Cefotetan

Cefotetan
Names
Trade namesApatef, Cefotan, others
Other namesCephotetan
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
Clinical data
Drug classCephamycin[1]
Main usesBacterial infections[1]
Side effectsLiver problems, allergic reactions, pain at the site of injection, low platelets[1]
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Pregnancy
category
  • US: B (No risk in non-human studies)
    Routes of
    use    		Injection
    External links
    AHFS/Drugs.comMonograph
    Legal
    Legal status
    Chemical and physical data
    FormulaC17H17N7O8S4
    Molar mass575.60 g·mol−1
    3D model (JSmol)
    SMILES
    • O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)C3S/C(S3)=C(/C(=O)N)C(=O)O)CSc4nnnn4C)C(=O)O
    InChI
    • InChI=1S/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+/m1/s1 checkY
    • Key:SRZNHPXWXCNNDU-IXOPCIAXSA-N checkY

    Cefotetan, sold under the brand name Cefotan among others, is an antibiotic used to treat bacterial infections.[1] This includes joint infections, pelvic inflammatory disease, intra abdominal infections, pneumonia, and skin infections.[1] It may also be used to prevent infection in people undergoing surgery.[2] It is given by injection into a vein or muscle.[1]

    Common side effects include liver problems, allergic reactions, pain at the site of injection, and low platelets.[1] Other side effects may include Clostridioides difficile infection and red blood cell breakdown.[1] Safety in pregnancy is unclear.[2] It is of the cephamycin and β-lactam class.[1] It may be grouped with second-generation cephalosporins.[1]

    Cefotetan was approved for medical use in the United States in 1985.[1] It is available as a generic medication.[1] In the United States 10 doses of 2 grams costs about 400 USD as of 2021.[3]

    Medical uses

    Spectrum of activity

    Cefotetan has a broad spectrum of activity and has been used to treat bacterial infections of the bone, skin, urinary tract, and lower respiratory tract. Notable species include Bacteroides, Streptococcus, and Escherichia. The following represents MIC susceptibility data for a few medically significant bacteria.[4]

    • Escherichia coli: 0.06 µg/mL
    • Bacteroides fragilis: ≤0.06 µg/mL - 512 µg/mL
    • Clostridium perfringens: 1 µg/mL - 4 µg/mL

    Dosage

    It is used at a dose of 1 to 6 grams per day.[2] It may be given once to twice per day.[2]

    Side effects

    The chemical structure of cefotetan, like that of several other cephalosporins, contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.[5]

    History

    It was developed by Yamanouchi.

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 12 "CefoTEtan Monograph for Professionals". Drugs.com. Archived from the original on 26 January 2021. Retrieved 30 December 2021.
    2. 1 2 3 4 "DailyMed - cefotan- cefotetan disodium injection, solution cefotan- cefotetan disodium injection, powder, for solution". dailymed.nlm.nih.gov. Archived from the original on 28 December 2021. Retrieved 30 December 2021.
    3. ↑ "Cefotetan Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 17 January 2021. Retrieved 30 December 2021.
    4. ↑ "Cefotetan Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). Toku-e. Archived (PDF) from the original on 2019-08-02. Retrieved 2021-03-07.
    5. ↑ Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Archived from the original on 2013-06-13. Retrieved 2009-07-03.
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