Latamoxef information

Latamoxef
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intramuscular, intravenous
ATC code	J01DD06 (WHO) ;
Pharmacokinetic data
Protein binding	35 to 50%
Metabolism	Nil
Elimination half-life	2 hours
Excretion	Mostly renal, unchanged; also biliary
Identifiers
	IUPAC name (6R,7R)-7-{[carboxy(4-hydroxyphenyl)acetyl]amino}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	64952-97-2 ;
PubChem CID	47499;
DrugBank	DB04570 ;
ChemSpider	43215 ;
UNII	VUF6C936Z3;
KEGG	D08109 ;
ChEBI	CHEBI:599928 ;
ChEMBL	ChEMBL74632 ;
CompTox Dashboard (EPA)	DTXSID9023338 ;
ECHA InfoCard	100.059.334
Chemical and physical data
Formula	C20H20N6O9S
Molar mass	520.47 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	117 to 122 °C (243 to 252 °F) (dec.)
	SMILES O=C2N1/C(=C(\CO[C@@H]1[C@]2(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O;
	InChI InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1 ; Key:JWCSIUVGFCSJCK-CAVRMKNVSA-N ;
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Latamoxef (or moxalactam) is an oxacephem antibiotic usually grouped with the cephalosporins. In oxacephems such as latamoxef, the sulfur atom of the cephalosporin core is replaced with an oxygen atom.

Latamoxef has been associated with prolonged bleeding time, and several cases of coagulopathy, some fatal, were reported during the 1980s.^[1]^[2] Latamoxef is no longer available in the United States. As with other cephalosporins with a methylthiotetrazole side chain, latamoxef causes a disulfiram reaction when mixed with alcohol. Additionally, the methylthiotetrazole side chain inhibits γ-carboxylation of glutamic acid; this can interfere with the actions of vitamin K.^{[citation needed]}

It has been described as a third-generation cephalosporin.^[3]

^ Weitekamp MR, Aber RC (January 1983). "Prolonged bleeding times and bleeding diathesis associated with moxalactam administration". JAMA. 249 (1): 69–71. doi:10.1001/jama.249.1.69. PMID 6217353.
^ Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M (November 1986). "Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients". Archives of Internal Medicine. 146 (11): 2159–2164. doi:10.1001/archinte.146.11.2159. PMID 3778044.
^ Salem RR, McIndoe A, Matkin JA, Lidou AC, Clarke A, Wood CB (June 1987). "The hematologic effects of latamoxef sodium when used as a prophylaxis during surgical treatment". Surgery, Gynecology & Obstetrics. 164 (6): 525–529. PMID 3296254.

[1] Weitekamp MR, Aber RC (January 1983). "Prolonged bleeding times and bleeding diathesis associated with moxalactam administration". JAMA. 249 (1): 69–71. doi:10.1001/jama.249.1.69. PMID 6217353.

[2] Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M (November 1986). "Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients". Archives of Internal Medicine. 146 (11): 2159–2164. doi:10.1001/archinte.146.11.2159. PMID 3778044.

[pmid3296254-3] Salem RR, McIndoe A, Matkin JA, Lidou AC, Clarke A, Wood CB (June 1987). "The hematologic effects of latamoxef sodium when used as a prophylaxis during surgical treatment". Surgery, Gynecology & Obstetrics. 164 (6): 525–529. PMID 3296254.

Latamoxef information

and 12 Related for: Latamoxef information

Latamoxef

Cephalosporin

Timeline of antibiotics

Antibiotic

Side effects of penicillin

Benzathine benzylpenicillin

ATC code J01

Avibactam

Epicillin

Cefozopran

Carumonam

Oxacephem

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Intramuscular, intravenous
ATC code	J01DD06 (WHO)
Pharmacokinetic data
Protein binding	35 to 50%
Metabolism	Nil
Elimination half-life	2 hours
Excretion	Mostly renal, unchanged; also biliary
Identifiers
IUPAC name (6R,7R)-7-{[carboxy(4-hydroxyphenyl)acetyl]amino}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	64952-97-2^Y
PubChem CID	47499
DrugBank	DB04570^N
ChemSpider	43215^Y
UNII	VUF6C936Z3
KEGG	D08109^Y
ChEBI	CHEBI:599928^N
ChEMBL	ChEMBL74632^Y
CompTox Dashboard (EPA)	DTXSID9023338
ECHA InfoCard	100.059.334
Chemical and physical data
Formula	C₂₀H₂₀N₆O₉S
Molar mass	520.47 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	117 to 122 °C (243 to 252 °F) (dec.)
SMILES O=C2N1/C(=C(\CO[C@@H]1[C@]2(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O
InChI InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1^Y Key:JWCSIUVGFCSJCK-CAVRMKNVSA-N^Y
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