Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H15N5O7S2 |
Molecular Weight | 453.45 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=CS1)C(=N\OCC(O)=O)\C(=O)N[C@H]2[C@H]3SCC(C=C)=C(N3C2=O)C(O)=O
InChI
InChIKey=OKBVVJOGVLARMR-QSWIMTSFSA-N
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
Molecular Formula | C16H15N5O7S2 |
Molecular Weight | 453.45 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall. Like all beta-lactam antibiotics, cefixime binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefixime interferes with an autolysin inhibitor. Cefixime is sold under the brand name Suprax, indicated for the treatment of:
Uncomplicated Urinary Tract Infections
Otitis Media
Pharyngitis and Tonsillitis
Acute Exacerbations of Chronic Bronchitis
Uncomplicated Gonorrhea (cervical/urethral)
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
9.91 pM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | SUPRAX Approved UseTo reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date1989 |
|||
Curative | SUPRAX Approved UseTo reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date1989 |
|||
Curative | SUPRAX Approved UseTo reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date1989 |
|||
Curative | SUPRAX Approved UseTo reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date1989 |
|||
Curative | SUPRAX Approved UseTo reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date1989 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.74 mg/L |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME ANHYDROUS serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.696 μg/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.837 μg/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
4.74 mg/L |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.68 mg/L |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.69 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.13 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.95 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
34.9 mg × h/L |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME ANHYDROUS serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
30.211 μg × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
15.864 μg × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
34.9 mg × h/L |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
49.5 mg × h/L |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.32 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.66 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
14.99 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.5 h |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME ANHYDROUS serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.479 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.461 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3.5 h |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.2 h |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.38 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFIXIME serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
35% |
400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CEFIXIME ANHYDROUS serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
35% |
CEFIXIME serum | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
800 mg 3 times / day multiple, oral Highest studied dose Dose: 800 mg, 3 times / day Route: oral Route: multiple Dose: 800 mg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
|
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Diarrhea, Vomiting... Other AEs: Nausea... AEs leading to discontinuation/dose reduction: Diarrhea (2.5%) Other AEs:Vomiting (0.8%) Increased urinary frequency (0.8%) Nausea (0.8%) Sources: |
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Hypersensitivity, Diarrhea, Clostridium difficile... AEs leading to discontinuation/dose reduction: Hypersensitivity Sources: Diarrhea, Clostridium difficile |
200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Other AEs: Perioral dermatitis... |
8 mg/kg 1 times / day multiple, oral Recommended Dose: 8 mg/kg, 1 times / day Route: oral Route: multiple Dose: 8 mg/kg, 1 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 0.8% | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Increased urinary frequency | 0.8% Disc. AE |
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Vomiting | 0.8% Disc. AE |
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Diarrhea | 2.5% Disc. AE |
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Diarrhea, Clostridium difficile | Disc. AE | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Hypersensitivity | Disc. AE | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Perioral dermatitis | 1 patient | 200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Double-blind comparison of cefixime and cefaclor in the treatment of acute otitis media in children. | 1991 |
|
[Clinical evaluation of cefixime in pediatric respiratory tract infections]. | 1991 Jan |
|
Cefixime compared with amoxicillin for treatment of acute otitis media. | 1991 Jul |
|
[Benign intracranial hypertension after treatment with pefloxacin]. | 1998 Aug |
|
Nephrotic syndrome following cefixime therapy in a 10-month-old girl: spontaneous resolution without corticosteroid treatment. | 1999 Oct |
|
Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center. | 2004 Oct |
|
IgE antibodies to betalactams: relationship between the triggering hapten and the specificity of the immune response. | 2006 Aug |
|
Investigation of the role of oligopeptide transporter PEPT1 and sodium/glucose cotransporter SGLT1 in intestinal absorption of their substrates using small GTP-binding protein Rab8-null mice. | 2009 Mar |
|
Diagnostic evaluation of hypersensitivity reactions to beta-lactam antibiotics in a large population of children. | 2014 Feb |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20093260
A mosaic penicillin-binding protein 2 (PBP 2) was found in a single isolate that exhibited the highest cefixime MIC (0.5 mg/L).
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:08:08 GMT 2025
by
admin
on
Mon Mar 31 18:08:08 GMT 2025
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Record UNII |
XZ7BG04GJX
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Record Status |
Validated (UNII)
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Record Version |
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Common Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English |
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WHO-ATC |
J01DD08
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NDF-RT |
N0000175488
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LIVERTOX |
NBK548358
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LIVERTOX |
NBK548666
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NDF-RT |
N0000011161
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SUB07395MIG
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DTXSID7022754
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SUB70432
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m3195
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DB00671
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XZ7BG04GJX
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79350-37-1
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5362065
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1546021
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XZ7BG04GJX
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5678
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C170534
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS |
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EXCRETED UNCHANGED |
Undergoes little if any metabolism
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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