(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 417
• Molecular Formular: C14H13N5O5S2
• Molecular Mass: 395.41352
• Monoisotopic Mass: 395.03581054
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N\O)/c2nc(sc2)N)C(=C(C1)C=C)C(=O)O
• Canonical SMILES: O/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C=C
• InChI: InChI=1S/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
• InChIKey: RTXOFQZKPXMALH-GHXIOONMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefdinir; omnicef
• Brand Name: Cefzon; Omnicef
• Synonyms: CFDN; Cefdirnir; Cefdinir; (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo--5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Omnicef; FK-482; BMY-28488; Cefdinir(Omnicef)

Database IDs

• CAS Number: 91832-40-5
• PubChem SID: 160963880; 46505573
• PubChem CID: 6915944

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7439805
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.769286
• LogD (pH = 7.4): -4.5017385
• Log P: -1.6689881
• Molar Refractivity: 94.3449 cm^3
• Polarizability: 35.26974 Å^3
• Polar Surface Area: 158.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.02
• LOG S: -3.65
• Solubility (Water): 8.78e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMF; DMSO
• Apperance: Pale Yellow Solid
• Melting Point: >180°C dec.
• Hydrophobicity(logP): -0.2

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00535

• Drug Groups: approved
• Description: Cefdinir (marketed by Abbott Laboratories under the brand name Omnicef) is a semi-synthetic, broad-spectrum antibiotic in the third generation of the cephalosporin class, proven effective for common bacterial infections of the ear, sinus, throat, and skin. It was approved by the U.S. Food and Drug Administration (FDA) in December of 1997.
• Indication: For the treatment of the respiratory, skin, soft tissue, and ENT infections caused by H. influenzae (including b-lactamase producing strains), H. parainfluenzae (including b-lactamase producing strains), S. pneumoniae (penicillin-susceptible strains), S. pyogenes, S. aureus (including b-lactamase producing strains), and M. catarrhalis.
• Pharmacology: Cefdinir is a third generation cephalosporin with a broad spectrum of activity against enteric gram-negative rods. Cefdinir is stable in the presence of some, but not all, b-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins are susceptible to cefdinir. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal.
• Toxicity: Information on cefdinir overdosage in humans is not available. In acute rodent toxicity studies, a single oral 5600-mg/kg dose produced no adverse effects. Toxic signs and symptoms following overdosage with other b-lactam antibiotics have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.
• Affected Organisms: Enteric gram-negative rods
• Biotransformation: Cefdinir is not appreciably metabolized. Activity is primarily due to parent drug.
• Absorption: Maximal plasma cefdinir concentrations occur 2 to 4 hours postdose following capsule or suspension administration. Estimated bioavailability of cefdinir capsules is 21% following administration of a 300 mg capsule dose, and 16% following administration of a 600 mg capsule dose. Estimated absolute bioavailability of cefdinir suspension is 25%. Absorption is reduced by approximately 15% when administered with a high fat meal.
• Half Life: 1.7 ± 0.6 hours
• Protein Binding: 60%-70%, binding is independent of concentration.
• Elimination: Cefdinir is not appreciably metabolized. Cefdinir is eliminated principally via renal excretion with a mean plasma elimination half-life (t?) of 1.7 (±0.6) hours.
• Distribution: * 0.35±0.29 L/kg [adult subjects]; * 0.67±0.38 L/kg [pediatric subjects (age 6 months to 12 years)]
• Clearance: * renal cl=2 +/- 1 mL/min/kg [healthy]
• References: Yamanaka H, Shimazaki J, Imai K, Sugiyama Y, Shida K: Effect of estrogen administration on activities of testosterone 5alpha-reductase, alkaline phosphatase and arginase in the ventral and the dorsolateral prostates of rats. Endocrinol Jpn. 1975 Aug;22(4):297-302. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1605

Research Area: Infection
Biological Activity:
Cefdinir (Omnicef) is a semi-synthetic, broad-spectrum antibiotic in the third generation of the cephalosporin class, which is proved to be effective for common bacterial infections of the ear, sinus, throat, and skin. It can be used to treat infections caused by several Gram-negative and Gram-positive bacteria. [1]

Toronto Research Chemicals - C242670

A Cephalosporin antibiotic structurally similar to Cefixime.

REFERENCES

• Yamanaka H, Shimazaki J, Imai K, Sugiyama Y, Shida K: Effect of estrogen administration on activities of testosterone 5alpha-reductase, alkaline phosphatase and arginase in the ventral and the dorsolateral prostates of rats. Endocrinol Jpn. 1975 Aug;22(4):297-302. Pubmed
• http://en.wikipedia.org/wiki/Cefdinir
• Inamoto, Y., et al.: J. Antibiot., 41, 828 (1988)