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| {{Short description|Chemical compound}} | |||
| {{Drugbox | {{Drugbox | ||
| | Watchedfields = changed | |||
| | verifiedrevid = |
| 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. |
| 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--> | ||
| | |
| CAS_number_Ref = {{cascite|correct|??}} | ||
| | CAS_number = 61622-34-2 | | CAS_number = 61622-34-2 | ||
| | ATC_prefix = J01 | | ATC_prefix = J01 | ||
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| | 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 | ||
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| | 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 | |
||
| ⚫ | * {{cite journal | |
||
| ==Medical uses== | |||
| ⚫ | * {{cite journal | |
||
| 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}} | ||
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| ] | ] | ||
| ] | ] | ||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
Latest revision as of 00:19, 19 October 2024
Chemical compound Pharmaceutical compound | |
 | |
| Clinical data | |
|---|---|
| Trade names | Pansporin |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Intravenous, intramuscular |
| ATC code | |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Bioavailability | 60% (intramuscular) |
| Protein binding | 40% |
| Metabolism | Nil |
| Elimination half-life | Approximately 1 hour |
| Excretion | Renal |
| Identifiers | |
IUPAC name
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.205.922  |
| Chemical and physical data | |
| Formula | C18H23N9O4S3 |
| Molar mass | 525.62 g·mol |
| 3D model (JSmol) | |
SMILES
| |
InChI
| |
| (verify) | |
Cefotiam is a parenteral third-generation cephalosporin antibiotic. It has broad-spectrum activity against Gram-positive and Gram-negative bacteria. As a beta-lactam, its bactericidal activity results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins.
It was patented in 1973 and approved for medical use in 1981.
Medical uses
This drug is indicated for prophylaxis for surgical infection, postoperative infections, bacterial , bone and joint infections, cholangitis, cholecystitis, peritonitis, prostatitis, pyelonephritis, respiratory tract infections, skin and soft tissue infections, cystitis, urethritis, and infections caused by susceptible organisms. It does not have activity against Pseudomonas aeruginosa.
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 renal impairment a dose reduction may be needed.
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.
- Bacteroides fragilis: - 16 - >128 μg/ml
- Clostridioides difficile: >128 μg/ml
- Staphylococcus aureus: 0.25 - 32 μg/ml
Adverse effects
Side effects include nausea and vomiting, diarrhoea, hypersensitivity reactions, nephrotoxicity, convulsions, CNS toxicity, hepatic dysfunction, haematologic disorders, pain at injection site, thrombophlebitis, pseudomembranous colitis, and superinfection with prolonged use.
Mechanism of action
Cefotiam inhibits the final cross-linking stage of peptidoglycan production, thus inhibiting bacterial cell wall synthesis. It has similar or less activity against Gram-positive staphylococci and streptococci, but is resistant to some beta-lactamases produced by Gram-negative bacteria. It is more active against many of the Enterobacteriaceae including Enterobacter, E. coli, Klebsiella, Salmonella and indole-positive Proteus species.
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).
References
- Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN 978-3-527-60749-5.
- "Cefotiam hydrochloride" (PDF). Susceptibilty and Resistance Data. TOKU-E. 24 February 2014. Archived from the original (PDF) on 2016-03-04. Retrieved 2014-02-06.
Further reading
- Müller R, Böttger C, Wichmann G (2003). "Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients". Arzneimittel-Forschung. 53 (2): 126–132. doi:10.1055/s-0031-1297083. PMID 12642969. S2CID 38768846.
- Kolben M, Mandoki E, Ulm K, Freitag K (January 2001). "Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section". European Journal of Clinical Microbiology & Infectious Diseases. 20 (1): 40–42. doi:10.1007/s100960000365. PMID 11245321. S2CID 26877334.
- Shimizu S, Chen KR, Miyakawa S (1996). "Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses". Dermatology. 192 (2): 174–176. doi:10.1159/000246352. PMID 8829507.