Cefditoren Pivoxil (also named ME-1207) is a broad-spectrum and 3rd-generation antibiotic against Gram-negative and Gram-positive bacteria. Cefditoren has MIC50/MIC90 results for Moraxella catarrhalis and Haemophilus influenzae of 0.12/0.5 and < or = 0.008/0.015 mg/mL, respectively. Cefditoren (MIC(90), 0.5 mg/mL) is 4- to 128-fold more active than comparison beta-lactams against the pneumoococci and was the most potent beta-lactam (including penicillin) versus beta-haemolytic streptococci. Cefditoren (MIC(90) in mg/mL/% susceptible) activity against all tested H. influenzae (0.03/100) and M. catarrhalis (0.06-0.5/100) is comparable to Cefixime and significantly greater than cefaclor.

Physicochemical Properties

Molecular Formula	C25H28N6O7S3
Molecular Weight	620.72
Exact Mass	620.118
Elemental Analysis	C, 48.38; H, 4.55; N, 13.54; O, 18.04; S, 15.50
CAS #	117467-28-4
Related CAS #	Cefditoren sodium;104146-53-4;Cefditoren-13C,d3
PubChem CID	6437877
Appearance	Light yellow to yellow solid powder
Density	1.6±0.1 g/cm3
Melting Point	207-209ºC
Index of Refraction	1.710
LogP	2.74
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	12
Heavy Atom Count	41
Complexity	1160
Defined Atom Stereocenter Count	2
SMILES	S1C([H])([H])C(/C(/[H])=C(/[H])\C2=C(C([H])([H])[H])N=C([H])S2)=C(C(=O)OC([H])([H])OC(C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])=O)N2C([C@]([H])([C@@]12[H])N([H])C(/C(/C1=C([H])SC(N([H])[H])=N1)=N\OC([H])([H])[H])=O)=O
InChi Key	AFZFFLVORLEPPO-UVYJNCLZSA-N
InChi Code	InChI=1S/C25H28N6O7S3/c1-12-15(41-10-27-12)7-6-13-8-39-21-17(29-19(32)16(30-36-5)14-9-40-24(26)28-14)20(33)31(21)18(13)22(34)37-11-38-23(35)25(2,3)4/h6-7,9-10,17,21H,8,11H2,1-5H3,(H2,26,28)(H,29,32)/b7-6-,30-16-/t17-,21-/m1/s1
Chemical Name	(pivaloyloxy)methyl(6R,7R)-7-((Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((Z)-2-(4-methylthiazol-5-yl)vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Synonyms	ME-1207; ME 1207; ME1207; CDTR-PI; Spectracef; Meiact.
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	β-lactam
ln Vitro	Cefditoren has MIC50/MIC90 results for Moraxella catarrhalis and Haemophilus influenzae of 0.12/0.5 and < or = 0.008/0.015 mg/mL, respectively. Cefditoren (MIC(90), 0.5 mg/mL) is 4- to 128-fold more active than comparison beta-lactams against the pneumoococci and was the most potent beta-lactam (including penicillin) versus beta-haemolytic streptococci. Cefditoren (MIC(90) in mg/mL/% susceptible) activity against all tested H. influenzae (0.03/100) and M. catarrhalis (0.06-0.5/100) is comparable to Cefixime and significantly greater than cefaclor. Cefditoren pharmacokinetics demonstrate a T(1/2) of 1.5-2 hours and C(max) values of 2.8 and 4.6 mg/mL, respectively with 200 or 400 mg doses of Cefditoren pivoxil. Cefditoren possesses a broad-spectrum of cidal antibacterial activity against both Gram-positive and Gram-negative species with stability to many beta-lactamases of clinical importance. Cefditoren is also effective against methicillin-susceptible strains of Staphylococcus aureus. Cefditoren has compared favorably against other orally administered antibiotics used against the most commonly isolated respiratory tract pathogens. Cefditoren up-regulates the expression levels of Mrp2, Bcrp and Oat2, and down-regulate P-gp and Oct1 mRNA expression.
ln Vivo
Animal Protocol
References	Diagn Microbiol Infect Dis.1998 Aug;31(4):573-8;Diagn Microbiol Infect Dis.2000 Jun;37(2):99-105;Drugs Exp Clin Res.1994;20(4):127-47.
Additional Infomation	Cefditoren pivoxil is the pivaloyloxymethyl ester prodrug of cefditoren. It has a role as a prodrug and an antibacterial drug. It is a pivaloyloxymethyl ester, a member of 1,3-thiazoles, an oxime O-ether and a member of cephams. It is functionally related to a cefditoren. Cefditoren Pivoxil is a semi-synthetic, broad-spectrum, beta-lactamase resistant, third-generation cephalosporin antibiotic with bactericidal activity. Cefditoren pivoxil is a prodrug that is rapidly hydrolyzed by intestinal esterases during absorption to the microbiologically active cefditoren, an active aminothiazolyl cephalosporin. Cefditoren inactivates penicillin binding proteins (PBPs) thereby interfering with peptidoglycan synthesis and inhibiting bacterial cell wall synthesis. Another consequence of beta-lactam exposure results in the loss of lipoteichoic acids from the cell wall. Lipoteichoic acids inhibit murein hydrolase activity and their absence from the cell wall triggers uncontrolled autolytic activity rendering bacterial cells susceptible to osmotic shock. This results in a reduction of cell wall stability and causes cell lysis. See also: Cefditoren (has active moiety).

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL ( ~161.1 mM )

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.03 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.03 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (4.03 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (4.03 mM)  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.6110 mL	8.0552 mL	16.1103 mL
	5 mM	0.3222 mL	1.6110 mL	3.2221 mL
	10 mM	0.1611 mL	0.8055 mL	1.6110 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.