Cefotaxime supplier | CasNO.63527-52-6

Name
Cefotaxime
EINECS 264-299-1
CAS No. 63527-52-6
Article Data47
CAS DataBase
Density 1.8 g/cm³
Solubility soluble in water
Melting Point
Formula C₁₆H₁₇N₅O₇S₂
Boiling Point
Molecular Weight 455.472
Flash Point
Transport Information
Appearance white power
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Zeefotax;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[(acetyloxy)methyl]-7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-,[6R-[6a,7b(Z)]]-;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)- (9CI);Cefabol;Cefotaxime acid;Ceftax;Claforan;Omnatax;Taxim;
PSA 227.05000
LogP 0.28750

Synthetic route

: 80756-85-0
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

: 957-68-6
7-Aminocephalosporanic acid

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
With TEA In dichloromethane at 20℃; for 1h; Substitution;	95%
With triethylamine In dichloromethane at 20℃; for 1h;	95%
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-Aminocephalosporanic acid With triethylamine In methanol at 0 - 5℃; Stage #2: With hydrogenchloride In methanol; water at 0 - 5℃; for 1h; pH=2.3 - 2.5;
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-Aminocephalosporanic acid With triethylamine In 1,2-dimethoxyethane at -5 - 0℃; Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water for 1h; pH=2.6 - 2.8; Product distribution / selectivity;

: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate

: 957-68-6
7-Aminocephalosporanic acid

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Stage #1: 7-Aminocephalosporanic acid With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 20℃; for 1h; Stage #2: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate In dichloromethane at 20℃; for 8h; Stage #3: With sodium hydroxide In dichloromethane; water at 15 - 20℃; pH=7.5 - 7.8;	94.4%
Stage #1: 7-Aminocephalosporanic acid With N,O-bis-(trimethylsilyl)-acetamide In DMF (N,N-dimethyl-formamide) at 20 - 25℃; Stage #2: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;	93.5%

: C21H16N6O3S

: 957-68-6
7-Aminocephalosporanic acid

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at -5 - 0℃; for 1h; Temperature;	93.1%

: 957-68-6
7-Aminocephalosporanic acid

: 207725-19-7
(2-Amino-thiazol-4-yl)-[(Z)-methoxyimino]-acetic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
With N,O-bis-dimethylsilyl acetamide In acetonitrile at 0 - 5℃; for 1.5h;	75.4%

: 7-[4-bromo-2(Z)-methoxyimino-3-oxobutyramido]-cephalosporanic acid

: 17356-08-0
thiourea

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Stage #1: 7-[4-bromo-2(Z)-methoxyimino-3-oxobutyramido]-cephalosporanic acid; thiourea With sodium acetate In dichloromethane; water for 2.5 - 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2.8;	40.3%

: 957-68-6
7-Aminocephalosporanic acid

: 64485-90-1
2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
(i) DCC, CH2Cl2, (ii) /BRN= 622638/, Et3N, (iii) aq. HCO2H; Multistep reaction;

: 65243-53-0
pyvaloyloxymethyl 7β-<2-(2-aminothiazol-4-yl)-(Z)-methoxyiminoacetamido>-3-acetoxymethyl-3-cephem-4-carboxylate

A: 63527-52-6
cefotaxime

B: 126747-48-6
(2R,6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid

C: (2R,6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Conditions

Conditions	Yield
With water In N,N-dimethyl-formamide at 37℃; Rate constant; phosphate buffer, var. pH;

...Expand

: 64485-88-7
ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / dimethylformamide / 3 h 2: aq. NaOH / dioxane / 0.5 h / Heating 3: (i) DCC, CH2Cl2, (ii) /BRN= 622638/, Et3N, (iii) aq. HCO2H View Scheme

: 65872-39-1
(Z)-γ-bromo-β-oxo-α-methoxyiminobutyric acid ethyl ester

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ethanol; H2O / 1 h / 20 °C 2: Et3N / dimethylformamide / 3 h 3: aq. NaOH / dioxane / 0.5 h / Heating 4: (i) DCC, CH2Cl2, (ii) /BRN= 622638/, Et3N, (iii) aq. HCO2H View Scheme

: 64485-89-8
ethyl (Z)-2-(methoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / dioxane / 0.5 h / Heating 2: (i) DCC, CH2Cl2, (ii) /BRN= 622638/, Et3N, (iii) aq. HCO2H View Scheme

: C15H16ClN3O8S

: 17356-08-0
thiourea

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Stage #1: C15H16ClN3O8S; thiourea With triethylamine In tetrahydrofuran; water at 20 - 25℃; for 4h; pH=7.5; Stage #2: With hydrogenchloride In water at 15 - 20℃; for 0.5h; pH=3 - 4.2;

: 71754-15-9
C15H16ClN3O8S

: 17356-08-0
thiourea

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Stage #1: C15H16ClN3O8S; thiourea With sodium acetate In tetrahydrofuran; water at 20℃; for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 10℃; for 1h; pH=2.5;

: 64486-19-7
7β-[2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Stage #1: 7β-[2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid With water; sodium carbonate; thiourea; isopropyl alcohol at 20 - 30℃; Stage #2: With hydrogenchloride; water In isopropyl alcohol at 20 - 30℃; for 2h; pH=2.7 - 3.0;

: 80756-85-0
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

: 957-68-6
7-Aminocephalosporanic acid

A: 63527-52-6
cefotaxime

B: 149-30-4
2-Mercaptobenzothiazole

Conditions

Conditions	Yield
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-Aminocephalosporanic acid With sodium 2-ethylhexanoate In water; acetonitrile at 6 - 8℃; for 12h; Stage #2: In water; acetonitrile pH=2.5 - 3.0;

...Expand

: 111230-59-2
4-chloro-2-methoxyimino-3-oxo-butyric acid

: 17356-08-0
thiourea

: 957-68-6
7-Aminocephalosporanic acid

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Stage #1: 4-chloro-2-methoxyimino-3-oxo-butyric acid With phosphorus pentachloride In dichloromethane at -5 - 0℃; for 1h; Stage #2: 7-Aminocephalosporanic acid With ammonia In water; acetone at -5 - 0℃; for 0.5 - 0.666667h; pH=6.5 - 7; Stage #3: thiourea With sodium acetate In water; acetone at 18 - 20℃; for 1h;

...Expand

: C13H11N5O2S2

: 957-68-6
7-Aminocephalosporanic acid

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Stage #1: C13H11N5O2S2; 7-Aminocephalosporanic acid With sodium hydrogensulfite; triethylamine In ethanol; dichloromethane; isopropyl alcohol at 5℃; pH=7 - 8; Stage #2: With hydrogenchloride In water; acetone at 10℃; for 1.5h; pH=2.5; Temperature;

: 10416-59-8
N,O-bis-(trimethylsilyl)-acetamide

: 57079-45-5
D-(-)-2-formyloxy-2-phenylacetyl chloride

: 7-amino-3-(4-methylthiazolyl)-3-cephem-4-carboxylic acid

: 141-78-6
ethyl acetate

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
at 20℃;

...Expand

: 91868-79-0
2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid

: 63527-52-6
cefotaxime

Conditions

Conditions	Yield
Multi-step reaction with 2 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 View Scheme

: 63527-52-6
cefotaxime

: 64485-93-4
cefotaxime sodium salt

Conditions

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%

: 63527-52-6
cefotaxime

: 79-04-9
chloroacetyl chloride

: 64486-19-7
7β-[2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
In N,N-dimethyl acetamide at 20℃; for 1h;	90.2%

: 63527-52-6
cefotaxime

: 908093-98-1
diazodiphenylmethane

: benzhydryl (6R,7R,Z)-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 0.75h; pH=3; Inert atmosphere;	80%

: 63527-52-6
cefotaxime

: 239468-67-8
5-[(4-methylquinolin-2-yloxy)methyl]-1,3,4-thiadiazole-2-thiol

: 7-{[(2-aminothiazol-4-yl)(methoxyimino)acetyl]amino}-3-{[5-[(4-methylquinolin-2-yloxy)methyl]-1,3,4-thiadiazol-2-ylthio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid for 0.0333333h; Condensation; microwave irradiation;	58%

: 63527-52-6
cefotaxime

: 239468-65-6
5-[(quinolin-8-yloxy)methyl]-1,3,4-thiadiazole-2-thiol

: 7-{[(2-aminothiazol-4-yl)(methoxyimino)acetyl]amino}-3-{[5-[(quinolin-8-yloxy)methyl]-1,3,4-thiadiazol-2-ylthio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid for 0.0166667h; Condensation; microwave irradiation;	54%

: 63527-52-6
cefotaxime

: 4741-45-1
furane-2-monocarboxylic acid

: 80370-57-6
ceftiofur

Conditions

Conditions	Yield
With methanesulfonic acid; sulfuric acid In acetonitrile at 15 - 20℃;	54%
With methanesulfonic acid In dichloromethane at 23 - 27℃;	47%
With methanesulfonic acid In ethyl acetate at 30℃;	47%

: 63527-52-6
cefotaxime

: 202116-95-8
5-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-1,3,4-thiadiazole-2-thiol

: 7-{[(2-aminothiazol-4-yl)(methoxyimino)acetyl]amino}-3-{[5-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-1,3,4-thiadiazol-2-ylthio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid for 0.025h; Condensation; microwave irradiation;	52%

: 63527-52-6
cefotaxime

: 202116-96-9
5-[(tetrazol-1-yl)methyl]-1,3,4-thiadiazole-2-thiol

: 7-{[(2-aminothiazol-4-yl)(methoxyimino)acetyl]amino}-3-{[5-[(tetrazol-1-yl)methyl]-1,3,4-thiadiazol-2-ylthio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid for 0.025h; Condensation; microwave irradiation;	48%

: 63527-52-6
cefotaxime

: 3724-43-4, 149409-22-3
Vilsmeier reagent

: C33H34N10O14S4

Conditions

Conditions	Yield
at 35℃; for 2.5h;	35.8%

: 63527-52-6
cefotaxime

: 24589-78-4
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

: 104498-86-4
C19H25N5O7S2Si

Conditions

Conditions	Yield
In dichloromethane at 40℃;

: 63527-52-6
cefotaxime

: 24589-78-4
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

: C20H31N5O6S2Si2

Conditions

Conditions	Yield
In dichloromethane for 1h;

: 63527-52-6
cefotaxime

: (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-bromomethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
In dichloromethane

: 63527-52-6
cefotaxime

: 86070-92-0
(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-iodomethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions

Conditions	Yield
In dichloromethane
With trimethylsilyl iodide; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide In dichloromethane at 20℃; for 0.5h; Substitution;

: 63527-52-6
cefotaxime

: 533-37-9
2,3-cyclopentenopyridine

: 84957-29-9, 97164-55-1, 130431-30-0
cefpirome

Conditions

Conditions	Yield
With potassium iodide In water at 70℃;

: 63527-52-6
cefotaxime

: 24589-78-4
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

: 83421-24-3
7β-<2-(2-aminothiazol-4yl)-2-(Z)-methoximinoacetamide>-3-iodomethyl-2-<(trimethylsilyloxy)carbonyl>cephalosporin

Conditions

Conditions	Yield
Stage #1: cefotaxime; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide In dichloromethane for 1h; Iodination; Stage #2: With trimethylsilyl iodide In dichloromethane for 0.5h; Condensation;

: 63527-52-6
cefotaxime

: 87239-81-4
cefpodoxime proxetil

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 90.2 percent / N,N-dimethyl-acetamide / 1 h / 20 °C 2: 65 percent / aq. NaHCO3; CaCl2*2H2O / 1.25 h / 70 °C 3: 2.4 g / dicyclohexylamine / N,N-dimethyl-acetamide / 0.75 h / 0 - 5 °C 4: 1.44 g / thiourea / N,N-dimethyl-acetamide / 3 h / 20 °C View Scheme

: 63527-52-6
cefotaxime

: 82618-67-5
7β-[2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90.2 percent / N,N-dimethyl-acetamide / 1 h / 20 °C 2: 65 percent / aq. NaHCO3; CaCl2*2H2O / 1.25 h / 70 °C View Scheme

: 63527-52-6
cefotaxime

: 620962-96-1
(6R,7R)-7-{2-[2-(2-Chloro-acetylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90.2 percent / N,N-dimethyl-acetamide / 1 h / 20 °C 2: 65 percent / aq. NaHCO3; CaCl2*2H2O / 1.25 h / 70 °C 3: 2.4 g / dicyclohexylamine / N,N-dimethyl-acetamide / 0.75 h / 0 - 5 °C View Scheme

: 63527-52-6
cefotaxime

: C19H21N7O5S3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: MSTFA; TMSI / CH2Cl2 / 0.5 h / 20 °C 2: 0.10 g / MSTFA / acetonitrile; tetrahydrofuran / 20 h / 20 °C View Scheme

: 63527-52-6
cefotaxime

: C20H23N7O5S3

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: MSTFA; TMSI / CH2Cl2 / 0.5 h / 20 °C 2: MSTFA / acetonitrile; tetrahydrofuran / 20 h / 20 °C View Scheme

: 63527-52-6
cefotaxime

: C22H20N8O5S2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CH2Cl2 / 1 h 1.2: Me3SiI / CH2Cl2 / 0.5 h 2.1: acetonitrile; tetrahydrofuran / 16 h / 20 °C View Scheme

Cefotaxime Specification

The Cefotaxime with CAS registry number of 63527-52-6 is also known as Cefotaximum. The IUPAC name is (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-carboxylic acid. Its EINECS registry number is 264-299-1. In addition, the formula is C₁₆H₁₇N₅O₇S₂ and the molecular weight is 455.47. This chemical is a white power.

Physical properties about Cefotaxime are: (1)ACD/LogP: 1.20; (2)# of Rule of 5 Violations: 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 12; (8)#H bond donors: 4; (9)#Freely Rotating Bonds: 8; (10)Index of Refraction: 1.778; (11)Molar Refractivity: 105.95 cm³; (12)Molar Volume: 252.8 cm³; (13)Surface Tension: 81.2 dyne/cm; (14)Density: 1.8 g/cm³.

Preparation of Cefotaxime: it is prepared by reaction of cephalosporin C. Firstly, cefotaxime is crystallizated after cracking, silicon esterification, condensation and hydrolysis. Secondly, add sodium acetate to get sodium. Product is obtained after bleaching, sterile filtration and crystallization.

Uses of Cefotaxime: it is used as antibacterial drugs and is a semi-synthetic oxime-type cephalosporins. It is used for infections of the respiratory tract, skin, bones, joints, urogenital system, meningitis, and septicemia. This chemical is used to produce 7b-(2-(2-Aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido)-3-acetoxymethyl-3-cephem-4-carboxylic acid sodium salt. The reaction occurs with reagent aq. NaHCO₃ and solvent ethanol. The yield is about 95.4%.

Cefotaxime is used to produce 7b-(2-(2-Aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido)-3-acetoxymethyl-3-cephem-4-carboxylic acid sodium salt.

You can still convert the following datas into molecular structure:
1. SMILES: O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=NOC)c3nc(sc3)N)COC(=O)C)C(=O)O
2. InChI: InChI=1/C16H17N5O7S2/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)/t10-,14-/m1/s1
3. InChIKey: GPRBEKHLDVQUJE-QMTHXVAHBP

Product Name

Cefotaxime

Synthetic route

Cefotaxime Specification

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