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SML2104

Sigma-Aldrich

Ambrisentan

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C22H22N2O4
CAS Number:
177036-94-1
Molecular Weight:
378.42
MDL number:
MFCD08672619
UNSPSC Code:
41121706
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +160 to +190°, c = 0.5 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CC1=CC(C)=NC(O[C@@H](C(C2=CC=CC=C2)(OC)C3=CC=CC=C3)C(O)=O)=N1

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)

InChI key

OUJTZYPIHDYQMC-UHFFFAOYSA-N

Biochem/physiol Actions

Ambrisentan is an endothelin receptor antagonist used in the treatment of pulmonary arterial hypertension (PAH). It is 200-fold selective for the the ETA receptor subtype with a Ki of 1 nM for ETA and a Ki of 195 nM for ETB.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1A

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Belinda N Rivera-Lebron et al.
Therapeutic advances in respiratory disease, 11(6), 233-244 (2017-04-21)
Pulmonary arterial hypertension (PAH) is a progressive disease defined by an elevation in pulmonary arterial pressure that can lead to right heart failure and death. Ambrisentan is a selective endothelin receptor antagonist approved for the treatment of idiopathic, heritable PAH
Johanna Weiss et al.
European journal of pharmacology, 660(2-3), 298-304 (2011-04-20)
The safety and effectiveness of drugs used to treat chronic diseases critically depend on their propensity to interact with co-administered drugs. Induction of enzymes and drug transporters involved in the clearance and distribution of drugs may critically reduce exposure with
James A Angus et al.
European journal of pharmacology, 804, 111-116 (2017-03-17)
Endothelin receptor antagonists are approved for pulmonary arterial hypertension. Development of selective ET Human isolated pulmonary (i.d. 5.5mm) and human radial (i.d. 3.23mm) artery ring segments were mounted in organ baths for isometric force measurement. Single concentration-contraction curves to endothelin-1
Ilenia Masi et al.
Cell reports, 34(9), 108800-108800 (2021-03-04)
Cancer cells use actin-based membrane protrusions, invadopodia, to degrade stroma and invade. In serous ovarian cancer (SOC), the endothelin A receptor (ETAR) drives invadopodia by a not fully explored coordinated function of β-arrestin1 (β-arr1). Here, we report that β-arr1 links
Sanah M Nkadimeng et al.
Scientific reports, 10(1), 22314-22314 (2020-12-20)
Prevalence of major depression in people with chronic heart failure is higher than in normal populations. Depression in heart failure has become a major issue. Psilocybin-containing mushrooms commonly known as magic mushrooms, have been used since ancient times for their

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