U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H21NO3
Molecular Weight 275.3428
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

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

SMILES

COC1=CC=C(C=C1OC2CCCC2)[C@H]3CNC(=O)C3

InChI

InChIKey=HJORMJIFDVBMOB-GFCCVEGCSA-N
InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)/t12-/m1/s1

HIDE SMILES / InChI

Description

S-enantiomer of rolipram is less active at inhibition of type 4 phosphodiesterase. Displays activity 10-fold less than R-rolipram.

CNS Activity

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 1136.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Stereospecific binding of the antidepressant rolipram to brain protein structures.
1986 Aug 7

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
It was examined the inhibitory effect of rolipram on rat brain phosphodiesterase 4 to determine the heterogeneity of the enzyme activity. Partial purification of various phosphodiesterases from the rat brain was performed by anion-exchange chromatography. The eluant was pooled into four fractions, two of which manifested cAMP-selective phosphodiesterase activity that was blocked by 10 microM of rolipram, indicating the presence of phosphodiesterase 4 in these fractions. The IC50 of rolipram (racemate) of these two fractions was 492 and 79 nM, respectively. The R-(-)-enantiomer of rolipram inhibited the cAMP-phosphodiesterase activity in the latter fraction 10 times more than did S-(+)-rolipram, and the inhibition of the former fraction was less stereospecific.
Name Type Language
ROLIPRAM, (S)-
Common Name English
(+)-ROLIPRAM
Preferred Name English
2-PYRROLIDINONE, 4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)-, (4S)-
Systematic Name English
(4S)-4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)-2-PYRROLIDINONE
Systematic Name English
(S)-ROLIPRAM
Common Name English
2-PYRROLIDINONE, 4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)-, (S)-
Systematic Name English
ROLIPRAM, (+)-
Common Name English
(S)-(+)-ROLIPRAM
Common Name English
Code System Code Type Description
PUBCHEM
158758
Created by admin on Mon Mar 31 21:01:31 GMT 2025 , Edited by admin on Mon Mar 31 21:01:31 GMT 2025
PRIMARY
DRUG BANK
DB03606
Created by admin on Mon Mar 31 21:01:31 GMT 2025 , Edited by admin on Mon Mar 31 21:01:31 GMT 2025
PRIMARY
CHEBI
59540
Created by admin on Mon Mar 31 21:01:31 GMT 2025 , Edited by admin on Mon Mar 31 21:01:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID30234634
Created by admin on Mon Mar 31 21:01:31 GMT 2025 , Edited by admin on Mon Mar 31 21:01:31 GMT 2025
PRIMARY
FDA UNII
H6G4VMQ24K
Created by admin on Mon Mar 31 21:01:31 GMT 2025 , Edited by admin on Mon Mar 31 21:01:31 GMT 2025
PRIMARY
CAS
85416-73-5
Created by admin on Mon Mar 31 21:01:31 GMT 2025 , Edited by admin on Mon Mar 31 21:01:31 GMT 2025
PRIMARY
SUBSTANCE RECORD
Structure of ROLIPRAM, (S)-
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966