Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H21N5O5S |
Molecular Weight | 479.508 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=CC=C1OC2=C(NS(=O)(=O)C3=CC=C(C)C=N3)N=C(N=C2OC)C4=CC=NC=C4
InChI
InChIKey=YBWLTKFZAOSWSM-UHFFFAOYSA-N
InChI=1S/C23H21N5O5S/c1-15-8-9-19(25-14-15)34(29,30)28-22-20(33-18-7-5-4-6-17(18)31-2)23(32-3)27-21(26-22)16-10-12-24-13-11-16/h4-14H,1-3H3,(H,26,27,28)
Molecular Formula | C23H21N5O5S |
Molecular Weight | 479.508 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Avosentan is an oral endothelin receptor A antagonist which was developed by Roche and then licensed by Speedel (now Novartis). The drug was tested in phase III of clinical trials in patients suffering from diabetic nephropathy, however drug development was terminated due to safety reasons: avosentan caused severe heart failure and even deaths.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL252 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22529820 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19279566 |
0.5 mg 1 times / day multiple, oral dose: 0.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AVOSENTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1883.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19279566 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AVOSENTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
228.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19279566 |
5 mg 1 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AVOSENTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
54.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19279566 |
1.5 mg 1 times / day multiple, oral dose: 1.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AVOSENTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
247 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19279566 |
0.5 mg 1 times / day multiple, oral dose: 0.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AVOSENTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
15646 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19279566 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AVOSENTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2106 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19279566 |
5 mg 1 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AVOSENTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
641 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19279566 |
1.5 mg 1 times / day multiple, oral dose: 1.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AVOSENTAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Dose-dependent acute and sustained renal effects of the endothelin receptor antagonist avosentan in healthy subjects. | 2009 Jun |
|
Unlike each drug alone, lisinopril if combined with avosentan promotes regression of renal lesions in experimental diabetes. | 2009 Nov |
|
Absolute bioavailability and pharmacokinetics of avosentan in man. | 2009 Sep |
|
Channels and transporters. Mini-symposium of the Division of Medicinal Chemistry (DMC) of the Swiss Chemical Society (SCS) at the Department of Chemistry, University of Basel, May 27, 2010. | 2010 |
|
Antiatherosclerotic and renoprotective effects of ebselen in the diabetic apolipoprotein E/GPx1-double knockout mouse. | 2010 Dec |
|
The endothelin receptor antagonist avosentan ameliorates nephropathy and atherosclerosis in diabetic apolipoprotein E knockout mice. | 2010 Jan |
|
Avosentan for overt diabetic nephropathy. | 2010 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23228194
Oral avosentan is administered once daily at doses of 25 or 50 mg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21281066
Porcine ciliary arteries were incubated with avosentan (10(-6) M and 10(-8) M) and then exposed, cumulatively, to increasing concentrations of endothelin-1 (10(-12) M-3 × 10(-8) M). Avosentan had a strong inhibitory effect on the endothelin-1-induced contractions. The inhibitory effect of 10(-6) M avosentan was significantly stronger than the effect of 10(-8) M avosentan.
Substance Class |
Chemical
Created
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Record UNII |
L94KSX715K
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Record Status |
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