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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H26N6O
Molecular Weight 354.4493
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SELICICLIB, (S)-

SMILES

CC[C@@H](CO)NC1=NC2=C(N=CN2C(C)C)C(NCC3=CC=CC=C3)=N1

InChI

InChIKey=BTIHMVBBUGXLCJ-HNNXBMFYSA-N
InChI=1S/C19H26N6O/c1-4-15(11-26)22-19-23-17(20-10-14-8-6-5-7-9-14)16-18(24-19)25(12-21-16)13(2)3/h5-9,12-13,15,26H,4,10-11H2,1-3H3,(H2,20,22,23,24)/t15-/m0/s1

HIDE SMILES / InChI
(S)-Seliciclib is enantiomer of the potent cyclin-dependent kinase (CDK) inhibitor Roscovitine. Roscovitine (racemic mixture) is an inhibitor of cell cyclin-dependent kinase (CDK)-2, CDK-4 and CDK-5, which are upregulated in stress conditions inducing apoptosis. (S)-Seliciclib potently inhibits Cyclin-dependent kinase 1. In vivo studies in rabbits demonstrated that both isomers (R- and S-) significantly reduce intraocular pressure (IOP). However, S- isomer was superior to R- isomer in lowering IOP and providing protection to retinal ganglionic cells.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
550.0 nM [IC50]
570.0 µM [EC50]
350.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of human immunodeficiency virus type-1 by cdk inhibitors.
2010-03-24
Inhibition of Toxoplasma gondii by indirubin and tryptanthrin analogs.
2008-12
Patents

Patents

Sample Use Guides

New Zealand White (albino) rabbits were used for activity evaluation. (S)-Seliciclib Was suspended in 4% (w/v) polyethylene glycol (PEG) 4000 at a concentration of 0.1%. Drug solution (50 mkL) was topically administered in the left eyes.
Route of Administration: Topical
The cultured retinal ganglion cell (RGC-5) line were used for activity evaluation. Cultures were maintained at 37 C in a humidified atmosphere of 95% air and 5% CO2. The RGC-5 cells were passaged by trypsinization every 3–4 days. The oxygen–glucose deprivation (OGD)-induced cell death assay involved seeding the cells at a density of 2 x 10^3 cells per well into 96-well plates, followed by incubation in a humidified atmosphere of 95% air and 5% CO2 at 37 C for 24 h. The OGD stress was induced by washing the cells with glucose-free DMEM (Invitrogen, Carlsbad, CA, USA) and then placing them in the same medium in a hypoxic incubator (94% N2, 5% CO2, and 1% O2) for 4 h. At the end of the OGD period, glucose solution and FBS were added at final concentrations of 4.5 mg/mL and 1%, respectively, and the cultures were returned to the incubator for an additional 16 h at the regular atmospheric oxygen level (reoxygenation). The roscovitine R-isomer or S-isomer ((S)-Seliciclib) was added to the culture immediately after replacement of the culture medium. At the end of this culture period, the cell viability was measured.
Name Type Language
(S)-SELICICLIB
Preferred Name English
SELICICLIB, (S)-
Common Name English
SELICICLIB (2S)-FORM [MI]
Common Name English
1-BUTANOL, 2-((9-(1-METHYLETHYL)-6-((PHENYLMETHYL)AMINO)-9H-PURIN-2-YL)AMINO)-, (2S)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID101133475
Created by admin on Mon Mar 31 22:57:49 GMT 2025 , Edited by admin on Mon Mar 31 22:57:49 GMT 2025
PRIMARY
FDA UNII
8C43G94891
Created by admin on Mon Mar 31 22:57:49 GMT 2025 , Edited by admin on Mon Mar 31 22:57:49 GMT 2025
PRIMARY
PUBCHEM
6603989
Created by admin on Mon Mar 31 22:57:49 GMT 2025 , Edited by admin on Mon Mar 31 22:57:49 GMT 2025
PRIMARY
MERCK INDEX
m9849
Created by admin on Mon Mar 31 22:57:49 GMT 2025 , Edited by admin on Mon Mar 31 22:57:49 GMT 2025
PRIMARY Merck Index
CAS
186692-45-5
Created by admin on Mon Mar 31 22:57:49 GMT 2025 , Edited by admin on Mon Mar 31 22:57:49 GMT 2025
PRIMARY