OLOMOUCINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H18N6O
Molecular Weight	298.343
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C=NC2=C1N=C(NCCO)N=C2NCC3=CC=CC=C3

InChI

InChIKey=GTVPOLSIJWJJNY-UHFFFAOYSA-N

InChI=1S/C15H18N6O/c1-21-10-18-12-13(17-9-11-5-3-2-4-6-11)19-15(16-7-8-22)20-14(12)21/h2-6,10,22H,7-9H2,1H3,(H2,16,17,19,20)

HIDE SMILES / InChI

Molecular Formula	C15H18N6O
Molecular Weight	298.343
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8626506 | https://www.ncbi.nlm.nih.gov/pubmed/7549905 | https://www.scbt.com/scbt/product/olomoucine-101622-51-9 | https://www.ncbi.nlm.nih.gov/pubmed/16000586 |

Olomoucine acts as a competitive inhibitor of ATP in cyclin-dependent kinase 1/2/5, and mitogen-activated protein kinase 1. Olomoucine is an anti-mitotic compound that induces cell death preferentially in cancer cell lines, but also at a slower rate in non-cancer cells. It has been studied pre-clinically in a number of cancer models but has not been reported in any human trials. Olomoucine has also seen some preliminary investigation in mouse models of Herpes Simplex Viral Encephalitis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclin-dependent kinase 2 23 Target ID: P24941 Gene ID: 1017.0 Gene Symbol: CDK2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7549905 \| https://www.ncbi.nlm.nih.gov/pubmed/7479711 \| https://www.ncbi.nlm.nih.gov/pubmed/7925396	Inhibitor 8504	7.0 µM [IC50]
Cyclin-dependent-like kinase 5 1 Target ID: Q00535 Gene ID: 1020.0 Gene Symbol: CDK5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7925396	Inhibitor 8504	3.0 µM [IC50]
Mitogen-activated protein kinase 1 3 Target ID: P28482 Gene ID: 5594.0 Gene Symbol: MAPK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7925396	Inhibitor 8504	25.0 µM [IC50]
Cyclin-dependent kinase 1 27 Target ID: P06493 Gene ID: 983.0 Gene Symbol: CDK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8626506	Inhibitor 8504	7.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: http://adis.springer.com/drugs/800008577 https://www.ncbi.nlm.nih.gov/pubmed/16000586 https://www.ncbi.nlm.nih.gov/pubmed/10602500 https://www.ncbi.nlm.nih.gov/pubmed/17094472	Primary		Preclinical	Unknown Approved Use Unknown
Herpes virus encephalitis 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27241721	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The role of protein kinase A and cyclin-dependent (CDC2) kinase in the control of basal and IGF-II-induced proliferation and secretory activity of chicken ovarian cells.	2006-03	16029936
Zinc(II) complexes with potent cyclin-dependent kinase inhibitors derived from 6-benzylaminopurine: synthesis, characterization, X-ray structures and biological activity.	2006-02	16386795
Activation of CYP1A1 gene expression during primary culture of mouse hepatocytes.	2005-12-15	16169145
Molecular models of protein kinase 6 from Plasmodium falciparum.	2005-12	16096806
Caspase 8/10 are not mediating apoptosis in neuroblastoma cells treated with CDK inhibitory drugs.	2005-11-07	16243312
Cdk2 activity is dispensable for triggering replicon initiation after transient hypoxia in T24 cells.	2005-11	16262700
During male pronuclei formation chromatin remodeling is uncoupled from nucleus decondensation.	2005-10-01	16088960
Cdk5-dependent regulation of glucose-stimulated insulin secretion.	2005-10	16155576
DNA damage induces cdk2 protein levels and histone H2B phosphorylation in SH-SY5Y neuroblastoma cells.	2005-09	16155345
Role of the cell cycle in the pathobiology of central nervous system trauma.	2005-09	16082214
Slowed N-type calcium channel (CaV2.2) deactivation by the cyclin-dependent kinase inhibitor roscovitine.	2005-09	15951378
Antiproliferative activity of olomoucine II, a novel 2,6,9-trisubstituted purine cyclin-dependent kinase inhibitor.	2005-08	16003486
In vitro and in vivo pharmacokinetic-pharmacodynamic relationships for the trisubstituted aminopurine cyclin-dependent kinase inhibitors olomoucine, bohemine and CYC202.	2005-07-01	16000586
Signaling pathways in ascidian oocyte maturation: effects of various inhibitors and activators on germinal vesicle breakdown.	2005-05	15921501
Resveratrol-induced apoptotic death in human U251 glioma cells.	2005-04	15827328
Cdk inhibition in human cells compromises chk1 function and activates a DNA damage response.	2005-02-01	15705874
CIL-102 interacts with microtubule polymerization and causes mitotic arrest following apoptosis in the human prostate cancer PC-3 cell line.	2005-01-28	15536083
Clinical anticancer drug development: targeting the cyclin-dependent kinases.	2005-01-17	15558073
Phosphorylated amyloid-beta: the toxic intermediate in alzheimer's disease neurodegeneration.	2005	15709490
N-glucosylation of cytokinins by glycosyltransferases of Arabidopsis thaliana.	2004-11-12	15342621
Phosphorylation of Sp1 by cyclin-dependent kinase 2 modulates the role of Sp1 in CTP:phosphocholine cytidylyltransferase alpha regulation during the S phase of the cell cycle.	2004-09-17	15247247
Mitogen-activated protein kinase regulates neurofilament axonal transport.	2004-09-15	15331628
Cell cycle arrest induced in human breast cancer cells by cyclin-dependent kinase inhibitors: a comparison of the effects exerted by roscovitine and olomoucine.	2004-09-06	15591654
Cyclin-dependent kinase inhibitors attenuate protein hyperphosphorylation, cytoskeletal lesion formation, and motor defects in Niemann-Pick Type C mice.	2004-09	15331409
Cdk5 regulates activation and localization of Src during corneal epithelial wound closure.	2004-08-15	15280426
Correlation between semaphorin3A-induced facilitation of axonal transport and local activation of a translation initiation factor eukaryotic translation initiation factor 4E.	2004-07-07	15240808
A novel CDK5-dependent pathway for regulating GSK3 activity and kinesin-driven motility in neurons.	2004-06-02	15152189
Roscovitine, olomoucine, purvalanol: inducers of apoptosis in maturing cerebellar granule neurons.	2004-05-15	15130771
Cell differentiation, caspase inhibition, and macromolecular synthesis blockage, but not BCL-2 or BCL-XL proteins, protect SH-SY5Y cells from apoptosis triggered by two CDK inhibitory drugs.	2004-04-15	15051486
Activation of cyclin-dependent kinase 5 is involved in axonal regeneration.	2004-03	15033170
Cassette dosing pharmacokinetics of a library of 2,6,9-trisubstituted purine cyclin-dependent kinase 2 inhibitors prepared by parallel synthesis.	2004-03	15026556
Development of an assay to screen for inhibitors of tau phosphorylation by cdk5.	2004-03	15006135
Xylocydine, a novel inhibitor of cyclin-dependent kinases, prevents the tumor necrosis factor-related apoptosis-inducing ligand-induced apoptotic cell death of SK-HEP-1 cells.	2004-03	14617691
Nuclear translocation of the Hsp70/Hsp90 organizing protein mSTI1 is regulated by cell cycle kinases.	2004-02-15	14754904
Angiostatin-induced inhibition of endothelial cell proliferation/apoptosis is associated with the down-regulation of cell cycle regulatory protein cdk5.	2004-02-01	14743398
Protection of renal cells from cisplatin toxicity by cell cycle inhibitors.	2004-02	12965891
Synergic effects of the cyclin-dependent kinase (CDK) inhibitor olomoucine and androgen-antagonist bicalutamide on prostatic cancer cell lines.	2004	15640940
Expression profiles of a human pancreatic cancer cell line upon induction of apoptosis search for modulators in cancer therapy.	2004	15557790
An inhibition of cyclin-dependent kinases that lengthens, but does not arrest, neuroepithelial cell cycle induces premature neurogenesis.	2003-12-15	14625388
Changes in the activities of hydroxysteroid dehydrogenases in mouse oocytes during meiotic maturation.	2003-12	14967895
The expression of retinoblastoma and Sp1 is increased by low concentrations of cyclin-dependent kinase inhibitors.	2003-12	14653808
Cdk5/p35 and Rho-kinase mediate ephrin-A5-induced signaling in retinal ganglion cells.	2003-11	14664814
Prevention of dopaminergic neuronal death by cyclic AMP in mixed neuronal/glial mesencephalic cultures requires the repression of presumptive astrocytes.	2003-09	12920193
Involvement of the transcription factor E2F1/Rb in kainic acid-induced death of murine cerebellar granule cells.	2003-08-19	12941462
Cdk2 activity is associated with depolarization of mitochondrial membrane potential during apoptosis.	2003-06-13	12767926
Roscovitine and other purines as kinase inhibitors. From starfish oocytes to clinical trials.	2003-06	12809528
Synthesis and biological evaluations of pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 inhibitors.	2003-05	12767603
Mixed ligand complexes of platinum(II) and palladium(II) with cytokinin-derived compounds Bohemine and Olomoucine: X-ray structure of [Pt(BohH+-N7)Cl(3)].9/5H2O [Boh=6-(benzylamino)-2-[(3-(hydroxypropyl)-amino]-9-isopropylpurine, Bohemine].	2003-04-01	12667701
Growth cones contain a dynamic population of neurofilament subunits.	2003-03	12589678
In vitro glycosidation potential towards olomoucine-type cyclin-dependent kinase inhibitors in rodent and primate microsomes.	2003	12899660

Patents

Sample Use Guides

In Vivo Use Guide

Pharmacokinetic properties were characterized in mice which were administered with 50 mg/kg of oral olomoucine.

Route of Administration: Oral

In Vitro Use Guide

Human MCF-7 and IMR-90 cell lines were grown in Dulbecco's modified Eagle's medium, and cell cycles were arrested at the G2/M or G0/G1 checkpoints respectively. Cells were released from cycle blocking and olomoucine (150 uM) was added after 4 hours. Treatment induces nuclear accumulation of wt p53 and a delocalization of nucleolin from the nucleolus in all cells regardless of cell cycle stage. This triggers rapid death of human tumor cells and a less rapid death of non-tumor cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:36:47 GMT 2025` Edited by `admin` on `Mon Mar 31 21:36:47 GMT 2025`
Record UNII	6A839B2HYS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OLOMOUCINE

Common Name

English

NSC-666096

Preferred Name

English

ETHANOL, 2-((9-METHYL-6-((PHENYLMETHYL)AMINO)-9H-PURIN-2-YL)AMINO)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID90144068