Cefixime
A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Cefixime are summarized together with 3D and 2D structures and relevant physico-chemical properties.
Table of Contents
What is the Cefixime?
The molecule Cefixime presents a molecular formula of C16H15N5O7S2 and its IUPAC name is (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.
Cefixime is a third-generation cephalosporin antibiotic. It is used to treat a wide range of bacterial infections, including bronchitis, pneumonia, urinary tract infections, and infections of the skin..
The chemical structure of cefixime is a beta-lactam antibiotic, which means it contains a four-membered beta-lactam ring. This ring gives cefixime its antimicrobial activity, as it is able to inhibit the synthesis of the bacterial cell wall..
Cefixime is classified as a broad-spectrum antibiotic, meaning it is effective against a wide range of bacteria. It is often used as a treatment option when other antibiotics have been ineffective or when the exact type of bacterial infection is unknown..
Cefixime is typically administered orally, in the form of a tablet or suspension. It is well absorbed in the gastrointestinal tract and has a high bioavailability, meaning it is readily available for use in the body..
One of the main advantages of cefixime is its low potential for causing allergic reactions. It is also relatively safe for use in children and pregnant women, although it should still be used with caution and only under the supervision of a healthcare provider..
Like all antibiotics, cefixime should only be used to treat bacterial infections. It is not effective against viral infections, such as the common cold or flu. Overuse and misuse of antibiotics can contribute to the development of antibiotic-resistant bacteria, so it is important to use them responsibly..
In conclusion, cefixime is a useful and effective antibiotic for the treatment of a wide range of bacterial infections. However, it should be used with caution and only under the supervision of a healthcare provider to help prevent the development of antibiotic resistance..
Cefixime is a third-generation cephalosporin antibiotic. It is used to treat a wide range of bacterial infections, including bronchitis, pneumonia, urinary tract infections, and infections of the skin..
The chemical structure of cefixime is a beta-lactam antibiotic, which means it contains a four-membered beta-lactam ring. This ring gives cefixime its antimicrobial activity, as it is able to inhibit the synthesis of the bacterial cell wall..
Cefixime is classified as a broad-spectrum antibiotic, meaning it is effective against a wide range of bacteria. It is often used as a treatment option when other antibiotics have been ineffective or when the exact type of bacterial infection is unknown..
Cefixime is typically administered orally, in the form of a tablet or suspension. It is well absorbed in the gastrointestinal tract and has a high bioavailability, meaning it is readily available for use in the body..
One of the main advantages of cefixime is its low potential for causing allergic reactions. It is also relatively safe for use in children and pregnant women, although it should still be used with caution and only under the supervision of a healthcare provider..
Like all antibiotics, cefixime should only be used to treat bacterial infections. It is not effective against viral infections, such as the common cold or flu. Overuse and misuse of antibiotics can contribute to the development of antibiotic-resistant bacteria, so it is important to use them responsibly..
Summary
From all the above, this molecule is a useful and effective antibiotic for the treatment of a wide range of bacterial infections. However, it should be used with caution and only under the supervision of a healthcare provider to help prevent the development of antibiotic resistance..
3D structure
Cartesian coordinates
Geometry of Cefixime in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.
2D drawing
Molecule descriptors
IUPAC name | (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
InChI code | InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1 |
InChI Key | OKBVVJOGVLARMR-QSWIMTSFSA-N |
SMILES | C=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\OCC(=O)O)c3csc(N)n3)[C@H]2SC1 |
Other names (synonyms)
IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.
One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.
Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.
In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.
- (-)-Cefixim
- (6R,7R)-7-((2-(2-AMINO-1,3-THIAZOL-4-YL)-2-(CARBOXYMETHOXYIMINO)ACETYL)AMINO)-3-ETHENYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
- (6R,7R)-7-((Z)-2-(2-Aminothiazol-4-yl)-2-((carboxymethoxy)imino)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (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)-(O-(carboxymethyl)oxime) trihydrate
- (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)-(O-(carboxymethyl)oxime)trihydrate
- (6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetyl}amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6R,7R)-7-[[(2z)-2-(2-amino-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid
- (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(carboxymethyl)oxy]imino}acetyl]amino}-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6S,7R)-7-[[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7r)-7-[-2-(2-amino-thiazol-4-yl)-2-carboxymethoxyimino-acetylamino]-8-oxo-3-vinyl-5-thia-1-aza-b
- 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, trihydrate, (6R-(6alpha,7beta(Z)))-
- 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, (6R,7R)-
- 50C371
- 79350-37-1
- 7beta-{(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido}-3-ethenyl-3,4-didehydrocepham-4-carboxylic acid
- A13697
- AB00513842
- AC-4350
- Anhydrous cefixime
- BDBM84007
- BPBio1_000622
- BRN 6025058
- BSPBio_000564
- C-2469
- C04
- C06881
- CCG-220462
- CEFIXIME
- CFIX
- CL 284,635
- CL 284635
- CL-284635
- CS-4820
- Cefixim
- Cefixima
- Cefixime
- Cefixime (INN)
- Cefixime Anhydrous
- Cefixime, Antibiotic for Culture Media Use Only
- Cefiximum
- Cefixoral
- Cefspan
- Cephoral
- Citropen
- D00258
- DB00671
- Denvar
- FK 027
- FK-027
- FR 17027
- FR-17027
- HMS2096M06
- HMS2234J21
- HMS3713M06
- HY-B1381
- MFCD00865020
- MLS002222332
- NCGC00179521-01
- NCGC00179521-03
- Necopen
- Oroken
- Prestwick3_000462
- Q27290799
- SMR001307271
- SR-01000760706
- SR-01000760706-4
- Suprax
- Tricef
- Unixime
- XZ7BG04GJX
- cid_5362065
- s4596
Reference codes for other databases
There exist several different chemical codes commonly used in orded to identify molecules:- CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
- Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
- ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
- PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
- RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
- ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
- CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.
- ZINC12503147
- UNII-XZ7BG04GJX
- AKOS015854940
- AKOS015961135
- BRD-K71059170-001-02-5
- BRD-K71059170-001-08-2
- DTXSID7022754
- CHEMBL1541
- CHEBI:472657
- SCHEMBL24945
Physico-Chemical properties
IUPAC name | (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
Molecular formula | C16H15N5O7S2 |
Molecular weight | 453.45 |
Melting point (ºC) | |
Boiling point (ºC) | |
Density (g/cm3) | |
Molar refractivity | 109.91 |
LogP | 0.4 |
Topological polar surface area | 238.1 |
LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.
The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.
TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.
In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.
For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.