Cefpodoxime supplier | CasNO.80210-62-4

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Cas Database

Name	Cefpodoxime	EINECS	N/A
CAS No.	80210-62-4	Density	1.785 g/cm³
PSA	209.98000	LogP	0.37080
Solubility	N/A	Melting Point	200-202 °C
Formula	C₁₅H₁₇N₅O₆S₂	Boiling Point	N/A
Molecular Weight	427.462	Flash Point	N/A
Transport Information	N/A	Appearance	off-white solid
Safety	22-36/37-45	Risk Codes	42/43
Molecular Structure		Hazard Symbols	Xn
Synonyms	5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-,[6R-[6a,7b(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-,(6R,7R)- (9CI);Cefpodoxime acid;R 3763;	Article Data	10

Cefpodoxime Synthetic route

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

: 24701-69-7
(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at -5 - 5℃; for 2h;	82.86%
With triethylamine In tetrahydrofuran at 0 - 5℃; for 2h;	82.86%
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In methanol at 8 - 12℃; Stage #2: With sulfuric acid In methanol; water at 0 - 20℃; pH=2.4 - 2.5; Product distribution / selectivity;
With triethylamine In methanol; water at 15 - 20℃;	81 mg

: 124-41-4
sodium methylate

: 75994-59-1
2-(2-amino-4-thiazolyl)-2-(Z)-methoxyiminoacetyl chloride

: 7-amino-3-chloromethyl-3-cephem-4-carboxylic acid

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
Stage #1: sodium methylate; 7-amino-3-chloromethyl-3-cephem-4-carboxylic acid With benzyltrihexylammonium chloride; potassium iodide In dimethyl sulfoxide at 15℃; for 8h; Stage #2: 2-(2-amino-4-thiazolyl)-2-(Z)-methoxyiminoacetyl chloride In dimethyl sulfoxide at 10℃; for 4h; Temperature; Solvent; Reagent/catalyst;	82.2%

: 82618-98-2
(6R,7R)-7-{2-(2-Amino-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 2,2-dimethyl-propionyloxymethyl ester

A: 126747-46-4
(2R,6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid

B: 80210-62-4
cefpodoxime

C: 126617-55-8
(2R,6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-methoxymethyl-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, add of bovin serum albumin (as protein);

: 957-68-6
7-Aminocephalosporanic acid

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanesulfonic acid / 5 - 12 °C 2: triethylamine / water; methanol / 15 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: methyl bisulfate / N,N-dimethyl-formamide; methanol / 5 h / 0 - 20 °C 2: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C View Scheme

: 15690-38-7
(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanesulfonic acid / acetonitrile / 5 - 40 °C 2: triethylamine / methanol; water / 15 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: methanesulfonic acid / 5 - 40 °C 2: triethylamine / methanol; water / 15 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: methanesulfonic acid / 5 - 40 °C 2: triethylamine / methanol; water / 15 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: methanesulfonic acid / 5 - 40 °C 2: triethylamine / methanol; water / 15 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / acetonitrile / 0.92 h / -20 - 25 °C 1.2: 25 °C 2.1: triethylamine / dichloromethane / 5 - 25 °C / pH 8 - 9 View Scheme

: (benzothiazol-2-yl)-2-(2-aminothiazol-4-yl)-Z-2-methoxyimino-thioacetate

: 24701-69-7
(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
Stage #1: (benzothiazol-2-yl)-2-(2-aminothiazol-4-yl)-Z-2-methoxyimino-thioacetate; (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In methanol; water at 15 - 20℃; Stage #2: With sulfuric acid In methanol; water

: 94088-75-2
2-(2-amino-1,3-thiazol-4-yl)-1-(1,3-benzothiazol-2-ylsulfanyl)-2-(methoxyimino)ethan-1-one

: 24701-69-7
(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 5 - 25℃; pH=8 - 9; Temperature;

: 65872-41-5
cefotaxime

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N-dimethyl acetamide / 0.08 h 1.2: 1.5 h / -11 - 15 °C 2.1: triethylamine / methanol / 0.5 h / -30 - 0 °C View Scheme

: C13H13N3O5S2

: 24701-69-7
(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
With triethylamine In methanol at -30 - 0℃; for 0.5h; Solvent;

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

: 15690-38-7
(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 149-73-5
trimethyl orthoformate

: 80210-62-4
cefpodoxime

Conditions

Conditions	Yield
Stage #1: trimethyl orthoformate With boron trifluoride diethyl etherate In acetonitrile at -30℃; for 1.58333h; Stage #2: (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid In acetonitrile at 25℃; for 0.25h; Stage #3: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With triethylamine In dichloromethane at 0℃; pH=8 - 9;

Yield

Stage #1: trimethyl orthoformate With boron trifluoride diethyl etherate In acetonitrile at -30℃; for 1.58333h;
Stage #2: (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid In acetonitrile at 25℃; for 0.25h;
Stage #3: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With triethylamine In dichloromethane at 0℃; pH=8 - 9;

Cefpodoxime Specification

The Cefpodoxime, with the CAS registry number 80210-62-4, is also known as 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-,(6R,7R)-. It belongs to the product categories of Various Metabolites and Impurities; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; Heterocycles; Sulfur & Selenium Compounds. This chemical's molecular formula is C₁₅H₁₇N₅O₆S₂ and molecular weight is 427.46. What's more, its systematic name is (6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Cefpodoxime is an oral third generation cephalosporin antibiotic. It is marketed as the prodrug cefpodoxime proxetil by Pharmacia & Upjohn under the trade name Vantin. It is commonly used to treat acute otitis media, pharyngitis, and sinusitis. This chemical also finds use as oral continuation therapy when intravenous cephalosporins (such as ceftriaxone) are no longer necessary for continued treatment.

Physical properties of Cefpodoxime are: (1)ACD/LogP: 0.938; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.80; (4)ACD/LogD (pH 7.4): -2.81; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 11; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.78; (13)Molar Refractivity: 100.498 cm³; (14)Molar Volume: 239.526 cm³ ; (15)Polarizability: 39.84 10-24cm³; (16)Surface Tension: 79.25 dyne/cm; (17)Density: 1.785 g/cm³

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(=N\OC)/c3nc(sc3)N)COC)C(=O)O
(2)Std. InChI: InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1
(3)Std. InChIKey: WYUSVOMTXWRGEK-HBWVYFAYSA-N

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