Identification
- Generic Name
- Rolipram
- DrugBank Accession Number
- DB01954
- Background
A phosphodiesterase inhibitor with antidepressant properties.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Rolipram (DB01954)
- Weight
- Average: 275.348
Monoisotopic: 275.15214354 - Chemical Formula
- C16H21NO3
- Synonyms
- 4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinone
- Rolipram
- Rolipramum
- External IDs
- BRN 1588548
- SB-95952
- ZK 62 711
- ZK-62711
- ZK-62771
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UcAMP-specific 3',5'-cyclic phosphodiesterase 4D Not Available Humans UcAMP-specific 3',5'-cyclic phosphodiesterase 4B Not Available Humans AcAMP-specific 3',5'-cyclic phosphodiesterase 4 (PDE4) inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Rolipram is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Rolipram is combined with Acenocoumarol. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Rolipram. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Rolipram. Agomelatine The risk or severity of adverse effects can be increased when Rolipram is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Rolipram. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Rolipram. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Rolipram. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Rolipram. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Rolipram. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- 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
- pyrrolidin-2-ones (CHEBI:104872)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- K676NL63N7
- CAS number
- 61413-54-5
- 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
- 4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
- SMILES
- COC1=C(OC2CCCC2)C=C(C=C1)C1CNC(=O)C1
References
- General References
- Not Available
- External Links
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Multiple Sclerosis 1 1 Completed Treatment Healthy Subjects (HS) / Major Depressive Disorder (MDD) 1 1 Completed Treatment Huntington's Disease (HD) 1 1, 2 Completed Basic Science Diseases of the Nervous System 1
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
Property Value Source Water Solubility 0.0672 mg/mL ALOGPS logP 2.51 ALOGPS logP 1.96 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 14.28 Chemaxon pKa (Strongest Basic) -1.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 47.56 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 76.16 m3·mol-1 Chemaxon Polarizability 30.29 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9822 Caco-2 permeable + 0.5695 P-glycoprotein substrate Substrate 0.5193 P-glycoprotein inhibitor I Non-inhibitor 0.8626 P-glycoprotein inhibitor II Non-inhibitor 0.9717 Renal organic cation transporter Non-inhibitor 0.7173 CYP450 2C9 substrate Non-substrate 0.7863 CYP450 2D6 substrate Non-substrate 0.6385 CYP450 3A4 substrate Substrate 0.645 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.651 Ames test Non AMES toxic 0.7253 Carcinogenicity Non-carcinogens 0.9475 Biodegradation Ready biodegradable 0.6993 Rat acute toxicity 2.1938 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9813 hERG inhibition (predictor II) Non-inhibitor 0.6511
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Components:
References
- Shalaby AM, Kamal SM: Effect of rolipram, a phosphodiesterase enzyme type-4 inhibitor, on gamma-amino butyric acid content of the frontal cortex in mice exposed to chronic mild stress. J Pharmacol Pharmacother. 2012 Apr;3(2):132-7. doi: 10.4103/0976-500X.95509. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51