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MedKoo Cat#: 317398 | Name: Cefpodoxime Proxetil
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Description:

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

Cefpodoxime Proxetil is an antibacterial with a broad spectrum activity. It is an oral, third generation cephalosporin, ester prodrug of the active free acid metabolite Cefpodoxime. It is active against most Gram-positive and Gram-negative organisms. It is commonly used to treat acute otitis media, pharyngitis, sinusitis, and gonorrhea. It also finds use as oral continuation therapy when intravenous cephalosporins (such as ceftriaxone) are no longer necessary for continued treatment. Currently, it is only marketed as generic preparations in the USA.

Chemical Structure

Cefpodoxime Proxetil
Cefpodoxime Proxetil
CAS#87239-81-4 (Proxetil)

Theoretical Analysis

MedKoo Cat#: 317398

Name: Cefpodoxime Proxetil

CAS#: 87239-81-4 (Proxetil)

Chemical Formula: C21H27N5O9S2

Exact Mass: 557.1250

Molecular Weight: 557.60

Elemental Analysis: C, 45.23; H, 4.88; N, 12.56; O, 25.82; S, 11.50

Price and Availability

Size Price Availability Quantity
50mg USD 150.00 Ready to Ship
100mg USD 250.00 Ready to ship
200mg USD 450.00 Ready to ship
500mg USD 950.00 Ready to ship
1g USD 1,650.00 Ready to ship
2g USD 2,950.00 Ready to ship
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Related CAS #
80210-62-4 (free acid) 82619-04-3 (sodium) 87239-81-4 (Proxetil) 79287-88-0 (HCl) 82623-37-8 (TFA)
Synonym
Cefpodoxime Proxetil; Vantin; Banan; Doxef; CS 807; cefpodoxime proxetil; cephalosporin 807; CS 807; CS-807; Doxef; U 76252; U-76,252; Toraxim;
IUPAC/Chemical Name
1-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
InChi Key
LTINZAODLRIQIX-ZFEISNGRSA-N
InChi Code
InChI=1S/C21H27N5O9S2/c1-9(2)33-21(30)35-10(3)34-19(29)15-11(6-31-4)7-36-18-14(17(28)26(15)18)24-16(27)13(25-32-5)12-8-37-20(22)23-12/h8-10,14,18H,6-7H2,1-5H3,(H2,22,23)(H,24,27)/b25-13+/t10?,14-,18-/m1/s1
SMILES Code
CC(C)OC(=O)OC(C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N/OC)/C3=CSC(=N3)N)COC
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
Biological target:
Cefpodoxime proxetil binds to penicillin binding proteins, which inhibits peptidoglycan synthesis, finally results in interfering bacterial cell wall biosynthesis.
In vitro activity:
Cefpodoxime proxetil was identified as the hit compound, and it was found for the first time that cefpodoxime proxetil might have neuroprotective activity as a NR2B-NMDAR antagonist. This study also found that cefpodoxime proxetil could suppress the NR2B upregulation induced by NMDA. Reference: J Biomol Struct Dyn. 2021 Jul;39(11):3975-3985. https://pubmed.ncbi.nlm.nih.gov/32448083/
In vivo activity:
In diabetic rats, the plasma exposure of cefpodoxime was significantly lowered due to enhanced glomerular filtration. There was significant (p < 0.01) decrease in maximum concentration and area under the curve of cefpodoxime by both oral and intravenous route, which was attributed to augmented clearance of cefpodoxime. Reference: Diabetes Metab Disord. 2022 Nov 22;22(1):385-392. https://pubmed.ncbi.nlm.nih.gov/37255782/
Solvent mg/mL mM
Solubility
DMSO 125.0 224.18
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 557.60 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.

Recalculate based on batch purity %
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:
1. Yurtdaş-Kırımlıoğlu G. Spray dried nanospheres for inclusion complexes of cefpodoxime proxetil with β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and methyl-β-cyclodextrin: improved dissolution and enhanced antibacterial activity. Drug Dev Ind Pharm. 2021 Aug;47(8):1261-1278. doi: 10.1080/03639045.2021.1989452. Epub 2021 Oct 15. PMID: 34606394. 2. Quan J, Ma C, Wang Y, Hu B, Zhang D, Zhang Z, Wang J, Cheng M. Repurposing of cefpodoxime proxetil as potent neuroprotective agent through computational prediction and in vitro validation. J Biomol Struct Dyn. 2021 Jul;39(11):3975-3985. doi: 10.1080/07391102.2020.1772884. Epub 2020 Jun 8. PMID: 32448083. 3. Mittal G, Jakhar P, Patel A, Bhagwat DP. Pharmacokinetic assessment of cefpodoxime proxetil in diabetic rats. J Diabetes Metab Disord. 2022 Nov 22;22(1):385-392. doi: 10.1007/s40200-022-01156-3. PMID: 37255782; PMCID: PMC10225406. 4. Mujeeb MA, Pardeshi ML. Pharmacokinetics of cefpodoxime proxetil with special reference to biochemical parameters, tissue residue, and spermatozoa motility in rats. Indian J Med Sci. 2011 Feb;65(2):43-9. PMID: 23196312.
In vitro protocol:
1. Yurtdaş-Kırımlıoğlu G. Spray dried nanospheres for inclusion complexes of cefpodoxime proxetil with β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and methyl-β-cyclodextrin: improved dissolution and enhanced antibacterial activity. Drug Dev Ind Pharm. 2021 Aug;47(8):1261-1278. doi: 10.1080/03639045.2021.1989452. Epub 2021 Oct 15. PMID: 34606394. 2. Quan J, Ma C, Wang Y, Hu B, Zhang D, Zhang Z, Wang J, Cheng M. Repurposing of cefpodoxime proxetil as potent neuroprotective agent through computational prediction and in vitro validation. J Biomol Struct Dyn. 2021 Jul;39(11):3975-3985. doi: 10.1080/07391102.2020.1772884. Epub 2020 Jun 8. PMID: 32448083.
In vivo protocol:
1. Mittal G, Jakhar P, Patel A, Bhagwat DP. Pharmacokinetic assessment of cefpodoxime proxetil in diabetic rats. J Diabetes Metab Disord. 2022 Nov 22;22(1):385-392. doi: 10.1007/s40200-022-01156-3. PMID: 37255782; PMCID: PMC10225406. 2. Mujeeb MA, Pardeshi ML. Pharmacokinetics of cefpodoxime proxetil with special reference to biochemical parameters, tissue residue, and spermatozoa motility in rats. Indian J Med Sci. 2011 Feb;65(2):43-9. PMID: 23196312.
1: Mahmood W, Ahmad I, Khan MA, Ali Shah SA, Ashraf M, Shahzad MI, Pervaiz I, Sajid-Ur-Rehman M, Khurshid U. Synthesis, characterization, molecular docking and biological evaluation of Schiff Base derivatives of cefpodoxime. Heliyon. 2022 Nov 2;8(11):e11332. doi: 10.1016/j.heliyon.2022.e11332. PMID: 36387450; PMCID: PMC9649975. 2: Gao YY, Sang KN, Li PP, Hao J, Zhang C, Li HJ, Zhou DG. Bioequivalence of two tablet formulations of cefpodoxime proxetil in beagle dogs. Front Vet Sci. 2022 Oct 14;9:1048823. doi: 10.3389/fvets.2022.1048823. PMID: 36311679; PMCID: PMC9614231. 3: Gupta A, Malik S, Kaminski M, Landman D, Quale JM. In Vitro and In Vivo Activity of Amoxicillin-Clavulanate Combined with Ceftibuten or Cefpodoxime Against Extended-Spectrum β-Lactamase-Producing Escherichia coli and Klebsiella pneumoniae. Microb Drug Resist. 2022 Apr;28(4):419-424. doi: 10.1089/mdr.2021.0025. PMID: 35451880. 4: Yurtdaş-Kırımlıoğlu G. Spray dried nanospheres for inclusion complexes of cefpodoxime proxetil with β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and methyl-β-cyclodextrin: improved dissolution and enhanced antibacterial activity. Drug Dev Ind Pharm. 2021 Aug;47(8):1261-1278. doi: 10.1080/03639045.2021.1989452. Epub 2021 Oct 15. PMID: 34606394. 5: Birgy A, Madhi F, Jung C, Levy C, Cointe A, Bidet P, Hobson CA, Bechet S, Sobral E, Vuthien H, Ferroni A, Aberrane S, Cuzon G, Beraud L, Gajdos V, Launay E, Pinquier D, Haas H, Desmarest M, Dommergues MA, Cohen R, Bonacorsi S; Group of the National Observatory of Urinary tract Infection due to ESBL-producing Enterobacteriaceae in children. Clavulanate combinations with mecillinam, cefixime or cefpodoxime against ESBL-producing Enterobacterales frequently associated with blaOXA-1 in a paediatric population with febrile urinary tract infections. J Antimicrob Chemother. 2021 Oct 11;76(11):2839-2846. doi: 10.1093/jac/dkab289. PMID: 34453533. 6: Sharma PK, Shukla VK, Kumar A. Physical Characterization and In Vitro Evaluation of Dissolution Rate from Cefpodoxime Proxetil Loaded Self Solidifying Solid SNEDDS. Curr Drug Deliv. 2022;19(3):395-406. doi: 10.2174/1567201818666210805153859. PMID: 34353259. 7: Dey KK, Ghosh M. Study of the structure and dynamics at various parts of the antibacterial drug molecule cefpodoxime proxetil. Solid State Nucl Magn Reson. 2021 Oct;115:101752. doi: 10.1016/j.ssnmr.2021.101752. Epub 2021 Jul 29. PMID: 34340119. 8: Yurtdaş-Kırımlıoğlu G. Development and characterization of lyophilized cefpodoxime proxetil-Pluronic® F127/polyvinylpyrrolidone K30 solid dispersions with improved dissolution and enhanced antibacterial activity. Pharm Dev Technol. 2021 Apr;26(4):476-489. doi: 10.1080/10837450.2021.1889584. Epub 2021 Mar 1. PMID: 33616480. 9: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Cefpodoxime. 2021 Jan 18. PMID: 30000458. 10: Wenzel M, Welte MN, Theissen LH, Wittler C, Hoeh B, Humke C, Preisser F, Würnschimmel C, Tilki D, Graefen M, Roos FC, Becker A, Karakiewicz PI, Chun FKH, Kluth LA, Mandel P. Comparison of Complication Rates with Antibiotic Prophylaxis with Cefpodoxime Versus Fluoroquinolones After Transrectal Prostate Biopsy. Eur Urol Focus. 2021 Sep;7(5):980-986. doi: 10.1016/j.euf.2020.11.006. Epub 2020 Dec 24. PMID: 33358884. 11: Shapiro AB, Moussa SH, Carter NM, Gao N, Miller AA. Ceftazidime-Avibactam Resistance Mutations V240G, D179Y, and D179Y/T243M in KPC-3 β-Lactamase Do Not Alter Cefpodoxime-ETX1317 Susceptibility. ACS Infect Dis. 2021 Jan 8;7(1):79-87. doi: 10.1021/acsinfecdis.0c00575. Epub 2020 Dec 8. PMID: 33291867. 12: Das N, Chadda RK. Hyperprolactinemic Galactorrhea Associated With Cefpodoxime in a Patient With Recurrent Depressive Disorder on Venlafaxine Monotherapy: A Case Report. J Clin Psychopharmacol. 2020 Nov/Dec;40(6):635-636. doi: 10.1097/JCP.0000000000001293. PMID: 33065718. 13: Quan J, Ma C, Wang Y, Hu B, Zhang D, Zhang Z, Wang J, Cheng M. Repurposing of cefpodoxime proxetil as potent neuroprotective agent through computational prediction and in vitro validation. J Biomol Struct Dyn. 2021 Jul;39(11):3975-3985. doi: 10.1080/07391102.2020.1772884. Epub 2020 Jun 8. PMID: 32448083. 14: Fan Y, Chen H, Huang Z, Zhu J, Wan F, Peng T, Pan X, Huang Y, Wu C. Taste- masking and colloidal-stable cubosomes loaded with Cefpodoxime proxetil for pediatric oral delivery. Int J Pharm. 2020 Feb 15;575:118875. doi: 10.1016/j.ijpharm.2019.118875. Epub 2019 Nov 22. PMID: 31765781. 15: Babu T, Panachiyil GM, Sebastian J, Shastry V. Drug Rash With Eosinophilia and Systemic Symptoms (DRESS) Syndrome Probably Related to Cefpodoxime: A Case Report. J Pharm Pract. 2021 Feb;34(1):163-165. doi: 10.1177/0897190019866094. Epub 2019 Aug 5. PMID: 31382812. 16: Pieper M, Schleich H, Gröger H. Isolation and characterization of side- products formed through ∆2-isomerization in the synthesis of cefpodoxime proxetil. J Antibiot (Tokyo). 2019 Sep;72(9):702-708. doi: 10.1038/s41429-019-0190-z. Epub 2019 Jun 19. PMID: 31217553. 17: Iqbal S, Hassan S, Hassan A, Ali M, Nazim U, Zaheer E, Ahmed A, Hussain K, Shereen -, Furqan H. In vitro Spectroscopic studies on drug interaction of cefpodoxime proxetil and H2 receptor blockers. Pak J Pharm Sci. 2019 Mar;32(2 (Supplementary)):881-887. PMID: 31103987. 18: Hassan S, Iqbal S, Zaheer E, Hassan A, Hamid S, Ali M, Akram A, Maroof SZ, Abedin S, Khan SJ. Development and validation of RP-HPLC method for simultaneous determination of cefpodoxime proxetil and H2 receptor antagonists in pharmaceutical dosage forms. Pak J Pharm Sci. 2019 Mar;32(2 (Supplementary)):839-844. PMID: 31103980. 19: Mostafa GAE, Al-Otaibi YH, Al-Badr AA. Cefpodoxime proxetil. Profiles Drug Subst Excip Relat Methodol. 2019;44:1-165. doi: 10.1016/bs.podrm.2019.02.001. Epub 2019 Apr 16. PMID: 31029216. 20: Krajcar N, Marić LS, Šarić D, Milić N, Tešović G. Cefpodoxime proxetil as a therapeutic option in switching therapy for infective endocarditis in children: case reports and literature review. J Chemother. 2019 Oct;31(6):354-358. doi: 10.1080/1120009X.2019.1603797. Epub 2019 Apr 22. PMID: 31007148.