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Details

Stereochemistry EPIMERIC
Molecular Formula C17H15N7O8S4.2Na
Molecular Weight 619.583
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFOTETAN DISODIUM

SMILES

[Na+].[Na+].[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)C4SC(S4)=C(C(N)=O)C([O-])=O)OC)C([O-])=O

InChI

InChIKey=ZQQALMSFFARWPK-GLHLDKNHSA-L
InChI=1S/C17H17N7O8S4.2Na/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);;/q;2*+1/p-2/b12-6-;;/t13?,15-,17+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C17H15N7O8S4
Molecular Weight 573.603
Charge -2
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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. It is FDA approved for the treatment of urinary tract infection, lower respiratory tract infection, skin and skin structure infections, gynecologic infection, intra-abdominal infection, and bone and joint infection; and for prophylaxis of postoperative infection. The bactericidal action of cefotetan results from inhibition of cell wall synthesis. The methoxy group in the 7-alpha position provides cefotetan with a high degree of stability in the presence of beta-lactamases including both penicillinases and cephalosporinase of gram-negative bacteria. Common adverse reactions include diarrhea and nausea. As with other cephalosporins, high concentrations of cefotetan may interfere with measurement of serum and urine creatinine levels.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CEFOTAN
Curative
CEFOTAN
Curative
CEFOTAN
Curative
CEFOTAN
Curative
CEFOTAN
Curative
CEFOTAN

Cmax

ValueDoseCo-administeredAnalytePopulation
237.75 μg/mL
2 g single, intravenous
CEFOTETAN plasma
Homo sapiens
69.49 μg/mL
0.5 g single, intravenous
CEFOTETAN plasma
Homo sapiens
132.03 μg/mL
1 g single, intravenous
CEFOTETAN plasma
Homo sapiens
147.58 μg/mL
1 g 2 times / day multiple, intravenous
CEFOTETAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1020.18 μg × h/mL
2 g single, intravenous
CEFOTETAN plasma
Homo sapiens
284.42 μg × h/mL
0.5 g single, intravenous
CEFOTETAN plasma
Homo sapiens
551.38 μg × h/mL
1 g single, intravenous
CEFOTETAN plasma
Homo sapiens
612.06 μg × h/mL
1 g 2 times / day multiple, intravenous
CEFOTETAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.27 h
2 g single, intravenous
CEFOTETAN plasma
Homo sapiens
4.21 h
0.5 g single, intravenous
CEFOTETAN plasma
Homo sapiens
4.39 h
1 g single, intravenous
CEFOTETAN plasma
Homo sapiens
4.3 h
1 g 2 times / day multiple, intravenous
CEFOTETAN plasma
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
The usual adult dosage is 1 or 2 grams of CEFOTAN (cefotetan disodium for injection) administered intravenously or intramuscularly or CEFOTAN (cefotetan injection) in the Galaxy plastic container (PL 2040) administered intravenously every 12 hours for 5 to 10 days. Urinary Tract: 500 mg every 12 hours IV or IM 1 or 2 g every 24 hours IV or IM 1 or 2 g every 12 hours IV or IM Skin & Skin Structure: Mild - Moderatea: 2 g every 24 hours IV 1 g every 12 hours IV or IM; Severe: 2 g every 12 hours IV
Route of Administration: Other
In Vitro Use Guide
Cefotetan was moderately active against the staphylococci (mean MIC 50, 7.6 to 26 micrograms/ml) and streptococci (mean MIC 50, 0.9 to 6.6 micrograms/ml).
Substance Class Chemical
Record UNII
0GXP746VXB
Record Status Validated (UNII)
Record Version