AMBRISENTAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H22N2O4
Molecular Weight	378.4211
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC([C@H](OC1=NC(C)=CC(C)=N1)C(O)=O)(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=OUJTZYPIHDYQMC-LJQANCHMSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H22N2O4
Molecular Weight	378.4211
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022081s029lbl.pdf

Ambrisentan (alternative Names: BSF 208075; GSK 1325760; GSK1325760A; Letairis) is an endothelin receptor antagonist that is selective for the endothelin type-A (ETA) receptor. The chemical name of ambrisentan is (+)-(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic acid. Ambrisentan is indicated for the treatment of pulmonary arterial hypertension. It is approved in Europe, Canada and the United States for use as a single agent to improve exercise ability and delay clinical worsening. In addition, it is approved in the United States for use in combination with tadalafil to reduce the risks of disease progression, hospitalization and to improve exercise ability. As an endothelin receptor antagonist, ambrisentan prevents endogenous endothelin peptide from constricting the muscles in blood vessels, allowing them to relax and permit a reduction in blood pressure. Endothelin-1 (ET-1) is a potent autocrine and paracrine peptide. Two receptor subtypes, ETA and ETB, mediate the effects of ET-1 in the vascular smooth muscle and endothelium. The primary actions of ETA are vasoconstriction and cell proliferation, while the predominant actions of ETB are vasodilation, antiproliferation, and ET-1 clearance. In patients with PAH, plasma ET-1 concentrations are increased as much as 10-fold and correlate with increased mean right atrial pressure and disease severity. ET-1 and ET-1 mRNA concentrations are increased as much as 9-fold in the lung tissue of patients with PAH, primarily in the endothelium of pulmonary arteries. These findings suggest that ET-1 may play a critical role in the pathogenesis and progression of PAH. Ambrisentan is a high-affinity (Ki=0.011 nM) ETA receptor antagonist with a high selectivity for the ETA versus ETB receptor (>4000-fold). The clinical impact of high selectivity for ETA is not known.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Endothelin receptor ET-B 11 Target ID: CHEMBL1785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19920913	Antagonist 2778
Endothelin receptor ET-A 19 Target ID: CHEMBL252 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19920913	Antagonist 2778		0.011 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pulmonary arterial hypertension 35 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022081s029lbl.pdf	Primary		Approved 8429	LETAIRIS Approved Use Letairis is indicated for the treatment of pulmonary arterial hypertension (PAH) (WHO Group 1): To improve exercise ability and delay clinical worsening. In combination with tadalafil to reduce the risks of disease progression and hospitalization for worsening PAH, and to improve exercise ability [see Clinical Studies (14.2) Launch Date 2007

C_max

Value	Dose	Co-administered	Analyte	Population
838.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19455620	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		AMBRISENTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
6976.5 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19455620	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		AMBRISENTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
18.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19455620	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		AMBRISENTAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022081s033lbl.pdf	steady-state, oral		AMBRISENTAN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
10 mg 1 times / day multiple, oral Highest studied dose Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf https://pubmed.ncbi.nlm.nih.gov/22506623	unhealthy, 45.6 years n = 17 Health Status: unhealthy Condition: pulmonary arterial hypertension Age Group: 45.6 years Sex: M+F Population Size: 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf https://pubmed.ncbi.nlm.nih.gov/22506623	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf https://pubmed.ncbi.nlm.nih.gov/22506623
100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf	healthy, adult Health Status: healthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf	pregnant, adult Health Status: pregnant Condition: pulmonary arterial hypertension Age Group: adult Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf	Other AEs: Fetal damage... Other AEs: Fetal damage (grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf	unhealthy, adult Health Status: unhealthy Condition: pulmonary arterial hypertension Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf	Other AEs: Liver injury... Other AEs: Liver injury (serious) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022081s000_LBL.pdf
5 mg 1 times / day multiple, oral (max) Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT02080637	unhealthy, children n = 13 Health Status: unhealthy Condition: heart defects Age Group: children Population Size: 13 Sources: https://clinicaltrials.gov/ct2/show/NCT02080637	Other AEs: Anemia, Hypertension... Other AEs: Anemia (below serious, 2 patients) Hypertension (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT02080637
10 mg 1 times / day steady, oral (max) Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00768300	unhealthy n = 329 Health Status: unhealthy Condition: Early Idiopathic Pulmonary Fibrosis Population Size: 329 Sources: https://clinicaltrials.gov/ct2/show/NCT00768300	Other AEs: Anaemia, Acute myocardial infarction... Other AEs: Anaemia (serious, 1 patient) Acute myocardial infarction (serious, 3 patients) Angina pectoris (serious, 1 patient) Angina unstable (serious, 1 patient) Atrial fibrillation (serious, 2 patients) Sinus tachycardia (serious, 1 patient) Cardiac failure congestive (serious, 4 patients) Cardiomegaly (serious, 1 patient) Dilatation atrial (serious, 1 patient) Tricuspid valve incompetence (serious, 1 patient) Palpitations (serious, 1 patient) Extrasystoles (serious, 1 patient) Electromechanical dissociation (serious, 1 patient) Acute vestibular syndrome (serious, 1 patient) Visual impairment (serious, 1 patient) Constipation (serious, 4 patients) Nausea (serious, 2 patients) Colonic polyp (serious, 1 patient) Small intestinal obstruction (serious, 1 patient) Upper gastrointestinal haemorrhage (serious, 1 patient) Oedema peripheral (serious, 4 patients) Oedema (serious, 1 patient) Pain (serious, 2 patients) Pyrexia (serious, 2 patients) Fatigue (serious, 2 patients) Catheter site haemorrhage (serious, 1 patient) Influenza like illness (serious, 1 patient) Hyperthermia (serious, 1 patient) Pharyngitis (serious, 1 patient) Sinusitis (serious, 1 patient) Pneumonia (serious, 9 patients) Bronchitis (serious, 3 patients) Bronchopneumonia (serious, 1 patient) Infection (serious, 1 patient) Cellulitis (serious, 2 patients) Sepsis (serious, 2 patients) Influenza (serious, 2 patients) Urinary tract infection (serious, 1 patient) Oral candidiasis (serious, 1 patient) Conjunctivitis viral (serious, 1 patient) Road traffic accident (serious, 1 patient) Fracture rib (serious, 1 patient) Electrocardiogram ST-T segment abnormal (serious, 1 patient) Electrocardiogram T wave inversion (serious, 1 patient) Computerised tomogram thorax abnormal (serious, 1 patient) Hyperkalaemia (serious, 4 patients) Hypokalaemia (serious, 2 patients) Hyperglycaemia (serious, 2 patients) Anorexia (serious, 1 patient) Diabetic ketoacidosis (serious, 1 patient) Hypophosphataemia (serious, 1 patient) Back pain (serious, 1 patient) Musculoskeletal pain (serious, 1 patient) Clubbing (serious, 1 patient) Pain in jaw (serious, 1 patient) Myalgia (serious, 1 patient) Squamous cell carcinoma (serious, 1 patient) Prostate cancer (serious, 1 patient) Prostate cancer metastatic (serious, 1 patient) Lung neoplasm malignant (serious, 1 patient) Headache (serious, 5 patients) Cerebrovascular accident (serious, 1 patient) Ischaemic stroke (serious, 1 patient) Somnolence (serious, 1 patient) Carotid artery stenosis (serious, 1 patient) Coma (serious, 1 patient) Grand mal convulsion (serious, 1 patient) Nerve compression (serious, 1 patient) Hypoaesthesia (serious, 1 patient) Anxiety (serious, 3 patients) Delirium (serious, 1 patient) Insomnia (serious, 1 patient) Renal failure acute (serious, 2 patients) Renal failure (serious, 1 patient) Benign prostatic hyperplasia (serious, 1 patient) Idiopathic pulmonary fibrosis (serious, 20 patients) Emphysema (serious, 2 patients) Pulmonary fibrosis (serious, 2 patients) Pulmonary alveolar haemorrhage (serious, 1 patient) Dyspnoea (serious, 17 patients) Respiratory arrest (serious, 1 patient) Cough (serious, 4 patients) Haemoptysis (serious, 4 patients) Productive cough (serious, 1 patient) Acute respiratory failure (serious, 5 patients) Respiratory failure (serious, 4 patients) Nasal congestion (serious, 4 patients) Allergic rhinitis (serious, 1 patient) Choking (serious, 1 patient) Rhinorrhoea (serious, 1 patient) Hypoxia (serious, 1 patient) Pneumothorax (serious, 1 patient) Pneumonitis (serious, 1 patient) Hiccups (serious, 1 patient) Pleurisy (serious, 1 patient) Hypotension (serious, 4 patients) Hypertension (serious, 3 patients) Subclavian vein thrombosis (serious, 1 patient) Flushing (serious, 1 patient) Hot flush (serious, 1 patient) Cardiac ventricular disorder (serious, 1 patient) Peripheral ischaemia (serious, 1 patient) Oedema peripheral (below serious, 73 patients) Upper respiratory tract infection (below serious, 47 patients) Headache (below serious, 47 patients) Dyspnoea (below serious, 40 patients) Nasopharyngitis (below serious, 37 patients) Idiopathic pulmonary fibrosis (below serious, 19 patients) Nasal congestion (below serious, 27 patients) Diarrhoea (below serious, 20 patients) Sinusitis (below serious, 20 patients) Back pain (below serious, 18 patients) Dizziness (below serious, 20 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00768300
10 mg 1 times / day steady, oral (max) Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT02290613	unhealthy n = 19 Health Status: unhealthy Condition: Arterial Hypertension Population Size: 19 Sources: https://clinicaltrials.gov/ct2/show/NCT02290613	Other AEs: Jaw fracture, Edema... Other AEs: Jaw fracture (serious, 1 patient) Edema (below serious, 8 patients) Diarrhea (below serious, 4 patients) Paraesthesia (below serious, 4 patients) Epistaxis (below serious, 3 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT02290613

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 788 OATP1B3 706 NTCP 34 BSEP 402 BCRP 699 P-gp 1461 MRP2 383 CYP2A6 707 CYP2C8 911 UGT1A1 204 UGT1A6 108 UGT1A9 116 UGT2B7 146	P-gp 1537 CYP2C19 991 UGT1A9 380 UGT2B7 389 UGT1A3 422 OATP1B1 406 MRP2 205 BSEP 52 CYP3A5 395	NTCP 2 BSEP 6 MRP2 111

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022081s041lbl.pdf Page: 12.0	no
BSEP 403	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 36.0	no
BSEP 403	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 36.0	no
MRP2 475	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 36.0	no
MRP2 475	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 36.0	no
NTCP 35	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 36.0	no
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 36, 61	no	no (co-administration study) Comment: ambrisentan had no inhibitory effect on the P-gp efflux of digoxin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 36, 61
NTCP 35	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 36.0	weak [IC50 100 uM]
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022081s041lbl.pdf Page: 12.0	weak [IC50 45 uM]
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022081s041lbl.pdf Page: 12.0	weak [IC50 47 uM]
UGT1A1 254	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 10, 55	weak [Inhibition 300 uM]
UGT1A6 141	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 10, 55	weak [Inhibition 300 uM]
UGT1A9 121	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 10, 55	weak [Inhibition 300 uM]
UGT2B7 157	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 10, 55, 64	weak [Inhibition 300 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_ClinPharmR_P1.pdf Page: 23.0	weak
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_ClinPharmR_P1.pdf Page: 23.0	weak
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_ClinPharmR_P1.pdf Page: 23.0	weak

Drug as victim

Target	Modality	Activity
BSEP 52	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 61.0	likely
MRP2 205	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 61.0	likely
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 9.0	yes
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 9.0	yes
CYP3A5 395	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 9.0	yes
OATP1B1 406	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022081s041lbl.pdf Page: 12.0	yes
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 61.0	yes
UGT1A3 422	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 9.0	yes
UGT1A9 380	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 9.0	yes
UGT2B7 389	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022081s000_PharmR_P1.pdf Page: 9.0	yes

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0024ZZ	http://www.aablocks.com/goods/Goods/detail?id=AA0024ZZ
AEchem Scientific Corp., USA	AE024026	http://www.aechemsc.com/info_products/AE024026.php
AK Scientific, Inc. (AKSCI)	66500	http://www.aksci.com/item_detail.php?cat=66500
Aaron Chemicals	AR0025RR	http://www.aaronchem.com/177036-94-1
Achemtek	0102-012312	http://www.achemtek.com/177036-94-1
Acorn PharmaTech	ACN-030051	http://www.acornpharmatech.com/
Adooq BioScience	A11291	https://www.adooq.com/ambrisentan.html
Alsachim	1485	http://www.alsachim.com/product-C2081-glo.bal-view.html
Anward	ANW-59416	http://www.anward.com/pro_result/45867
ApexBio Technology	B2075	http://www.apexbt.com/ambrisentan-26523.html
AstaTech, Inc.	FD7219	http://www.astatechinc.com/CPSResult.php?CRNO=37302
Aurora Fine Chemicals LLC	A24.076.624	http://online.aurorafinechemicals.com/info?ID=A24.076.624
Aurum Pharmatech LLC	K-5435	http://www.Aurumpharmatech.com/Product/ProductDetails/K_5435
AvaChem Scientific	2664	http://www.avachem.com/productSearch.asp?2664
Axon MedChem	1648	https://www.axonmedchem.com/product/1648
BLD Pharm	BD118907	http://www.bldpharm.com/products/177036-94-1.html
BioSynth	J-519579	https://www.biosynth.com/en/products/all-products/products/J-519579.html
Boerchem	BC224510	http://www.boerchem.com/?product_37829.html
CSNpharm	CSN10496	https://www.csnpharm.com/products/ambrisentan.html
Capot Chemical	18318	http://www.capotchem.com/en/18318.htm
Capot Chemical	PubChem18318	http://www.capotchem.com/en/18318.htm
Chem Scene	CS-0447	http://www.chemscene.com/177036-94-1.html
ChemMol	30114223	http://www.chemmol.com/chemmol/30114223.html
ChemMol	44007214	http://www.chemmol.com/chemmol/44007214.html
Chemspace	CSSB00015191759	https://chem-space.com/CSSB00015191759
Clearsynth	CS-O-00462	https://www.clearsynth.com/en/CSO00462.html
Excenen	EX-A3315	https://www.excenen.com/searchresultlist.php?id=177036-94-1
Hairui	HR136588	http://www.hairuichem.com/en/product/177036-94-1.html
LGC Standards	MM3756.00-0250	https://www.lgcstandards.com/US/en/p/MM3756.00-0250
Lab Network	LN00130941	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00130941
Matrix Scientific	149338	https://www.matrixscientific.com/149338.html
MedChem Express	HY-13209	https://www.medchemexpress.com/Ambrisentan.html
Oakwood	221767	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=102766&ExtHyperLink=1
Smolecule	S518340	http://www.smolecule.com/products/s518340
Synblock Inc	SB17358	http://www.synblock.com/product/177036-94-1.html
TCI (Tokyo Chemical Industry)	A2966	http://www.tcichemicals.com/eshop/en/us/commodity/A2966/index.html
THE BioTek	bt-258891	https://www.thebiotek.com/product/inhibitors/bt-258891
Tocris	5828	https://www.tocris.com/products/ambrisentan_5828
TripleBond	CA0131	http://www.triplebond-canada.com/prod/1093/
VladaChem	VL279151-25MG	https://www.vladachem.com/product.php?products=177036-94-1
Yuhao Chemical	JZ1234	http://www.chemyuhao.com/177036-94-1.html
abcr GmbH	AB436215	http://www.abcr.com/shop/en/AB436215
eNovation Chemicals	K09791	https://www.enovationchem.com/ProductDetails.asp?ProductID=K09791
iChemical	EBD31205	http://www.ichemical.com/products/177036-94-1.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Endothelin A-receptor blockade in experimental diabetes improves glucose balance and gastrointestinal function.	2002 Aug	12193138
Effect of the novel endothelin(A) receptor antagonist LU 208075 on contraction and relaxation of isolated rat basilar artery.	2002 Aug	12193134
Ambrisentan (Myogen).	2002 Oct	12431023
Administration of a selective endothelin-a receptor antagonist (BSF 208075) improves hepatic warm ischemia/reperfusion injury in pigs.	2002 Sep	12270450
Endothelin receptor antagonists in pulmonary arterial hypertension.	2004 Jun 16	15194180
Novel benzo[1,4]diazepin-2-one derivatives as endothelin receptor antagonists.	2004 May 20	15139756
Drug Insight: endothelin-receptor antagonists for pulmonary arterial hypertension in systemic rheumatic diseases.	2005 Dec	16932638
Improvement of postischemic hepatic microcirculation after endothelinA receptor blockade--endothelin antagonism influences platelet-endothelium interactions.	2005 Feb	15694814
[Emerging therapies for the treatment of pulmonary arterial hypertension].	2005 Jun	15965806
Endothelin antagonism prevents diabetic retinopathy in NOD mice: a potential role of the angiogenic factor adrenomedullin.	2006 Jun	16741057
Profile of past and current clinical trials involving endothelin receptor antagonists: the novel "-sentan" class of drug.	2006 Jun	16740981
Medical therapies for chronic thromboembolic pulmonary hypertension: an evolving treatment paradigm.	2006 Sep	16963540
Ambrisentan, a non-peptide endothelin receptor antagonist.	2006 Spring	16939634
Therapeutic targets in systemic sclerosis.	2007	17767744
Gateways to clinical trials.	2007 Mar	17440629
Endothelin receptor antagonists in the treatment of pulmonary arterial hypertension.	2007 Mar	17338931
Pathophysiological role of platelets in acute experimental pancreatitis: influence of endothelin A receptor blockade.	2007 Mar	17093924
Expert opinion on available options treating pulmonary arterial hypertension.	2007 Oct	17927481
Systematic review of randomised, double-blind clinical trials of oral agents conducted in patients with pulmonary arterial hypertension.	2007 Oct	17877662
Therapeutic challenges for systemic sclerosis: facts and future targets.	2007 Sep	17911460
Ambrisentan.	2007 Sep	17907344
New drugs: ambrisentan, temsirolimus, and eculizumab.	2007 Sep-Oct	17848357
Ambrisentan.	2008	18840007
Endothelin receptor antagonism: role in the treatment of pulmonary arterial hypertension related to scleroderma.	2008	18681488
Acute right ventricular failure in the setting of acute pulmonary embolism or chronic pulmonary hypertension: a detailed review of the pathophysiology, diagnosis, and management.	2008 Feb	19924277
The status of pulmonary arterial hypertension in 2008.	2008 Jun 10	18541751
Ambrisentan for the treatment of pulmonary arterial hypertension: results of the ambrisentan in pulmonary arterial hypertension, randomized, double-blind, placebo-controlled, multicenter, efficacy (ARIES) study 1 and 2.	2008 Jun 10	18506008
Gateways to clinical trials.	2008 Mar	18560631
The endothelin system as a therapeutic target in cardiovascular disease: great expectations or bleak house?	2008 Mar	17965745
Pulmonary arterial hypertension: on the way to a manageable disease.	2008 Sep	18729002
Therapeutic methods used in patients with Eisenmenger syndrome.	2009	19950085
Cost-utility of treatments for pulmonary arterial hypertension: a Markov state-transition decision analysis model.	2009	19715380
Bosentan in the treatment of pulmonary arterial hypertension with the focus on the mildly symptomatic patient.	2009	19688101
Oral therapies for the treatment of pulmonary arterial hypertension: a population-based cost-minimization analysis.	2009	19558194
Treatment of pediatric pulmonary hypertension.	2009	19554091
Endothelin-1 inhibition by ambrisentan as a potential treatment adjunct after debulking surgery in epithelial ovarian cancer.	2009	19544975
Ambrisentan: new drug. Too risky in mildly symptomatic pulmonary hypertension.	2009 Apr	19585715
Gateways to clinical trials.	2009 Apr	19536362
Use of inhaled iloprost in an infant with bronchopulmonary dysplasia and pulmonary artery hypertension.	2009 Aug	19949642
Ambrisentan, an endothelin receptor type A-selective endothelin receptor antagonist, for the treatment of pulmonary arterial hypertension.	2009 Aug	19601701
[Endothelin receptor antagonists - their role in pulmonary medicine].	2009 Dec	20032843
No clinically relevant pharmacokinetic and safety interactions of ambrisentan in combination with tadalafil in healthy volunteers.	2009 Dec	19455620
Ambrisentan therapy in patients with pulmonary arterial hypertension who discontinued bosentan or sitaxsentan due to liver function test abnormalities.	2009 Jan	18812445
Gateways to clinical trials.	2009 Jun	19649342
Small-molecule endothelin receptor antagonists: a review of patenting activity across therapeutic areas.	2009 Jun	19517317
Effect of ketoconazole on the pharmacokinetic profile of ambrisentan.	2009 Jun	19389876
The pharmacokinetics and pharmacodynamics of warfarin in combination with ambrisentan in healthy volunteers.	2009 May	19552747
Gateways to clinical trials.	2009 Nov	20094643
Can we improve outcome of congenital diaphragmatic hernia?	2009 Sep	19669650
Pharmacotherapy in pulmonary arterial hypertension: a systematic review and meta-analysis.	2010 Jan 29	20113497

Patents

Sample Use Guides

In Vivo Use Guide

5 mg once daily, and consider increasing the dose to 10 mg once daily if 5 mg is tolerated. Tablets may be administered with or without food.

Route of Administration: Oral

In Vitro Use Guide

The effect of the novel and ET(A) receptor selective antagonist LU 208075 (AMBRISENTAN) was characterized by the contraction and relaxation induced by ET-1 and bigET-1 on rat basilar artery. Concentration-effect curves were constructed by cumulative application of ET-1 or bigET-1 in the presence of LU 208075 (10(-7)M, 10(-6)M, and 10(-5)M). The effect of LU 208075 was determined by the pA(2) value. The contraction by ET-1 and bigET-1 was inhibited by LU 208075 in a dose-dependent manner.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:32:57 GMT 2023` Edited by `admin` on `Sat Dec 16 17:32:57 GMT 2023`
Record UNII	HW6NV07QEC
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AMBRISENTAN

Official Name

English

AMBRISENTAN [MI]

Common Name

English

(+)-(2S)-2-((4,6-DIMETHYLPYRIMIDIN-2-YL)OXY)-3-METHOXY-3,3-DIPHENYLPROPANOIC ACID

Systematic Name

English

AMBRISENTAN [JAN]

Common Name

English

GSK1325760

Code

English

AMBRISENTAN [ORANGE BOOK]

Common Name

English

GSK-1325760

Code

English

LU-208075

Code

English

LETAIRIS

Brand Name

English

VOLIBRIS

Brand Name

English

AMBRISENTAN [MART.]

Common Name

English

GSK1325760A

Code

English

ambrisentan [INN]

Common Name

English

AMBRISENTAN [EMA EPAR]

Common Name

English

Ambrisentan [WHO-DD]

Common Name

English

GSK-1325760A

Code

English

AMBRISENTAN [VANDF]

Common Name

English

AMBRISENTAN, (+)-

Common Name

English

Classification Tree Code System Code

WHO-ATC

C02KX52