Compounds > avosentan
Page last updated: 2024-08-02 12:01:17

avosentan

Description

Avosentan: structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID9912992
CHEMBL ID3989834
SCHEMBL ID2742679
MeSH IDM0534901

Synonyms (38)

Synonym
HY-15195
ro 67-0565; spp-301
AVOSENTAN,CAS:290815-26-8
avosentan
5-methylpyridine-2-sulfonic acid (6-methoxy-5-(2-methoxyphenoxy)-2-(pyridin-4-yl)pyrimidin-4-yl)amide
spp301
L001646
FT-0662342
spp 301
2-pyridinesulfonamide, n-(6-methoxy-5-(2-methoxyphenoxy)-2-(4-pyridinyl)-4-pyrimidinyl)-5-methyl-
ro 67-0565
l94ksx715k ,
290815-26-8
avosentan [inn]
unii-l94ksx715k
CS-0625
n-[6-methoxy-5-(2-methoxyphenoxy)-2-pyridin-4-ylpyrimidin-4-yl]-5-methylpyridine-2-sulfonamide
gtpl8260
spp-301
n-(6-methoxy-5-(2-methoxyphenoxy)-2-(pyridin-4-yl)pyrimidin-4-yl)-5-methylpyridine-2-sulfonamide
ro-67-0565
5-methyl-pyridine-2-sulfonic acid [6-methoxy-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide
YBWLTKFZAOSWSM-UHFFFAOYSA-N
5-methyl-pyridine-2-sulfonic acid[6-methoxy-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide
SCHEMBL2742679
AC-33590
DTXSID30183330
NCGC00379058-01
ro670565
CHEMBL3989834
n-(6-methoxy-5-(2-methoxyphenoxy)-2-(pyridin-4-yl)-pyrimidin-4-yl)-5-methylpyridine-2-sulfonamide
Q27074636
BCP28417
2-pyridinesulfonamide, n-[6-methoxy-5-(2-methoxyphenoxy)-2-(4-pyridinyl)-4-pyrimidinyl]-5-methyl-
HMS3741G07
F84811
MS-28915
bdbm50532577

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
cytochrome P450 family 3 subfamily A polypeptide 4Homo sapiens (human)Potency3.3786AID1645841
GVesicular stomatitis virusPotency26.8370AID1645842
Interferon betaHomo sapiens (human)Potency26.8370AID1645842
HLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)Potency26.8370AID1645842
Inositol hexakisphosphate kinase 1Homo sapiens (human)Potency26.8370AID1645842
cytochrome P450 2C9, partialHomo sapiens (human)Potency26.8370AID1645842

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Endothelin receptor type BHomo sapiens (human)IC500.9000AID1626368; AID1626373
Endothelin-1 receptorHomo sapiens (human)IC500.0022AID1626371; AID1626372

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
ISSN: 1521-0111		A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
ISSN: 2472-5560		Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
ISSN: 1091-6490		Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
ISSN: 1091-6490		Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
ISSN: 1521-0111		A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1626371Displacement of 125I-ET1 from ETA receptor (unknown origin) expressed in CHO cells2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
ISSN: 1464-3405		From bosentan (Tracleer®) to macitentan (Opsumit®): The medicinal chemistry perspective.
AID1626368Displacement of radioligand from ETB receptor in human placenta cell membranes2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
ISSN: 1464-3405		From bosentan (Tracleer®) to macitentan (Opsumit®): The medicinal chemistry perspective.
AID1626372Antagonist activity at ETA receptor (unknown origin) in presence of ET12016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
ISSN: 1464-3405		From bosentan (Tracleer®) to macitentan (Opsumit®): The medicinal chemistry perspective.
AID1626373Antagonist activity at ETB receptor (unknown origin) in presence of ET12016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
ISSN: 1464-3405		From bosentan (Tracleer®) to macitentan (Opsumit®): The medicinal chemistry perspective.

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's9 (31.03)29.6817
2010's17 (58.62)24.3611
2020's3 (10.34)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials10 (34.48%)5.53%
Reviews8 (27.59%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (37.93%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
sulfamethoxazole
1
isoxazoles;
substituted aniline;
sulfonamide antibiotic;
sulfonamide		antibacterial agent;
antiinfective agent;
antimicrobial agent;
drug allergen;
EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor;
EC 2.5.1.15 (dihydropteroate synthase) inhibitor;
environmental contaminant;
epitope;
P450 inhibitor;
xenobiotic		201620168.0low000010
bosentan anhydrous
1
primary alcohol;
pyrimidines;
sulfonamide		antihypertensive agent;
endothelin receptor antagonist		201620168.0low000010
ro 46-2005
1
201620168.0low000010
tezosentan
1
201620168.0low000010
lu 135252
1
201620168.0low000010
tbc-11251
1
benzodioxoles201620168.0low000010
ro 46-8443
1
201620168.0medium000010
ro 47-8634
1
201620168.0high000010
clazosentan
1
201620168.0low000010
lu 208075
1
diarylmethane201620168.0low000010
bms 193884
1
201620168.0medium000010
zibotentan
1
phenylpyridine201620168.0low000010
macitentan
1
aromatic ether;
organobromine compound;
pyrimidines;
ring assembly;
sulfamides		antihypertensive agent;
endothelin receptor antagonist;
orphan drug		201620168.0low000010
act-132577
1
aromatic ether;
organobromine compound;
pyrimidines;
sulfamides		antihypertensive agent;
drug metabolite;
endothelin receptor antagonist;
xenobiotic metabolite		201620168.0low000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
pyridoxamine
2
aminoalkylpyridine;
hydroxymethylpyridine;
monohydroxypyridine;
vitamin B6		Escherichia coli metabolite;
human metabolite;
iron chelator;
mouse metabolite;
nephroprotective agent;
plant metabolite;
Saccharomyces cerevisiae metabolite		2010201412.0low000110
pimagedine
1
guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor		2010201014.0low000100
ketoconazole
1
dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine		2006200618.0low100100
pentoxifylline
1
oxopurine2010201014.0low000100
ethinyl estradiol
1
17-hydroxy steroid;
3-hydroxy steroid;
terminal acetylenic compound		xenoestrogen2006200618.0low100100
valine
1
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite		2014201410.0low000010
thiophenes
2
mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent2011201312.0low000020
isoxazoles
2
isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene		2011201312.0low000020
hydrazine
1
azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor2010201014.0low000100
pyridoxamine dihydrochloride
1
hydrochloride;
vitamin B6		Escherichia coli metabolite;
human metabolite;
iron chelator;
mouse metabolite;
nephroprotective agent;
plant metabolite;
Saccharomyces cerevisiae metabolite		2014201410.0low000010
levonorgestrel
1
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
terminal acetylenic compound		contraceptive drug;
female contraceptive drug;
progestin;
synthetic oral contraceptive		2006200618.0low100100
quinapril
1
dicarboxylic acid monoester;
ethyl ester;
isoquinolines;
tertiary carboxamide		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
prodrug		2010201014.0low000100
valsartan
1
biphenylyltetrazole;
monocarboxylic acid amide;
monocarboxylic acid		angiotensin receptor antagonist;
antihypertensive agent;
environmental contaminant;
xenobiotic		2014201410.0low000010
bosentan anhydrous
2
primary alcohol;
pyrimidines;
sulfonamide		antihypertensive agent;
endothelin receptor antagonist		201720215.0low000011
tezosentan
1
201720177.0low000010
atrasentan
5
pyrrolidines201120219.2medium000041
lu 135252
2
2011201710.0low000020
tbc-11251
2
benzodioxoles2011201312.0low000020
bq 123
1
cyclic peptide2011201113.0low000010
lisinopril
1
dipeptideEC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor2009200915.0low000100
glucuronyl glucosamine glycan sulfate
1
2014201410.0low000010
angiotensinogen
1
2014201410.0low000010
endothelin-1
2
2011201312.0low000020
cardiovascular agents
1
2005200519.0low100100
piperidines
1
2011201113.0low000010
transforming growth factor beta
1
2010201014.0low000100
alt-946
1
2010201014.0high000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Albuminuria0
4
2009202110.2low100121
Alloxan Diabetes0
1
2009200915.0low000100
Atherogenesis0
1
2010201014.0low000100
Atherosclerosis0
1
2010201014.0low000100
Bilateral Headache0
1
2006200618.0low100100
Blood Pressure, High0
1
201720177.0low000010
Body Weight0
2
2009201014.5low200200
Cardiac Failure0
3
201020219.0low200111
Chronic Kidney Diseases0
2
2013201410.5low000020
Chronic Kidney Failure0
3
2010201411.7low200120
Congenital Zika Syndrome0
1
202020204.0low000010
Diabetes Mellitus, Adult-Onset0
2
201420216.5low100011
Diabetes Mellitus, Type 20
2
201420216.5low100011
Diabetic Angiopathies0
1
2010201014.0low000100
Diabetic Glomerulosclerosis0
11
2009202112.4medium300641
Diabetic Nephropathies1
11
2009202112.4medium300641
Disease Exacerbation0
2
2010201014.0low100200
Disease Models, Animal0
3
2010202010.3low000120
Electrolytes0
1
2009200915.0low100100
Emesis0
1
2006200618.0low100100
Exanthem0
1
2006200618.0low100100
Exanthema0
1
2006200618.0low100100
Facial Injuries0
1
2006200618.0low100100
Glaucoma0
1
2011201113.0low000010
Headache0
1
2006200618.0low100100
Heart Failure0
3
201020219.0low200111
Hyperglycemia0
1
2010201014.0low000100
Hyperglycemia, Postprandial0
1
2010201014.0low000100
Hyperlipemia0
1
2010201014.0low000100
Hyperlipidemias0
1
2010201014.0low000100
Hypertension0
1
201720177.0low000010
Hypertension, Renal0
1
2014201410.0low000010
Intraocular Pressure0
1
2011201113.0low000010
Kidney Diseases0
1
2011201113.0low000010
Kidney Failure, Chronic0
3
2010201411.7low200120
Nasal Catarrh0
1
2006200618.0low100100
Nephritis0
1
2014201410.0low000010
Proteinuria0
4
2010201113.5low100220
Renal Insufficiency, Chronic0
2
2013201410.5low000020
Rhinitis0
1
2006200618.0low100100
Vomiting0
1
2006200618.0low100100
Water-Electrolyte Imbalance0
1
2010201014.0low100100
Weight Gain0
1
2014201410.0low100010
Zika Virus Infection0
1
202020204.0low000010

Safety/Toxicity (1)

ArticleYear
Efficacy and safety of endothelin receptor antagonists in type 2 diabetic kidney disease: A systematic review and meta-analysis of randomized controlled trials.
Diabetic medicine : a journal of the British Diabetic Association, , Volume: 38, Issue:1		2021

Pharmacokinetics (6)

ArticleYear
Absolute bioavailability and pharmacokinetics of avosentan in man.
International journal of clinical pharmacology and therapeutics, , Volume: 47, Issue:9		2009
Influence of food intake on the pharmacokinetics of avosentan in man.
International journal of clinical pharmacology and therapeutics, , Volume: 46, Issue:9		2008
Influence of avosentan (SPP3OI) on the pharmacokinetics of a second generation oral contraceptive containing ethinylestradiol and levonorgestrel in healthy female volunteers.
International journal of clinical pharmacology and therapeutics, , Volume: 44, Issue:12		2006
Pharmacokinetic interaction between ketoconazole and SPP301 in healthy volunteers.
International journal of clinical pharmacology and therapeutics, , Volume: 44, Issue:7		2006
Multiple-dose pharmacokinetics, pharmacodynamics and tolerability of the oral ET(A) endothelin-receptor antagonist SPP301 in man.
International journal of clinical pharmacology and therapeutics, , Volume: 43, Issue:4		2005
Pharmacokinetics and pharmacodynamics of the ETA-selective endothelin receptor antagonist SPP301 in healthy human subjects.
Journal of clinical pharmacology, , Volume: 44, Issue:1		2004

Bioavailability (2)

ArticleYear
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology, , Volume: 96, Issue:5		2019
Absolute bioavailability and pharmacokinetics of avosentan in man.
International journal of clinical pharmacology and therapeutics, , Volume: 47, Issue:9		2009

Dosage (4)

ArticleYear
Efficacy and safety of endothelin receptor antagonists in type 2 diabetic kidney disease: A systematic review and meta-analysis of randomized controlled trials.
Diabetic medicine : a journal of the British Diabetic Association, , Volume: 38, Issue:1		2021
Endothelin antagonists for diabetic and non-diabetic chronic kidney disease.
British journal of clinical pharmacology, , Volume: 76, Issue:4		2013
Effect of SPP 301, an endothelin antagonist, on intraocular pressure in glaucomatous monkey eyes.
Current eye research, , Volume: 36, Issue:1		2011
Avosentan reduces albumin excretion in diabetics with macroalbuminuria.
Journal of the American Society of Nephrology : JASN, , Volume: 20, Issue:3		2009