Cefoxitin acid

A semisynthetic cephamycin antibiotic with broad-spectrum bactericidal activity against susceptible Gram-positive, Gram-negative, and anaerobic bacteria. Cefoxitin inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins and preventing peptidoglycan cross-linking. Its 7α-methoxy group provides increased stability against certain β-lactamases. Cefoxitin is used clinically, primarily as its sodium salt, to treat intra-abdominal, pelvic, respiratory tract, and other susceptible infections, as well as for surgical infection prophylaxis

CAS Number: 35607-66-0

Molecular Mass: 427.5 g/mol

Formula: C₁₆H₁₇N₃O₇S₂

Smiles: CO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@@H]21

Synonymes:

Cefoxitin acid, cefoxitin, 35607-66-0, Cefoxitina, Cefoxitine, CEPHOXITIN, Cefoxitinum, Rephoxitin, Mefoxitin, Cenomycin, ceftoxitin, 6OEV9DX57Y, DTXSID1022764, J01DC01, CHEBI:209807, (6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, DTXCID002764, MK306, (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7S)-3-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, (6R,7S)-, MK 306, (6R,7S)-3-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-((2-thiophen-2-ylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7S)-4-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-((thiophen-2-enyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7S)-4-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-enyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, (6R,7S)-, RefChem:57281, J01DA05, 252-641-2, Mefoxin, MFCD00072014, CFX, CHEMBL996, 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, (6R-cis)-, Cefoxitin S-Oxide, C16H17N3O7S2, (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7S)-3-(Hydroxymethyl)-7-methoxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid carbamate (ester), CAS-35607-66-0, MK-306, NCGC00183034-01, Cefoxitine [INN-French], Cefoxitinum [INN-Latin], Cefoxitina [INN-Spanish], UNII-6OEV9DX57Y, Cefoxotin, Cefoxitin [USAN:INN:BAN], 4kow, (6R,7S)-3-(Hydroxymethyl)-7-methoxy-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid carbamate (ester), EINECS 252-641-2, Cefoxitin (Standard), Spectrum_001399, CEFOXITIN [INN], CEFOXITIN [MI], Cefoxitin (USAN/INN), CEFOXITIN [USAN], Prestwick0_000832, Prestwick1_000832, Prestwick2_000832, Prestwick3_000832, Spectrum2_000676, Spectrum3_001491, Spectrum4_000153, Spectrum5_001145, CEFOXITIN [VANDF], Epitope ID:116201, C06887, CEFOXITIN [USP-RS], CEFOXITIN [WHO-DD], SCHEMBL15971, BSPBio_000783, BSPBio_003101, KBioGR_000626, KBioSS_001879, DivK1c_000576, SPBio_000771, SPBio_002704, BPBio1_000863, orb1705512, CEFOXITIN [ORANGE BOOK], GTPL10937, HY-B1825R, KBio1_000576, KBio2_001879, KBio2_004447, KBio2_007015, KBio3_002601, NINDS_000576, HY-B1825, MSK10014, Tox21_113009, BDBM50335563, EBC-27061, s5951, AKOS022185232, Tox21_113009_1, DB01331, DS-5384, Cefoxitin for peak identification A CRS, IDI1_000576, NCGC00093351-06, 73356-24-8, DA-62189, FC144348, SY115637, SBI-0051927.P002, C3598, CS-0013876, NS00004232, (6R,7R)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7S)-3-Carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7S)-4-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6S,7R)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6S,7R)-4-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-Carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-Carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid anion, 3-Carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-3-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid anion, D02345, T20643, EN300-7405307, F793555, Q2353907, BRD-K70976396-236-25-2, BRD-K70976396-236-26-0, (6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7S)-3-[[(Aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylic Acid, (6R,7S)-3-{[(aminocarbonyl)oxy]methyl}-7-(methyloxy)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(carbamoyloxy)methyl]-7alpha-methoxy-7beta-[(thiophen-2-yl)acetamido]-3,4-didehydrocepham-4-carboxylic acid, 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, (6R-cis)-, Cefoxitin Impurity 1, (6R,7S)-3-((Carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Bioactivity: Second-generation cephamycin (β-lactam) antibiotic; bacterial penicillin-binding protein (PBP) inhibitor; inhibitor of peptidoglycan cell wall synthesis

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Propanol	278.15	-	1.215	[95]
1-Propanol	283.15	-	1.464	[95]
1-Propanol	288.15	-	1.642	[95]
1-Propanol	293.15	-	1.93	[95]
1-Propanol	298.15	-	2.239	[95]
1-Propanol	303.15	-	2.784	[95]
1-Propanol	308.15	-	3.162	[95]
Acetonitrile	278.15	-	3.763	[95]
Acetonitrile	283.15	-	4.062	[95]
Acetonitrile	288.15	-	4.332	[95]
Acetonitrile	293.15	-	4.724	[95]
Acetonitrile	298.15	-	5.023	[95]
Acetonitrile	303.15	-	5.444	[95]
Acetonitrile	308.15	-	6.068	[95]
Ethanol	278.15	-	3.006	[95]
Ethanol	283.15	-	3.583	[95]
Ethanol	288.15	-	4.441	[95]
Ethanol	293.15	-	5.418	[95]
Ethanol	298.15	-	6.216	[95]
Ethanol	303.15	-	7.457	[95]
Ethanol	308.15	-	8.483	[95]
Ethyl acetate	278.15	-	1.02	[95]
Ethyl acetate	283.15	-	1.069	[95]
Ethyl acetate	288.15	-	1.131	[95]
Ethyl acetate	293.15	-	1.166	[95]
Ethyl acetate	298.15	-	1.226	[95]
Ethyl acetate	303.15	-	1.278	[95]
Ethyl acetate	308.15	-	1.369	[95]
Isopropanol	278.15	-	0.25	[95]
Isopropanol	283.15	-	0.4063	[95]
Isopropanol	288.15	-	0.6148	[95]
Isopropanol	293.15	-	0.8428	[95]
Isopropanol	298.15	-	1.032	[95]
Isopropanol	303.15	-	1.342	[95]
Isopropanol	308.15	-	1.726	[95]
Methanol	278.15	-	61.0	[95]
Methanol	283.15	-	70.67	[95]
Methanol	288.15	-	82.56	[95]
Methanol	293.15	-	97.93	[95]
Methanol	298.15	-	116.4	[95]
Methanol	303.15	-	136.2	[95]
Methanol	308.15	-	157.3	[95]

Molecule 3D descriptors

Descriptor	Value
PMI1	2042.6335
PMI2	5039.1682
PMI3	5619.7487
NPR1	0.3635
NPR2	0.8967
RadiusOfGyration	3.8545
InertialShapeFactor	0.0004
Eccentricity	0.9316
Asphericity	0.2741
SpherocityIndex	0.3093
PBF	1.0811