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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H38N2O6
Molecular Weight 510.6218
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATRASENTAN

SMILES

CCCCN(CCCC)C(=O)CN1C[C@@H]([C@H]([C@@H]1C2=CC=C(OC)C=C2)C(O)=O)C3=CC=C4OCOC4=C3

InChI

InChIKey=MOTJMGVDPWRKOC-QPVYNBJUSA-N
InChI=1S/C29H38N2O6/c1-4-6-14-30(15-7-5-2)26(32)18-31-17-23(21-10-13-24-25(16-21)37-19-36-24)27(29(33)34)28(31)20-8-11-22(35-3)12-9-20/h8-13,16,23,27-28H,4-7,14-15,17-19H2,1-3H3,(H,33,34)/t23-,27-,28+/m1/s1

HIDE SMILES / InChI

Description

Atrasentan (ABT-627, A-127722) is a selective endothelin A receptor antagonist. Atrasentan is being developed by AbbVie as an oral treatment for diabetic nephropathies.Abbott Laboratories was conducting clinical development of atrasentan for the treatment of certain cancers, including phase II trials for prostate cancer. However, no recent development has been reported for cancer indications and development is presumed to be discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
69.0 pM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
89 ng/mL
5 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
0.28 ng/mL
0.25 mg single, oral
ATRASENTAN plasma
Homo sapiens
4.12 ng/mL
1.75 mg single, oral
ATRASENTAN plasma
Homo sapiens
1.72 ng/mL
0.75 mg single, oral
ATRASENTAN plasma
Homo sapiens
242 ng/mL
30 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
358 ng/mL
20 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
489 ng/mL
75 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
819 ng/mL
60 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
544 ng/mL
45 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
62 ng/mL
10 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
580 ng × h/mL
5 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
0.71 ng × h/mL
0.25 mg single, oral
ATRASENTAN plasma
Homo sapiens
13.07 ng × h/mL
1.75 mg single, oral
ATRASENTAN plasma
Homo sapiens
5.31 ng × h/mL
0.75 mg single, oral
ATRASENTAN plasma
Homo sapiens
1492 ng × h/mL
30 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
1591 ng × h/mL
20 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
2338 ng × h/mL
75 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
3162 ng × h/mL
60 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
5354 ng × h/mL
45 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
536 ng × h/mL
10 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
34.1 h
5 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
32 h
30 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
40.9 h
20 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
36.1 h
75 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
32.6 h
60 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
30 h
45 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens
23.2 h
10 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1.2%
75 mg 1 times / day multiple, oral
ATRASENTAN plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
0.75, or 1.75 mg daily for 8 weeks atrasentan is generally safe and effective in reducing residual albuminuria and may ultimately improve renal outcomes in patients with type 2 diabetic nephropathy.
Route of Administration: Oral
In Vitro Use Guide
Atrasentan (ABT-627, A-127722) exhibits a dose-dependent inhibition of ET-1-induced arachidonic acid release in human pericardium smooth muscle cells with a pA2 value of 10.5 and inhibits ET-1-induced vasoconstriction in isolated rat aorta with a pA2 value of 9.2.