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Prexasertib

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

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Identification

Generic Name
Prexasertib
DrugBank Accession Number
DB12008
Background

Prexasertib has been used in trials studying the treatment and basic science of mCRPC, Leukemia, Neoplasm, breast cancer, and Ovarian Cancer, among others.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 365.397
Monoisotopic: 365.16002288
Chemical Formula
C18H19N7O2
Synonyms
  • Prexasertib
External IDs
  • ACR 368
  • ACR-368
  • ACR368
  • LY-2606368
  • LY2606368
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ASerine/threonine-protein kinase Chk1
inhibitor
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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Toxicity

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.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Prexasertib dihydrochloride9RFT476U2L1234015-54-3Not applicable
Prexasertib mesylate monohydrateS4D3L195S41234015-57-6Not applicable

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Pyrazoles
Direct Parent
Phenylpyrazoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Anisoles / Aminopyrazines / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Secondary amines / Nitriles / Azacyclic compounds
show 2 more
Substituents
Alkyl aryl ether / Amine / Aminopyrazine / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonitrile / Cyanide / Ether
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
820NH671E6
CAS number
1234015-52-1
InChI Key
DOTGPNHGTYJDEP-UHFFFAOYSA-N
InChI
InChI=1S/C18H19N7O2/c1-26-14-4-2-5-15(27-7-3-6-19)18(14)13-8-16(25-24-13)23-17-11-21-12(9-20)10-22-17/h2,4-5,8,10-11H,3,6-7,19H2,1H3,(H2,22,23,24,25)
IUPAC Name
5-({5-[2-(3-aminopropoxy)-6-methoxyphenyl]-1H-pyrazol-3-yl}amino)pyrazine-2-carbonitrile
SMILES
COC1=CC=CC(OCCCN)=C1C1=CC(NC2=CN=C(C=N2)C#N)=NN1

References

General References
Not Available
PubChem Compound
46700756
PubChem Substance
347828326
ChemSpider
32738771
BindingDB
50524300
ChEMBL
CHEMBL3544911
ZINC
ZINC000095837013
Wikipedia
Prexasertib

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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2CompletedTreatmentAdvanced Malignant Neoplasm1somestatusstop reasonjust information to hide
2CompletedTreatmentOvarian Cancer1somestatusstop reasonjust information to hide
2CompletedTreatmentSmall Cell Lung Cancer (SCLC)1somestatusstop reasonjust information to hide
2CompletedTreatmentTriple-Negative Breast Cancer1somestatusstop reasonjust information to hide
2TerminatedTreatmentBreast Cancer / Ovarian Cancer / Prostate Cancer1somestatusstop reasonjust information to hide

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0496 mg/mLALOGPS
logP1.77ALOGPS
logP0.73Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)10.02Chemaxon
pKa (Strongest Basic)9.85Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area134.76 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity100.65 m3·mol-1Chemaxon
Polarizability37.99 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0009000000-6a46e63c255e6d968a72
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0096000000-179d13423f9e09aadb36
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-0019000000-818029bf20bce20121ba
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0191000000-f3da8774fc8c31030385
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-054x-2097000000-a7a3a365ccca8ce9d52f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0190000000-6aa4602814f765e553e5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-180.8927
predicted
DeepCCS 1.0 (2019)
[M+H]+183.3521
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.86092
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine/threonine-protein kinase Chk1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine/threonine-protein kinase which is required for checkpoint-mediated cell cycle arrest and activation of DNA repair in response to the presence of DNA damage or unreplicated DNA (PubMed:11535615, PubMed:12399544, PubMed:12446774, PubMed:14559997, PubMed:14988723, PubMed:15311285, PubMed:15650047, PubMed:15665856, PubMed:32357935). May also negatively regulate cell cycle progression during unperturbed cell cycles (PubMed:11535615, PubMed:12399544, PubMed:12446774, PubMed:14559997, PubMed:14988723, PubMed:15311285, PubMed:15650047, PubMed:15665856). This regulation is achieved by a number of mechanisms that together help to preserve the integrity of the genome (PubMed:11535615, PubMed:12399544, PubMed:12446774, PubMed:14559997, PubMed:14988723, PubMed:15311285, PubMed:15650047, PubMed:15665856). Recognizes the substrate consensus sequence [R-X-X-S/T] (PubMed:11535615, PubMed:12399544, PubMed:12446774, PubMed:14559997, PubMed:14988723, PubMed:15311285, PubMed:15650047, PubMed:15665856). Binds to and phosphorylates CDC25A, CDC25B and CDC25C (PubMed:12676583, PubMed:12676925, PubMed:12759351, PubMed:14559997, PubMed:14681206, PubMed:19734889, PubMed:9278511). Phosphorylation of CDC25A at 'Ser-178' and 'Thr-507' and phosphorylation of CDC25C at 'Ser-216' creates binding sites for 14-3-3 proteins which inhibit CDC25A and CDC25C (PubMed:9278511). Phosphorylation of CDC25A at 'Ser-76', 'Ser-124', 'Ser-178', 'Ser-279' and 'Ser-293' promotes proteolysis of CDC25A (PubMed:12676583, PubMed:12676925, PubMed:12759351, PubMed:14681206, PubMed:19734889, PubMed:9278511). Phosphorylation of CDC25A at 'Ser-76' primes the protein for subsequent phosphorylation at 'Ser-79', 'Ser-82' and 'Ser-88' by NEK11, which is required for polyubiquitination and degradation of CDCD25A (PubMed:19734889, PubMed:20090422, PubMed:9278511). Inhibition of CDC25 leads to increased inhibitory tyrosine phosphorylation of CDK-cyclin complexes and blocks cell cycle progression (PubMed:9278511). Also phosphorylates NEK6 (PubMed:18728393). Binds to and phosphorylates RAD51 at 'Thr-309', which promotes the release of RAD51 from BRCA2 and enhances the association of RAD51 with chromatin, thereby promoting DNA repair by homologous recombination (PubMed:15665856). Phosphorylates multiple sites within the C-terminus of TP53, which promotes activation of TP53 by acetylation and promotes cell cycle arrest and suppression of cellular proliferation (PubMed:10673501, PubMed:15659650, PubMed:16511572). Also promotes repair of DNA cross-links through phosphorylation of FANCE (PubMed:17296736). Binds to and phosphorylates TLK1 at 'Ser-743', which prevents the TLK1-dependent phosphorylation of the chromatin assembly factor ASF1A (PubMed:12660173, PubMed:12955071). This may enhance chromatin assembly both in the presence or absence of DNA damage (PubMed:12660173, PubMed:12955071). May also play a role in replication fork maintenance through regulation of PCNA (PubMed:18451105). May regulate the transcription of genes that regulate cell-cycle progression through the phosphorylation of histones (By similarity). Phosphorylates histone H3.1 (to form H3T11ph), which leads to epigenetic inhibition of a subset of genes (By similarity). May also phosphorylate RB1 to promote its interaction with the E2F family of transcription factors and subsequent cell cycle arrest (PubMed:17380128). Phosphorylates SPRTN, promoting SPRTN recruitment to chromatin (PubMed:31316063). Reduces replication stress and activates the G2/M checkpoint, by phosphorylating and inactivating PABIR1/FAM122A and promoting the serine/threonine-protein phosphatase 2A-mediated dephosphorylation and stabilization of WEE1 levels and activity (PubMed:33108758)
Specific Function
ATP binding
Gene Name
CHEK1
Uniprot ID
O14757
Uniprot Name
Serine/threonine-protein kinase Chk1
Molecular Weight
54433.115 Da
References
  1. Hsu WH, Zhao X, Zhu J, Kim IK, Rao G, McCutcheon J, Hsu ST, Teicher B, Kallakury B, Dowlati A, Zhang YW, Giaccone G: Checkpoint Kinase 1 Inhibition Enhances Cisplatin Cytotoxicity and Overcomes Cisplatin Resistance in SCLC by Promoting Mitotic Cell Death. J Thorac Oncol. 2019 Jun;14(6):1032-1045. doi: 10.1016/j.jtho.2019.01.028. Epub 2019 Feb 14. [Article]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at October 20, 2016 21:10 / Updated at August 26, 2024 19:23