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CAS No.: | 64485-93-4 |
---|---|
Name: | Cefotaxime sodium |
Article Data: | 17 |
Molecular Structure: | |
Formula: | C16H16N5NaO7S2 |
Molecular Weight: | 477.454 |
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 |
Solubility: | Soluble in water. |
Appearance: | White to pale yellow crystalline powder |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 42/43 |
Safety: | 22-36/37 |
PSA: | 229.88000 |
LogP: | -1.04720 |
cefotaxime
cefotaxime sodium salt
Conditions | Yield |
---|---|
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 acetate | 88.7% |
cefotaxime
cefotaxime sodium salt
Conditions | Yield |
---|---|
With sodium acetate trihydrate In water; acetone |
7-Aminocephalosporanic acid
cefotaxime sodium salt
Conditions | Yield |
---|---|
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; |
2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid
(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cefotaxime sodium salt
Conditions | Yield |
---|---|
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 |
2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid
cefotaxime sodium salt
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
In methanol for 1h; Reflux; | 77% |
Conditions | Yield |
---|---|
at 20℃; for 6h; | 72% |
Conditions | Yield |
---|---|
With methanesulfonic acid In acetonitrile at 20℃; for 3h; | 25% |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water pH=4.5; | 24% |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water pH=4.5; | 24% |
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
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.
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, |
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: Xn,Xi(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
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 .