Details
Stereochemistry | ACHIRAL |
Molecular Formula | C30H24N4O8 |
Molecular Weight | 568.5336 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC1=NC2=C(N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NOC(=O)N5)C(=CC=C2)C(=O)OCC6=C(C)OC(=O)O6
InChI
InChIKey=QJFSABGVXDWMIW-UHFFFAOYSA-N
InChI=1S/C30H24N4O8/c1-3-38-28-31-23-10-6-9-22(27(35)39-16-24-17(2)40-30(37)41-24)25(23)34(28)15-18-11-13-19(14-12-18)20-7-4-5-8-21(20)26-32-29(36)42-33-26/h4-14H,3,15-16H2,1-2H3,(H,32,33,36)
Molecular Formula | C30H24N4O8 |
Molecular Weight | 568.5336 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/200796s006lbl.pdfhttps://www.takeda.com/news/2011/20110322_3837.htmlCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23487168
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/200796s006lbl.pdfhttps://www.takeda.com/news/2011/20110322_3837.html
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23487168
TAK-536 (generic name: azilsartan) is an angiotensin II type 1 receptor blocker, discovered by Takeda and its mechanism of action is to lower blood pressure by inhibiting action of a vasopressor hormone Angiotensin II. Angiotensin II type 1 receptor antagonists have become an important drug class in the treatment of hypertension and heart failure. TAK-536 is in phase III clinical trial for treatment hypertension. This drug also known as active metabolite of the prodrug azilsartan medoxomil (also known as azilsartan kamedoxomil), but in some countries azilsartan rather than its prodrug is used for oral treatment.
Originator
Sources: https://www.takeda.com/news/2011/20110224_3831.htmlhttps://www.takeda.com/news/2011/20110322_3837.html
Curator's Comment: # Takeda
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P30556 Gene ID: 185.0 Gene Symbol: AGTR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=22346296 |
0.62 nM [IC50] | ||
Target ID: CHEMBL227 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17485025 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EDARBI Approved UseIndicated for the treatment of hypertension to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. Edarbi may be used either alone or in combination with other antihypertensive agents. Launch Date2011 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5355.71 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27514506/ |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: Chlorthalidone |
AZILSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
141.3 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN METABOLITE M-I plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
191.3 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN METABOLITE M-I plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
227.7 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN METABOLITE M-II plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
179.3 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN METABOLITE M-II plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
888.3 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
831.3 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
46688.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27514506/ |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: Chlorthalidone |
AZILSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1420.5 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN METABOLITE M-I plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
1592.7 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN METABOLITE M-I plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
1986.5 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN METABOLITE M-II plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
3526 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN METABOLITE M-II plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
6350.3 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
5 mg single, oral dose: 5 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
|
6871.7 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02451150 |
10 mg single, oral dose: 10 mg route of administration: oral experiment type: single co-administered: |
AZILSARTAN plasma | Homo sapiens population: unhealthy age: Children sex: food status: Fed |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27514506/ |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: Chlorthalidone |
AZILSARTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
80 mg 1 times / day unknown, oral dose: 80 mg route of administration: Oral experiment type: UNKNOWN co-administered: |
AZILSARTAN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
80 mg 1 times / day multiple, oral (max) Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.187 |
unhealthy, 50.4+/-10.2 n = 179 Health Status: unhealthy Condition: Hypertension Age Group: 50.4+/-10.2 Sex: M+F Population Size: 179 Sources: Page: p.187 |
Disc. AE: Dizziness, Fatigue... AEs leading to discontinuation/dose reduction: Dizziness (3.35%) Sources: Page: p.187Fatigue (2.79%) |
320 mg 1 times / day multiple, oral Overdose Dose: 320 mg, 1 times / day Route: oral Route: multiple Dose: 320 mg, 1 times / day Sources: Page: p.6 |
healthy Health Status: healthy Sources: Page: p.6 |
|
80 mg 1 times / day multiple, oral (max) Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.4 |
unhealthy n = 2146 Health Status: unhealthy Condition: Hypertension Population Size: 2146 Sources: Page: p.4 |
Disc. AE: Hypotension orthostatic... AEs leading to discontinuation/dose reduction: Hypotension orthostatic (0.4%) Sources: Page: p.4 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fatigue | 2.79% Disc. AE |
80 mg 1 times / day multiple, oral (max) Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.187 |
unhealthy, 50.4+/-10.2 n = 179 Health Status: unhealthy Condition: Hypertension Age Group: 50.4+/-10.2 Sex: M+F Population Size: 179 Sources: Page: p.187 |
Dizziness | 3.35% Disc. AE |
80 mg 1 times / day multiple, oral (max) Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.187 |
unhealthy, 50.4+/-10.2 n = 179 Health Status: unhealthy Condition: Hypertension Age Group: 50.4+/-10.2 Sex: M+F Population Size: 179 Sources: Page: p.187 |
Hypotension orthostatic | 0.4% Disc. AE |
80 mg 1 times / day multiple, oral (max) Recommended Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.4 |
unhealthy n = 2146 Health Status: unhealthy Condition: Hypertension Population Size: 2146 Sources: Page: p.4 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
Page: 9, 46-47, (ClinPharm) 15, 17-18 |
no [IC50 >100 uM] | |||
Page: 9, 46-47, (ClinPharm) 15, 17-18 |
no [IC50 >100 uM] | |||
Page: 9, 46-47, (ClinPharm) 15, 17-18 |
no [IC50 >100 uM] | |||
Page: 9, 46-47, (ClinPharm) 15, 17-18, 58-59 |
no [IC50 >100 uM] | no (co-administration study) Comment: Human liver microsomes (Phenacetin O-deethylation), Maximum inhibition = 5.1%; Coadministration of Azilsartan medoxomil (80 mg QD for 6 days) did not significantly affect Caffeine (200 mg QD on Day 6, CYP1A2 substrate) AUC and Cmax. Page: 9, 46-47, (ClinPharm) 15, 17-18, 58-59 |
||
Page: 9, 46-47, (ClinPharm) 15, 17-18, 77-78 |
no [IC50 >100 uM] | no (co-administration study) Comment: Human liver microsomes (Paclitaxel 6a-hydroxylation), Maximum inhibition = 10.1%; Pioglitazone does not affect systemic exposure to Azilzartan, and systemic exposure to pioglitazone is not affected by Azilzartan. Page: 9, 46-47, (ClinPharm) 15, 17-18, 77-78 |
||
Page: 9, 46-47, (ClinPharm) 15, 17-18, 58-59, 66-68 |
no [IC50 >100 uM] | no (co-administration study) Comment: Human liver microsomes (Diclofenac 4'-hydroxylation), Inhibited CYP2C9 activities at 30 (14.4%) and 100 mcM (37.9%); Human CYP expressing microsomes derived from B-lymphoblastoid cells (tolbutamide hydroxylation); Coadministration of Azilsartan medoxomil (80 mg QD for 6 days) did not significantly affect Tolbutamide (500 mg QD on Day 6, CYP2C9 substrate) AUC and Cmax.; Azilzartan dose not affect the pharmacokinetics and pharmacodynamics of warfarin and is not expected to significantly affect systemic exposure to other CYP 2C9 substartes. Page: 9, 46-47, (ClinPharm) 15, 17-18, 58-59, 66-68 |
||
Page: 9, 46-47, (ClinPharm) 15, 17-18, 58-59 |
no [IC50 >100 uM] | no (co-administration study) Comment: Human liver microsomes (Bufuralol 1'-hydroxylation), Maximum inhibition = 5.1%; Coadministration of Azilsartan medoxomil (80 mg QD for 6 days) did not significantly affect Dextromethorphan (30 mg QD on Day 6, CYP2D6 substrate) AUC and Cmax. Page: 9, 46-47, (ClinPharm) 15, 17-18, 58-59 |
||
Page: 9, 46-47, (ClinPharm) 15, 17-18, 58-59, 73-74 |
no [IC50 >100 uM] | no (co-administration study) Comment: Human liver microsomes (Midazolam 17-hydroxylation, Testosterone 6b-hydroxylation), Maximum inhibition = /<0%; Coadministration of Azilsartan medoxomil(80 mg QD for 6 days) did not significantly affect Midazolam (4 mg QD on Day 6, CYP3A4 substrate) AUC and Cmax.; Amlodipine does not affect systemic exposure to Azilzartan, and systemic exposure to amlodipine is not affected by Azilzartan. Page: 9, 46-47, (ClinPharm) 15, 17-18, 58-59, 73-74 |
||
Page: 9, 45-46, (ClinPharm) 16, 19 |
unlikely | |||
Page: 35, (ClinPharm) 22-23, 58-59, 62-63 |
unlikely | weak (co-administration study) Comment: Caco-2 cells (After incubation at 37°C for 2 hours with Azilzartan (at 0, 20, 100, and 500 μmol/L), efflux ratios of digoxin were 6.4, 7.0, 6.6, and 7.23. These results show that Azilsartan had no inhibitory effect on P-gp-mediated efflux activity.; Coadministration of Azilsartan medoxomil (80 mg QD for 6 days) did not significantly affect Fexofenadine (60 mg QD on Day 6, P-gp substrate) AUC and Cmax.; Coadminitration of Azilzartan (80 mg QD for 10 days) increased Digoxin (200 mcg QD for 10 days) AUC0-tau by 2.87% and decreased Cmax by 5.71%. Page: 35, (ClinPharm) 22-23, 58-59, 62-63 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200796Orig1s000PharmR.pdf#page=35 Page: 35.0 |
inconclusive | |||
Page: 9, 45, (ClinPharm) 14, 64-65, 69-70 |
major | yes (co-administration study) Comment: O-dealkylation to form Azilsartan M-II primarily by CYP2C9, Incubation of 14C-AZILSARTAN with microsomes from baculovirus-infected insect cellsexpressuing human CYP isoforms (elimination and formation (M-1 & M-II) rate); Human liver microsomes (16 donors); Clearance of Azilzartan (40 mg QD on Days 1 & 10) is reduced when co-administered with fluconazole (200 mg QD on Days 4-10), a CYP 2C9 inhibitor. This is evident from the ~ 40% increase in AUC, but only ~ 14% increase in Cmax. However, this is not of clinical significance given the flat D-R relationship for Azilzartan and the absence of serious adverse events.; Systemic exposure to glyburide (5 mg QD on DAy 8) is not affected by Azilzartan (40 mg QD for 8 days). Page: 9, 45, (ClinPharm) 14, 64-65, 69-70 |
||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200796Orig1s000ClinPharmR.pdf#page=14 Page: (ClinPharm) 14 |
yes | |||
Page: 9, 45, (ClinPharm) 14, 64-65 |
yes | yes (co-administration study) Comment: Incubation of 14C-AZILSARTAN with microsomes from baculovirus-infected insect cellsexpressuing human CYP isoforms (elimination and formation (M-1 & M-II) rate); Human liver microsomes (16 donors); When co-administered with ketoconazole (400 mg QD on Days 4-10), Cmax of Azilzartan (40 mg QD on Day 1 & 10) decreased by ~ 30% and AUC by ~ 20%. However, the reason for this is not apparent. Page: 9, 45, (ClinPharm) 14, 64-65 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/200796Orig1s000PharmR.pdf#page=30 Page: 8, 30 |
PubMed
Title | Date | PubMed |
---|---|---|
TAK-536, a new AT1 receptor blocker, improves glucose intolerance and adipocyte differentiation. | 2007 May |
|
Differential pharmacology and benefit/risk of azilsartan compared to other sartans. | 2012 |
|
A systematic comparison of the properties of clinically used angiotensin II type 1 receptor antagonists. | 2013 Apr |
|
Azilsartan, aliskiren, and combination antihypertensives utilizing renin-angiotensin-aldosterone system antagonists. | 2014 Sep-Oct |
Substance Class |
Chemical
Created
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Record UNII |
LL0G25K7I2
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Validated (UNII)
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WHO-ATC |
C09CA09
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NCI_THESAURUS |
C66930
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EMA ASSESSMENT REPORTS |
EDARBI (AUTHORIZED: HYPERTENSION)
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WHO-ATC |
C09DA09
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IPREZIV (WITHDRAWN: HYPERTENSION)
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WHO-VATC |
QC09CA09
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m2173
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1091642
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SUB31560
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UU-32
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CHEMBL2028661
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |