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 Date1.15102083E12 |
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 |
---|---|---|
Gateways to clinical trials. | 2004 May |
|
[New drugs--hope for salvage patients?]. | 2005 Apr 25 |
|
Anti-HIV agents. What the future holds for TMC114. | 2005 Aug-Sep |
|
Anti-HIV agents. Interactions with TMC114. | 2005 Aug-Sep |
|
Protease inhibitors: the current status. | 2005 Dec |
|
[Protease inhibitors]. | 2005 Dec |
|
Development of a capillary electrophoretic method for the separation of diastereoisomers of a new human immunodeficiency virus protease inhibitor. | 2005 Feb |
|
TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates. | 2005 Jun |
|
TMC114/ritonavir substitution for protease inhibitor(s) in a non-suppressive antiretroviral regimen: a 14-day proof-of-principle trial. | 2005 Jun 10 |
|
New protease inhibitor TMC-114. Preliminary 24-week late breaker results of the phase II trial. | 2005 Mar-Apr |
|
New PI may offer hope to triple class patients. | 2005 May |
|
Molecular basis for substrate recognition and drug resistance from 1.1 to 1.6 angstroms resolution crystal structures of HIV-1 protease mutants with substrate analogs. | 2005 Oct |
|
Structure-based design of novel HIV-1 protease inhibitors to combat drug resistance. | 2006 Aug 24 |
|
Screening and selecting for optimized antiretroviral drugs: rising to the challenge of drug resistance. | 2006 Dec |
|
Enantioselective synthesis and selective monofunctionalization of (4R,6R)-4,6- dihydroxy-2,8-dioxabicyclo[3.3.0]octane. | 2006 Dec 7 |
|
Effectiveness of nonpeptide clinical inhibitor TMC-114 on HIV-1 protease with highly drug resistant mutations D30N, I50V, and L90M. | 2006 Feb 23 |
|
Prezista (darunavir, TMC-114) approved; may be important treatment advance. | 2006 Jan-Jun |
|
The clinical pharmacology of antiretrovirals in development. | 2006 Jun |
|
XVI International AIDS Conference: Part 2. | 2006 Nov |
|
New HIV treatment. | 2006 Sep-Oct |
|
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 |
|
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 |
|
Darunavir (TMC114): a new HIV-1 protease inhibitor. | 2007 Aug |
|
Darunavir: a second-generation protease inhibitor. | 2007 Aug 1 |
|
A novel substrate-based HIV-1 protease inhibitor drug resistance mechanism. | 2007 Jan |
|
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 |
|
Prezista gets EU approval. | 2007 Mar |
|
Darunavir: an overview of an HIV protease inhibitor developed to overcome drug resistance. | 2007 Mar |
|
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 |
|
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 |
|
Lessons Learned From 2 Patients With Multidrug-Resistant HIV-1 Infection Successfully Treated With a Darunavir-Containing Antiretroviral Treatment Regimen. | 2007 Sep |
|
Tipranavir: a new option for the treatment of drug-resistant HIV infection. | 2007 Sep 15 |
|
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
Wed Jul 05 23:54:22 UTC 2023
by
admin
on
Wed Jul 05 23:54:22 UTC 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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WHO-ATC |
J05AR14
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NDF-RT |
N0000000246
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WHO-VATC |
QJ05AE10
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NCI_THESAURUS |
C783
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206361-99-1
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DTXSID0046779
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YO603Y8113
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N0000190114
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PRIMARY | Cytochrome P450 3A Inhibitors [MoA] | ||
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Darunavir
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DARUNAVIR
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7788
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CHEMBL1323
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YO603Y8113
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RR-31
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M4099
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SUB25394
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C65364
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100000089367
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460132
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213039
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C482292
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Related Record | Type | Details | ||
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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 |
Related Record | Type | Details | ||
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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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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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