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64485-93-4

Basic Information
CAS No.: 64485-93-4
Name: Cefotaxime sodium
Molecular Structure:
Molecular Structure of 64485-93-4 (Cefotaxime sodium)
Formula: C16H16N5NaO7S2
Molecular Weight: 477.48
Synonyms: cefotaxim sodium salt;Cefotaxime Sodium (Sterile);Cefotaxime free acid;RU 24662;Liquiritin;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;sodium [6R-[6α,7β(Z)]]-3-(acetoxymethyl)-7-[(2-aminothiazol-4-yl)(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;Sodium (6R,7R)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 7(sup 2)-(Z)-(O-methyloxime), acetate (ester);Claforan (TN);Sodium 7-(2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)cephalosporanate;Cefotaxime sodium (JP14/USP);HR 756;Claforan sodium;Cefotaxime sodium salt;sodium (6R,7R)-3-(acetyloxymethyl)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;63527-52-6;Cefotaxime Sodium. Sterile;Cefotaxima [INN-Spanish];Cefotaxime sodium [USAN:JAN];sodium (6R,7R)-3-(acetyloxymethyl)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;Sodium (6R-(6alpha,7beta(Z)))-3-(acetoxymethyl)-7-((2-aminothiazol-4-yl)(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate;Prestwick_823;RU 24756;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)-;(+)-Cefotaxime sodium salt;Sodium cefotaxime;Tolycar;(6S,7S)-3-(acetyloxymethyl)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, monosodium salt, (6R-(6alpha,7beta(Z)))-;Cefotaxime Sodium sterile;
EINECS: 264-915-9
Density: 1.8 g/cm3
Melting Point: 162-163 °C
Boiling Point:
Flash Point:
Solubility: Soluble in water.
Appearance: White to pale yellow crystalline powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 42/43
Safety: 22-36/37
Transport Information:
PSA: 229.88000
LogP: -1.04720
Synthetic route
63527-52-6

cefotaxime

64485-93-4

cefotaxime sodium salt

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol Substitution;95.4%
With sodium isooctanoate; sodium sulfite In water; acetone at 5 - 10℃; for 0.5h;95%
With triethylamine; sodium 2-ethylhexanoic acid In methanol; ethyl acetate88.7%
64485-93-4

cefotaxime sodium salt

Conditions
ConditionsYield
With sodium acetate trihydrate In water; acetone
957-68-6

7-Aminocephalosporanic acid

64485-93-4

cefotaxime sodium salt

Conditions
ConditionsYield
Stage #1: 7-Aminocephalosporanic acid In water; acetone at 10℃; for 10h; Large scale;
Stage #2: With sodium hydroxide In water; acetone at 10 - 15℃; pH=9.5; Temperature; pH-value; Large scale;
91868-79-0

2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid

36923-17-8

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

64485-93-4

cefotaxime sodium salt

Conditions
ConditionsYield
Stage #1: 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid With dmap; dicyclohexyl-carbodiimide In ethanol at 20℃; for 0.5h;
Stage #2: With 1-hydroxy-pyrrolidine-2,5-dione In ethanol at 20℃; for 0.5h;
Stage #3: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Further stages;
2.59 g
91868-79-0

2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid

64485-93-4

cefotaxime sodium salt

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2.5 h / 2 - 25 °C
2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / -5 - 0 °C
3: sodium sulfite; sodium isooctanoate / water; acetone / 0.5 h / 5 - 10 °C
View Scheme

silver nitrate

64485-93-4

cefotaxime sodium salt

C32H32Ag2N10O14S4

Conditions
ConditionsYield
In methanol for 1h; Reflux;77%

tin(ll) chloride

64485-93-4

cefotaxime sodium salt

Sn(2+)*Cl(1-)*C16H16N5O7S2(1-)*H2O

Conditions
ConditionsYield
at 20℃; for 6h;72%
4741-45-1

furane-2-monocarboxylic acid

64485-93-4

cefotaxime sodium salt

80370-57-6

ceftiofur

Conditions
ConditionsYield
With methanesulfonic acid In acetonitrile at 20℃; for 3h;25%
2687-43-6

O-benzylhydoxylamine hydrochloride

64485-93-4

cefotaxime sodium salt

C23H24N6O7S2

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water pH=4.5;24%

N-methyl-O-allylhydroxylamine hydrochloride

64485-93-4

cefotaxime sodium salt

C20H24N6O7S2

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water pH=4.5;24%
38945-21-0

O-allylhydroxylamine hydrochloride

64485-93-4

cefotaxime sodium salt

C19H22N6O7S2

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water pH=4.5;16%
71925-14-9

O-benzyl-N-methylhydroxylamine hydrochloride

64485-93-4

cefotaxime sodium salt

C24H26N6O7S2

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water pH=4.5;14%
64485-93-4

cefotaxime sodium salt

A

104301-63-5

2-<<(2-amino-4-thiazolyl)((Z)-methoxyimino)acetyl>amino>acetoaldehyde

B

(Z)-4-Acetoxy-2-amino-3-mercaptomethyl-but-2-enoic acid

Conditions
ConditionsYield
With sodium hydroxide at 95℃; for 0.416667h;
64485-93-4

cefotaxime sodium salt

(E)-3-Acetoxymethyl-2-imino-4-(7-nitro-benzo[1,2,5]oxadiazol-4-ylsulfanyl)-but-3-enoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aq. NaOH / 0.42 h / 95 °C
2.1: Na2B4O7*10H2O / H2O
2.2: H2O; acetone / 0.5 h / 25 °C
View Scheme
101234-94-0

1-Cyclopropyl-4-thiopyridone

64485-93-4

cefotaxime sodium salt

(6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(1-cyclopropylpyridinium-4-yl)thiomethyl]-ceph-3-em-4-carboxylate

Conditions
ConditionsYield
With sodium iodide In water; acetone; acetonitrile
88-89-1

2,4,6-Trinitrophenol

64485-93-4

cefotaxime sodium salt

C16H16N5O7S2(1-)*C6H3N3O7*Na(1+)

Conditions
ConditionsYield
In methanol at 20℃; for 2h;
87-88-7

3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone

64485-93-4

cefotaxime sodium salt

C16H16N5O7S2(1-)*Na(1+)*C6H2Cl2O4

Conditions
ConditionsYield
In methanol at 20℃; for 2h;
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

64485-93-4

cefotaxime sodium salt

C16H16N5O7S2(1-)*Na(1+)*C8Cl2N2O2

Conditions
ConditionsYield
In methanol at 20℃; for 2h;
1518-16-7

7,7',8,8'-tetracyanoquinodimethane

64485-93-4

cefotaxime sodium salt

C16H16N5O7S2(1-)*Na(1+)*C12H4N4

Conditions
ConditionsYield
In methanol at 20℃; for 2h;
7758-99-8

copper(II) sulfate

64485-93-4

cefotaxime sodium salt

Cu(2+)*C16H16N5O7S2(1-)*Na(1+)

Conditions
ConditionsYield
In aq. acetate buffer at 60℃; for 0.666667h; pH=5.5; pH-value; Concentration; Temperature; Solvent;

cadmium sulfate

64485-93-4

cefotaxime sodium salt

Cd(2+)*C16H16N5O7S2(1-)*Na(1+)

Conditions
ConditionsYield
In aq. buffer at 40℃; for 0.666667h; pH=11; pH-value; Concentration; Temperature; Solvent;
64485-93-4

cefotaxime sodium salt

C16H16N5O7S2(1-)*Na(1+)*0.25H2O

Conditions
ConditionsYield
With water In methanol80.87 g
Raw Materials
63527-52-6
Downstream Products
80370-57-6
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    Cefotaxime Sodium CAS NO.64485-93-4

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    CAS NO.: 64485-93-4 EINECS NO.: 264-915-9 MF: C16H16N5NaO7S2 MW: 477.45 Appearance:White crystalline powder Specification:99%min Standard: EP/BP/USP Odor: odorless Appearance:White powder Storage:Store in cool and dry place, away

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    64485-93-4

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    64485-93-4

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    Cefotaxime Sodium for Injection CAS NO.64485-93-4

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Chemistry

Empirical Formula: C16H17N5O7S2
Molecular Weight: 455.4655 
EINECS: 264-915-9 
Index of Refraction: 1.778
Density: 1.8 g/cm3
Melting point: 162-163 °C(lit.)
Storage tempreture: 2-8 °C
Appearance: White to pale yellow crystalline powder
Structure of Cefotaxime sodium (CAS NO.64485-93-4):
                             
IUPAC Name: Sodium (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)[O-].[Na+]
Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)[O-].[Na+]
InChI: InChI=1S/C16H17N5O7S2.Na/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8;/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26);/q;+1/p-1/b20-9-;/t10-,14-;/m1./s1
InChIKey: AZZMGZXNTDTSME-JUZDKLSSSA-M
Product Category of Cefotaxime sodium (CAS NO.64485-93-4): API;Antibiotics for Research and Experimental Use;Biochemistry;Antibiotic Explorer;Heterocycles;Intermediates & Fine Chemicals;Sulfur & Selenium Compounds

Uses

 Cefotaxime sodium (CAS NO.64485-93-4) can be used as antibiotic medicine for the treatment of respiratory, urinary, intestinal and biliary tract, skin and soft tissue, burns, and bone and joint infections and other diseases.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 1800mg/kg/18D (1800mg/kg) BLOOD: AGRANULOCYTOSIS Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 739, 1983.
dog LD50 intramuscular > 716mg/kg (716mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 349, 1982.
dog LD50 intravenous > 1500mg/kg (1500mg/kg)   Journal of Antimicrobial Chemotherapy. Vol. 6(Suppl,
mouse LD50 intraperitoneal 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. APP-8, 1982.
mouse LD50 intravenous 6845mg/kg (6845mg/kg)   Antibiotiki i Khimioterapiya. Antibiotics and Chemotherapy. Vol. 35(5), Pg. 25, 1990.
mouse LD50 oral > 20gm/kg (20000mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
BEHAVIORAL: ATAXIA
Chemotherapy Vol. 28(Suppl,
mouse LD50 subcutaneous 12950mg/kg (12950mg/kg)   Drugs in Japan Vol. 6, Pg. APP-8, 1982.
rabbit LD50 intravenous 1880mg/kg (1880mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
BEHAVIORAL: ATAXIA
Chemotherapy Vol. 28(Suppl,
rat LD50 intramuscular > 2gm/kg (2000mg/kg)   Chemotherapy Vol. 28(Suppl,
rat LD50 intraperitoneal 10gm/kg (10000mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
BEHAVIORAL: ATAXIA
Chemotherapy Vol. 28(Suppl,
rat LD50 intravenous 7gm/kg (7000mg/kg)   Drugs in Japan Vol. 6, Pg. APP-8, 1982.
rat LD50 oral > 20gm/kg (20000mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)
BEHAVIORAL: ATAXIA
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 28(Suppl,
rat LD50 subcutaneous 18400mg/kg (18400mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)
BEHAVIORAL: ATAXIA
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 28(Suppl,

Safety Profile

Moderately toxic by intravenous and intramuscular routes. Mildly toxic by ingestion and intraperitoneal routes. Human systemic effects by intravenous route: agranulocytosis. An experimental teratogen. When heated to decomposition it emits toxic fumes of SOx, NOx and Na2O.
Hazard Codes: HarmfulXn,IrritantXi(Harmful)
Risk Statements:
R42/43 (May cause sensitization by inhalation and skin contact )
Safety Statements:
S22:Do not breathe dust  
S36/37 :Wear suitable protective clothing and gloves
WGK Germany: 2

Specification

 Cefotaxime sodium , its cas register number is 64485-93-4. It also can be called Claforan ; CTX ; and [6R-[6alpha,7beta(z)]]-3-[(Acetyloxy)methyl]-[[(2-amine-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid monosodium salt .