Cefditoren pivoxil | CAS#117467-28-4 (pivoxil) | cephalosporin antibiotic

MedKoo Cat#: 319527 | Name: Cefditoren pivoxil

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Cefditoren pivoxil

CAS#117467-28-4 (pivoxil)

Theoretical Analysis

MedKoo Cat#: 319527

Name: Cefditoren pivoxil

CAS#: 117467-28-4 (pivoxil)

Chemical Formula: C25H28N6O7S3

Exact Mass: 620.1182

Molecular Weight: 620.71

Elemental Analysis: C, 48.38; H, 4.55; N, 13.54; O, 18.04; S, 15.50

Price and Availability

Size	Price	Availability
100mg	USD 450.00	2 Weeks
200mg	USD 750.00	2 Weeks
500mg	USD 1,650.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,250.00	2 Weeks

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Related CAS #

104145-95-1 (free base) 117467-28-4 (pivoxil) 442852-27-9 (tosylate) 442852-31-5 (oxalate) 442852-33-7 (sulfate) 1448435-17-3 (pivoxil HCl) 442852-29-1 (mesylate)

Synonym

ME-1207; ME 1207; ME1207; CDTR-PI; Cefditoren pivoxil; trade name Spectracef; Meiact.

IUPAC/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

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

SMILES Code

CC1=C(SC=N1)/C=C\C2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)OCOC(=O)C(C)(C)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Cefditoren Pivoxil (ME-1207) is a broad-spectrum antibiotic against Gram-negative and Gram-positive bacteria.

In vitro activity:

Cefditoren was compared to cefaclor, cefixime, and penicillins against 1 435 recently isolated strains of streptococci (312 Streptococcus pneumoniae, 165 viridans group streptococci, 142 beta-haemolytic streptococci), Haemophilus influenzae (521 strains), and Moraxella catarrhalis (295 strains). Streptococcus pneumoniae and viridans group streptococci had penicillin nonsusceptible rates of 37.8 and 35.8%, respectively. Cefditoren (MIC(90) in microg/ml/% susceptible) activity against all tested H. influenzae (0.03/100) and M. catarrhalis (0.06-0.5/100) was comparable to cefixime and significantly greater than cefaclor. Cefditoren (MIC(90), 0.5 microg/ml) was 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 pharmacokinetics demonstrate a T(1/2) of 1.5-2 h and C(max) values of 2.8 and 4.6 microg/ml, respectively with 200 or 400 mg doses of cefditoren pivoxil; plasma concentrations exceed 1 microg/ml for 4 to 6 hours (33-50% of dosing interval). Consequently, a susceptible MIC of </= 1 microg/ml or </= 2 microg/ml was proposed with zone diameter correlates of >/= 18 and >/= 15 mm (5-microg disk) for all cited fastidious species tested. Categorical agreement between MIC and disk tests was 94.6 to 100% with a correlation coefficient (r) range of 0.50 to 0.90 for streptococci. H. influenzae intermethod comparison results using the same interpretive criteria were in complete agreement, but exhibited a low r = 0.39. Cefditoren clearly possesses the most potent activity among currently studied oral cephalosporins or penicillin against commonly isolated bacterial pathogens causing bronchitis, pneumonia, sinusitis, or pharyngitis and was active against nearly all penicillin-resistant streptococci at </= 0.5 microg/ml. Reference: Diagn Microbiol Infect Dis. 2000 Jun;37(2):99-105. https://linkinghub.elsevier.com/retrieve/pii/S0732-8893(00)00136-X

In vivo activity:

Groups of mice were challenged with a lethal dose of the corresponding strain and 1 h later antibiotic treatment was initiated, with administration at 8 h intervals for a total of 6 doses. Treatment with 50 mg/kg of cefditoren in animals infected with Strain 1 or 100 mg/kg in animals infected with Strain 2 produced 100% survival rates, while in those infected with Strain 3, the 100 mg/kg regimen only produced 60% survival (Tables 1 and 2). The highest cefditoren doses that produced the lowest survival rate (i.e, antibiotic non-protective doses - A-np) were 12.5 mg/kg for Strain 1 (0% survival) and 50 mg/kg for Strain 2 (0% survival) and 3 (20% survival). Cefditoren t>MIC values linked to high survival rates markedly decreased in pre-immunized animals and therefore with specific antibodies in the systemic circulation: from ≈35% (≈19% free) to ≈25% (≈15% free) for Strains 1 and 2, and from 27.3% (15.8% free) to 22.4% (12.7% free) for Strain 3. Overall, cefditoren t>MIC values linked to survival (90% for Strain 1 and 60% for Strains 2 and 3) in pre-immunized animals with the HS-np dilution were associated with <10% survival rates in non-immunized animals. Reference: PLoS One. 2010 Aug 10;5(8):e12041. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/20706584/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	161.10

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 620.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

In vitro protocol:

1. Johnson DM, Biedenbach DJ, Beach ML, Pfaller MA, Jones RN. Antimicrobial activity and in vitro susceptibility test development for cefditoren against Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus species. Diagn Microbiol Infect Dis. 2000 Jun;37(2):99-105. doi: 10.1016/s0732-8893(00)00136-x. PMID: 10863104. 2. Jones RN, Pfaller MA, Jacobs MR, Appelbaum PC, Fuchs PC. Cefditoren in vitro activity and spectrum: a review of international studies using reference methods. Diagn Microbiol Infect Dis. 2001 Sep-Oct;41(1-2):1-14. doi: 10.1016/s0732-8893(01)00274-7. PMID: 11687308.

In vivo protocol:

1. Cafini F, Yuste J, Giménez MJ, Sevillano D, Aguilar L, Alou L, Ramos-Sevillano E, Torrico M, González N, García E, Coronel P, Prieto J. Enhanced in vivo activity of cefditoren in pre-immunized mice against penicillin-resistant S. pneumoniae (serotypes 6B, 19F and 23F) in a sepsis model. PLoS One. 2010 Aug 10;5(8):e12041. doi: 10.1371/journal.pone.0012041. PMID: 20706584; PMCID: PMC2919394.

1: Venugopalarao G, Lakshmipathy R, Sarada NC. Preparation and characterization of cefditoren pivoxil-loaded liposomes for controlled in vitro and in vivo drug release. Int J Nanomedicine. 2015 Oct 1;10 Suppl 1:149-57. doi: 10.2147/IJN.S79994. eCollection 2015. PubMed PMID: 26491316; PubMed Central PMCID: PMC4599605. 2: Poachanukoon O, Tangsathapornpong A, Tanuchit S. A Comparison of Cefditoren Pivoxil 8-12 mg/kg/day and Cefditoren Pivoxil 16-20 mg/kg/day in Treatment of Children With Acute Presumed Bacterial Rhinosinusitis: A Prospective, Randomized, Investigator-Blinded, Parallel-Group Study. Clin Exp Otorhinolaryngol. 2015 Jun;8(2):129-35. doi: 10.3342/ceo.2015.8.2.129. Epub 2015 May 13. PubMed PMID: 26045911; PubMed Central PMCID: PMC4451537. 3: Gawande VT, Bothara KG, Singh A, Mahajan AA. Identification and Characterization of Hydrolytic Degradation Products of Cefditoren Pivoxil using LC and LC-MS/TOF. Indian J Pharm Sci. 2015 Jan-Feb;77(1):75-82. PubMed PMID: 25767321; PubMed Central PMCID: PMC4355885. 4: Alarfaj NA, Aly FA, El-Tohamy MF. Application of silver nanoparticles to the chemiluminescence determination of cefditoren pivoxil using the luminol-ferricyanide system. Luminescence. 2015 Feb;30(1):91-7. doi: 10.1002/bio.2696. Epub 2014 May 22. PubMed PMID: 24850667. 5: Matsumoto K, Sato N, Mitomi N, Shitara Y, Shibasaki S. Population pharmacokinetics of cefditoren pivoxil in non-infected adults. Jpn J Antibiot. 2014 Feb;67(1):49-66. PubMed PMID: 24809208. 6: Matsumoto K, Sato N, Mitomi N, Shibasaki S. Population pharmacokinetic analysis of cefditoren pivoxil in pediatric patients with infection. Jpn J Antibiot. 2013 Dec;66(6):357-75. PubMed PMID: 24649799. 7: Monmaturapoj T, Montakantikul P, Mootsikapun P, Tragulpiankit P. A prospective, randomized, double dummy, placebo-controlled trial of oral cefditoren pivoxil 400mg once daily as switch therapy after intravenous ceftriaxone in the treatment of acute pyelonephritis. Int J Infect Dis. 2012 Dec;16(12):e843-9. doi: 10.1016/j.ijid.2012.07.009. Epub 2012 Aug 28. PubMed PMID: 22951426. 8: Nandy M, Mandal A, Tripathi SK, Chakrabarti A. Cefditoren pivoxil associated rash and arthralgia in a child. Indian J Pharmacol. 2012 May;44(3):419-20. doi: 10.4103/0253-7613.96354. PubMed PMID: 22701261; PubMed Central PMCID: PMC3371474. 9: Kim H, Chu K, Jung KH, Lee ST, Kim JM, Lee SK. Acquired encephalopathy associated with carnitine deficiency after cefditoren pivoxil administration. Neurol Sci. 2012 Dec;33(6):1393-6. doi: 10.1007/s10072-012-0939-7. Epub 2012 Jan 19. PubMed PMID: 22258360. 10: Tsumura N, Nagai K, Hidaka H, Otsu Y, Tanaka Y, Ikezawa S, Honma S, Shindo S, Ubukata K. [Antibiotic therapy against acute tonsillopharyngitis in children due to group A beta-hemolytic streptococci: comparison of clinical efficacy, the bactericidal effects, and effects on oral flora between cefditoren pivoxil for 5 days and amoxicillin for 10 days]. Jpn J Antibiot. 2011 Jun;64(3):179-90. Japanese. PubMed PMID: 21861309. 11: Kawamata S, Yamada H, Sato Y, Sasagawa Y, Iwama Y, Matumoto M. [Evaluation of the safety and efficacy of cefditoren pivoxil fine granules for pediatric use in pediatric patients with laryngopharyngitis and tonsillitis caused by Streptococcus pyogenes]. Jpn J Antibiot. 2010 Aug;63(4):299-311. Japanese. PubMed PMID: 21298863. 12: Kawamata S, Yamada H, Sato Y, Sasagawa Y, Iwama Y, Matumoto M. [Evaluation of the safety and efficacy of cefditoren pivoxil fine granules for pediatric use in pediatric patients with acute otitis media]. Jpn J Antibiot. 2010 Jun;63(3):207-23. Japanese. PubMed PMID: 20976878. 13: Manaktala C, Singh AK, Verma M, Sachdeva A, Sharma H, Roy A, Jalali RK, Gowrishankar R, Kumar A, Kumar AS, Jayaraman AM, Swarnkar B, Srinivas CR, Nayak C, Duttaroy D, Umrigar D, Jesudanam M, Maheshwari N, Shetty P, Singh RP, Ghate S, Sacchidanand S, Tolat S, Bhoira S, Marfatia Y. Efficacy and tolerability of cefditoren pivoxil in uncomplicated skin and skin structure infections in Indian patients. Indian J Dermatol. 2009;54(4):350-6. doi: 10.4103/0019-5154.57612. PubMed PMID: 20101337; PubMed Central PMCID: PMC2807712. 14: Kikuta H, Shibata M, Nakata S, Yamanaka T, Sakata H, Akizawa K, Kobayashi K. Comparative Study of 5-Day and 10-Day Cefditoren Pivoxil Treatments for Recurrent Group A beta-Hemolytic Streptococcus pharyngitis in Children. Int J Pediatr. 2009;2009:863608. doi: 10.1155/2009/863608. Epub 2009 Mar 5. PubMed PMID: 20041005; PubMed Central PMCID: PMC2778142. 15: Poachanukoon O, Kitcharoensakkul M. Efficacy of cefditoren pivoxil and amoxicillin/clavulanate in the treatment of pediatric patients with acute bacterial rhinosinusitis in Thailand: a randomized, investigator-blinded, controlled trial. Clin Ther. 2008 Oct;30(10):1870-9. doi: 10.1016/j.clinthera.2008.10.001. PubMed PMID: 19014842. 16: Ozaki T, Nishimura N, Suzuki M, Narita A, Watanabe N, Ahn J, Koyama N, Ushida H, Nakane K, Yasuda N, Funahashi K. Five-day oral cefditoren pivoxil versus 10-day oral amoxicillin for pediatric group A streptococcal pharyngotonsillitis. J Infect Chemother. 2008 Jun;14(3):213-8. doi: 10.1007/s10156-008-0602-7. Epub 2008 Jun 24. PubMed PMID: 18574657. 17: Sakata H. [A multicenter study of 7-day cefditoren pivoxil treatment for group A streptococcal infection]. Jpn J Antibiot. 2007 Oct;60(5):257-63. Japanese. PubMed PMID: 18198654. 18: Sevillano D, Aguilar L, Alou L, Giménez MJ, Torrico M, González N, Cafini F, Relaño MT, Coronel P, Prieto J. Urine bactericidal activity against Escherichia coli isolates exhibiting different resistance phenotypes/genotypes in an in vitro pharmacodynamic model simulating urine concentrations obtained after oral administration of a 400-milligram single dose of cefditoren-pivoxil. Antimicrob Agents Chemother. 2008 Mar;52(3):1184-6. Epub 2007 Dec 26. PubMed PMID: 18160517; PubMed Central PMCID: PMC2258530. 19: Granizo JJ, Giménez MJ, Barberán J, Coronel P, Gimeno M, Aguilar L. The efficacy of cefditoren pivoxil in the treatment of lower respiratory tract infections, with a focus on the per-pathogen bacteriologic response in infections caused by Streptococcus pneumoniae and Haemophilus influenzae: a pooled analysis of seven clinical trials. Clin Ther. 2006 Dec;28(12):2061-9. Review. PubMed PMID: 17296462. 20: Hernández-Martin J, Romá E, Salavert M, Doménech L, Poveda JL. [Cefditoren pivoxil: A new oral cephalosporin for skin, soft tissue and respiratory tract infections]. Rev Esp Quimioter. 2006 Sep;19(3):231-46. Review. Spanish. PubMed PMID: 17099791.