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Cephradine (monohydrate)

CAT: 0804-HY-128449-01Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-128449-01Size:100 mg
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Description
Cephradine (Cefradine) monohydrate is a broad-spectrum and orally active cephalosporin. Cephradine monohydrate is active against both grampositive and gram-negative pathogens and effective in eradicating most penicillinase-producing organisms known to be resistant to penicillin G, penicillin V, and ampicillin. Cephradine monohydrate has been used in the research of genitourinary, gastrointestinal and respiratory tract infections, and in infections of the skin and soft tissues. Cephradine monohydrate blocks solar-ultraviolet induced skin inflammation through direct inhibition of TOPK[1][2][3].
CAS Number
75975-70-1
Product Name Alternative
Cefradine (monohydrate)
UNSPSC
12352005
Target
Antibiotic; Bacterial; TOPK
Type
Reference compound
Related Pathways
Anti-infection; Cell Cycle/DNA Damage
Applications
COVID-19-immunoregulation
Field of Research
Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/cephradine-monohydrate.html
Purity
91.02
Solubility
10 mM in DMSO
Smiles
O=C(C(N12)=C(C)CS[C@]2([H])[C@H](NC([C@H](N)C3=CCC=CC3)=O)C1=O)O.[H]O[H]
Molecular Formula
C16H21N3O5S
Molecular Weight
367.42
References & Citations
[1]Schwinghammer TL, et al. Pharmacokinetics of cephradine administered intravenously and orally to young and elderly subjects. J Clin Pharmacol. 1990;30 (10) :893-899|[2]Caloza DL Jr, et al. Intravenous use of cephradine and cefazolin against serious infections. Antimicrob Agents Chemother. 1979;15 (1) :119-122.|[3]Kang S, et al. In Vitro and In Vivo Antimicrobial Activity of Antibiotic-Conjugated Carriers with Rapid pH-Responsive Release Kinetics. Adv Healthc Mater. 2019;8 (14) :e1900247.|[4]Fan X, et al. Cefradine blocks solar-ultraviolet induced skin inflammation through direct inhibition of T-LAK cell-originated protein kinase. Oncotarget. 2016;7 (17) :24633-24645.
Shipping Conditions
Room Temperature
Storage Conditions
Store at room temperature, keep dry and cool
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
β-lactam

Chemical Information

Cephradine Monohydrate

Cephradine Monohydrate is the monohydrate form of cephradine, a beta-lactam, first-generation cephalosporin antibiotic with bactericidal activity. Cephradine monohydrate binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. PBPs participate in the terminal stages of assembling the bacterial cell wall, and in reshaping the cell wall during cell division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

CAS Number75975-70-1
PubChem CID21124775
IUPAC 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;hydrate
Molecular FormulaC16H21N3O5S
Molecular Weight367.4
Topological Polar Surface Area139
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Heavy Atom Count25
Formal Charge0
Complexity697
SMILES
CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CCC=CC3)N)SC1)C(=O)O.O
InChI
InChI=1S/C16H19N3O4S.H2O/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);1H2/t10-,11-,15-;/m1./s1
InChIKey
VHNPSPMQGXQSET-CYJZLJNKSA-N
Chemical Structure
2D Structure
2D structure of Cephradine Monohydrate
CAS: 75975-70-1
CID: 21124775
Formula: C16H21N3O5S
MW: 367.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight367.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass367.12019195
Monoisotopic Mass367.12019195
Topological Polar Surface Area139 Ų
Heavy Atom Count25
Formal Charge0
Complexity697
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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