Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H5N3O |
Molecular Weight | 123.1127 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=CN=CC=N1
InChI
InChIKey=IPEHBUMCGVEMRF-UHFFFAOYSA-N
InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634eCurator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00339
https://en.wikipedia.org/wiki/Pyrazinamide
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00339
https://en.wikipedia.org/wiki/Pyrazinamide
Pyrazinamide is indicated for the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents. (The current recommendation of the CDC for drug-susceptible disease is to use a six-month regimen for initial treatment of active tuberculosis, consisting of isoniazid, rifampin and pyrazinamide given for 2 months, followed by isoniazid and rifampin for 4 months. Pyrazinamide should only be used in conjunction with other effective antituberculous agents. Pyrazinamide diffuses into M. tuberculosis, where the enzyme pyrazinamidase converts pyrazinamide to the active form pyrazinoic acid. Under acidic conditions, the pyrazinoic acid that slowly leaks out converts to the protonated conjugate acid, which is thought to diffuse easily back into the bacilli and accumulate. The net effect is that more pyrazinoic acid accumulates inside the bacillus at acid pH than at neutral pH. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids. However, this theory was thought to have been discounted. However, further studies reproduced the results of FAS I inhibition as the putative mechanism first in whole cell assay of replicating M. tuberculosis bacilli which have shown that pyrazinoic acid and its ester inhibit the synthesis of fatty acids . This study was followed by in vitro assay of tuberculous FAS I enzyme that tested the activity with pyrazinamide, pyrazinoic acid and several classes of pyrazinamide analogs. Pyrazinamide and its analogs inhibited the activity of purified FAS I. It has also been suggested that the accumulation of pyrazinoic acid disrupts membrane potential and interferes with energy production, necessary for survival of M. tuberculosis at an acidic site of infection. Pyrazinoic acid has also been shown to bind to the ribosomal protein S1 (RpsA) and inhibit trans-translation. This may explain the ability of the drug to kill dormant mycobacteria
CNS Activity
Curator's Comment: Drugs like isoniazid, pyrazinamide and cycloserine cross the blood brain barrier (BBB) freely, but the behavior of rifampicin, ethambutol and streptomycin is less predictable in the presence of inflamed meninges. The CSF concentration of these drugs is at least equal to or higher than those in the noninflamed meninges
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2011 Sources: http://www.drugbank.ca/drugs/DB00339 |
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Target ID: CHEMBL2363965 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21835980 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | PYRAZINAMIDE Approved UsePyrazinamide Launch Date3.7065601E10 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
38.2 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23629715 |
27.8 mg/kg bw 3 times / day steady-state, oral dose: 27.8 mg/kg bw route of administration: Oral experiment type: STEADY-STATE co-administered: Isoniazid | Rifampicin | Ethambutol |
PYRAZINAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
38.7 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2737233 |
27 mg/kg bw single, oral dose: 27 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PYRAZINAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
344 mg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23629715 |
27.8 mg/kg bw 3 times / day steady-state, oral dose: 27.8 mg/kg bw route of administration: Oral experiment type: STEADY-STATE co-administered: Isoniazid | Rifampicin | Ethambutol |
PYRAZINAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
520 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2737233 |
27 mg/kg bw single, oral dose: 27 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PYRAZINAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23629715 |
27.8 mg/kg bw 3 times / day steady-state, oral dose: 27.8 mg/kg bw route of administration: Oral experiment type: STEADY-STATE co-administered: Isoniazid | Rifampicin | Ethambutol |
PYRAZINAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Co-administed with:: ofloxacin, p.o(800 mg/day; 6 months) Sources: |
healthy n = 16 |
Disc. AE: Arthralgia, Distress gastrointestinal... AEs leading to discontinuation/dose reduction: Arthralgia (43.75%) Sources: Distress gastrointestinal (37.5%) Pruritus (25%) Fatigue (25%) Generalized maculopapular rash (18.8%) Insomnia (18.8%) Vertigo (12.5%) |
20 mg/kg 1 times / day multiple, oral Recommended Dose: 20 mg/kg, 1 times / day Route: oral Route: multiple Dose: 20 mg/kg, 1 times / day Co-administed with:: rifampin, p.o(600 mg/d; 2 months) Sources: Page: p.643 |
unhealthy n = 207 Health Status: unhealthy Condition: Tuberculosis Sex: M+F Population Size: 207 Sources: Page: p.643 |
Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity (5.8%) Sources: Page: p.643 |
30 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 30 mg/kg, 1 times / day Route: oral Route: multiple Dose: 30 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Tuberculosis Sources: |
Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Vertigo | 12.5% Disc. AE |
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Co-administed with:: ofloxacin, p.o(800 mg/day; 6 months) Sources: |
healthy n = 16 |
Generalized maculopapular rash | 18.8% Disc. AE |
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Co-administed with:: ofloxacin, p.o(800 mg/day; 6 months) Sources: |
healthy n = 16 |
Insomnia | 18.8% Disc. AE |
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Co-administed with:: ofloxacin, p.o(800 mg/day; 6 months) Sources: |
healthy n = 16 |
Fatigue | 25% Disc. AE |
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Co-administed with:: ofloxacin, p.o(800 mg/day; 6 months) Sources: |
healthy n = 16 |
Pruritus | 25% Disc. AE |
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Co-administed with:: ofloxacin, p.o(800 mg/day; 6 months) Sources: |
healthy n = 16 |
Distress gastrointestinal | 37.5% Disc. AE |
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Co-administed with:: ofloxacin, p.o(800 mg/day; 6 months) Sources: |
healthy n = 16 |
Arthralgia | 43.75% Disc. AE |
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Co-administed with:: ofloxacin, p.o(800 mg/day; 6 months) Sources: |
healthy n = 16 |
Hepatotoxicity | 5.8% Disc. AE |
20 mg/kg 1 times / day multiple, oral Recommended Dose: 20 mg/kg, 1 times / day Route: oral Route: multiple Dose: 20 mg/kg, 1 times / day Co-administed with:: rifampin, p.o(600 mg/d; 2 months) Sources: Page: p.643 |
unhealthy n = 207 Health Status: unhealthy Condition: Tuberculosis Sex: M+F Population Size: 207 Sources: Page: p.643 |
Hepatotoxicity | Disc. AE | 30 mg/kg 1 times / day multiple, oral (max) Recommended Dose: 30 mg/kg, 1 times / day Route: oral Route: multiple Dose: 30 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Tuberculosis Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Serial counts of Mycobacterium tuberculosis in sputum as surrogate markers of the sterilising activity of rifampicin and pyrazinamide in treating pulmonary tuberculosis. | 2001 |
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The molecular basis of resistance to isoniazid, rifampin, and pyrazinamide in Mycobacterium tuberculosis. | 2001 |
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[Effectiveness of chemotherapy of intrathoracic tuberculosis in children: late follow-up data]. | 2001 |
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Pancreatic mass caused by Mycobacterium tuberculosis with reduced drug sensitivity. | 2001 Apr |
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Pulmonary tuberculosis in Kumasi, Ghana: presentation, drug resistance, molecular epidemiology and outcome of treatment. | 2001 Apr-Jun |
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[Functional role of the red nucleus in the cerebral cortex-cerebellum-spinal cord communication system]. | 2001 Apr-Jun |
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Renal handling of uric acid assessed by means of pharmacological tests in obese women. | 2001 Aug |
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Rifampicin allergy confirmed by an intradermal test, but with a negative patch test. | 2001 Aug |
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Update: Fatal and severe liver injuries associated with rifampin and pyrazinamide for latent tuberculosis infection, and revisions in American Thoracic Society/CDC recommendations--United States, 2001. | 2001 Aug 31 |
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Can serial qualitative polymerase chain reaction monitoring predict outcome of pulmonary tuberculosis treatment? | 2001 Dec |
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[Treatment outcomes of multidrug-resistant tuberculosis--comparison between success and failure cases]. | 2001 Dec |
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Isonicotinic acid hydrazide induced anagen effluvium and associated lichenoid eruption. | 2001 Dec |
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Pyrazinamide use as a method of estimating under-reporting of tuberculosis. | 2001 Dec |
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Side effects of antituberculosis treatment. | 2001 Dec |
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Postantibiotic effects of antituberculosis agents alone and in combination. | 2001 Dec |
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New mutations in pncA of in vitro selected pyrazinamide-resistant strains of Mycobacterium tuberculosis. | 2001 Fall |
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Pattern of some haematological indices in newly diagnosed pulmonary tuberculosis cases in Iwo, Nigeria: diagnostic and therapeutic implications. | 2001 Jan-Mar |
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Reintroducing antituberculosis therapy after Stevens-Johnson syndrome in human immunodeficiency virus-infected patients with tuberculosis: role of desensitization. | 2001 Jul |
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[Multiple intracranial tuberculomas in infancy]. | 2001 Jul 1-15 |
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Tuberculosis and HIV infection: epidemiology, immunology, and treatment. | 2001 Jul-Aug |
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Antimycobacterial plant terpenoids. | 2001 Nov |
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Pyrazinamide induced photoallergy. | 2001 Nov |
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Tuberculous meningitis: is a 6-month treatment regimen sufficient? | 2001 Nov |
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Tuberculosis infection in Chinese patients undergoing continuous ambulatory peritoneal dialysis. | 2001 Nov |
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Rapamycin and less immunosuppressive analogs are toxic to Candida albicans and Cryptococcus neoformans via FKBP12-dependent inhibition of TOR. | 2001 Nov |
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Crystal structure and mechanism of catalysis of a pyrazinamidase from Pyrococcus horikoshii. | 2001 Nov 27 |
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Duration of efficacy of treatment of latent tuberculosis infection in HIV-infected adults. | 2001 Nov 9 |
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[Orchiectomy for tuberculous epididymitis: a report of two cases with intractable to antituberculosis treatment]. | 2001 Oct |
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Characterization of pncA mutations of pyrazinamide-resistant Mycobacterium tuberculosis in Korea. | 2001 Oct |
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Characterisation of the pncA gene in Mycobacterium tuberculosis isolates from Gauteng, South Africa. | 2001 Oct |
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Treatment of tuberculosis in Haiti. | 2001 Oct |
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Hepatotoxicity from rifampin plus pyrazinamide: lessons for policymakers and messages for care providers. | 2001 Oct 1 |
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Antitubercular drugs (isoniazid, rifampin and pyrazinamide): hepatobiliary reactions. | 2001 Oct 2 |
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[Vesical uric acid lithiasis in a child with renal hypouricemia]. | 2001 Sep |
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Safety of an ofloxacin-based antitubercular regimen for the treatment of tuberculosis in patients with underlying chronic liver disease: a preliminary report. | 2001 Sep |
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Intramedullary tuberculoma of the conus medullaris: case report and review of the literature. | 2001 Sep |
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Modulating effect of Liv.100, an ayurvedic formulation on antituberculosis drug-induced alterations in rat liver microsomes. | 2001 Sep |
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Tuberculosis: guidelines changed for latent TB treatment. | 2001 Sep 21 |
|
From the Centers for Disease Control and Prevention. Update: Fatal and severe liver injuries associated with Rifampin and Pyrazinamide for latent tuberculosis infection, and revisions in American Thoracic Society/CDC recommendations--United States, 2001. | 2001 Sep 26 |
|
US guidelines for treatment of latent tuberculosis revised. | 2001 Sep 8 |
|
Treatment of childhood tuberculosis with a six month directly observed regimen of only two weeks of daily therapy. | 2002 Feb |
|
Tuberculosis presenting as immune thrombocytopenic purpura. | 2002 Feb |
|
Conditions that may affect the results of susceptibility testing of Mycobacterium tuberculosis to pyrazinamide. | 2002 Jan |
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Susceptibility testing of Mycobacterium tuberculosis to pyrazinamide. | 2002 Jan |
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High rates of tuberculosis in end-stage renal failure: the impact of international migration. | 2002 Jan |
|
Surveillance for antimicrobial resistance in Croatia. | 2002 Jan |
|
Rapidly progressive glomerulonephritis due to rifampicin therapy. | 2002 Jan |
|
Liquid chromatographic determination of isoniazid, pyrazinamide and rifampicin from pharmaceutical preparations and blood. | 2002 Jan 25 |
|
Therapeutic isoniazid monitoring using a simple high-performance liquid chromatographic method with ultraviolet detection. | 2002 Jan 5 |
|
Tuberculoma of the conus medullaris: case report. | 2002 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e
Curator's Comment: Three grams per day should not be exceeded. The CDC (Center for Disease Control ) recommendations do not exceed 2 g per day when given as a daily regimen
15 to 30 mg/kg once daily
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C280
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WHO-VATC |
QJ04AM05
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4 (ISO/PYR/RIF)
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WHO-ATC |
J04AM06
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WHO-ATC |
J04AK01
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WHO-ATC |
J04AM05
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4 (ETH/ISO/PYR/RIF)
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4
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WHO-VATC |
QJ04AM06
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LIVERTOX |
NBK547856
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NDF-RT |
N0000175483
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WHO-VATC |
QJ04AK01
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FDA ORPHAN DRUG |
6585
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DTXSID9021215
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CHEMBL614
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2328
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Pyrazinamide
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PYRAZINAMIDE
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PYRAZINAMIDE
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Sparingly soluble in water; slightly soluble in ethanol (~750 g/l) TS. Category: Antituberculosis drug. Storage: Pyrazinamide should be kept in a well-closed container. Definition: Pyrazinamide contains not less than 98.5% and not more than 101.0% of C5H5N3O, calculated with reference to the anhydrous substance. | ||
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202-717-6
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1046
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SUB10163MIG
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786
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7287
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D011718
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3576
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2KNI5N06TI
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14911
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45285
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100000080846
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DB00339
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98-96-4
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8987
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m9337
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1585006
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2KNI5N06TI
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C29395
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)