Cefepime(BMY-28142) - Moligand™, ≥98% , CAS No.88040-23-7

CAS: 88040-23-7 Cat. No.: C304822 Molecular Weight: 480.56 EC Number: 643-019-5

GRADE & PURITY Moligand™, ≥98%

Synonyms

AKOS016014147 | Cefepime [USAN:INN:BAN] | CEFEPIME [USAN] | Pyrrolidinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-1-methyl-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))- |

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

AKOS016014147 | Cefepime [USAN:INN:BAN] | CEFEPIME [USAN] | Pyrrolidinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-1-methyl-, hydroxide, inner salt, (6R-(6alpha, 7beta(Z)))- |

Specifications & Purity

Moligand™, ≥98%

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488195573
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195573
• Canonical Smiles: C[N+]1(CCCC1)CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)[O-]
• IUPAC Name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• InChIKey: HVFLCNVBZFFHBT-ZKDACBOMSA-N
• INCHI: 1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1
• Isomeric SMILES: C[N+]1(CCCC1)CC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)[O-]
• Molecular Weight: 480.56
• Reaxy-Rn: 10773275
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10773275&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Lactams
      • Subclass Beta lactams
        • Level5 Cephems
          • Level6 Cephalosporins
            • Level7 3'-quaternary ammonium cephalosporins

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Lactams
• Subclass: Beta lactams
• Intermediate Tree Nodes: Cephems - Cephalosporins
• Direct Parent: 3'-quaternary ammonium cephalosporins
• Alternative Parents: N-acyl-alpha amino acids and derivatives 2,4-disubstituted thiazoles 1,3-thiazines 2-amino-1,3-thiazoles N-alkylpyrrolidines Heteroaromatic compounds Tetraalkylammonium salts Tertiary carboxylic acid amides Carboxylic acid salts Azetidines Secondary carboxylic acid amides Amino acids Carboxylic acids Monocarboxylic acids and derivatives Dialkylthioethers Thiohemiaminal derivatives Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Primary amines
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3'-quaternary ammonium cephalosporin - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - 2,4-disubstituted 1,3-thiazole - Meta-thiazine - N-alkylpyrrolidine - 1,3-thiazol-2-amine - Tertiary carboxylic acid amide - Thiazole - Quaternary ammonium salt - Pyrrolidine - Tetraalkylammonium salt - Azole - Heteroaromatic compound - Carboxylic acid salt - Carboxamide group - Amino acid - Amino acid or derivatives - Secondary carboxylic acid amide - Azetidine - Azacycle - Carboxylic acid derivative - Dialkylthioether - Carboxylic acid - Monocarboxylic acid or derivatives - Hemithioaminal - Thioether - Amine - Organopnictogen compound - Organic oxygen compound - Organic salt - Carbonyl group - Organic nitrogen compound - Organic oxide - Organic zwitterion - Organonitrogen compound - Organooxygen compound - Primary amine - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 3'-quaternary ammonium cephalosporins. These are cephalosporins that are substituted at the 3'-position by a quaternary ammonium group.
• External Descriptors: cephalosporin - oxime O-ether

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

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ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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Associated Targets(non-human)

bla Beta-lactamase TEM (457 Activities)

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mrdA Penicillin-binding protein 2 (41 Activities)

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mrcB Penicillin-binding protein 1B (40 Activities)

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blaZ Beta-lactamase (285 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Enterococcus durans (113 Activities)

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Streptococcus pneumoniae (31063 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Burkholderia cepacia (649 Activities)

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Pseudomonas fluorescens (1630 Activities)

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Pseudomonas putida (467 Activities)

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Enterobacter cloacae (7976 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Proteus vulgaris (5823 Activities)

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Providencia rettgeri (925 Activities)

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Providencia sp. (46 Activities)

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Salmonella typhimurium (15756 Activities)

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Shigella flexneri (1836 Activities)

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Haemophilus parainfluenzae (65 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Staphylococcus haemolyticus (1695 Activities)

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Acinetobacter (437 Activities)

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Acinetobacter baumannii (41033 Activities)

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Acinetobacter calcoaceticus (618 Activities)

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Acinetobacter sp. (243 Activities)

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Moraxella catarrhalis (3334 Activities)

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Enterobacteriaceae (669 Activities)

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Citrobacter (156 Activities)

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Citrobacter koseri (193 Activities)

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Citrobacter freundii (1864 Activities)

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Enterobacter (462 Activities)

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Klebsiella aerogenes (4963 Activities)

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Escherichia coli (133304 Activities)

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Klebsiella oxytoca (929 Activities)

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Klebsiella sp. (156 Activities)

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Morganella morganii (1291 Activities)

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Proteus mirabilis (3894 Activities)

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Providencia stuartii (425 Activities)

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Salmonella (646 Activities)

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Serratia marcescens (3237 Activities)

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Shigella (221 Activities)

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Shigella sonnei (625 Activities)

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Aeromonas sp. (29 Activities)

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Haemophilus influenzae (8812 Activities)

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Pasteurella sp. (35 Activities)

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Streptococcus agalactiae (1777 Activities)

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Streptococcus pyogenes (16140 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 480.600 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 480.125 Da
• Monoisotopic Mass: 480.125 Da
• Topological Polar Surface Area: 204.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 869.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Li Zhang, Hongbo Mo, Chuan Wang, Xiaofeng Li, Shuai Jiang, Weigang Fan, Yagang Zhang.  (2023)  Synthesis and Properties of Cefixime Core–Shell Magnetic Nano-Molecularly Imprinted Materials.  Polymers,  15  (22): (4464).  [PMID:38006188] [10.3390/polym15224464]

2. Xiaojie Xu, Jiahui Zuo, Huajing Zeng, Yuan Zhao, Zengjie Fan.  (2023)  Improving Osseointegration Potential of 3D Printed PEEK Implants with Biomimetic Periodontal Ligament Fiber Hydrogel Surface Modifications.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202308811]

3. Yexuan Mao, Yichao Fan, Ran Yang, Youyi Wang, Qingyue Li, Meng Dang, Xianqing Huang, Lianjun Song, Pingan Zhang, Miao Song, Liang Liu, Linli Wang, Shun Yu, Qiuyan Zhao, Xiya Zhang.  (2023)  A highly sensitive electrochemical sensor derived from peptide amphiphilic inspired self-assembled, ordered gold nanoparticles for determination of 22 β-lactams.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2023.142669]

4. Lan Sugui, Li Zhirong, Su Aiqiu, Peng Yanhong, Liao Yanke, Liu Xuemei, Tan Qiang.  (2021)  Study on the mechanisms of the cross-resistance to TET, PIP, and GEN in Staphylococcus aureus mediated by the Rhizoma Coptidis extracts.  JOURNAL OF ANTIBIOTICS,  74  (5): (330-336).  [PMID:33500562] [10.1038/s41429-021-00407-4]

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