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Cefixime

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Name

Cefixime

EINECS 616-684-4
CAS No. 79350-37-1 Density 1.85 g/cm3
PSA 238.05000 LogP 0.36520
Solubility 55.11 mg/L in water Melting Point 218-225 °C
Formula C16H15N5O7S2 Boiling Point N/A
Molecular Weight 453.456 Flash Point N/A
Transport Information N/A Appearance white to off white powder or off white crystal powder
Safety 22-36/37-45 Risk Codes 42/43
Molecular Structure Molecular Structure of 79350-37-1 (Cefixime) Hazard Symbols HarmfulXn
Synonyms

(-)-Cefixim;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, (6R,7R)-;(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefspan;Suprax (TN);Cefixima [Spanish];Cefixim;FR 17027;Cephoral;Cefixime (JP14/USP);Cefiximum [Latin];Cefixoral;Unixime;(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefixime Micronized;

Article Data 6

Cefixime Synthetic route

88621-01-6

7-{2-[(2-aminothiazol)-4-yl]-2-[(Z)(methoxycarbonyl)methoxyimino]acetamido}-3-vinyl-ceph-3-em-4-carboxylic acid

79350-37-1

cefixime

Conditions
ConditionsYield
Stage #1: 7-{2-[(2-aminothiazol)-4-yl]-2-[(Z)(methoxycarbonyl)methoxyimino]acetamido}-3-vinyl-ceph-3-em-4-carboxylic acid With sodium hydroxide; water at 0 - 5℃; for 0.0833333h;
Stage #2: With hydrogenchloride In water at 34 - 36℃; pH=2.3; Product distribution / selectivity;
With sodium hydrogencarbonate; sodium hydroxide In water at 0 - 15℃; for 0.25h;162 g
80544-17-8

2-(2-aminothiazol-4-yl)-2-[(Z)-methoxycarbonylmethoxyimino]acetic acid

79350-37-1

cefixime

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,4-diaza-bicyclo[2.2.2]octane; tributyl-amine / dichloromethane / -5 - 20 °C / 7125.71 Torr
2: sodium hydroxide; sodium hydrogensulfite / tetrahydrofuran; water / 6 h / 5 - 10 °C
3: sodium hydroxide; sodium hydrogencarbonate / water / 0.25 h / 0 - 15 °C
View Scheme

7-Amino-3-vinyl-3-cephem-4-carboxylic acid

2-(2-amino-4-thiazolyl)-2-(carboxymethoxy)iminoacetyl chloride

79350-37-1

cefixime

Conditions
ConditionsYield
at 10℃; for 5h; Temperature;4.7 g
90-02-8

salicylaldehyde

79350-37-1

cefixime

1312673-65-6

8-(2-carboxymethoxyimino-2-{2-[(2-hydroxybenzylidene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: salicylaldehyde; cefixime With potassium hydroxide In methanol for 0.5h; pH=7 - 8; Reflux;
Stage #2: With acetic acid In methanol pH=7;
85%
98-01-1

furfural

79350-37-1

cefixime

1312673-67-8

8-(2-carboxymethoxyimino-2-{2-[(furan-2-ylmethylene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: furfural; cefixime With potassium hydroxide In methanol for 0.5h; pH=7 - 8; Reflux;
Stage #2: With acetic acid In methanol pH=7;
80%
1003-29-8

2-pyrrole aldehyde

79350-37-1

cefixime

1312673-69-0

8-(2-carboxymethoxyimino-2-{2-[(1H-pyrrol-2-ylmethylene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: 2-pyrrole aldehyde; cefixime With potassium hydroxide In methanol for 0.5h; pH=7 - 8; Reflux;
Stage #2: With acetic acid In methanol pH=7;
78%
98-03-3

thiophene-2-carbaldehyde

79350-37-1

cefixime

1312673-68-9

8-(2-carboxymethoxyimino-2-{2-[(thiophen-2-ylmethylene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: thiophene-2-carbaldehyde; cefixime With potassium hydroxide In methanol for 0.5h; pH=7 - 8; Reflux;
Stage #2: With acetic acid In methanol pH=7;
78%
79350-37-1

cefixime

98-09-9

benzenesulfonyl chloride

7-[2-(2-benzenesulfonylamino-thiazol-4-yl)-2-carboxymethoxyimino-acetylamino]-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; pH=6 - 8;75.8%
79350-37-1

cefixime

121-60-8

p-acetylaminobenzenesulfonyl chloride

7-{2-[2-(4-acetylaminobenzenesulfonylamino)-thiazol-4-yl]-2-carboxymethoxyimino-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; pH=6 - 8;69.8%
79350-37-1

cefixime

(R,R)-α-<(Z)-2-(2-amino-4-thiazolyl)-2-(carboxymethoxyimino)acetamido>-4-carboxy-5,6-dihydro-5-ethylidene-2H-1,3-thiazine-2-acetic acid

Conditions
ConditionsYield
With sodium hydroxide In water for 4h; Ambient temperature; pH 12;15%
In water at 25℃; Rate constant; Mechanism; pH 9;

Cefixime Specification

The Cefixime, with the CAS registry number 79350-37-1, has the IUPAC name of (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethyloxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Being a kind of white or light yellow crystalline powder with no odour, it is easily soluble in ethanol or dimethylsulfoxide, slightly soluble in acetone while insoluble in hexane, acetic acid or water. And its product categories are including Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds.

The physical properties of this chemical are as follows: (1)ACD/LogP: 1.00; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -3.61; (4)ACD/LogD (pH 7.4): -3.78; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 12; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 184.48; (13)Index of Refraction: 1.811; (14)Molar Refractivity: 105.6 cm3; (15)Molar Volume: 244.4 cm3; (16)Polarizability: 41.86×10-24 cm3; (17)Surface Tension: 89.9 dyne/cm; (18)Density: 1.85 g/cm3; (19)Exact Mass: 453.041289; (20)MonoIsotopic Mass: 453.041289; (21)Topological Polar Surface Area: 238; (22)Heavy Atom Count: 30; (23)Complexity: 861.

As to its usage, it is widely applied in many ways. It could be used in the third generation oral cephalosporins broad-spectrum antibiotic, with good antibacterial action to the streptococcus, Gram-negative bacteria, colibacillus, pneumobacillus, and proteus mirabilis. It could also be used to treat pharyngitis, gonorrhes and tonsilitis.
 
When you are dealing with this chemical, you should be much more cautious. For being a kind of harmful chemical, it may cause damage to health and may cause sensitisation by inhalation and skin contact. Therefore, you should wear suitable protective clothing and gloves and if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Then do not breathe dust.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O
(2)Isomeric SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
(3)InChI: InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
(4)InChIKey: OKBVVJOGVLARMR-QSWIMTSFSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 3200mg/kg (3200mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: STRUCTURAL OR FUNCTIONAL CHANGES IN URETER
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
dog LD50 oral > 600mg/kg (600mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 intravenous 4420mg/kg (4420mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 intravenous 6990mg/kg (6990mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.

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