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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
Molecular Formula C16H21NO3
Molecular Weight 275.3428
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:49:53 UTC 2023
Edited
by admin
on Sat Dec 16 01:49:53 UTC 2023
Record UNII
H6G4VMQ24K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROLIPRAM, (S)-
Common 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
(+)-ROLIPRAM
Common Name English
(S)-(+)-ROLIPRAM
Common Name English
Code System Code Type Description
PUBCHEM
158758
Created by admin on Sat Dec 16 01:49:53 UTC 2023 , Edited by admin on Sat Dec 16 01:49:53 UTC 2023
PRIMARY
DRUG BANK
DB03606
Created by admin on Sat Dec 16 01:49:53 UTC 2023 , Edited by admin on Sat Dec 16 01:49:53 UTC 2023
PRIMARY
CHEBI
59540
Created by admin on Sat Dec 16 01:49:53 UTC 2023 , Edited by admin on Sat Dec 16 01:49:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID30234634
Created by admin on Sat Dec 16 01:49:53 UTC 2023 , Edited by admin on Sat Dec 16 01:49:53 UTC 2023
PRIMARY
FDA UNII
H6G4VMQ24K
Created by admin on Sat Dec 16 01:49:53 UTC 2023 , Edited by admin on Sat Dec 16 01:49:53 UTC 2023
PRIMARY
CAS
85416-73-5
Created by admin on Sat Dec 16 01:49:53 UTC 2023 , Edited by admin on Sat Dec 16 01:49:53 UTC 2023
PRIMARY
Related Record Type Details
Structure of ROLIPRAM
RACEMATE -> ENANTIOMER
NIH
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