Identification

Generic Name
(S)-Rolipram
DrugBank Accession Number
DB03606
Background

A phosphodiesterase inhibitor with antidepressant properties. [PubChem]

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 275.348
Monoisotopic: 275.15214354
Chemical Formula
C16H21NO3
Synonyms
  • (+)-rolipram
  • (S)-(+)-rolipram
  • S-rolipram

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UcAMP-specific 3',5'-cyclic phosphodiesterase 4DNot AvailableHumans
UcAMP-specific 3',5'-cyclic phosphodiesterase 4B
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
Adverseeffects
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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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
Phenylpyrrolidines
Direct Parent
Phenylpyrrolidines
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / Pyrrolidine-2-ones / Pyrroles / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
2-pyrrolidone / 3-phenylpyrrolidine / Alkyl aryl ether / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
rolipram (CHEBI:59540)
Affected organisms
Not Available

Chemical Identifiers

UNII
H6G4VMQ24K
CAS number
85416-73-5
InChI Key
HJORMJIFDVBMOB-GFCCVEGCSA-N
InChI
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
IUPAC Name
(4S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
SMILES
[H][C@@]1(CNC(=O)C1)C1=CC=C(OC)C(OC2CCCC2)=C1

References

General References
Not Available
PubChem Compound
158758
PubChem Substance
46507984
ChemSpider
139651
BindingDB
50042056
ChEBI
59540
ChEMBL
CHEMBL325795
ZINC
ZINC000002000919
Therapeutic Targets Database
DNC000017
PharmGKB
PA153906323

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0672 mg/mLALOGPS
logP2.51ALOGPS
logP1.96ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.28ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.16 m3·mol-1ChemAxon
Polarizability30.34 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9822
Caco-2 permeable+0.5695
P-glycoprotein substrateSubstrate0.5193
P-glycoprotein inhibitor INon-inhibitor0.8626
P-glycoprotein inhibitor IINon-inhibitor0.9717
Renal organic cation transporterNon-inhibitor0.7173
CYP450 2C9 substrateNon-substrate0.7863
CYP450 2D6 substrateNon-substrate0.6385
CYP450 3A4 substrateSubstrate0.645
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.651
Ames testNon AMES toxic0.7253
CarcinogenicityNon-carcinogens0.9475
BiodegradationReady biodegradable0.6993
Rat acute toxicity2.1938 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9813
hERG inhibition (predictor II)Non-inhibitor0.6511
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0390000000-257b025de2f19ed55c18

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name
PDE4D
Uniprot ID
Q08499
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Molecular Weight
91114.1 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging f...
Gene Name
PDE4B
Uniprot ID
Q07343
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Molecular Weight
83342.695 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52