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| CAS No.: | 50370-12-2 |
|---|---|
| Name: | Cefadroxil |
| Molecular Structure: | |
|
|
|
| Formula: | C16H17N3O5S |
| Molecular Weight: | 363.394 |
| Synonyms: | 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[amino(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-, [6R-[6a,7b(R*)]]-;Bidocef;Cefadrox;Cefadroxil;Cefadur;Cephadroxil;Cipadur;D-Cefadroxil;Helicef;Neucef;Sumacef;Ultracef;Cefadroxil anhydrous; |
| EINECS: | 256-555-6 |
| Density: | 1.592 g/cm3 |
| Melting Point: | 197°C (rough estimate) |
| Boiling Point: | 789.861 °C at 760 mmHg |
| Flash Point: | 431.492 °C |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 36/37/38-42/43 |
| Safety: | 26-36 |
| PSA: | 158.26000 |
| LogP: | 1.17960 |
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- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; ethyl acetate at 5℃; for 0.5h; pH=4; | 95% |
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| Multistep reaction.; | 94% |
- 22252-43-3, 26395-99-3, 70287-30-8, 72059-35-9
3-deacetyloxy-7-aminocephalosporanic acid
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| Stage #1: 3-deacetyloxy-7-aminocephalosporanic acid; ((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride With triethylamine In dichloromethane; water at -40 - 0℃; for 3h; Stage #2: With hydrogenchloride In dichloromethane; water for 1h; Stage #3: With sodium hydroxide In dichloromethane; water at 0℃; for 2h; pH=3.2; | 83% |
- 37763-23-8
D-2-p-hydroxyphenylglycine methyl ester
- 26395-99-3
7-aminodesacetoxycephalosporanic acid
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| immobilised Pen G acylase In water Enzymatic reaction; |
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water |
- 22252-43-3, 26395-99-3, 70287-30-8, 72059-35-9
3-deacetyloxy-7-aminocephalosporanic acid
- 78858-51-2
C16H19NO7
B
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| Stage #1: 3-deacetyloxy-7-aminocephalosporanic acid With 1H-imidazole; chloro-trimethyl-silane In dichloromethane for 3 - 4h; Heating / reflux; Stage #2: C16H19NO7 In DMF (N,N-dimethyl-formamide); dichloromethane at -45 - -20℃; for 2.5h; Stage #3: With hydrogenchloride In DMF (N,N-dimethyl-formamide); dichloromethane; water at 0 - 5℃; for 0.25h; |
- 22252-43-3, 26395-99-3, 70287-30-8, 72059-35-9
3-deacetyloxy-7-aminocephalosporanic acid
- 37763-23-8
D-2-p-hydroxyphenylglycine methyl ester
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| With formic acid; ammonia; immobilized Pen-G acylase mutant Phe-24-Ala In water at 12℃; for 2.5h; pH=7.3; Product distribution / selectivity; Enzymatic reaction; | |
| With penicillin acylasefrom Escherichia coli; water | |
| With penicillin G acylase immobilized on polymer microspheres supported Fe3O4 at 30℃; for 18h; Temperature; Ionic liquid; Enzymatic reaction; |
- 22252-43-3, 26395-99-3, 70287-30-8, 72059-35-9
3-deacetyloxy-7-aminocephalosporanic acid
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| With penicillin acylasefrom Escherichia coli; water |
- 61969-53-7
2,5-dihydroxy-N-(2-hydroxyethyl)benzamide
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| With air; sodium acetate buffer at 20℃; for 3h; pH=5.6; | 88% |
- 677-25-8
ethylenesulfonyl fluoride
- 50370-12-2
cefadroxil
| Conditions | Yield |
|---|---|
| In ethanol at 50℃; | 86% |
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Specification
The Cefadroxil, with the CAS registry number 50370-12-2, is also known as 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2R)-amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6R,7R)-. It belongs to the product categories of Active Pharmaceutical Ingredients; Alphabetic; C; CA - CGForensic and Veterinary Standards; Drugs & Metabolites; Neat Compounds. Its EINECS registry number is 256-555-6. This chemical's molecular formula is C16H17N3O5S and molecular weight is 363.39. What's more, both its IUPAC name and systematic name are the same which is called (6R,7R)-7-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. It should be stored in a cool, dry and well-ventilated place. Cefadroxil is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections. It is a bactericidal antibiotic.
Physical properties about Cefadroxil are: (1)ACD/LogP: -0.248; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -2.74; (4)ACD/LogD (pH 7.4): -3.40; (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: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 158.26 Å2; (13)Index of Refraction: 1.728; (14)Molar Refractivity: 90.944 cm3; (15)Molar Volume: 228.229 cm3; (16)Polarizability: 36.053×10-24cm3; (17)Surface Tension: 90.455 dyne/cm; (18)Density: 1.592 g/cm3; (19)Flash Point: 431.492 °C; (20)Enthalpy of Vaporization: 120.499 kJ/mol; (21)Boiling Point: 789.861 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
Preparation of Cefadroxil: this chemical can be prepared by cefadroxil. The yield is 94 %.
Uses of Cefadroxil: it is used to produce other chemicals. For example, it can react with acetic acid anhydride to get N-acetylcefadroxil. The reaction needs ambient temperature. The reaction time is 15 hours and yield is 53.3 %.
When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health. It is irritating to eyes, respiratory system and skin. It may cause sensitisation by inhalation and skin contact. Therefore, you should wear suitable protective clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
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@@H](c3ccc(O)cc3)N)C)C(=O)O
(2) InChI: InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1
(3) InChIKey: BOEGTKLJZSQCCD-UEKVPHQBSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | oral | > 2gm/kg (2000mg/kg) | Japanese Journal of Antibiotics. Vol. 35, Pg. 2736, 1982. | |
| mouse | LD50 | intraperitoneal | > 6gm/kg (6000mg/kg) | Japanese Journal of Antibiotics. Vol. 35, Pg. 2736, 1982. | |
| mouse | LD50 | intravenous | > 1500mg/kg (1500mg/kg) | Infection. Vol. 8(Suppl, | |
| mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Japanese Journal of Antibiotics. Vol. 35, Pg. 2736, 1982. | |
| mouse | LD50 | subcutaneous | > 8gm/kg (8000mg/kg) | Japanese Journal of Antibiotics. Vol. 35, Pg. 2736, 1982. | |
| rabbit | LD50 | oral | > 6gm/kg (6000mg/kg) | Japanese Journal of Antibiotics. Vol. 35, Pg. 2736, 1982. | |
| rat | LD50 | intraperitoneal | > 6gm/kg (6000mg/kg) | Japanese Journal of Antibiotics. Vol. 35, Pg. 2736, 1982. | |
| rat | LD50 | intravenous | > 1gm/kg (1000mg/kg) | Infection. Vol. 8(Suppl, | |
| rat | LD50 | oral | > 10gm/kg (10000mg/kg) | Drugs in Japan Vol. -, Pg. 552, 1990. | |
| rat | LD50 | subcutaneous | > 8gm/kg (8000mg/kg) | Japanese Journal of Antibiotics. Vol. 35, Pg. 2736, 1982. |