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
Structure for Atrasentan (DB06199)
- Weight
- Average: 510.6218
Monoisotopic: 510.272986958 - Chemical Formula
- C29H38N2O6
- Synonyms
- Atrasentan
- External IDs
- ABT-627
Pharmacology
- Indication
Investigated for use/treatment in prostate cancer and cancer/tumors (unspecified).
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Not Available
- Mechanism of action
Target Actions Organism UEndothelin-1 receptor Not Available Humans - 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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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetylcysteine The excretion of Atrasentan can be decreased when combined with Acetylcysteine. Aminohippuric acid The excretion of Atrasentan can be decreased when combined with Aminohippuric acid. Amprenavir The excretion of Atrasentan can be decreased when combined with Amprenavir. Apalutamide The excretion of Atrasentan can be increased when combined with Apalutamide. Asunaprevir The excretion of Atrasentan can be decreased when combined with Asunaprevir. Atazanavir The excretion of Atrasentan can be decreased when combined with Atazanavir. Atorvastatin The excretion of Atrasentan can be decreased when combined with Atorvastatin. Axitinib The excretion of Atrasentan can be decreased when combined with Axitinib. Beclomethasone dipropionate The excretion of Atrasentan can be decreased when combined with Beclomethasone dipropionate. Belumosudil The excretion of Atrasentan can be decreased when combined with Belumosudil. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Atrasentan Hydrochloride E4G31X93ZA 195733-43-8 IJFUJIFSUKPWCZ-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
- External Links
- PubChem Compound
- 159594
- ChemSpider
- 140321
- BindingDB
- 50051007
- ChEBI
- 135810
- ChEMBL
- CHEMBL9194
- ZINC
- ZINC000003812144
- Wikipedia
- Atrasentan
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Endothelial Dysfunction 1 3 Completed Treatment Metastatic Cancers / Prostate Cancer 1 3 Completed Treatment Prostate Cancer 2 3 Completed Treatment Prostatic Neoplasms 1 3 Recruiting Treatment IgA Nephropathy (IgAN) / Immunoglobulin A Nephropathy 1 3 Terminated Treatment Diabetic Nephropathy 1 2 Completed Other Diabetes / Renal Dysfunction 1 2 Completed Treatment Adenocarcinoma of the Prostate / Prostate Cancer 1 2 Completed Treatment Chronic Kidney Disease (CKD) / Diabetic Nephropathy 4 2 Completed Treatment Prostatic Neoplasms 1
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
Property Value Source Water Solubility 0.0321 mg/mL ALOGPS logP 4.09 ALOGPS logP 1.76 ChemAxon logS -4.2 ALOGPS pKa (Strongest Acidic) 3.02 ChemAxon pKa (Strongest Basic) 8.17 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 88.54 Å2 ChemAxon Rotatable Bond Count 12 ChemAxon Refractivity 140.14 m3·mol-1 ChemAxon Polarizability 55.33 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9485 Blood Brain Barrier + 0.6335 Caco-2 permeable - 0.5191 P-glycoprotein substrate Substrate 0.836 P-glycoprotein inhibitor I Inhibitor 0.7581 P-glycoprotein inhibitor II Inhibitor 0.8119 Renal organic cation transporter Non-inhibitor 0.7707 CYP450 2C9 substrate Non-substrate 0.821 CYP450 2D6 substrate Non-substrate 0.8057 CYP450 3A4 substrate Substrate 0.7436 CYP450 1A2 substrate Non-inhibitor 0.9696 CYP450 2C9 inhibitor Non-inhibitor 0.7407 CYP450 2D6 inhibitor Non-inhibitor 0.7773 CYP450 2C19 inhibitor Inhibitor 0.5209 CYP450 3A4 inhibitor Inhibitor 0.771 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5707 Ames test Non AMES toxic 0.6721 Carcinogenicity Non-carcinogens 0.8803 Biodegradation Not ready biodegradable 0.962 Rat acute toxicity 2.4252 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9465 hERG inhibition (predictor II) Non-inhibitor 0.5396
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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]
- 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]
- 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