Cephradine (free base)
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MedKoo CAT#: 317450

CAS#: 38821-53-3 (free base)

Description: Cephradine (free base) is a semi-synthetic cephalosporin antibiotic. Cefradin inhibits the last stage of bacterial cell wall synthesis by binding to certain penicillin-binding proteins which results in cell lysis. Cell lysis is mediated by bacterial cell wall autolytic enzymes. Cefradin may interfere with autolysin inhibitors.

Chemical Structure

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Cephradine (free base)
CAS# 38821-53-3 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317450
Name: Cephradine (free base)
CAS#: 38821-53-3 (free base)
Chemical Formula: C16H19N3O4S
Exact Mass: 0.00
Molecular Weight: 349.400
Elemental Analysis: C, 55.00; H, 5.48; N, 12.03; O, 18.32; S, 9.18

Price and Availability

Size Price Availability Quantity
1g USD 285 2 weeks
5g USD 650 2 weeks
10g USD 950 2 weeks
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Related CAS #: 31828-50-9 (dihydrate)   38821-53-3 (free base)   57584-26-6 (sodium)  

Synonym: Cephradine; Alpharma Brand of Cephradine; Anspor; Bouchara Brand of Cephradine; Bristol-Myers Squibb Brand of Cefradine; Cefradine; Cephradine; Cephradine Dihydrate; Cephradine, Non Stoichiometric Hydrate; Cephradine, Non-Stoichiometric Hydrate; Dexef; Dexo Brand of Cephradine; Dihydrate, Cephradine; Galen Brand of Cephradine; Kelsef; Maxisporin; Nicef; Non-Stoichiometric Hydrate Cephradine; Reig Jofre Brand of Cephradine; Sefril; Septa Brand of Cephradine; Septacef; SQ 11436; SQ-11436; SQ11436; Squibb Brand of Cephradine; Velocef; Velosef; Yamanouchi Brand of Cephradine; Zeefra Gé

IUPAC/Chemical Name: (6R,7R)-7-[[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChi Key: RDLPVSKMFDYCOR-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)

SMILES Code: CC1=C(N2C(C(C2=O)NC(=O)C(C3=CCC=CC3)N)SC1)C(=O)O

Appearance: Solid powder

Purity: >90% (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: Cefradine is a beta-lactam, first-generation cephalosporin antibiotic with bactericidal activity.
In vitro activity: The relative viability (OD600) of S. aureus was measured after 12 h of treatment with free cephradine (CP) and β-CD–MCM–CP at pH 7.4 (Figure 4A) and pH 5.5 (Figure 4B). S. aureus was generally more viable at pH 7.4 than at pH 5.5. After free CP incubation, bacterial viability rapidly increased at antibiotic concentrations below the MIC of 0.70 µg mL−1 at both pH 7.4 and pH 5.5. In contrast, the inhibitory effect of β-CD–MCM–CP on bacterial viability differed significantly under different pH conditions. At pH 7.4, the MIC of β-CD–MCM–CP was 2.0 µg mL−1, approximately three times higher than that of free CP. However, at pH 5.5, β-CD–MCM–CP had almost the same antibacterial effect as free CP with an MIC of 0.70 µg mL−1 (Table 1). The CP-conjugated carrier thus exhibited a clear pH-responsive toxicity against S. aureus. Reference: Mater. 2019 Jul;8(14):e1900247. https://doi.org/10.1002/adhm.201900247
In vivo activity: The in vivo activity of β-CD–MCM–CP was evaluated in subcutaneous abscess models using nondiabetic mice (Balb/c; Figure S9, Supporting Information) and diabetic mice (C57BLKs-Jdb/db; Figure S10, Supporting Information). Figure 7A presents a simplified diagram of the animal experiment. CP and β-CD–MCM–CP were subcutaneously injected into the mice 5 days after infection. CP was injected at a dose of 25 mg kg−1 day−1 for 5 days, and β-CD–MCM–CP containing the same amount of CP was injected in the same manner. The β-CD–MCM carrier and the simple mixture of β-CD–MCM and CP (C + C) at the same molar amount and ratio as β-CD–MCM–CP were also injected as positive controls. Figure 7F,G presents the abscess grade scores and bacterial counts in the abscesses collected from non-insulin-dependent diabetes mellitus model mice. Unlike the nondiabetic mice, there was a significant difference in abscess scores, with those of the CP and β-CD–MCM–CP groups significantly lower than those of the saline-treated and carrier-only groups. A similarly significant reduction in the bacterial counts in the abscesses was observed in the groups treated with CP, β-CD–MCM–CP, and C + C. However, there was no significant difference in abscess scores and bacterial counts between CP, β-CD–MCM–CP, and C + C groups. In this case, the carrier-only exhibited no antimicrobial effect. Reference: Mater. 2019 Jul;8(14):e1900247. https://doi.org/10.1002/adhm.201900247

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 4.0 10.88

Preparing Stock Solutions

The following data is based on the product molecular weight 349.40 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. Kang S, Park GH, Kim S, Kim J, Choi Y, Huang Y, Lee Y, Choi TH. In Vitro and In Vivo Antimicrobial Activity of Antibiotic-Conjugated Carriers with Rapid pH-Responsive Release Kinetics. Adv Healthc Mater. 2019 Jul;8(14):e1900247. doi: 10.1002/adhm.201900247. Epub 2019 May 13. PMID: 31081217. 2. Silver MS, Counts GW, Zeleznik D, Turck M. Comparison of in vitro antibacterial activity of three oral cephalosporins: cefaclor, cephalexin, and cephradine. Antimicrob Agents Chemother. 1977 Nov;12(5):591-6. doi: 10.1128/AAC.12.5.591. PMID: 921255; PMCID: PMC429981.
In vivo protocol: 1. Kang S, Park GH, Kim S, Kim J, Choi Y, Huang Y, Lee Y, Choi TH. In Vitro and In Vivo Antimicrobial Activity of Antibiotic-Conjugated Carriers with Rapid pH-Responsive Release Kinetics. Adv Healthc Mater. 2019 Jul;8(14):e1900247. doi: 10.1002/adhm.201900247. Epub 2019 May 13. PMID: 31081217.

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1: Zhang H, Xie H, Chen J, Zhang S. Prediction of hydrolysis pathways and
kinetics for antibiotics under environmental pH conditions: a quantum chemical
study on cephradine. Environ Sci Technol. 2015 Feb 3;49(3):1552-8. doi:
10.1021/es505383b. Epub 2015 Jan 26. PubMed PMID: 25590945.


2: Bashir S, Akhtar S, Hussain S, Malik F, Mahmood S, Erum A, Ruqiatulain U.
Appraisal of multifarious brands of Cephradine for their in vitro antibacterial
activity against varied microorganisms. Pak J Pharm Sci. 2013 Sep;26(5):953-9.
PubMed PMID: 24035952.


3: Wu MT, Pei SN. Development of cephradine-induced acquired factor V inhibitors:
a case report. Ann Pharmacother. 2010 Oct;44(10):1673-6. doi: 10.1345/aph.1P324.
Epub 2010 Aug 31. PubMed PMID: 20807866.


4: Lu C, Zhang N, Li J, Li Q. Colorimetric detection of cephradine in
pharmaceutical formulations via fluorosurfactant-capped gold nanoparticles.
Talanta. 2010 Apr 15;81(1-2):698-702. doi: 10.1016/j.talanta.2010.01.006. Epub
2010 Jan 11. PubMed PMID: 20188984.


5: Choi SJ, Ryu JH, Lee HW, Lee MJ, Seo JH, Tak SK, Lee KT. Rapid and simple
method for determination of cephradine in human plasma using liquid
chromatography-tandem mass spectrometry (LC-MS/MS): application to the
bioequivalence study. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Dec
1;877(31):4059-64. doi: 10.1016/j.jchromb.2009.10.011. Epub 2009 Oct 12. PubMed
PMID: 19854118.


6: Liu YM, Xuan CS, Li WY, Feng J. [Study of cefadroxil and cephradine charge
transfer process by fluorescence quenching method]. Guang Pu Xue Yu Guang Pu Fen
Xi. 2009 Feb;29(2):441-5. Chinese. PubMed PMID: 19445223.


7: Foster DR, Yee S, Bleske BE, Carver PL, Shea MJ, Menon SS, Ramachandran C,
Welage LS, Amidon GL. Lack of interaction between the peptidomimetic substrates
captopril and cephradine. J Clin Pharmacol. 2009 Mar;49(3):360-7. doi:
10.1177/0091270008329554. PubMed PMID: 19246733.


8: Shoaib MH, Shaikh D, Yousuf RI, Naqvi BS, Hashmi K. Pharmacokinetic study of
cephradine in Pakistani healthy male volunteers. Pak J Pharm Sci. 2008
Oct;21(4):400-6. PubMed PMID: 18930862.


9: Chohan ZH, Jaffery MF. Synthesis, Characterization and Biological Evaluation
of Co(II), Cu(II), Ni(II) and Zn(II) Complexes With Cephradine. Met Based Drugs.
2000;7(5):265-9. doi: 10.1155/MBD.2000.265. PubMed PMID: 18475955; PubMed Central
PMCID: PMC2365234.


10: Wu Z, Feng B, Weng J, Qu S, Wang J, Lu X. Biomimetic apatite coatings on
titanium coprecipitated with cephradine and salviae miltlorrhizae. J Biomed Mater
Res B Appl Biomater. 2008 Feb;84(2):486-92. PubMed PMID: 17635037.


11: Arayne MS, Sultana N, Afzal M. Cephradine antacids interaction studies. Pak J
Pharm Sci. 2007 Jul;20(3):179-84. PubMed PMID: 17545100.


12: Sohn YT, Park SH. Crystal form of cephradine. Arch Pharm Res. 2006
Feb;29(2):178-82. PubMed PMID: 16526284.


13: Sultana N, Arayne MS, Afzal M. Synthesis and antibacterial activity of
cephradine metal complexes : part II complexes with cobalt, copper, zinc and
cadmium. Pak J Pharm Sci. 2005 Jan;18(1):36-42. PubMed PMID: 16431381.


14: Sultana N, Arayne MS, Afzal M. Synthesis and antibacterial activity of
cephradine metal complexes: part I complexes with magnesium, calcium, chromium
and manganese. Pak J Pharm Sci. 2003 Jan;16(1):59-72. PubMed PMID: 16414567.


15: Zhong J, Shen Z, Yang Y, Chen J. Preparation and characterization of uniform
nanosized cephradine by combination of reactive precipitation and liquid
anti-solvent precipitation under high gravity environment. Int J Pharm. 2005 Sep
14;301(1-2):286-93. PubMed PMID: 16054788.


16: Cui F, Shi J, Bai X. [Enzymatic synthesis of cephradine]. Wei Sheng Wu Xue
Bao. 1998 Aug;38(4):300-3. Chinese. PubMed PMID: 12549419.


17: Takishima J, Onishi H, Machida Y. Prolonged intestinal absorption of
cephradine with chitosan-coated ethylcellulose microparticles in rats. Biol Pharm
Bull. 2002 Nov;25(11):1498-502. PubMed PMID: 12419970.


18: de Fijter CW, ter Wee PM, Oe LP, Verbrugh HA. Intraperitoneal ciprofloxacin
and rifampicin versus cephradine as initial treatment of (C)APD-related
peritonitis: a prospective randomized multicenter comparison (CIPPER trial).
Perit Dial Int. 2001 Sep-Oct;21(5):480-6. PubMed PMID: 11757832.


19: Ovalle A, Martínez MA, Wolff M, Cona E, Valderrama O, Villablanca E, Lobos L.
[Prospective, randomized, comparative study of the efficacy, safety and cost of
cefuroxime versus cephradine in acute pyelonephritis during pregnancy]. Rev Med
Chil. 2000 Jul;128(7):749-57. Spanish. PubMed PMID: 11050836.


20: Johnson VM, Allanson JP, Causon RC. Determination of the cephalosporin
antibiotic cephradine in human plasma by high-performance liquid chromatography
with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2000 Mar
31;740(1):71-80. PubMed PMID: 10798295.