| Version |
2.5 |
| Creation Date |
2007-06-30 17:52:27 |
| Update Date |
2009-06-23 18:08:15 |
| Primary Accession Number |
DB01330 |
| Secondary Accession Number |
Not Available |
| Name |
Cefotetan |
| Drug Type |
|
| Description |
A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms. [PubChem] |
| Synonyms |
- Cefotetanum [inn-latin]
|
| Brand Names |
- Cefotan
- Yamatetan
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
(7S)-7-[[4-(1-amino-3-hydroxy-1,3-dioxopropan-2-ylidene)1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Chemical Formula |
C17H17N7O8S4 |
| Chemical Structure |
 |
| CAS Registry Number |
69712-56-7 |
| InChI Identifier |
InChI=1/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15?,17-/m0/s1/f/h19,27,29H,18H2 |
| InChI Key |
SRZNHPXWXCNNDU-DIGKKDMYDI |
| KEGG Drug |
D00260  |
| KEGG Compound |
C06886 |
| PubChem Compound |
50614 |
| PubChem Substance |
11011827 |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA448854 |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
Not Available |
| RxList Link |
http://www.rxlist.com/cgi/generic/cefotet.htm |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Cefotetan |
| FDA Label |
|
| Material Safety Data Sheet (MSDS) |
Not Available |
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
575.6190 |
| Monoisotopic Molecular Weight |
575.0021 |
| State |
Solid |
| Melting Point |
Not Available |
| Experimental Water Solubility |
Not Available
Source: PhysProp
|
| Predicted Water Solubility |
5.21e-01 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
Not Available
Source: PhysProp
|
| Predicted LogP |
-0.64
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-3.04
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
Not Available |
| pKa/Isoelectric Point |
Not Available |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download |
| SDF File |
Show | Download |
| PDB File |
Show | Download |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
CO[C@]1(NC(=O)C2S\C(S2)=C(\C(N)=O)C(O)=O)[C@@H]2SCC(CSC3=NN=NN3C)=C(N2C1=O)C(O)=O |
| Canonical SMILES |
COC1(NC(=O)C2SC(S2)=C(C(N)=O)C(O)=O)C2SCC(CSC3=NN=NN3C)=C(N2C1=O)C(O)=O |
| Drug Category |
- Anti-Bacterial Agents
- Cephalosporins
|
| ATC Codes |
|
| AHFS Codes |
Not Available |
| Indication |
For prophylaxis and treatment of bacterial infections. |
| Pharmacology |
Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms. |
| Mechanism of Action |
The bactericidal action of cefotetan results from inhibition of cell wall synthesis. |
| Absorption |
Not Available |
| Toxicity |
Not Available |
| Protein Binding |
Cefotetan is 88% plasma protein bound. |
| Biotransformation |
No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug. |
| Half Life |
In volunteers with reduced renal function, the plasma half-life of cefotetan is prolonged |
| Dosage Forms |
| Form |
Route |
| Injection, solution |
Intramuscular |
| Injection, solution |
Intravenous |
|
| Patient Information |
Show |
| Contraindications |
Show |
| Interactions |
Show |
| Drug Interactions |
| Drug |
Interaction |
| Acenocoumarol |
The cephalosporin increases the anticoagulant effect |
| Amikacin |
Increased risk of nephrotoxicity |
| Anisindione |
The cephalosporin increases the anticoagulant effect |
| Dicumarol |
The cephalosporin increases the anticoagulant effect |
| Gentamicin |
Increased risk of nephrotoxicity |
| Kanamycin |
Increased risk of nephrotoxicity |
| Neomycin |
Increased risk of nephrotoxicity |
| Netilmicin |
Increased risk of nephrotoxicity |
| Probenecid |
Probenecid increases the antibiotic's level |
| Streptomycin |
Increased risk of nephrotoxicity |
| Tobramycin |
Increased risk of nephrotoxicity |
| Warfarin |
The cephalosporin increases the anticoagulant effect |
|
| Food Interactions |
- Avoid alcohol as it can cause a disulfiram effect.
|
| Pathways |
Not Available
|
| General References |
- Wikipedia
- RxList
|
| Organisms Affected |
- Enteric bacteria and other eubacteria
|
