Details
Stereochemistry | ACHIRAL |
Molecular Formula | C32H39NO2 |
Molecular Weight | 469.6576 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)C1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)OC(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=MJJALKDDGIKVBE-UHFFFAOYSA-N
InChI=1S/C32H39NO2/c1-32(2,3)28-18-16-25(17-19-28)30(34)15-10-22-33-23-20-29(21-24-33)35-31(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-9,11-14,16-19,29,31H,10,15,20-24H2,1-3H3
Molecular Formula | C32H39NO2 |
Molecular Weight | 469.6576 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/19032340
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340
Ebastine is an antihistamine which blocks H1-receptors through its carboxylic acid metabolite. Ebastine is indicated for the treatment of allergic rhinitis and chronic idiopathic urticaria.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11328664
Curator's Comment: Ebastine BBB transport was studied on rats, mice and bovine brain. Ebastine has shown limmited transport, while its active metabolite, carebastine, was effectively transported by P-gp.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/19032340 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EBATROL Approved UseUnknown |
|||
Primary | EBATROL Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
53.4 ng/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAREBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
97.7 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAREBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.71 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.98 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.31 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.49 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.91 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.58 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.15 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: sex: MALE food status: UNKNOWN |
|
5.97 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1417 ng × h/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAREBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2630 ng × h/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAREBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
16.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
30.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
14.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
28.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
16.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: sex: MALE food status: UNKNOWN |
|
25.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.1 h |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAREBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
17.6 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAREBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
24.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
24.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
23.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: sex: MALE food status: UNKNOWN |
|
37.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17518511/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EBASTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.1% |
EBASTINE serum | Homo sapiens |
||
2.3% |
CAREBASTINE plasma | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
40 mg 1 times / day single, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: single Dose: 40 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
|
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: |
Other AEs: Headache, Drowsiness... Other AEs: Headache (7.9%) Sources: Drowsiness (3%) dry mouth (2.1%) |
60 mg single, oral Overdose |
healthy |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
dry mouth | 2.1% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: |
Drowsiness | 3% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: |
Headache | 7.9% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 10.964 uM] | ||||
inconclusive [IC50 15.4871 uM] | ||||
no [EC50 3.0901 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no | ||||
no | ||||
no | ||||
yes [IC50 13.8029 uM] | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
major | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes [Km 0.75 uM] | ||||
yes [Km 1.3 uM] | ||||
yes [Km 21.9 uM] | ||||
yes [Km 3 uM] | ||||
yes [Km 3.85 uM] | ||||
yes [Km 5.56 uM] | ||||
yes [Km 7.63 uM] | ||||
yes [Km 7.67 uM] | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Mechanism responsible for epileptogenic activity by first-generation H1-antagonists in rats. | 2000 Dec 22 |
|
Safety of antihistamines in children. | 2001 |
|
Problems of heart rate correction in assessment of drug-induced QT interval prolongation. | 2001 Apr |
|
Transport characteristics of ebastine and its metabolites across human intestinal epithelial Caco-2 cell monolayers. | 2001 Aug |
|
Blockade of eosinophil migration and airway hyperresponsiveness by cPLA2-inhibition. | 2001 Feb |
|
Simultaneous determination of the histamine H1-receptor antagonist ebastine and its two metabolites, carebastine and hydroxyebastine, in human plasma using high-performance liquid chromatography. | 2001 Jun 5 |
|
Urticaria to cetirizine. | 2002 |
|
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations]. | 2002 |
|
Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes. | 2002 Jan |
|
[Effect of H1 histamine receptor antagonists on T cell functions]. | 2003 Nov |
|
A study comparing the inhibitory effects of single and repeated oral doses of ebastine and fexofenadine against histamine-induced skin reactivity. | 2003 Nov |
|
Fixed drug eruption due to loratadine. | 2003 Sep-Oct |
|
Pharmacokinetics and safety of ebastine in patients with impaired hepatic function compared with healthy volunteers: a phase I open-label study. | 2004 |
|
Efficacy and safety of ebastine 20 mg compared to loratadine 10 mg once daily in the treatment of seasonal allergic rhinitis: a randomized, double-blind, placebo-controlled study. | 2004 Apr |
|
A review of the second-generation antihistamine ebastine for the treatment of allergic disorders. | 2004 Aug |
|
Anti-inflammatory activity of H1-receptor antagonists: review of recent experimental research. | 2004 Jan |
|
Pharmacological management of allergic rhinitis in the elderly: safety issues with oral antihistamines. | 2005 |
|
Management of persistent allergic rhinitis: evidence-based treatment with levocetirizine. | 2005 Dec |
|
Identification and functional characterization of novel CYP2J2 variants: G312R variant causes loss of enzyme catalytic activity. | 2005 Feb |
|
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic. | 2005 Mar |
|
Safety of ebastine. | 2005 Mar |
|
[Cardiac arrest following treatment with non-cardiologic QT-interval-increasing medications]. | 2005 May 2 |
|
Comparison of inhibition of cutaneous histamine reaction of ebastine fast-dissolving tablet [20 mg] versus desloratadine capsule [5 mg]: a randomized, double-blind, double-dummy, placebo-controlled, three-period crossover study in healthy, nonatopic adults. | 2007 Dec |
|
[Ebastine-induced hepatotoxicity]. | 2007 Oct |
|
Rupatadine in allergic rhinitis and chronic urticaria. | 2008 Apr |
|
Granular parakeratosis presenting with facial keratotic papules. | 2008 Jan-Feb |
|
Probing ligand binding modes of human cytochrome P450 2J2 by homology modeling, molecular dynamics simulation, and flexible molecular docking. | 2008 May 1 |
|
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS). | 2008 Sep |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/21437146
In vitro, ebastine and carebastine were shown to block the release of anti-IgE-induced eicosanoids LTC4/D4 and PGD2. Ebastine inhibited release of the two mediators by 30% at clinically relevant concentrations (IC30 = 2.57–9.6 umol/L).
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:05:44 GMT 2025
by
admin
on
Mon Mar 31 18:05:44 GMT 2025
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Record UNII |
TQD7Q784P1
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
R06AX22
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WHO-VATC |
QR06AX22
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NCI_THESAURUS |
C29578
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CHEMBL305660
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m4801
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90729-43-4
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Ebastine
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DB11742
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23796
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100000092562
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TQD7Q784P1
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DTXSID6046472
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EBASTINE
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Y-98
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C058249
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C77437
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SUB06435MIG
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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ACTIVE MOIETY |