Cefotetan

Cefotetan
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Routes of; administration	Injection
ATC code	J01DC05 (WHO) ;
Legal status
Legal status	US: ℞-only ;
Identifiers
	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;
CAS Number	69712-56-7 ;
PubChem CID	53025;
DrugBank	DB01330 ;
ChemSpider	47904 ;
UNII	48SPP0PA9Q;
KEGG	D00260 ;
ChEBI	CHEBI:3499 ;
ChEMBL	ChEMBL474579 ;
CompTox Dashboard (EPA)	DTXSID1022762 ;
ECHA InfoCard	100.067.337
Chemical and physical data
Formula	C17H17N7O8S4
Molar mass	575.60 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:SRZNHPXWXCNNDU-IXOPCIAXSA-N ;
	(verify)

Cefotetan is an injectable antibiotic of the cephamycin type for prophylaxis and treatment of bacterial infections. It is often grouped together with second-generation cephalosporins and has a similar antibacterial spectrum, but with additional anti-anaerobe coverage.

Cefotetan was developed by Yamanouchi. It is marketed outside Japan by AstraZeneca with the brand names Apatef and Cefotan.

Adverse 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.^[1]

Spectrum of bacterial susceptibility

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.^[2]

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

References

^ 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. Retrieved 2009-07-03.
^ "Cefotetan Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). Toku-e.

External links

Cefotan official web site run by AstraZeneca US
Cefotetan entry in RxList

[Goldfrank-1] 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. Retrieved 2009-07-03.

[2] "Cefotetan Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). Toku-e.

[1]

[2]

Clinical data

AHFS/Drugs.com	Consumer Drug Information
Routes of administration	Injection
ATC code	J01DC05 (WHO)
Legal status
Legal status	US: ℞-only
Identifiers
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
CAS Number	69712-56-7
PubChem CID	53025
DrugBank	DB01330
ChemSpider	47904
UNII	48SPP0PA9Q
KEGG	D00260
ChEBI	CHEBI:3499
ChEMBL	ChEMBL474579
CompTox Dashboard (EPA)	DTXSID1022762
ECHA InfoCard	100.067.337
Chemical and physical data
Formula	C₁₇H₁₇N₇O₈S₄
Molar mass	575.60 g·mol⁻¹
3D model (JSmol)	Interactive image
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 Key:SRZNHPXWXCNNDU-IXOPCIAXSA-N
(verify)