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MedKoo Cat#: 329114 | Name: Cefcapene Pivoxil Hydrochloride hydrate
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Description:

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

Cefcapene Pivoxil Hydrochloride, also known as Flomox and S-1108, is a cephalosporin antibiotic used as antibacterials.

Chemical Structure

Cefcapene Pivoxil Hydrochloride hydrate
Cefcapene Pivoxil Hydrochloride hydrate
CAS#147816-24-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 329114

Name: Cefcapene Pivoxil Hydrochloride hydrate

CAS#: 147816-24-8 (HCl)

Chemical Formula: C23H30ClN5O8S2

Exact Mass: 0.0000

Molecular Weight: 604.09

Elemental Analysis: C, 45.73; H, 5.01; Cl, 5.87; N, 11.59; O, 21.19; S, 10.61

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
200mg USD 650.00 2 Weeks
500mg USD 1,150.00 2 Weeks
1g USD 1,850.00 2 Weeks
2g USD 2,650.00 2 Weeks
5g USD 4,250.00 2 Weeks
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Related CAS #
105889-45-0 (free base) 147816-24-8 (HCl)
Synonym
Cefcapene Pivoxil Hydrochloride; S-1108; S 1108; S1108; Flomox; Flumax
IUPAC/Chemical Name
(6R,7R)-(Pivaloyloxy)methyl 7-((Z)-2-(2-aminothiazol-4-yl)pent-2-enamido)-3-((carbamoyloxy)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride hydrate
InChi Key
LUXIJPQYUCFVAL-XRLCNELCSA-N
InChi Code
InChI=1S/C23H29N5O8S2.ClH.H2O/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4;;/h6,9,14,18H,5,7-8,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29);1H;1H2/b12-6-;;/t14-,18-;;/m1../s1
SMILES Code
O=C(C(N12)=C(COC(N)=O)CS[C@]2([H])[C@H](NC(/C(C3=CSC(N)=N3)=C\CC)=O)C1=O)OCOC(C(C)(C)C)=O.[H]Cl.[H]O[H]
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
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
Related CAS# 135889-00-8 (Cefcapene) 147816-24-8 (Cefcapene Pivoxil Hydrochloride hydrate)
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cefcapene Pivoxil is the pivalate ester prodrug form of cefcapene, a semi-synthetic third-generation cephalosporin with antibacterial activity.
In vitro activity:
The influence of metabolism on transepithelial flux of the prodrug cefcapene pivoxil hydrochloride (CFPN-PI) as well as its active metabolite CFPN was studied using Caco-2 cells. The rate of transport of each drug across Caco-2 monolayers appeared to be linear with time (data not shown). The results are given in Table 2. Higher Papp values were obtained for prodrugs than for active acids. When CFPN-PI was added to the apical side of the monolayers, only CFPN appeared and CFPN-PI was not detected in the basolateral side. Intracellular degradation of prodrugs resulted in intracellular accumulation. From the results of studies on transport of CFPN, it was concluded that no intracellular entrapment occurred. Reference: Antimicrob Agents Chemother. 2004 Jul;48(7):2604-9. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/15215116/
In vivo activity:
Permeation of CFPN-PI across a Caco-2 monolayer and a rat intestine using the system was also studied. The time courses of the permeation of CFPN-PI into the receiver compartment are shown in Fig. 3b. When 15 mg of CFPN-PI was added, CFPN produced from CFPN-PI was detected in the receiver compartment of the side-by-side diffusion chamber, but CFPN-PI was below the detectable limit. The calculation of the amount of decomposition of CFPN-PI was based on the amount of CFPN that was produced by hydrolysis of CFPN-PI. In the case of a Caco-2 monolayer, 2.53 μg of decomposed CFPN-PI was estimated based on the amount of CFPN produced (2.22 μg). The cumulative permeation of CFPN-PI was calculated to be 0.0168%. On the other hand, in the case of rat intestine, it was estimated that 4.28 μg of CFPN-PI was decomposed into CFPN (3.76 μg), and the cumulative permeation was 0.0285%. As found in our previous studies, relatively water-soluble drugs that permeated across a Caco-2 monolayer at cumulative permeation rate of more than 0.03% or at a rate over 0.04% in the rat intestine can be almost completely absorbed in humans. When the cumulative permeation rate across a Caco-2 monolayer is lower than 0.03% or below 0.04% in the rat intestine, there is a good linear correlation between cumulative permeation across a Caco-2 monolayer and oral absorption in humans (R = 0.967) or between cumulative permeation across a rat intestine and oral absorption in humans (R = 0.959). Based on these results, the oral absorption of CFPN-PI is predicted to be 66.5% in the Caco-2 model and 77.1% in the rat intestine model (Fig. 4). Laboratory prediction of oral absorption is categorized by <40% in laboratory tests as poor, 40 to 60% as moderate, and >60% as good. The results were shown in Table 3. Reference: Antimicrob Agents Chemother. 2004 Jul;48(7):2604-9. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/15215116/
Solvent mg/mL mM comments
Solubility
DMSO 125.0 206.92
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 604.09 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:
In vitro protocol:
1. He X, Sugawara M, Takekuma Y, Miyazaki K. Absorption of ester prodrugs in Caco-2 and rat intestine models. Antimicrob Agents Chemother. 2004 Jul;48(7):2604-9. doi: 10.1128/AAC.48.7.2604-2609.2004. PMID: 15215116; PMCID: PMC434205. 2. Sekiya Y, Eguchi M, Nakamura M, Ubukata K, Omura S, Matsui H. Comparative efficacies of different antibiotic treatments to eradicate nontypeable Haemophilus influenzae infection. BMC Infect Dis. 2008 Feb 7;8:15. doi: 10.1186/1471-2334-8-15. PMID: 18254980; PMCID: PMC2276502.
In vivo protocol:
1. He X, Sugawara M, Takekuma Y, Miyazaki K. Absorption of ester prodrugs in Caco-2 and rat intestine models. Antimicrob Agents Chemother. 2004 Jul;48(7):2604-9. doi: 10.1128/AAC.48.7.2604-2609.2004. PMID: 15215116; PMCID: PMC434205. 2. Sekiya Y, Eguchi M, Nakamura M, Ubukata K, Omura S, Matsui H. Comparative efficacies of different antibiotic treatments to eradicate nontypeable Haemophilus influenzae infection. BMC Infect Dis. 2008 Feb 7;8:15. doi: 10.1186/1471-2334-8-15. PMID: 18254980; PMCID: PMC2276502.
1: Iwata E, Tachibana A, Kusumoto J, Takata N, Hasegawa T, Akashi M. Does prophylactic antibiotic administration for tooth extraction affect PT-INR in patients taking warfarin? BMC Oral Health. 2020 Nov 19;20(1):331. doi: 10.1186/s12903-020-01326-w. PMID: 33213431; PMCID: PMC7678308. 2: Sakaida T, Tanimoto I, Matsubara A, Nakamura M, Morita A. Unique skin manifestations of COVID-19: Is drug eruption specific to COVID-19? J Dermatol Sci. 2020 Jul;99(1):62-64. doi: 10.1016/j.jdermsci.2020.05.002. Epub 2020 May 16. PMID: 32425356; PMCID: PMC7229941. 3: Okamoto K, Asano S, Yamamoto T, Toyono T, Yamaguchi R, Okada Y, Okugawa S, Suzuki H, Moriya K, Aihara M. Poor penetration of cefcapene into aqueous humor after oral administration of cefcapene pivoxil to patients undergoing cataract surgery. J Infect Chemother. 2020 Feb;26(2):312-315. doi: 10.1016/j.jiac.2019.08.004. Epub 2019 Aug 31. PMID: 31481306. 4: Tatebe Y, Koyama T, Mikami N, Kitamura Y, Sendo T, Hinotsu S. Hypoglycemia associated with pivalate-conjugated antibiotics in young children: A retrospective study using a medical and pharmacy claims database in Japan. J Infect Chemother. 2020 Jan;26(1):86-91. doi: 10.1016/j.jiac.2019.07.013. Epub 2019 Aug 7. PMID: 31401031. 5: Hanai S, Iwata M, Terasawa T. Relapsing Hypoglycemia Associated with Hypocarnitinemia Following Treatment with Cefcapene Pivoxil in an Elderly Man. Intern Med. 2019 Oct 1;58(19):2891-2894. doi: 10.2169/internalmedicine.2339-18. Epub 2019 Jun 27. PMID: 31243204; PMCID: PMC6815901. 6: Taniwaki M, Katsutani S, Yamasaki M, Kawamoto K, Funaishi K, Matsumoto Y, Matsumoto N, Ohashi N, Hattori N. Acquired factor V inhibitor after antibiotic treatment in a patient with pneumonia: a case report. Ann Hematol. 2019 Aug;98(8):1989-1990. doi: 10.1007/s00277-019-03638-6. Epub 2019 Feb 12. PMID: 30747247. 7: Irie S, Anno T, Kawasaki F, Shigemoto R, Kaneto H, Kaku K, Okimoto N. Acute exacerbation of chronic osteomyelitis triggered by aggravation of type 2 diabetes mellitus: a case report. J Med Case Rep. 2019 Jan 7;13(1):7. doi: 10.1186/s13256-018-1954-y. PMID: 30621795; PMCID: PMC6323657. 8: Sone Y, Namiki T, Tokoro S, Miura K, Yokozeki H. A case of neutrophilic dermatoses including pyoderma gangrenosum as a continuous disease spectrum to SAPHO syndrome. Clin Exp Dermatol. 2018 Oct;43(7):829-831. doi: 10.1111/ced.13620. Epub 2018 May 13. PMID: 29756300. 9: Iwata K, Fukuchi T, Hirai M, Yoshimura K, Kanatani Y. Prevalence of inappropriate antibiotic prescriptions after the great east Japan earthquake, 2011. Medicine (Baltimore). 2017 Apr;96(15):e6625. doi: 10.1097/MD.0000000000006625. PMID: 28403114; PMCID: PMC5403111. 10: Deguchi T, Shimomura Y, Hayashi R, Orime M, Tomiyama K, Abe R. Cross- reactivity of cephalosporins: allergic immediate hypersensitivity to ceftriaxone in a cefcapene pivoxil-sensitized patient. Eur J Dermatol. 2017 Apr 1;27(2):187-189. doi: 10.1684/ejd.2016.2938. PMID: 27934618. 11: Kondo M, Akachi S, Yamazoe N, Yamanaka K, Mizutani H. Case with cellulitis, lymphangitis and subcutaneous nodule suspected due to Rickettsia japonica carrying tick bite. J Dermatol. 2017 Oct;44(10):1182-1183. doi: 10.1111/1346-8138.13666. Epub 2016 Oct 27. PMID: 27786374. 12: Kawakami Y, Katayama T, Kishida M, Oda W, Inoue Y. A Case of Streptobacillus moniliformis Infection with Cutaneous Leukocytoclastic Vasculitis. Acta Med Okayama. 2016 Oct;70(5):377-381. doi: 10.18926/AMO/54596. PMID: 27777430. 13: Murakami M, Masuda K, Utsunomiya R, Oda F, Namba C, Sayama K. Cefcapene Pivoxil Hydrochloride Is a Potentially New Treatment for Palmoplantar Pustulosis with Pustulotic Arthro-Osteitis. Dermatology. 2015;231(4):304-11. doi: 10.1159/000439401. Epub 2015 Oct 7. PMID: 26440444. 14: Maeda A, Ishiguro N, Kawashima M. The pathogenetic role of rod-shaped bacteria containing intracellular granules in the vellus hairs of a patient with perioral dermatitis: A comparison with perioral corticosteroid-induced rosacea. Australas J Dermatol. 2016 Aug;57(3):225-8. doi: 10.1111/ajd.12344. Epub 2015 Apr 20. PMID: 25894304. 15: Nasu T, Suzuki M, Uetake K, Kubota M. Newborn hypocarnitinemia due to long- term transplacental pivalic acid passage. Pediatr Int. 2014 Oct;56(5):772-4. doi: 10.1111/ped.12305. PMID: 25335995. 16: Iketani Y, Hata Y, Yamamoto N, Oguri T. [Case of the abscess type cutaneous nocardiosis]. Med Mycol J. 2014;55(1):J19-23. Japanese. doi: 10.3314/mmj.55.j19. PMID: 24682099. 17: Yamazato S, Nakai N, Katoh N. Positive skin prick test to cefcapene pivoxil hydrochloride hydrate: a case report. Allergol Int. 2013 Jun;62(2):263-4. doi: 10.2332/allergolint.12-LE-0524. Epub 2013 Apr 25. PMID: 23612491. 18: Zalewski P, Cielecka-Piontek J, Garbacki P, Jelińska A, Karaźniewicz-Łada M. Stability-Indicating HPLC Method for the Determination of Cefcapene Pivoxil. Chromatographia. 2013 Apr;76(7-8):387-391. doi: 10.1007/s10337-012-2318-1. Epub 2012 Sep 18. PMID: 23555152; PMCID: PMC3612177. 19: Duan HF, Ding L, Li XB, Hu LL, Wen AD, Leng Y, Liu Z. Determination of cefcapene acid by LC-MS and their application to a pharmacokinetic study in healthy Chinese volunteers. J Pharm Anal. 2013 Apr;3(2):84-92. doi: 10.1016/j.jpha.2012.09.006. Epub 2012 Oct 7. PMID: 29403801; PMCID: PMC5760932. 20: Sakamoto N, Nakamura-Uchiyama F, Kobayashi K, Takasaki T, Ogasawara Y, Ando S, Iwabuchi S, Ohnishi K. Severe murine typhus with shock and acute respiratory failure in a Japanese traveler after returning from Thailand. J Travel Med. 2013 Jan-Feb;20(1):50-3. doi: 10.1111/j.1708-8305.2012.00678.x. Epub 2012 Nov 30. PMID: 23279232