Misplaced Pages

Cefotiam: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 20:49, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 00:19, 19 October 2024 edit undo2601:642:c303:f370:845f:745f:fee:4663 (talk) The 
(59 intermediate revisions by 35 users not shown)
Line 1: Line 1:
{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Watchedfields = changed
| verifiedrevid = 443509780 | verifiedrevid = 460024199
| IUPAC_name = (6''R'',7''R'')-7-{<br>amino}-3-{<br>sulfanylmethyl}-8-oxo-5-thia-1-azabicyclo<br>oct-2-ene-2-carboxylic acid | IUPAC_name = (6''R'',7''R'')-7-{<br>amino}-3-{<br>sulfanylmethyl}-8-oxo-5-thia-1-azabicyclo<br>oct-2-ene-2-carboxylic acid
| image = Cefotiam.svg | image = Cefotiam.jpg
| width = 250 | width = 250
| image2 = Cefotiam.svg

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Pansporin
| Drugs.com = {{drugs.com|international|cefotiam}} | Drugs.com = {{drugs.com|international|cefotiam}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
Line 13: Line 15:
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD --> | legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only --> | legal_US = <!-- OTC / Rx-only -->
| legal_status = | legal_status = Rx-only
| routes_of_administration = ], intramuscular | routes_of_administration = ], ]

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 60% (]) | bioavailability = 60% (intramuscular)
| protein_bound = 40% | protein_bound = 40%
| metabolism = Nil | metabolism = Nil
| elimination_half-life = Approximately 1 hour | elimination_half-life = Approximately 1 hour
| excretion = ] | excretion = ]

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 61622-34-2 | CAS_number = 61622-34-2
| ATC_prefix = J01 | ATC_prefix = J01
Line 43: Line 43:
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1296 | ChEMBL = 1296

<!--Chemical data--> <!--Chemical data-->
| C=18 | H=23 | N=9 | O=4 | S=3 | C=18 | H=23 | N=9 | O=4 | S=3
| smiles = CN(C)CCN1N=NN=C1SCC1=C(N2(SC1)(NC(=O)CC1=CSC(N)=N1)C2=O)C(O)=O
| molecular_weight = 525.631 g/mol
| smiles = O=C2N1/C(=C(\CS12NC(=O)Cc3nc(sc3)N)CSc4nnnn4CCN(C)C)C(=O)O
| InChI = 1/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1
| InChIKey = QYQDKDWGWDOFFU-IUODEOHRBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1 | StdInChI = 1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1
Line 55: Line 51:
| StdInChIKey = QYQDKDWGWDOFFU-IUODEOHRSA-N | StdInChIKey = QYQDKDWGWDOFFU-IUODEOHRSA-N
}} }}
<!-- Definition and medical uses -->
'''Cefotiam''' is a second-generation ] ].
'''Cefotiam''' is a ] third-generation ] ]. It has broad-spectrum activity against ] and ] bacteria. As a ], its bactericidal activity results from the inhibition of cell wall synthesis via affinity for ].


<!-- Society and culture -->
==External links==
It was patented in 1973 and approved for medical use in 1981.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=494 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA494 |language=en}}</ref>
⚫ * {{cite journal | author = Müller R, Böttger C, Wichmann G | title = Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. | journal = Arzneimittelforschung | volume = 53 | issue = 2 | pages = 126–32 | year = 2003 | pmid = 12642969}}

⚫ * {{cite journal | author = Kolben M, Mandoki E, Ulm K, Freitag K | title = Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section. | journal = Eur J Clin Microbiol Infect Dis | volume = 20 | issue = 1 | pages = 40–2 | year = 2001 | pmid = 11245321 | doi = 10.1007/s100960000365}}
==Medical uses==
⚫ * {{cite journal | author = Shimizu S, Chen K, Miyakawa S | title = Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. | journal = Dermatology | volume = 192 | issue = 2 | pages = 174–6 | year = 1996 | pmid = 8829507 | doi = 10.1159/000246352}}
This drug is indicated for prophylaxis for surgical infection, postoperative infections, bacterial , bone and joint infections, ], ], ], ], ], respiratory tract infections, skin and soft tissue infections, ], ], and infections caused by susceptible organisms. It does not have activity against '']''.{{cn|date=March 2023}}

===Dosage===
For adults, the dose is up to 6 grams daily by intravenous or intramuscular route in divided doses according to the severity of infection. In patients with ] a dose reduction may be needed.{{cn|date=March 2023}}

===Spectrum of bacterial susceptibility===
Cefotiam has a broad spectrum of activity and has been used to treat infections caused by several enteric bacteria and bacteria responsible for causing skin infections. The following represents MIC susceptibility data for a few medically significant bacteria.
* '']'': - 16 - >128 μg/ml
* '']'': >128 μg/ml
* '']'': 0.25 - 32 μg/ml
<ref>{{Cite web |url=http://www.toku-e.com/Assets/MIC/Cefotiam%20hydrochloride.pdf |title=Cefotiam hydrochloride | work = Susceptibilty and Resistance Data | publisher = TOKU-E | date = 24 February 2014 |access-date=2014-02-06 |archive-url=https://web.archive.org/web/20160304002457/http://www.toku-e.com/Assets/MIC/Cefotiam%20hydrochloride.pdf |archive-date=2016-03-04 |url-status=dead }}</ref>

==Adverse effects==
Side effects include nausea and vomiting, diarrhoea, hypersensitivity reactions, ], convulsions, CNS toxicity, hepatic dysfunction, haematologic disorders, pain at injection site, thrombophlebitis, ], and ] with prolonged use.{{cn|date=March 2023}}

==Mechanism of action==
Cefotiam inhibits the final cross-linking stage of ] production, thus inhibiting bacterial cell wall synthesis. It has similar or less activity against Gram-positive ] and ], but is resistant to some ] produced by Gram-negative bacteria. It is more active against many of the ] including ''], ], ], ]'' and ] '']'' species.{{cn|date=March 2023}}

In clinical use, high concentrations of cefotiam are observed in several tissues (kidney, heart, ear, prostate, and genital tract), as well as in fluids and secretions (bile, ascitic fluid).{{cn|date=March 2023}}

== References ==
{{reflist}}

== Further reading ==
{{refbegin}}
⚫ * {{cite journal | vauthors = Müller R, Böttger C, Wichmann G | title = Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients | journal = Arzneimittel-Forschung | volume = 53 | issue = 2 | pages = 126–132 | year = 2003 | pmid = 12642969 | doi = 10.1055/s-0031-1297083 | s2cid = 38768846 }}
⚫ * {{cite journal | vauthors = Kolben M, Mandoki E, Ulm K, Freitag K | title = Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section | journal = European Journal of Clinical Microbiology & Infectious Diseases | volume = 20 | issue = 1 | pages = 40–42 | date = January 2001 | pmid = 11245321 | doi = 10.1007/s100960000365 | s2cid = 26877334 }}
⚫ * {{cite journal | vauthors = Shimizu S, Chen KR, Miyakawa S | title = Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses | journal = Dermatology | volume = 192 | issue = 2 | pages = 174–176 | year = 1996 | pmid = 8829507 | doi = 10.1159/000246352 }}
{{refend}}


{{antibiotic-stub}}
{{CephalosporinAntiBiotics}} {{CephalosporinAntiBiotics}}


Line 68: Line 93:
] ]
] ]
]

]
]
]