NAV

Atrasentan

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Atrasentan
DrugBank Accession Number
DB06199
Background

Atrasentan is a substance that is being studied in the treatment of cancer. It belongs to the family of drugs called endothelin-1 protein receptor antagonists. It is a novel, selective endothelin A receptor antagonist (SERA).

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 510.6218
Monoisotopic: 510.272986958
Chemical Formula
C29H38N2O6
Synonyms
  • Atrasentan
External IDs
  • ABT-627
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Pharmacology

Indication

Investigated for use/treatment in prostate cancer and cancer/tumors (unspecified).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEndothelin-1 receptorNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
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interactions in your software
AcetylcysteineThe excretion of Atrasentan can be decreased when combined with Acetylcysteine.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Atrasentan is combined with Ambroxol.
Aminohippuric acidThe excretion of Atrasentan can be decreased when combined with Aminohippuric acid.
AmprenavirThe excretion of Atrasentan can be decreased when combined with Amprenavir.
ApalutamideThe serum concentration of Atrasentan can be decreased when it is combined with Apalutamide.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Atrasentan HydrochlorideE4G31X93ZA195733-43-8IJFUJIFSUKPWCZ-SQMFDTLJSA-N
International/Other Brands
Xinlay

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
Phenylpyrrolidines
Direct Parent
Phenylpyrrolidines
Alternative Parents
Alpha amino acids and derivatives / Benzodioxoles / Anisoles / Pyrrolidine carboxylic acids / Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Aralkylamines / N-alkylpyrrolidines / Pyrroles
show 12 more
Substituents
2-phenylpyrrolidine / Acetal / Alkyl aryl ether / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Anisole / Aralkylamine / Aromatic heteropolycyclic compound
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
V6D7VK2215
CAS number
173937-91-2
InChI Key
MOTJMGVDPWRKOC-QPVYNBJUSA-N
InChI
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
IUPAC Name
(2R,3R,4S)-4-(2H-1,3-benzodioxol-5-yl)-1-[(dibutylcarbamoyl)methyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid
SMILES
CCCCN(CCCC)C(=O)CN1C[C@@H]([C@H]([C@@H]1C1=CC=C(OC)C=C1)C(O)=O)C1=CC2=C(OCO2)C=C1

References

General References
Not Available
PubChem Compound
159594
ChemSpider
140321
BindingDB
50051007
ChEBI
135810
ChEMBL
CHEMBL9194
ZINC
ZINC000003812144
Wikipedia
Atrasentan

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3Active Not RecruitingTreatmentImmunoglobulin A Nephropathy1
3CompletedTreatmentEndothelial Dysfunction1
3CompletedTreatmentMetastatic Cancer / Prostate Cancer1
3CompletedTreatmentNeoplasms of the Prostate1
3CompletedTreatmentProstate Cancer2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0321 mg/mLALOGPS
logP4.09ALOGPS
logP1.76Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.02Chemaxon
pKa (Strongest Basic)8.17Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area88.54 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity140.14 m3·mol-1Chemaxon
Polarizability55.33 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9485
Blood Brain Barrier+0.6335
Caco-2 permeable-0.5191
P-glycoprotein substrateSubstrate0.836
P-glycoprotein inhibitor IInhibitor0.7581
P-glycoprotein inhibitor IIInhibitor0.8119
Renal organic cation transporterNon-inhibitor0.7707
CYP450 2C9 substrateNon-substrate0.821
CYP450 2D6 substrateNon-substrate0.8057
CYP450 3A4 substrateSubstrate0.7436
CYP450 1A2 substrateNon-inhibitor0.9696
CYP450 2C9 inhibitorNon-inhibitor0.7407
CYP450 2D6 inhibitorNon-inhibitor0.7773
CYP450 2C19 inhibitorInhibitor0.5209
CYP450 3A4 inhibitorInhibitor0.771
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5707
Ames testNon AMES toxic0.6721
CarcinogenicityNon-carcinogens0.8803
BiodegradationNot ready biodegradable0.962
Rat acute toxicity2.4252 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9465
hERG inhibition (predictor II)Non-inhibitor0.5396
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0400590000-0176d913534344aab9a1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000390000-ecafc89d0f505e90a257
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0100920000-7ce749853d88712a274c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0204890000-44858ce00292408b35f0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-2313910000-adb404f020d593868a29
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-0235910000-71c615353eaaa0ff30ec
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-212.15227
predicted
DeepCCS 1.0 (2019)
[M+H]+213.97717
predicted
DeepCCS 1.0 (2019)
[M+Na]+219.58344
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Endothelin-1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
Receptor for endothelin-1. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of binding affinities for ET-A is:...
Gene Name
EDNRA
Uniprot ID
P25101
Uniprot Name
Endothelin-1 receptor
Molecular Weight
48721.76 Da
References
  1. Nelson J, Bagnato A, Battistini B, Nisen P: The endothelin axis: emerging role in cancer. Nat Rev Cancer. 2003 Feb;3(2):110-6. [Article]
  2. Cella D, Petrylak DP, Fishman M, Teigland C, Young J, Mulani P: Role of quality of life in men with metastatic hormone-refractory prostate cancer: how does atrasentan influence quality of life? Eur Urol. 2006 May;49(5):781-9. Epub 2006 Jan 19. [Article]
  3. Chichorro JG, Zampronio AR, Souza GE, Rae GA: Orofacial cold hyperalgesia due to infraorbital nerve constriction injury in rats: reversal by endothelin receptor antagonists but not non-steroidal anti-inflammatory drugs. Pain. 2006 Jul;123(1-2):64-74. Epub 2006 Mar 24. [Article]

Drug created at March 19, 2008 16:17 / Updated at February 21, 2021 18:52