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Cefdinir
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Name

Cefdinir

 EINECS 643-088-1
CAS No. 91832-40-5 Density 1.89 g/cm3
PSA 211.75000 LogP 0.73820
Solubility Soluble in water Melting Point >180 °C dec
Formula C14H13N5O5S2 Boiling Point N/A
Molecular Weight 395.42 Flash Point N/A
Transport Information N/A Appearance Pale yellow solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 91832-40-5 (Cefdinir) Hazard Symbols N/A
Synonyms

Cefzon;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl) (hydroxyimino)acetyl)amino)-3-ethenyl-8-oxo-, (6R-(6alpha,7beta(Z)))-;Cefdinirum [INN-Latin];(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyimino-acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefdinir [USAN:INN];(6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyimino-acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefzon (TN);Omnicef;(-)-(6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-oxime;Omnicef (TN);Cefdinyl;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylic acid,7-[[(2Z)-(2-amino-4- thiazolyl)(hydroxyimino)acetyl]amino]-3- ethenyl-8-oxo-,(6R,7R)-;

Article Data 31

Cefdinir Synthetic route

7-amino-3-vinylcephalosporin-4-carboxylic acid p-nitrobenzyl ester

1-[(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetoxy]benzotriazole

91832-40-5

cefdinir

Conditions
ConditionsYield
Stage #1: 7-amino-3-vinylcephalosporin-4-carboxylic acid p-nitrobenzyl ester With N-cyclohexyl-cyclohexanamine In water; isopropyl alcohol; acetonitrile at 5 - 10℃; for 0.166667h;
Stage #2: 1-[(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetoxy]benzotriazole In water; isopropyl alcohol; acetonitrile at 20℃; Further stages;		98%

potassium syn-7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate tetrahydrate

91832-40-5

cefdinir

Conditions
ConditionsYield
With hydrogenchloride In water at 25 - 30℃; for 2h; pH=2.4 - 2.5;90%
104797-47-9

S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate

79349-82-9

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

91832-40-5

cefdinir

Conditions
ConditionsYield
Stage #1: S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In tetrahydrofuran at 20 - 23℃; for 5h;
Stage #2: With hydrogenchloride; methoxybenzene In tetrahydrofuran; dichloromethane at -25 - -20℃; for 1.5h;		88.6%
Stage #1: S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In tetrahydrofuran; water at 20℃; for 4 - 6h;
Stage #2: With potassium carbonate In water at 20℃; for 0.5 - 0.75h; pH=8.0 - 8.2;
Stage #3: With sulfuric acid In water pH=2 - 2.5;
Stage #1: S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid In tetrahydrofuran for 0.166667h;
Stage #2: With water; triethylamine In tetrahydrofuran; dichloromethane at 15 - 25℃; for 3 - 4h;
Stage #3: With sulfuric acid; water In tetrahydrofuran; dichloromethane at 35 - 40℃; for 2h; pH=2.4 - 2.5;
79349-82-9

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

143183-03-3

S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate

91832-40-5

cefdinir

Conditions
ConditionsYield
Stage #1: (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate With triethylamine In N,N-dimethyl acetamide at 15 - 20℃; for 4h;
Stage #2: With hydrogenchloride; methoxybenzene In dichloromethane; N,N-dimethyl acetamide at -15 - -10℃; for 2h;		85.8%
128454-32-0

7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

91832-40-5

cefdinir

Conditions
ConditionsYield
With formic acid at 20℃; for 3h;2.54 g
127770-93-8

C16H15N5O6S2

91832-40-5

cefdinir

Conditions
ConditionsYield
With ammonium chloride; water; potassium carbonate at 18 - 22℃; pH=8 - 8.2;
128454-32-0

7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

A

3-methyl cefdinir

B

Cefdinir sulfoxide

C

(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(Z)-(hydroxyimino)acetamido]-3-vinyl-2-cephem-4-carboxylic acid

D

91832-40-5

cefdinir

Conditions
ConditionsYield
With trifluoroacetic acid at 10 - 15℃; for 4h; Further byproducts.;A n/a
B n/a
C n/a
D 39.5 g

C16H15N5O6S2*C6H15N

A

3-methyl cefdinir

B

C14H15N5O6S2

C

91832-40-5

cefdinir

D

7β-[(E)-2-(2-amino-4-thiazolyl)-2-(hydroxyimino)acetamido]-3-vinylcephem-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: C16H15N5O6S2*C6H15N With ammonium chloride; potassium carbonate In tetrahydrofuran at 20 - 25℃; for 0.166667h; pH=5;
Stage #2: With sulfuric acid at 20 - 40℃; pH=2.5 - 2.6; Further stages. Title compound not separated from byproducts.;		A n/a
B n/a
C 160 g
D n/a
104797-47-9

S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate

91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran; H2O / 6 h / 15 - 20 °C
2: ammonium chloride; potassium carbonate; water / 18 - 22 °C / pH 8 - 8.2
View Scheme

(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetic acid

91832-40-5

cefdinir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / triphenylphosphine; triethylamine / CH2Cl2 / 0.5 h / 10 - 30 °C
2: triethylamine / tetrahydrofuran; H2O / 6 h / 15 - 20 °C
3: ammonium chloride; potassium carbonate; water / 18 - 22 °C / pH 8 - 8.2
View Scheme

Cefdinir Chemical Properties

Molecular Structure of Cefdinir (CAS NO.91832-40-5):

IUPAC Name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Formula: C14H13N5O5S2
Molecular Weight: 395.413520 g/mol
H bond acceptors: 10
H bond donors: 5
Freely Rotating Bonds: 6
Polar Surface Area: 158.18 Å2
Index of Refraction: 1.861
Molar Refractivity: 94.14 cm3
Molar Volume: 208.6 cm3
Surface Tension: 94.6 dyne/cm
Density: 1.89 g/cm3
Appearance: White to Light yellow  crystalline powder, odorless or slightly smelly
Melting Point: >180°C dec
Insolubility: ethanol, ether,water
Storage temp: Room temp
Categories of cefdinir (CAS NO.91832-40-5): Miscellaneous Biochemicals; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds
InChI
InChI=1/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
Smiles
N12[C@@H]([C@@H](NC(\C(c3csc(n3)N)=N/O)=O)C2=O)SCC(=C1C(O)=O)C=C

Cefdinir History

 Cefdinir (CAS NO.91832-40-5) is approved by the U.S. Food and Drug Administration in December 1997.

Cefdinir Uses

 Cefdinir (CAS NO.91832-40-5) is  a semi-synthetic broad-spectrum antibiotic used for infectious impetigo, erysipelas, subcutaneous abscesses, mastitis, trauma and post-operative superficial infection, pharyngitis, acute bronchitis, pneumonia, tonsillitis, gonococcal urethritis, intrauterine infection.

Cefdinir Toxicity Data With Reference

1.    

orl-rat LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
2.    

ipr-rat LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
3.    

scu-rat LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
4.    

ivn-rat LD50:>2 g/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
5.    

orl-mus LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
6.    

ipr-mus LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
7.    

scu-mus LD50:>5600 mg/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
8.    

ivn-mus LD50:>2 g/kg

     IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 23 (1992),93.
9.    

orl-dog LD50:>1 g/kg

     NIIRDN    Drugs in Japan. Ethical Drugs, 6th Edition 1982 . Edited by Japan Pharmaceutical Information Center. (Yakugyo Jiho Co., Ltd.,Tokyo, Japan.: )1995,667.

Cefdinir Safety Profile

 Moderately toxic by ingestion and intravenous routes. Low toxicity by intraperitoneal and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx and SOx.

Cefdinir Specification

 Cefdinir , with CAS number of 91832-40-5, can be called (-)-(6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-8-oxo-3-
vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-oxime ; Cefdinirum . It is a pale yellow solid.

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