CAS No.91832-40-5,Cefdinir Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	91832-40-5
Name:	Cefdinir
Article Data:	31

Formula:	C₁₄H₁₃N₅O₅S₂
Molecular Weight:	395.42
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)-;
EINECS:	643-088-1
Density:	1.89 g/cm³
Melting Point:	>180 °C dec
Solubility:	Soluble in water
Appearance:	Pale yellow solid
PSA:	211.75000
LogP:	0.73820

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With formic acid at 20℃; for 3h;	2.54 g

: 127770-93-8
C16H15N5O6S2

: 91832-40-5
cefdinir

Conditions

Conditions	Yield
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

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

...Expand

: 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

Conditions	Yield
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

...Expand

: 104797-47-9
S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate

: 91832-40-5
cefdinir

Conditions

Conditions	Yield
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

Conditions	Yield
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

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Chemistry

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

History

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

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.

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.

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 NO_x and SO_x.

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.