Rolipram

Identification

Name
Rolipram
Accession Number
DB01954  (EXPT02804)
Type
Small Molecule
Groups
Investigational
Description

A phosphodiesterase inhibitor with antidepressant properties.

Structure
Thumb
Synonyms
  • 4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinone
  • Rolipramum
External IDs
BRN 1588548 / SB-95952 / ZK 62 711 / ZK-62711 / ZK-62771
Categories
UNII
K676NL63N7
CAS number
61413-54-5
Weight
Average: 275.348
Monoisotopic: 275.15214354
Chemical Formula
C16H21NO3
InChI Key
HJORMJIFDVBMOB-UHFFFAOYSA-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)
IUPAC Name
3-[3-(cyclopentyloxy)-4-methoxyphenyl]-3,4-dihydro-2H-pyrrol-5-ol
SMILES
COC1=C(OC2CCCC2)C=C(C=C1)C1CN=C(O)C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcAMP-specific 3',5'-cyclic phosphodiesterase 4DNot AvailableHuman
UcAMP-specific 3',5'-cyclic phosphodiesterase 4BNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Rolipram.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D01783
PubChem Compound
5092
PubChem Substance
46508075
ChemSpider
4913
BindingDB
14361
ChEBI
104872
ChEMBL
CHEMBL63
PharmGKB
PA153906323

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers / Major Depressive Disorder (MDD)1
1CompletedTreatmentHuntington's Disease (HD)1
2CompletedTreatmentDisseminated Sclerosis1

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 Solubility0.0239 mg/mLALOGPS
logP3.16ALOGPS
logP2.05ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.83ChemAxon
pKa (Strongest Basic)6.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.05 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.69 m3·mol-1ChemAxon
Polarizability30.07 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-0090000000-560244a4d0d6418f226c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0090000000-9507b0584062362f343b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a6u-0590000000-63d3f57e5eff4592ddd0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-1690000000-748a69ba652840c85f95
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0590000000-1ce7657ef60958653797
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f89-3910000000-38dfbb97597c517723c3

Taxonomy

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
3-phenylpyrrolidine / Phenoxy compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid / 2-pyrrolidone / Pyrrolidone
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrrolidin-2-ones (CHEBI:104872)

Targets

Kind
Protein
Organism
Human
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
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:51