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64544-07-6

Basic Information
CAS No.: 64544-07-6
Name: Cefuroxime 1-acetoxyethyl ester
Article Data: 7
Molecular Structure:
Molecular Structure of 64544-07-6 (Cefuroxime 1-acetoxyethyl ester)
Formula: C20H22N4O10S
Molecular Weight: 510.481
Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-furanyl(methoxyimino)acetyl]amino]-8-oxo-,1-(acetyloxy)ethyl ester, (6R,7R)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-,1-(acetyloxy)ethyl ester, [6R-[6a,7b(Z)]]-;Altacef;Bioracef;CCI15641;Cefaks;Cefazine;Ceftin;Cefurax;Cefuroxime axetil;Elobact;Forcef;Oraxim;Zinat;Zinnat;
EINECS: 259-560-1
Density: 1.61 g/cm3
Melting Point: 175-180 °C
Boiling Point: 250°C (rough estimate)
Appearance: white to pale yellow powder
Risk Codes: R36/37/38
PSA: 214.36000
LogP: 0.86080
Synthetic route
40258-78-4

1-bromoethyl acetate

55268-75-2

Cefuroxime

64544-07-6

cefuroxime axetil

Conditions
ConditionsYield
With N,N-dimethyl-formamide; copper dichloride In ethyl acetate at 8 - 30℃; for 1.5h; Temperature; Concentration;98.2%
97232-96-7

trans-cefuroxime axetil

64544-07-6

cefuroxime axetil

Conditions
ConditionsYield
In methanol; water at 25℃; Kinetics; Quantum yield; Irradiation;
40258-78-4

1-bromoethyl acetate

55268-75-2

Cefuroxime

A

108-20-3

di-isopropyl ether

B

64544-07-6

cefuroxime axetil

Conditions
ConditionsYield
With hydrogenchloride; potassium carbonate In ethyl acetate; N,N-dimethyl-formamide
64544-07-6

cefuroxime axetil

97232-96-7

trans-cefuroxime axetil

Conditions
ConditionsYield
In methanol; water at 25℃; Kinetics; Quantum yield; Irradiation;
In propylene glycol for 4h; Solvent; UV-irradiation;4.7 g
64544-07-6

cefuroxime axetil

A

cefuroxime sodium

B

Δ-2-cefuroxime axetil

C

(6R,7R)-7-[(Z)-2-(2-furyl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-2-cephem-4-carboxylic acid

Conditions
ConditionsYield
In phosphate buffer at 37℃; for 24h; pH=7.4; Product distribution; Kinetics; Further Variations:; Solvents;
64544-07-6

cefuroxime axetil

Δ-2-cefuroxime axetil

Conditions
ConditionsYield
With morpholine In dichloromethane at 20℃; for 7h; Solvent; Reagent/catalyst;5.9 g
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  • Cefuroxime Axetil

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    Cefuroxime Axetil

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    GMP/DMF/COS/CEP Storage:20°C Package:as client requirement Application:It is the 1-(acetyloxy) ethyl ester of Cefuroxime (C248060), an injectable second generation cephalosporin with an excellent antibacterial activity. Transportation:Express, Air ,S

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Standards and Recommendations

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.

Specification

The Cefuroxime Axetil with CAS registry number of 64544-07-6 is also known as Cefuroxime 1-acetoxyethyl ester. The IUPAC name is 1-Acetyloxyethyl(6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate. Its EINECS registry number is 259-560-1. In addition, the formula is C20H22N4O10S and the molecular weight is 510.47. This chemical is a white to pale yellow powder and should be stored in sealed containers in cool, dry place and away from oxidizing agents.

Physical properties about Cefuroxime Axetil are: (1)ACD/LogP: 1.22; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 1.22; (4)ACD/LogD (pH 7.4): 1.17; (5)ACD/BCF (pH 5.5): 4.96; (6)ACD/BCF (pH 7.4): 4.42; (7)ACD/KOC (pH 5.5): 109.43; (8)ACD/KOC (pH 7.4): 97.52; (9)#H bond acceptors: 14; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 182.79Å2; (13)Index of Refraction: 1.665; (14)Molar Refractivity: 117.51 cm3; (15)Molar Volume: 316.3 cm3; (16)Surface Tension: 63.8 dyne/cm; (17)Density: 1.61 g/cm3.

Preparation of Cefuroxime Axetil: it is prepared by reaction of cefuroxime. Sodium of cefuroxime reacts with 1-ethyl bromoacetate to generate the product.

Uses of Cefuroxime Axetil: it has antibacterial activity for a variety of gram-positive bacteria, gram-negative bacteria and anaerobic bacteria. It's also mainly used in clinical respiratory infections, urinary tract infections, gonococcal infections, skin and soft tissue infections caused by susceptible strains.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(OC(=O)C)OC(=O)C1=C(CSC2N1C(=O)C2NC(=O)C(=NOC)C3=CC=CO3)COC(=O)N
2. Isomeric SMILES: CC(OC(=O)C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N\OC)/C3=CC=CO3)COC(=O)N
3. InChI: InChI=1S/C20H22N4O10S/c1-9(25)33-10(2)34-19(28)15-11(7-32-20(21)29)8-35-18-14(17(27)24(15)18)22-16(26)13(23-30-3)12-5-4-6-31-12/h4-6,10,14,18H,7-8H2,1-3H3,(H2,21,29)(H,22,26)/b23-13-/t10?,14-,18-/m1/s1
4. InChIKey: KEJCWVGMRLCZQQ-YJBYXUATSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

GASTROINTESTINAL: NAUSEA OR VOMITING
Chemotherapy Vol. 34(Suppl,
mouse LD50 intraperitoneal 510mg/kg (510mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 34(Suppl,
mouse LD50 oral > 10gm/kg (10000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 34(Suppl,
mouse LD50 subcutaneous 1840mg/kg (1840mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Chemotherapy Vol. 34(Suppl,
rabbit LD50 oral 200mg/kg (200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Chemotherapy Vol. 34(Suppl,
rat LD50 intraperitoneal 950mg/kg (950mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 34(Suppl,
rat LD50 oral > 10gm/kg (10000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Chemotherapy Vol. 34(Suppl,
rat LD50 subcutaneous 2500mg/kg (2500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 34(Suppl,