(S)-Rolipram
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Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- (S)-Rolipram
- DrugBank Accession Number
- DB03606
- Background
A phosphodiesterase inhibitor with antidepressant properties. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 275.348
Monoisotopic: 275.15214354 - Chemical Formula
- C16H21NO3
- Synonyms
- (+)-rolipram
- (S)-(+)-rolipram
- S-rolipram
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism A3',5'-cyclic-AMP phosphodiesterase 4A inhibitorHumans A3',5'-cyclic-AMP phosphodiesterase 4B inhibitorHumans U3',5'-cyclic-AMP phosphodiesterase 4D Not Available 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!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.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
- External Links
- 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
Clinical Trial & Rare Diseases Add-on Data Package
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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 30.34 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.4813041 predictedDarkChem Lite v0.1.0 [M-H]- 163.41418 predictedDeepCCS 1.0 (2019) [M+H]+ 175.6929041 predictedDarkChem Lite v0.1.0 [M+H]+ 165.77266 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.1887041 predictedDarkChem Lite v0.1.0 [M+Na]+ 171.8658 predictedDeepCCS 1.0 (2019)
Targets
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1. Details3',5'-cyclic-AMP phosphodiesterase 4A
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Hydrolyzes the second messenger 3',5'-cyclic AMP (cAMP), which is a key regulator of many important physiological processes
- Specific Function
- 3',5'-cyclic-AMP phosphodiesterase activity
- Gene Name
- PDE4A
- Uniprot ID
- P27815
- Uniprot Name
- 3',5'-cyclic-AMP phosphodiesterase 4A
- Molecular Weight
- 98142.155 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. Details3',5'-cyclic-AMP phosphodiesterase 4B
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes (PubMed:15260978). May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents
- Specific Function
- 3',5'-cyclic-AMP phosphodiesterase activity
- Gene Name
- PDE4B
- Uniprot ID
- Q07343
- Uniprot Name
- 3',5'-cyclic-AMP 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. Details3',5'-cyclic-AMP phosphodiesterase 4D
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes
- Specific Function
- 3',5'-cyclic-AMP phosphodiesterase activity
- Gene Name
- PDE4D
- Uniprot ID
- Q08499
- Uniprot Name
- 3',5'-cyclic-AMP phosphodiesterase 4D
- Molecular Weight
- 91114.1 Da
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:21