		Cefaclor is contraindicated in case of hypersensitivity (i.e. allergy) to cephalosporins.{{cn|date=March 2023}}
	==Side effects==		==Side effects==
			]
	The principal ] of the cephalosporins is hypersensitivity. Up to about 10% of penicillin-sensitive patients will also be allergic to the cephalosporins, depending on the cephalosporin generation. Allergic reactions may present as, for example, rashes, ] (itching), ], ]-like reactions with rashes, fever and ], and ]. The frequency and severity of ]-like reactions in children has led researchers to question its role in pediatric illness.<ref>{{cite journal |author=King BA, Geelhoed GC |title=Adverse skin and joint reactions associated with oral antibiotics in children: the role of cefaclor in serum sickness-like reactions |journal=J Paediatr Child Health |volume=39 |issue=9 |pages=677–81 |year=2003 |month=December |pmid=14629499 |url=http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1034-4810&date=2003&volume=39&issue=9&spage=677 |doi=10.1046/j.1440-1754.2003.00267.x}}</ref> ] Other side effects include gastrointestinal disturbances (e.g. diarrhea, nausea and vomiting, abdominal discomfort, disturbances in liver enzymes, transient ] and cholestatic jaundice), ], and ]. Rare side effects include ] and blood disorders (including ], ], ], ] and ]); reversible ]; ], ], sleep disturbances, ], ], ], and ]. ] has been reported. In the UK, The Committee on the Safety of Medicines (]) has warned that the risk of diarrhea and rarely antibiotic-associated colitis are more likely with higher doses.
			The principal ] of the cephalosporins is hypersensitivity. Penicillin-sensitive patients may also be allergic to the cephalosporins, depending on the side chain and it's relation to the penicillin allergy. Most patients with penicillin allergy can tolerate the majority of cephalosporins without allergic reactions. The previous percentage of 10% cross reactivity rates are a gross overestimation.<ref>Zagursky RJ, Pichichero ME. Cross-reactivity in β-Lactam Allergy </ref> Allergic reactions may present as, for example, rashes, ] (itching), ], ]s with rashes, fever and ], and ]. The frequency and severity of ]-like reactions in children has led researchers to question its role in pediatric illness.<ref>{{cite journal | vauthors = King BA, Geelhoed GC | title = Adverse skin and joint reactions associated with oral antibiotics in children: the role of cefaclor in serum sickness-like reactions | journal = Journal of Paediatrics and Child Health | volume = 39 | issue = 9 | pages = 677–681 | date = December 2003 | pmid = 14629499 | doi = 10.1046/j.1440-1754.2003.00267.x | s2cid = 25762196 }}</ref> Other side effects include gastrointestinal disturbances (e.g. diarrhea, nausea and vomiting, abdominal discomfort, disturbances in liver enzymes, transient ] and cholestatic jaundice), ], and ]. Rare side effects include ] and blood disorders (including ], ], ], ] and ]); reversible ]; ], ], sleep disturbances, ], ], ], and ]. ] has been reported. In the UK, The Committee on the Safety of Medicines (]) has warned that the risk of diarrhea and rarely antibiotic-associated colitis are more likely with higher doses.{{cn|date=March 2023}}
	==Interactions with other medications==
	===Coumarins===
	] possibly enhance the ] effect of ] (e.g. ]) - change in patient's clinical condition, particularly associated with liver disease, intercurrent illness, or drug administration, necessitates more frequent testing of ], and dose adjustment as necessary.
			===Pregnancy and breastfeeding===
	===Probenecid===
			Cefaclor is passed into the ] in small quantities, but is generally accepted to be safe to take during ].<ref>{{cite web| work = LactMED|title=Summary of Cefaclor's use during lactation|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~gthK7d:1 |publisher = U.S. National Library of Medicine|access-date=22 May 2011}}</ref> Cefaclor is not known to be harmful in ].<ref name="Breast feeding and Cefaclor">{{cite journal | vauthors = Ito S, Blajchman A, Stephenson M, Eliopoulos C, Koren G | title = Prospective follow-up of adverse reactions in breast-fed infants exposed to maternal medication | journal = American Journal of Obstetrics and Gynecology | volume = 168 | issue = 5 | pages = 1393–1399 | date = May 1993 | pmid = 8498418 | doi = 10.1016/s0002-9378(11)90771-6 }}</ref>
	Excretion of ] is reduced by ] (resulting in increased concentrations of drug in the ]).
	===Antacids===
	Absorption of cefaclor is reduced by ]; therefore antacids should not be taken at the same time as cefaclor.
			== Interactions ==
	absorption of cefaclor is reduced by H2 blockers ; therefore antacids should not be taken at the same time as cefaclor
			===Coumarins===
	==Safety in pregnancy and breastfeeding==
			] possibly enhance the ] effect of ] (e.g. ]) - change in patient's clinical condition, particularly associated with liver disease, intercurrent illness, or drug administration, necessitates more frequent testing of ], and dose adjustment as necessary.{{cn|date=March 2023}}
	Cefaclor is passed into the ] in small quantities, but is generally accepted to be safe to take during ]. Cefaclor is not known to be harmful in ].
	==Cefaclor CD==		===Probenecid===
			Excretion of ] is reduced by ] (resulting in increased concentrations of drug in the ]).{{cn|date=March 2023}}
	Cefaclor CD is a ] form of Cefaclor which releases the drug to the body over a longer period of time, which means that doses can be taken less frequently, with steadier levels of the drug in the bloodstream. Sustained release is useful with Cefaclor as it has a very short half-life.
			===Antacids===
			Absorption of cefaclor is reduced by ]. Therefore antacids should not be taken right before or at the same time as cefaclor.<ref>{{Cite web|url=https://www.drugs.com/mtm/ceclor.html|title = Ceclor Uses, Side Effects & Warnings | work = Drugs.com }}</ref><ref>{{cite journal | vauthors = Satterwhite JH, Cerimele BJ, Coleman DL, Hatcher BL, Kisicki J, DeSante KA | title = Pharmacokinetics of cefaclor AF: effects of age, antacids and H2-receptor antagonists | journal = Postgraduate Medical Journal | volume = 68 | pages = S3–S9 | year = 1992 | issue = Suppl 3 | pmid = 1287615 }}</ref>
	==References==		== References ==
	{{Reflist}}		{{Reflist}}
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