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Cefdinir

Cefdinir structure

CAS No:
91832-40-5
Formula:
C14H13N5O5S2
Chemical Name:
Cefdinir
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-,(6R,7R)-;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-[6α,7β(Z)]]-;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)-;(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;FK 482;BMY 28488;Cefdinir;CI 983;Cefzon;CFDN;Adcef;Omnicef;Cefnil;Cefdiel;Kefnir;Zinir
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Cefdinir (Omnicef) is a semi-synthetic, broad-spectrum antibiotic, which is proved to be effective for common bacterial infections of the ear, sinus, throat, and skin.Target: AntibacterialCefdinir is a third generation oral cephalosporin antibiotic. 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

A third-generation oral cephalosporin antibacterial agent that is used to treat bacterial infections of the respiratory tract and skin.

Cefdinir Basic Attributes

Molecular Weight：

395.41

Exact Mass：

395.41

EC Number：

1312995-182-4

DSSTox ID：

DTXSID8046084

ATC Code：

J - Antiinfectives for systemic use

HScode：

2941905990

Characteristics

PSA：

212

XLogP3：

-3.47

Appearance：

Solid

Density：

1.9±0.1 g/cm3

Melting Point：

170 °C (decomp)

Boiling Point：

708.82°C

Refractive Index：

1.862

Water Solubility：

soluble in water;dilute HCl: slightly soluble

Storage Conditions：

room temp

Toxicity：

LD50 orl-rat: >5600 mg/kg IYKEDH 23,93,1992

PKA：

9.7None

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

RTECS Number：

XI0367250

GHS Classification：

|Danger|H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

7-(2 (2-aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic acid

Cefdinir Use and Manufacturing

Methods of Manufacturing

Using 7-ACA as the raw material, after protecting the 7-position amino group and the 2-position carboxyl group, and then reacting with triphenylphosphine to obtain a phosphide, it performs Wittig reaction with formaldehyde under alkaline conditions to obtain a 3-position vinyl derivative (I ). Treatment with hydrochloric acid frees the 7-position amino group to obtain compound (II). In the presence of N-trimethylsilylacetamide, compound (II) and 4-bromoacetoacetyl bromide were reacted in ethyl acetate at -10°C for 1h to obtain the acylated product (Ⅲ) in 88% yield . Compound (III) was nitrosated in dichloromethane and acetic acid with an aqueous solution of sodium nitrite at -5°C for 30 min, and then urea was added to destroy excess sodium nitrite to obtain hydroxylamine compound (IV) in quantitative yield. Compound (IV) is reacted with thiourea in N, N-dimethylacetamide at 5°C for 1 hour, and cyclized to obtain compound (V). The crude compound (V) was reacted with trifluoroacetic acid at 5°C for 1 h in anisole, and then recrystallized with water to obtain cefdinir in 45% yield [based on compound (IV)].

Uses

antihypertensive, ACE inhibitor

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:395.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:5
Exact Mass:395.03581088
Monoisotopic Mass:395.03581088
Topological Polar Surface Area:212
Heavy Atom Count:26
Complexity:739
Defined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Dimethylacetamide

Ethyl acetate

Trifluoroacetic acid

Price Analysis

Make your Cefdinir purchase based on the price and market insights! ECHEMI provides professional market insights with prices for you to make a better choice. Learn more on Cefdinir prices .

Drug Function and Efficacy

It has a wide antibacterial spectrum against Gram-positive and Gram-negative bacteria, especially against Staphylococcus and Streptococcus among Gram-positive bacteria. It has stronger antibacterial activity than previous oral cephalosporins, and its mode of action is bactericidal. It is stable to β-lactamases produced by various bacteria, and also has excellent antibacterial activity against β-lactamase-producing bacteria. The mechanism of action is to prevent the synthesis of bacterial cell walls. It has a strong affinity for penicillin-binding proteins (PBP) 1 (1a, 1bs), 2, and 3, but the active sites for different bacteria are different.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Cefdinir
Indication	Caution is required when using this product with the following drugs. Drug signs, symptoms, treatment mechanisms and risk factors Iron preparations may reduce the absorption of cefdinir by about 10%, so it is recommended to avoid co-administration with such drugs. If co-administration cannot be avoided, the interval between the two doses should be greater than 3 hours This product can combine with iron ions in the intestine to form a complex that is difficult to absorb. Warfarin potassium The effect of warfarin potassium may be enhanced, but there are no reports of interaction between the two. This product may inhibit the production of vitamin K by intestinal bacteria. Antacids (containing aluminum or magnesium) can reduce the absorption of cefdinir and weaken its effect, so antacids should be used 2 hours after taking this product. The mechanism is not clear.

Cefdinir

Indication

Caution is required when using this product with the following drugs. Drug signs, symptoms, treatment mechanisms and risk factors Iron preparations may reduce the absorption of cefdinir by about 10%, so it is recommended to avoid co-administration with such drugs. If co-administration cannot be avoided, the interval between the two doses should be greater than 3 hours This product can combine with iron ions in the intestine to form a complex that is difficult to absorb. Warfarin potassium The effect of warfarin potassium may be enhanced, but there are no reports of interaction between the two. This product may inhibit the production of vitamin K by intestinal bacteria. Antacids (containing aluminum or magnesium) can reduce the absorption of cefdinir and weaken its effect, so antacids should be used 2 hours after taking this product. The mechanism is not clear.

Cefdinir Capsules
Ingredients	Chemical name: (-)-(6R, 7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetylamino]-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.
Indication	This product should be used with caution when used in combination with the following drugs. The signs, symptoms and treatment of iron preparations are that it may reduce the absorption of cefdinir by about 10%, so it is recommended to avoid co-administration with such drugs. If co-administration cannot be avoided, the interval between the two administrations should be greater than 3 hours; Mechanism and risk factors: This product can combine with iron ions in the intestine to form a complex that is difficult to absorb. The signs, symptoms and treatment of warfarin potassium are that the effect of warfarin potassium may be enhanced, but there are no reports of interaction between the two; Mechanism and risk factors: This product may inhibit the production of vitamin K by intestinal bacteria. The signs, symptoms and treatment of antacids (containing aluminum or magnesium) are that it may reduce the absorption of cefdinir and weaken its effect, so antacids should be used 2 hours after taking this product. The mechanism and risk factors are not clear.
Specifications	0.1g (calculated based on 2 pieces of C14H13N505)

Cefdinir Dispersible Tablets
Ingredients	Cefdinir
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	0.1g (based on C14H13N5O5S2)
Manufacturer	Hainan Rizhongtian Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Parabolic Drugs Ltd.

Japan
Active
Sandoz GmbH

Austria
Active
Guangzhou Tosun Pharmaceutical Ltd

China
Active

See More Registered Holders

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