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[ CAS No. 58-71-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 58-71-9
Chemical Structure| 58-71-9
Structure of 58-71-9 * Storage: {[proInfo.prStorage]}

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Product Details of [ 58-71-9 ]

CAS No. :58-71-9 MDL No. :MFCD00072025
Formula : C16H15N2NaO6S2 Boiling Point : -
Linear Structure Formula :- InChI Key :VUFGUVLLDPOSBC-XRZFDKQNSA-M
M.W : 418.42 Pubchem ID :23675321
Synonyms :
Cefalotin sodium;Cefalothin (sodium salt);Lilly 38253;Keflin;38253;Sodium cephalotin
Chemical Name :Sodium (6R,7R)-3-(acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Calculated chemistry of [ 58-71-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.38
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 96.18
TPSA : 169.38 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : -11.13
Log Po/w (XLOGP3) : -0.41
Log Po/w (WLOGP) : -1.12
Log Po/w (MLOGP) : 0.66
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : -2.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.78
Solubility : 6.87 mg/ml ; 0.0164 mol/l
Class : Very soluble
Log S (Ali) : -2.68
Solubility : 0.869 mg/ml ; 0.00208 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.36
Solubility : 1.84 mg/ml ; 0.0044 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.48

Safety of [ 58-71-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P342+P311 UN#:2811
Hazard Statements:H317-H334 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 58-71-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 58-71-9 ]

[ 58-71-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6490-42-2 ]
  • 2-N hydrochloric acid [ No CAS ]
  • [ 58-71-9 ]
  • [ 58909-55-0 ]
  • [ 767230-97-7 ]
  • [ 58909-53-8 ]
YieldReaction ConditionsOperation in experiment
3.5 g (42%) With pyridine; diphosphorus pentasulfide; In ethanol; water; acetic acid; Chlorine was led into a solution of 9.9 g of 1-ethyl-uracil in 150 ml of glacial acetic acid until iodine-potassium-starch paper reacted positively and 1-ethyl-uracil was no longer detectable by thin-layer chromatography (ca. 0.5 hours). The mixture was evaporated in vacuo at 40 and the crystalline residue recrystallized from 300 ml of ethanol; yield 10.0 g (81%) of colorless, fine needles of 1-ethyl-5-chlorouracil; melting point 244-247. 1.74 Grams of 1-ethyl-5-chlorouracil were mixed with 4.44 g of phosphorus pentasulfide and 0.1 ml of water and the mixture treated with 30 ml of pyridine and boiled at reflux for 3.75 hours. The mixture was then evaporated in vacuo at 40, the residue suspended in 30 ml of water and treated with 30 ml of 2-N hydrochloric acid. the crystals obtained were filtered off under suction, washed with water and recrystallized from 1-ethyl-5-chloro-1,2-dihydro-4-mercapto-2-oxo-pyrimidine; melting point 217-220. In a manner analogous to that described in Example 1 6.27 g of cephalothin sodium salt were reacted 3.04 g of 1-ethyl-5-chloro-1,2-dihydro-4-mercapto-2-oxo-pyrimidine prepared above to give (7R)-3-[[(1-ethyl-5-chloro-1,2-dihydro-2-oxo-4-pyrimidinyl)-thio]methyl]-7-[2-(2-thienyl)-acetamido]-3-cephem-4-carboxylic acid as the sodium salt; yield 3.5 g (42%); melting point from 185 (decomposition); [α]D20 = -95.2 (c = 0.394 in water).
  • 2
  • [ 56-95-1 ]
  • [ 58-71-9 ]
  • chlorhexidine dicephalothin [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In water; butan-1-ol; at 20℃; for 48.0h; General procedure: The synthesis and physical characterization of four beta-lactam-based chlorhexidine GUMBOS, namely chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-cephalothin and chlorhexidinedi-oxacillin, were performed using methods previously reported by Cole et al. (2013) [24], but with slight modification. Briefly, stoichiometric amounts of <strong>[56-95-1]chlorhexidine diacetate</strong> and beta-lactam antibiotic, with the latter in slight excess, was stirred for 48 h at room temperature in a butanol:water (1:1) mixture to ensure the complete formation of the beta-lactam-based chlorhexidine GUMBOS. After removing butanol from the GUMBOS products, they were purified by washing several times with cold deionized water and dried overnight with a high vacuum. The structures of chlorhexidine di-ampicillin, chlorhexidine carbenicillin, chlorhexidine di-oxacillin and chlorhexidine di-cephalothin (Figure 1) were mainly confirmed by NMR, mass spectrometry and elemental analysis, among other spectroscopic data.
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