Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H37N3O7S |
Molecular Weight | 547.664 |
Optical Activity | ( - ) |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12OCC[C@@]1([H])[C@H](CO2)OC(=O)N[C@@H](CC3=CC=CC=C3)[C@H](O)CN(CC(C)C)S(=O)(=O)C4=CC=C(N)C=C4
InChI
InChIKey=CJBJHOAVZSMMDJ-HEXNFIEUSA-N
InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
Molecular Formula | C27H37N3O7S |
Molecular Weight | 547.664 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23708741 | http://adisinsight.springer.com/drugs/800016726
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23708741 | http://adisinsight.springer.com/drugs/800016726
Darunavir (trade name Prezista) is an orally active bis-furan-sulfonamide inhibitor of human immunodeficiency virus (HIV-1) protease. Darunavir was developed by Tibotec Pharmaceuticals (now Janssen R&D Ireland). Darunavir is indicated for the treatment of HIV-1 infection in adult and pediatric patients 3 years of age and older. The drug is co-administered with low-dose ritonavir and other anti-HIV agents. It is the only antiretroviral that has been registered at two different doses, 800/100 mg once-daily or 600/100 mg twice-daily, allowing its administration throughout the entire course of HIV disease, from naive subjects without any HIV-1 resistance to heavily treatment-experienced subjects with widespread triple-class family resistance.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15479840 |
4.5 pM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PREZISTA Approved UsePREZISTA is a human immunodeficiency virus (HIV-1) protease inhibitor indicated for the treatment of HIV-1 infection in adult patients. PREZISTA is also indicated for the treatment of HIV-1 infection in pediatric patients 3 years of age and older. PREZISTA must be co-administered with ritonavir (PREZISTA/ritonavir) and with other antiretroviral agents. Launch Date2006 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5272 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21926632/ |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
93026 ng × h/mL |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
124698 ng × h/mL |
600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
57055 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21926632/ |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
126377 ng × h/mL |
600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15 h |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
15 h |
600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5% |
600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir |
DARUNAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.227 |
unhealthy, 43 n = 127 Health Status: unhealthy Condition: HIV-1 infection Age Group: 43 Sex: M+F Population Size: 127 Sources: Page: p.227 |
Disc. AE: Headache, Gastrointestinal disorder NOS... AEs leading to discontinuation/dose reduction: Headache (grade 3, 0.79%) Sources: Page: p.227Gastrointestinal disorder NOS (5.51%) |
3200 mg single, oral Overdose Dose: 3200 mg Route: oral Route: single Dose: 3200 mg Sources: Page: p.22 |
healthy Health Status: healthy Sources: Page: p.22 |
|
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Disc. AE: Drug-induced hepatitis, Hepatitis acute... AEs leading to discontinuation/dose reduction: Drug-induced hepatitis Sources: Page: p.1Hepatitis acute Cytolytic hepatitis Reaction skin (grade 1-3) Stevens-Johnson syndrome Toxic epidermal necrolysis Diabetes mellitus Hyperglycemia Fat redistribution Fat tissue increased Immune reconstitution syndrome |
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.8 |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (grade 1-2, 0.5%) Sources: Page: p.8 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal disorder NOS | 5.51% Disc. AE |
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.227 |
unhealthy, 43 n = 127 Health Status: unhealthy Condition: HIV-1 infection Age Group: 43 Sex: M+F Population Size: 127 Sources: Page: p.227 |
Headache | grade 3, 0.79% Disc. AE |
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.227 |
unhealthy, 43 n = 127 Health Status: unhealthy Condition: HIV-1 infection Age Group: 43 Sex: M+F Population Size: 127 Sources: Page: p.227 |
Cytolytic hepatitis | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Diabetes mellitus | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Drug-induced hepatitis | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Fat redistribution | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Fat tissue increased | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Hepatitis acute | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Hyperglycemia | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Immune reconstitution syndrome | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Stevens-Johnson syndrome | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Toxic epidermal necrolysis | Disc. AE | 800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Reaction skin | grade 1-3 Disc. AE |
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Rash | grade 1-2, 0.5% Disc. AE |
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.8 |
PubMed
Title | Date | PubMed |
---|---|---|
New HIV treatment. | 2006 Sep-Oct |
|
Clinical pharmacokinetics of darunavir. | 2007 |
|
Pharmacokinetics of darunavir/ritonavir and TMC125 alone and coadministered in HIV-negative volunteers. | 2007 |
|
Pharmacokinetic interaction between TMC114/r and efavirenz in healthy volunteers. | 2007 |
|
Fast and simultaneous determination of darunavir and eleven other antiretroviral drugs for therapeutic drug monitoring: method development and validation for the determination of all currently approved HIV protease inhibitors and non-nucleoside reverse transcriptase inhibitors in human plasma by liquid chromatography coupled with electrospray ionization tandem mass spectrometry. | 2007 |
|
Pharmacokinetics of darunavir (TMC114) and atazanavir during coadministration in HIV-negative, healthy volunteers. | 2007 |
|
Antiretroviral treatment of HIV infection: Swedish recommendations 2007. | 2007 |
|
Anti-HIV drugs. | 2007 |
|
AIDS in the Third World: how to stop the HIV infection? | 2007 |
|
Key reports from the XV International HIV Drug Resistance Workshop 2006. | 2007 |
|
When and how to use tipranavir and darunavir. | 2007 Apr |
|
The effect of different meal types on the pharmacokinetics of darunavir (TMC114)/ritonavir in HIV-negative healthy volunteers. | 2007 Apr |
|
Efficacy and safety of darunavir-ritonavir at week 48 in treatment-experienced patients with HIV-1 infection in POWER 1 and 2: a pooled subgroup analysis of data from two randomised trials. | 2007 Apr 7 |
|
Darunavir: promising initial results. | 2007 Apr 7 |
|
Darunavir (TMC114): a new HIV-1 protease inhibitor. | 2007 Aug |
|
Development of therapeutics for AIDS: structure-based molecular targeting. | 2007 Aug |
|
Darunavir: a second-generation protease inhibitor. | 2007 Aug 1 |
|
Overview of boosted protease inhibitors in treatment-experienced HIV-infected patients. | 2007 Dec |
|
Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV. | 2007 Dec 15 |
|
Darunavir (TMC114) approved by the FDA. | 2007 Feb |
|
Efficacy and safety of TMC114/ritonavir in treatment-experienced HIV patients: 24-week results of POWER 1. | 2007 Feb 19 |
|
48-week study results show DRV's staying power. | 2007 Jan |
|
Anti-HIV agents. Darunavir and some antidepressants. | 2007 Jan |
|
Pharmacokinetics and antiretroviral response to darunavir/ritonavir and etravirine combination in patients with high-level viral resistance. | 2007 Jul 11 |
|
Efficacy and safety of darunavir-ritonavir compared with that of lopinavir-ritonavir at 48 weeks in treatment-experienced, HIV-infected patients in TITAN: a randomised controlled phase III trial. | 2007 Jul 7 |
|
Efficacy and safety of TMC125 (etravirine) in treatment-experienced HIV-1-infected patients in DUET-1: 24-week results from a randomised, double-blind, placebo-controlled trial. | 2007 Jul 7 |
|
No patient left behind--better treatments for resistant HIV infection. | 2007 Jul 7 |
|
Safety, tolerability, and efficacy of darunavir (TMC114) with low-dose ritonavir in treatment-experienced, hepatitis B or C co-infected patients in POWER 1 and 3. | 2007 Jul-Aug |
|
A novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI), GRL-98065, is potent against multiple-PI-resistant human immunodeficiency virus in vitro. | 2007 Jun |
|
Prezista gets EU approval. | 2007 Mar |
|
Editorial comment: impact of darunavir for salvage therapy. | 2007 Mar |
|
Darunavir: an overview of an HIV protease inhibitor developed to overcome drug resistance. | 2007 Mar |
|
Consensus recommendation from a group of German experts for the use of enfuvirtide in heavily pretreated HIV patients. | 2007 Mar 26 |
|
Tibotec and Aspen collaborate on Prezista. | 2007 May |
|
HIV-1 subtype B protease and reverse transcriptase amino acid covariation. | 2007 May |
|
Relative antiviral efficacy of ritonavir-boosted darunavir and ritonavir-boosted tipranavir vs. control protease inhibitor in the POWER and RESIST trials. | 2007 May |
|
Prediction of clinical benefits of ritonavir-boosted TMC114 from treatment effects on CD4 counts and HIV RNA. | 2007 May |
|
Key amprenavir resistance mutations counteract dramatic efficacy of darunavir in highly experienced patients. | 2007 May 31 |
|
Analysis of treatment costs for HIV RNA reductions and CD4 increases for darunavir versus other antiretrovirals in treatment-experienced, HIV-infected patients. | 2007 May-Jun |
|
Prevalence of darunavir resistance mutations in HIV-1-infected patients failing other protease inhibitors. | 2007 Oct |
|
Quantification of darunavir (TMC114) in human plasma by high-performance liquid chromatography with ultra-violet detection. | 2007 Oct 1 |
|
Predicting HIV care costs using CD4 counts from clinical trials. | 2007 Sep |
|
Lessons Learned From 2 Patients With Multidrug-Resistant HIV-1 Infection Successfully Treated With a Darunavir-Containing Antiretroviral Treatment Regimen. | 2007 Sep |
|
Safety and efficacy of darunavir (TMC114) with low-dose ritonavir in treatment-experienced patients: 24-week results of POWER 3. | 2007 Sep 1 |
|
Tipranavir: a new option for the treatment of drug-resistant HIV infection. | 2007 Sep 15 |
|
Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization. | 2007 Sep 28 |
|
Potent new antiviral compound shows similar inhibition and structural interactions with drug resistant mutants and wild type HIV-1 protease. | 2007 Sep 6 |
|
Darunavir offers potent new combo when used with enfuvirtide in ritonavir-boosted regimen. | 2007 Winter |
|
Design of HIV protease inhibitors targeting protein backbone: an effective strategy for combating drug resistance. | 2008 Jan |
|
Quality control of protease inhibitors. | 2008 Jun |
Sample Use Guides
Treatment-naïve adult patients and treatment-experienced adult patients with no darunavir resistance associated substitutions:
800 mg (two 400 mg tablets) taken with ritonavir 100 mg once daily and with food. Treatment-experienced adult patients with at least one darunavir resistance associated substitution: 600 mg (one 600 mg tablet) taken with ritonavir 100 mg twice daily and with food. Pediatric patients (3 to less than 18 years of age and weighing at
least 10 kg): dosage of PREZISTA and ritonavir is based on body weight and should not exceed the treatmentexperienced adult dose. Do not use once daily dosing in pediatric patients. PREZISTA should be taken with ritonavir twice daily and with food.
Route of Administration:
Oral
Darunavir exhibits activity against laboratory strains and clinical isolates of HIV-1 and laboratory strains of HIV-2 in acutely infected T-cell lines, human peripheral blood mononuclear cells and human monocytes/macrophages with median EC50 values ranging from 1.2 to 8.5 nM (0.7 to 5.0 ng/mL). Darunavir demonstrates antiviral activity in cell culture against a broad panel of HIV-1 group M (A, B, C, D, E, F, G), and group O primary isolates with EC50 values ranging from less than 0.1 to 4.3 nM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:28:19 GMT 2023
by
admin
on
Fri Dec 15 16:28:19 GMT 2023
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Record UNII |
YO603Y8113
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
J05AE10
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LIVERTOX |
NBK547994
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NDF-RT |
N0000175889
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J05AR14
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N0000000246
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QJ05AE10
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NCI_THESAURUS |
C783
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206361-99-1
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DTXSID0046779
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N0000190114
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Darunavir
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SUB25394
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460132
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213039
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C482292
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METABOLIC ENZYME -> SUBSTRATE | |||
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SOLVATE->ANHYDROUS | |||
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METABOLIC ENZYME -> INHIBITOR |
Ki
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SOLVATE->ANHYDROUS |
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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TARGET ORGANISM->INHIBITOR |
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SALT/SOLVATE -> PARENT |
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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TRANSPORTER -> INHIBITOR | |||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
FECAL
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS |
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
FECAL; URINE
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METABOLITE -> PARENT |
FECAL; URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
FECAL; URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
PLASMA
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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