Temocillin

Temocillin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01CA17 (WHO) ;
Identifiers
	IUPAC name (2S,5R,6S)-6-[(Carboxy-3-thienylacetyl)amino]- 6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0] heptane-2-carboxylic acid,;
CAS Number	66148-78-5 ;
PubChem CID	171758;
ChemSpider	150149 ;
UNII	03QB156W6I;
KEGG	D06064 ;
ChEBI	CHEBI:51817 ;
CompTox Dashboard (EPA)	DTXSID201009398 ;
ECHA InfoCard	100.060.148
Chemical and physical data
Formula	C16H18N2O7S2
Molar mass	414.45 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]2N3C(=O)[C@@](OC)(NC(=O)C(c1ccsc1)C(=O)O)[C@H]3SC2(C)C;
	InChI InChI=1S/C16H18N2O7S2/c1-15(2)9(12(22)23)18-13(24)16(25-3,14(18)27-15)17-10(19)8(11(20)21)7-4-5-26-6-7/h4-6,8-9,14H,1-3H3,(H,17,19)(H,20,21)(H,22,23)/t8?,9-,14+,16-/m0/s1 ; Key:BVCKFLJARNKCSS-DWPRYXJFSA-N ;
	(verify)

Temocillin is a β-lactamase-resistant penicillin^[1]^[2] introduced by Beecham, marketed by Eumedica Pharmaceuticals as Negaban. It is used primarily for the treatment of multiple drug-resistant, Gram-negative bacteria.
It is actually a 6-methoxy Ticarcillin; it is also a carboxypenicillin.^[3]

^ Andrews JM, Jevons G, Walker R, Ashby J, Fraise AP (July 2007). "Temocillin susceptibility by BSAC methodology". The Journal of Antimicrobial Chemotherapy. 60 (1): 185–187. doi:10.1093/jac/dkm179. PMID 17550891.
^ Van Landuyt HW, Pyckavet M, Lambert A, Boelaert J (October 1982). "In vitro activity of temocillin (BRL 17421), a novel beta-lactam antibiotic". Antimicrobial Agents and Chemotherapy. 22 (4): 535–540. doi:10.1128/aac.22.4.535. PMC 183789. PMID 7181470.
^ Chanal M, Sirot J, Cluzel M, Joly B, Glanddier Y (June 1983). "[In vitro study of the bacteriostatic and bactericidal activity of temocillin (BRL 17421)]". Pathologie-Biologie (in French). 31 (6): 467–470. PMID 6348653.

[pmid17550891-1] Andrews JM, Jevons G, Walker R, Ashby J, Fraise AP (July 2007). "Temocillin susceptibility by BSAC methodology". The Journal of Antimicrobial Chemotherapy. 60 (1): 185–187. doi:10.1093/jac/dkm179. PMID 17550891.

[pmid7181470-2] Van Landuyt HW, Pyckavet M, Lambert A, Boelaert J (October 1982). "In vitro activity of temocillin (BRL 17421), a novel beta-lactam antibiotic". Antimicrobial Agents and Chemotherapy. 22 (4): 535–540. doi:10.1128/aac.22.4.535. PMC 183789. PMID 7181470.

[pmid6348653-3] Chanal M, Sirot J, Cluzel M, Joly B, Glanddier Y (June 1983). "[In vitro study of the bacteriostatic and bactericidal activity of temocillin (BRL 17421)]". Pathologie-Biologie (in French). 31 (6): 467–470. PMID 6348653.

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