Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C19H24N2O2 |
| Molecular Weight | 312.4061 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C(C1CCCCC1)N2CC3N(CCC4=CC=CC=C34)C(=O)C2
InChI
InChIKey=FSVJFNAIGNNGKK-UHFFFAOYSA-N
InChI=1S/C19H24N2O2/c22-18-13-20(19(23)15-7-2-1-3-8-15)12-17-16-9-5-4-6-14(16)10-11-21(17)18/h4-6,9,15,17H,1-3,7-8,10-13H2
| Molecular Formula | C19H24N2O2 |
| Molecular Weight | 312.4061 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB01058Curator's Comment: description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018714s013lbl.pdf
https://en.wikipedia.org/wiki/Praziquantel
Sources: http://www.drugbank.ca/drugs/DB01058
Curator's Comment: description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018714s013lbl.pdf
https://en.wikipedia.org/wiki/Praziquantel
Praziquantel, marketed as Biltricide, is an anthelmintic used in humans and animals for the treatment of tapeworms and flukes. Specifically, it is effective against schistosoma, Clonorchis sinensis the fish tape worm Diphyllobothrium latum. Praziquantel works by causing severe spasms and paralysis of the worms' muscles. This paralysis is accompanied - and probably caused - by a rapid Ca 2+ influx inside the schistosome. Morphological alterations are another early effect of praziquantel. These morphological alterations are accompanied by an increased exposure of schistosome antigens at the parasite surface. The worms are then either completely destroyed in the intestine or passed in the stool. An interesting quirk of praziquantel is that it is relatively ineffective against juvenile schistosomes. While initially effective, effectiveness against schistosomes decreases until it reaches a minimum at 3-4 weeks. Effectiveness then increases again until it is once again fully effective at 6-7 weeks. Glutathione S-transferase (GST), an essential detoxification enzyme in parasitic helminths, is a major vaccine target and a drug target against schistosomiasis. Schistosome calcium ion channels are currently the only known target of praziquantel. The antibiotic rifampicin decreases plasma concentrations of praziquantel. Carbamazepine and phenytoin are reported to reduce the bioavailability of praziquantel. Chloroquine reduces the bioavailability of praziquantel. The drug cimetidine heightens praziquantel bioavailability.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/9646011
Curator's Comment: Praziquantel permeates the blood-brain barrier, thus explaining its effectiveness on parenchymal brain cysticercosis. Plasma concentrations of the drug are increased when a high carbohydrate diet is administered.
Originator
Sources: http://www.future-science.com/doi/10.4155/fmc.15.11
Curator's Comment: # in the laboratories of Bayer AG and Merck KGaA
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363079 Sources: http://www.drugbank.ca/drugs/DB01058 |
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Target ID: CHEMBL2363080 Sources: http://www.drugbank.ca/drugs/DB01058 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | BILTRICIDE Approved Usefor the treatment of infections due to: all species of schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini (approval of this indication was based on studies in which the two species were not differentiated Launch Date1984 |
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| Curative | BILTRICIDE Approved Usefor the treatment of infections due to: all species of schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini (approval of this indication was based on studies in which the two species were not differentiated Launch Date1984 |
|||
| Curative | BILTRICIDE Approved Usefor the treatment of infections due to: all species of schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini (approval of this indication was based on studies in which the two species were not differentiated Launch Date1984 |
|||
| Curative | BILTRICIDE Approved Usefor the treatment of infections due to: all species of schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini (approval of this indication was based on studies in which the two species were not differentiated Launch Date1984 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27152952/ |
25 mg/kg 3 times / day multiple, oral dose: 25 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRAZIQUANTEL, (R)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27152952/ |
25 mg/kg 3 times / day multiple, oral dose: 25 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRAZIQUANTEL, (S)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.83 μg/mL |
40 mg/kg single, oral dose: 40 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PRAZIQUANTEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27152952/ |
25 mg/kg 3 times / day multiple, oral dose: 25 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRAZIQUANTEL, (R)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27152952/ |
25 mg/kg 3 times / day multiple, oral dose: 25 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRAZIQUANTEL, (S)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.02 μg × h/mL |
40 mg/kg single, oral dose: 40 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PRAZIQUANTEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27152952/ |
25 mg/kg 3 times / day multiple, oral dose: 25 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRAZIQUANTEL, (R)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27152952/ |
25 mg/kg 3 times / day multiple, oral dose: 25 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRAZIQUANTEL, (S)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.99 h |
40 mg/kg single, oral dose: 40 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PRAZIQUANTEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
20% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27152952/ |
25 mg/kg 3 times / day multiple, oral dose: 25 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRAZIQUANTEL, (S)- plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12451431/ |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12451431/ |
no | |||
| no | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
Page: 2, 3, 4, 5, 7 |
yes | yes (co-administration study) Comment: praziquantel AUC decreased 23% and Cmax y 35% Page: 2, 3, 4, 5, 7 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Control of Echinococcus granulosus in Uruguay: evaluation of different treatment intervals for dogs. | 2002-02-04 |
|
| The effect of Nigella sativa oil against the liver damage induced by Schistosoma mansoni infection in mice. | 2002-01 |
|
| Evidence against rapid emergence of praziquantel resistance in Schistosoma haematobium, Kenya. | 2001-12-19 |
|
| Diphyllobothrium latum infection after eating domestic salmon flesh. | 2001-12 |
|
| Control of clonorchiasis by repeated treatments with praziquantel. | 2001-12 |
|
| Current progress in the development and use of artemether for chemoprophylaxis of major human schistosome parasites. | 2001-12 |
|
| Acidic vesicles of Schistosoma mansoni. | 2001-12 |
|
| The potential of artemether for the control of schistosomiasis. | 2001-12 |
|
| Isolation and identification of 8-hydroxypraziquantel as a metabolite of the antischistosomal drug praziquantel. | 2001-12 |
|
| Optimization of the single-day praziquantel therapy for neurocysticercosis. | 2001-11-27 |
|
| Development and validation of a 'tablet pole' for the administration of praziquantel in sub-Saharan Africa. | 2001-11-15 |
|
| Efficacy of praziquantel against Schistosoma japonicum: field evaluation in an area with repeated chemotherapy compared with a newly identified endemic focus in Hunan, China. | 2001-11-15 |
|
| Artesunate and praziquantel for the treatment of Schistosoma haematobium infections: a double-blind, randomized, placebo-controlled study. | 2001-11-15 |
|
| [Tactics of wide use of praziquantel in the complex of measures for prevention of opisthorchiasis. 3. General approach for ambulatory treatment of patients with opisthorchiasis in disease reservoirs]. | 2001-11-13 |
|
| Just another hemoptysis or a fluke? | 2001-11 |
|
| Urinary schistosomiasis in southern Ghana: a logistic regression approach to data from a community-based integrated control program. | 2001-11 |
|
| Are poor responses to praziquantel for the treatment of Schistosoma mansoni infections in Senegal due to resistance? An overview of the evidence. | 2001-11 |
|
| Impact of schistosomiasis on patient and graft outcome after renal transplantation: 10 years' follow-up. | 2001-11 |
|
| Prospects in medical management of Echinococcus granulosus. | 2001-10-27 |
|
| [Anemia, eosinophilia and generalized weakness in a 20-year old African]. | 2001-10-15 |
|
| Human susceptibility to Schistosoma japonicum in China correlates with antibody isotypes to native antigens. | 2001-10-03 |
|
| [Subretinal granuloma, retinal vasculitis and keratouveitis with secondary open-angle glaucoma in schistosomiasis]. | 2001-10 |
|
| A baseline study on the importance of bovines for human Schistosoma japonicum infection around Poyang Lake, China. | 2001-10 |
|
| Reinfection with Schistosoma haematobium following school-based chemotherapy with praziquantel in four highly endemic villages in Côte d'Ivoire. | 2001-10 |
|
| Acute colonic obstruction due to schistosomiasis in conjunction with ingestion of mangos. | 2001-10 |
|
| Failure of one-day praziquantel treatment in patients with multiple neurocysticercosis lesions. | 2001-10 |
|
| Medical treatment for neurocysticercosis characterized by giant subarachnoid cysts. | 2001-09-20 |
|
| Tropical warts. | 2001-09-08 |
|
| Spinal-cord involvement in the hepato-splenic form of Schistosoma mansoni infection. | 2001-09 |
|
| Combined praziquantel and albendazole chemoprophylaxis in experimental hydatidosis. | 2001-09 |
|
| Susceptibility of Schistosoma japonicum to praziquantel in China. | 2001-09 |
|
| In vitro effects of isoprinosine and a dipeptide methyl ester on Echinococcus multilocularis protoscoleces. | 2001-09 |
|
| In vitro responses of praziquantel-resistant and -susceptible Schistosoma mansoni to praziquantel. | 2001-09 |
|
| Counterfeit praziquantel. | 2001-08-25 |
|
| Depletion of praziquantel in plasma and muscle tissue of cultured rockfish Sebastes schlegeli after oral and bath treatment. | 2001-08-02 |
|
| Praziquantel--quality, dosages and markers of resistance. | 2001-08 |
|
| Pharmacokinetics and microsomal oxidation of praziquantel and its effects on the P450 system in three-month-old lambs infested by Fasciola hepatica. | 2001-08 |
|
| Acanthoparyphium tyosenense: the discovery of human infection and identification of its source. | 2001-08 |
|
| A rare case of eosinophilic pleuritis due to sparganosis. | 2001-08 |
|
| A comparative trial of albendazole alone versus combination of albendazole and praziquantel for treatment of Trichuris trichiura infection. | 2001-06 |
|
| Schistosoma mansoni and Biomphalaria: past history and future trends. | 2001 |
|
| [Schistosomiasis of the spinal cord. Case report]. | 2001 |
|
| Primary hydatid cyst of the axillary region: report of a case. | 2001 |
|
| Replacing oxamniquine by praziquantel against Schistosoma mansoni infection in a rural community from the sugar-cane zone of Northeast Brazil: an epidemiological follow-up. | 2001 |
|
| The impact of repeated treatment with praziquantel of schistosomiasis in children under six years of age living in an endemic area for Schistosoma haematobium infection. | 2001 |
|
| T cell clones from Schistosoma haematobium infected and exposed individuals lacking distinct cytokine profiles for Th1/Th2 polarisation. | 2001 |
|
| Schistosomiasis epidemiology and control: how did we get here and where should we go? | 2001 |
|
| Voltammetric determination of praziquantel in tablets and biological fluids. | 2001 |
|
| Evaluation of efficacy of school-based anthelmintic treatments against anaemia in children in the United Republic of Tanzania. | 2001 |
|
| Optimising the benefits of anthelmintic treatment in children. | 2001 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: The recommended dose for clonorchiasis and opisthorchiasis is: 25 mg/kg bodyweight three times a day as a one day treatment, at intervals of not less than 4 hours and not more than 6 hours. The tablets should be washed down unchewed with water during meals.
For schistosomiasis: 20 mg/kg body weight three times a day as a one day treatment, at intervals of not less than 4 hours and not more than 6 hours.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3998507
To discern whether stage-specific resistance of Schistosoma mansoni to praziquantel occurs in vitro, was determined minimal effective concentrations (MECs) of drug needed to increase motor activity, produce contraction and/or paralysis, and cause tegumental vesiculation of developmental stages from day 0 to day 42 of S. mansoni. Recovery of these stages from exposure to praziquantel in vitro was also evaluated. MECs of praziquantel inducing increased motor activity and muscular contraction or paralysis or both were 0.005-0.01 ug/ml, irrespective of the stage examined.
| Substance Class |
Chemical
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6490C9U457
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EMA VETERINARY ASSESSMENT REPORTS |
PROFENDER [AUTHORIZED]
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CFR |
21 CFR 520.1872
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CFR |
21 CFR 520.1870
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WHO-ESSENTIAL MEDICINES LIST |
6.1.3
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EMA VETERINARY ASSESSMENT REPORTS |
BROADLINE(AUTHORIZED)
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CFR |
21 CFR 520.1200
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CFR |
21 CFR 520.1871
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CFR |
21 CFR 522.1870
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WHO-VATC |
QP52AA01
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CFR |
21 CFR 520.1199
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WHO-VATC |
QP52AA51
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LIVERTOX |
NBK548916
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CFR |
21 CFR 520.903D
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CFR |
21 CFR 520.1453
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WHO-ESSENTIAL MEDICINES LIST |
6.1.1
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CFR |
21 CFR 520.1445
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NDF-RT |
N0000175481
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EMA VETERINARY ASSESSMENT REPORTS |
PROFENDER [AUTHORIZED]
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CFR |
21 CFR 520.1447
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WHO-ATC |
P02BA01
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NCI_THESAURUS |
C250
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CFR |
21 CFR 520.1198
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FDA ORPHAN DRUG |
19487
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CFR |
21 CFR 524.775
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757285
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D011223
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1554603
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100000081420
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CHEMBL976
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Praziquantel
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259-559-6
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SUB10008MIG
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DB01058
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4891
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55268-74-1
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PRAZIQUANTEL
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PRAZIQUANTEL
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PRIMARY | Description: A white or almost white, crystalline powder; odourless or with a faint characteristic odour. Solubility: Very slightly soluble in water; freely soluble in ethanol (~750 g/l) TS. Category: Antischistosomal drug. Storage: Praziquantel should be kept in a well-closed container, protected from light. Definition: Praziquantel contains not less than 98.5% and not more than 101.0% of C19H24N2O2, calculated with reference to thedried substance. | ||
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m9107
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PRIMARY | Merck Index | ||
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2241
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6490C9U457
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8628
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3895
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C47683
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DTXSID9021182
Created by
admin on Mon Mar 31 19:00:58 GMT 2025 , Edited by admin on Mon Mar 31 19:00:58 GMT 2025
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PRIMARY |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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TARGET ORGANISM->INHIBITOR |
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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| Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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