Ambrisentan (CED0005299)

Record Information

Version

1.0

Creation Date

2016-05-22 05:38:50 UTC

Update Date

2026-08-21 21:52:27 UTC

Accession Number

CHEM018899

Identification

Common Name

Ambrisentan

Class

Small Molecule

Description

Ambrisentan is an organic compound with the formula C22H22N2O4 and an average molecular weight of 378.43 g/mol. Ambrisentan belongs to the diphenylmethanes, a subclass of benzene and substituted derivatives within the organic compounds. This compound is utilized within healthcare, pharmaceuticals, and veterinary products as an antihypertensive and is administered via the oral exposure route. In terms of its biological activity, it acts on two recorded protein targets, serving as an antagonist of the Endothelin receptor type B (EDNRB) and the Endothelin-1 receptor (EDNRA).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Letairis	Kegg
Volibris	Kegg
(+)-(2S)-2-((4,6-Dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoic acid	MeSH
(2S)-2-(4,6-Dimethylpyrimidin-2-yl)oxy-3-methoxy-3,3-diphenylpropanoate	Generator
Ambrisentan	MeSH
(2S)-2-[(4,6-Dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoate	Generator

Chemical Formula

C₂₂H₂₂N₂O₄

Average Molecular Mass

378.428 g/mol

Monoisotopic Mass

378.158 g/mol

CAS Registry Number

177036-94-1

IUPAC Name

(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic acid

Traditional Name

ambrisentan

SMILES

COC([C@H](OC1=NC(C)=CC(C)=N1)C(O)=O)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26)22(27-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1

InChI Key

OUJTZYPIHDYQMC-LJQANCHMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
3-phenylpropanoic-acid
Benzylether
Alkyl aryl ether
Monosaccharide
Pyrimidine
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	3.9	ALOGPS
logP	3.5	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	2.48	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.54 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	104.17 m³·mol⁻¹	ChemAxon
Polarizability	38.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fb9-0519000000-334b60bcbe0d4e18e21c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-680ff5817e39ab02ea53	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-1109000000-4b9d77ab0d09d403d9f2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-7902000000-25ea1a5c6976b2c5edf4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0059-0009000000-af71ea92f7e0b973d113	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-005a-0139000000-228646252ca3fc3d901a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uxs-1590000000-a262b3c1deeff226fbd5	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1103.0	Log mg/kg	[620:2000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
289	Antihypertensives	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

2 pathways

Ambrisentan Drug Metabolism Action Pathway

Ambrisentan Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Interleukin-36 gamma	Q9NZH8	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Acetolactate synthase	Q8S3J0	Bromus tectorum	Predicted (SEA)	4.35956
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	334.207
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	586.827
Click to view 3D structure	Aldo-keto reductase family 1 member C3	P42330	Humans	Predicted (SEA)	254.1
Click to view 3D structure	Aldo-keto reductase family 1 member C2	P52895	Humans	Predicted (SEA)	203.498
Click to view 3D structure	Prostaglandin G/H synthase 1	P05979	Ovis aries	Predicted (SEA)	322.296
Click to view 3D structure	ACCase	H9BT73	Alopecurus japonicus	Predicted (SEA)	41.2601
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	4449.86
Click to view 3D structure	Platelet-activating factor acetylhydrolase	Q60963	Mus musculus	Predicted (SEA)	77.6935
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	4619.42
Click to view 3D structure	Protein RecA	P9WHJ3	Mycobacterium tuberculosis	Predicted (SEA)	1046.84
Click to view 3D structure	G-protein coupled receptor 55	Q9Y2T6	Humans	Predicted (SEA)	440.159
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	1399.5
Click to view 3D structure	Pantothenate synthetase	P9WIL5	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	47.0209
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	4101.64
Click to view 3D structure	Mitogen-activated protein kinase 14	Q16539	Humans	Predicted (SEA)	3087.5
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	2728.07
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	2571.36
Click to view 3D structure	Acetyl-coenzyme A synthetase, cytoplasmic	Q9NR19	Humans	Predicted (SEA)	74.0346
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	1231.73
Click to view 3D structure	Peroxisome proliferator-activated receptor alpha	Q07869	Humans	Predicted (SEA)	943.299
Click to view 3D structure	Pancreatic alpha-amylase	P00689	Rattus norvegicus	Predicted (SEA)	18.8395
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	1779.63
Click to view 3D structure	cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	Humans	Predicted (SEA)	819.052