Page last updated: 2024-12-06

Pyrrolidine-1-carbonitrile

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID73737
CHEMBL ID262697
CHEBI ID195083

Synonyms (30)

Synonym
1-pyrrolidinecarbonitrile
1530-88-7
nsc-44225
nsc44225
n-cyanopyrrolidine
inchi=1/c5h8n2/c6-5-7-3-1-2-4-7/h1-4h
pyrrolidine-1-carbonitrile
bdbm50095495
cyano-pyrrolidine
CHEMBL262697 ,
CHEBI:195083
A809393
1-cyanopyrrolidine
AKOS006227753
einecs 216-234-3
nsc 44225
FT-0607667
tetramethylenecyanamide
PS-9344
DTXSID90165192
mfcd00003165
J-008980
cyanopyrrolidine
DVF8MV7L37
P2337
AMY41640
T71834
CS-0155293
EN300-251955
SY050800
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrrolidinesAny of a class of heterocyclic amines having a saturated five-membered ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Procathepsin LHomo sapiens (human)IC50 (µMol)2.79240.00021.66619.5100AID51224; AID570625
Cathepsin BHomo sapiens (human)IC50 (µMol)20.05950.00021.845310.0000AID50270; AID570624
Cathepsin SHomo sapiens (human)IC50 (µMol)25.11890.00021.319110.0000AID570626
Gastrin/cholecystokinin type B receptorHomo sapiens (human)IC50 (µMol)4.00000.00010.36154.0000AID51224
Cathepsin KHomo sapiens (human)IC50 (µMol)2.27300.00010.848210.0000AID241950; AID48398; AID48399; AID48404; AID48405; AID48411; AID570623
Cathepsin KHomo sapiens (human)Ki2.10000.00000.15372.1000AID238235
Dipeptidyl peptidase 1Homo sapiens (human)IC50 (µMol)25.11890.03473.151510.0000AID570622
Gastrin/cholecystokinin type B receptorMus musculus (house mouse)IC50 (µMol)4.00000.00031.33674.0000AID51224
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (57)

Processvia Protein(s)Taxonomy
adaptive immune responseProcathepsin LHomo sapiens (human)
proteolysisProcathepsin LHomo sapiens (human)
protein autoprocessingProcathepsin LHomo sapiens (human)
fusion of virus membrane with host plasma membraneProcathepsin LHomo sapiens (human)
receptor-mediated endocytosis of virus by host cellProcathepsin LHomo sapiens (human)
antigen processing and presentationProcathepsin LHomo sapiens (human)
antigen processing and presentation of exogenous peptide antigen via MHC class IIProcathepsin LHomo sapiens (human)
collagen catabolic processProcathepsin LHomo sapiens (human)
zymogen activationProcathepsin LHomo sapiens (human)
enkephalin processingProcathepsin LHomo sapiens (human)
fusion of virus membrane with host endosome membraneProcathepsin LHomo sapiens (human)
CD4-positive, alpha-beta T cell lineage commitmentProcathepsin LHomo sapiens (human)
symbiont entry into host cellProcathepsin LHomo sapiens (human)
antigen processing and presentation of peptide antigenProcathepsin LHomo sapiens (human)
proteolysis involved in protein catabolic processProcathepsin LHomo sapiens (human)
elastin catabolic processProcathepsin LHomo sapiens (human)
macrophage apoptotic processProcathepsin LHomo sapiens (human)
cellular response to thyroid hormone stimulusProcathepsin LHomo sapiens (human)
positive regulation of apoptotic signaling pathwayProcathepsin LHomo sapiens (human)
positive regulation of peptidase activityProcathepsin LHomo sapiens (human)
immune responseProcathepsin LHomo sapiens (human)
proteolysisCathepsin BHomo sapiens (human)
thyroid hormone generationCathepsin BHomo sapiens (human)
collagen catabolic processCathepsin BHomo sapiens (human)
epithelial cell differentiationCathepsin BHomo sapiens (human)
regulation of apoptotic processCathepsin BHomo sapiens (human)
decidualizationCathepsin BHomo sapiens (human)
symbiont entry into host cellCathepsin BHomo sapiens (human)
proteolysis involved in protein catabolic processCathepsin BHomo sapiens (human)
cellular response to thyroid hormone stimulusCathepsin BHomo sapiens (human)
toll-like receptor signaling pathwayCathepsin SHomo sapiens (human)
adaptive immune responseCathepsin SHomo sapiens (human)
proteolysisCathepsin SHomo sapiens (human)
apoptotic processCathepsin SHomo sapiens (human)
response to acidic pHCathepsin SHomo sapiens (human)
protein processingCathepsin SHomo sapiens (human)
antigen processing and presentationCathepsin SHomo sapiens (human)
antigen processing and presentation of exogenous peptide antigen via MHC class IICathepsin SHomo sapiens (human)
extracellular matrix disassemblyCathepsin SHomo sapiens (human)
collagen catabolic processCathepsin SHomo sapiens (human)
basement membrane disassemblyCathepsin SHomo sapiens (human)
antigen processing and presentation of peptide antigenCathepsin SHomo sapiens (human)
proteolysis involved in protein catabolic processCathepsin SHomo sapiens (human)
cellular response to thyroid hormone stimulusCathepsin SHomo sapiens (human)
positive regulation of cation channel activityCathepsin SHomo sapiens (human)
positive regulation of peptidase activityCathepsin SHomo sapiens (human)
immune responseCathepsin SHomo sapiens (human)
positive regulation of apoptotic signaling pathwayCathepsin SHomo sapiens (human)
gastric acid secretionGastrin/cholecystokinin type B receptorHomo sapiens (human)
cell surface receptor signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationGastrin/cholecystokinin type B receptorHomo sapiens (human)
positive regulation of cell population proliferationGastrin/cholecystokinin type B receptorHomo sapiens (human)
cholecystokinin signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
pH reductionGastrin/cholecystokinin type B receptorHomo sapiens (human)
digestive tract developmentGastrin/cholecystokinin type B receptorHomo sapiens (human)
gland developmentGastrin/cholecystokinin type B receptorHomo sapiens (human)
collagen catabolic processCathepsin KHomo sapiens (human)
mitophagyCathepsin KHomo sapiens (human)
intramembranous ossificationCathepsin KHomo sapiens (human)
proteolysisCathepsin KHomo sapiens (human)
thyroid hormone generationCathepsin KHomo sapiens (human)
apoptotic processCathepsin KHomo sapiens (human)
response to organic cyclic compoundCathepsin KHomo sapiens (human)
extracellular matrix disassemblyCathepsin KHomo sapiens (human)
collagen catabolic processCathepsin KHomo sapiens (human)
response to insulinCathepsin KHomo sapiens (human)
cellular response to zinc ion starvationCathepsin KHomo sapiens (human)
bone resorptionCathepsin KHomo sapiens (human)
response to ethanolCathepsin KHomo sapiens (human)
proteolysis involved in protein catabolic processCathepsin KHomo sapiens (human)
negative regulation of cartilage developmentCathepsin KHomo sapiens (human)
cellular response to tumor necrosis factorCathepsin KHomo sapiens (human)
cellular response to transforming growth factor beta stimulusCathepsin KHomo sapiens (human)
mononuclear cell differentiationCathepsin KHomo sapiens (human)
positive regulation of apoptotic signaling pathwayCathepsin KHomo sapiens (human)
positive regulation of peptidase activityCathepsin KHomo sapiens (human)
immune responseCathepsin KHomo sapiens (human)
T cell mediated cytotoxicityDipeptidyl peptidase 1Homo sapiens (human)
proteolysisDipeptidyl peptidase 1Homo sapiens (human)
apoptotic processDipeptidyl peptidase 1Homo sapiens (human)
immune responseDipeptidyl peptidase 1Homo sapiens (human)
response to organic substanceDipeptidyl peptidase 1Homo sapiens (human)
negative regulation of myelinationDipeptidyl peptidase 1Homo sapiens (human)
positive regulation of proteolysis involved in protein catabolic processDipeptidyl peptidase 1Homo sapiens (human)
positive regulation of microglial cell activationDipeptidyl peptidase 1Homo sapiens (human)
positive regulation of apoptotic signaling pathwayDipeptidyl peptidase 1Homo sapiens (human)
proteolysis involved in protein catabolic processDipeptidyl peptidase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
fibronectin bindingProcathepsin LHomo sapiens (human)
cysteine-type endopeptidase activityProcathepsin LHomo sapiens (human)
protein bindingProcathepsin LHomo sapiens (human)
collagen bindingProcathepsin LHomo sapiens (human)
cysteine-type peptidase activityProcathepsin LHomo sapiens (human)
histone bindingProcathepsin LHomo sapiens (human)
proteoglycan bindingProcathepsin LHomo sapiens (human)
serpin family protein bindingProcathepsin LHomo sapiens (human)
cysteine-type endopeptidase activator activity involved in apoptotic processProcathepsin LHomo sapiens (human)
cysteine-type endopeptidase activityCathepsin BHomo sapiens (human)
protein bindingCathepsin BHomo sapiens (human)
collagen bindingCathepsin BHomo sapiens (human)
peptidase activityCathepsin BHomo sapiens (human)
cysteine-type peptidase activityCathepsin BHomo sapiens (human)
proteoglycan bindingCathepsin BHomo sapiens (human)
fibronectin bindingCathepsin SHomo sapiens (human)
cysteine-type endopeptidase activityCathepsin SHomo sapiens (human)
serine-type endopeptidase activityCathepsin SHomo sapiens (human)
collagen bindingCathepsin SHomo sapiens (human)
laminin bindingCathepsin SHomo sapiens (human)
proteoglycan bindingCathepsin SHomo sapiens (human)
cysteine-type endopeptidase activator activity involved in apoptotic processCathepsin SHomo sapiens (human)
cholecystokinin receptor activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
protein bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
gastrin receptor activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
peptide hormone bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
type B gastrin/cholecystokinin receptor bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
1-phosphatidylinositol-3-kinase regulator activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
fibronectin bindingCathepsin KHomo sapiens (human)
cysteine-type endopeptidase activityCathepsin KHomo sapiens (human)
serine-type endopeptidase activityCathepsin KHomo sapiens (human)
protein bindingCathepsin KHomo sapiens (human)
collagen bindingCathepsin KHomo sapiens (human)
cysteine-type peptidase activityCathepsin KHomo sapiens (human)
proteoglycan bindingCathepsin KHomo sapiens (human)
cysteine-type endopeptidase activator activity involved in apoptotic processCathepsin KHomo sapiens (human)
serine-type endopeptidase activityDipeptidyl peptidase 1Homo sapiens (human)
protein bindingDipeptidyl peptidase 1Homo sapiens (human)
cysteine-type peptidase activityDipeptidyl peptidase 1Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 1Homo sapiens (human)
peptidase activator activity involved in apoptotic processDipeptidyl peptidase 1Homo sapiens (human)
phosphatase bindingDipeptidyl peptidase 1Homo sapiens (human)
chloride ion bindingDipeptidyl peptidase 1Homo sapiens (human)
identical protein bindingDipeptidyl peptidase 1Homo sapiens (human)
protein-folding chaperone bindingDipeptidyl peptidase 1Homo sapiens (human)
cysteine-type endopeptidase activityDipeptidyl peptidase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (30)

Processvia Protein(s)Taxonomy
extracellular regionProcathepsin LHomo sapiens (human)
extracellular spaceProcathepsin LHomo sapiens (human)
nucleusProcathepsin LHomo sapiens (human)
lysosomeProcathepsin LHomo sapiens (human)
multivesicular bodyProcathepsin LHomo sapiens (human)
Golgi apparatusProcathepsin LHomo sapiens (human)
plasma membraneProcathepsin LHomo sapiens (human)
apical plasma membraneProcathepsin LHomo sapiens (human)
endolysosome lumenProcathepsin LHomo sapiens (human)
chromaffin granuleProcathepsin LHomo sapiens (human)
lysosomal lumenProcathepsin LHomo sapiens (human)
intracellular membrane-bounded organelleProcathepsin LHomo sapiens (human)
collagen-containing extracellular matrixProcathepsin LHomo sapiens (human)
extracellular exosomeProcathepsin LHomo sapiens (human)
endocytic vesicle lumenProcathepsin LHomo sapiens (human)
extracellular spaceProcathepsin LHomo sapiens (human)
lysosomeProcathepsin LHomo sapiens (human)
collagen-containing extracellular matrixCathepsin BHomo sapiens (human)
extracellular regionCathepsin BHomo sapiens (human)
extracellular spaceCathepsin BHomo sapiens (human)
lysosomeCathepsin BHomo sapiens (human)
external side of plasma membraneCathepsin BHomo sapiens (human)
apical plasma membraneCathepsin BHomo sapiens (human)
endolysosome lumenCathepsin BHomo sapiens (human)
melanosomeCathepsin BHomo sapiens (human)
perinuclear region of cytoplasmCathepsin BHomo sapiens (human)
collagen-containing extracellular matrixCathepsin BHomo sapiens (human)
extracellular exosomeCathepsin BHomo sapiens (human)
peptidase inhibitor complexCathepsin BHomo sapiens (human)
ficolin-1-rich granule lumenCathepsin BHomo sapiens (human)
extracellular spaceCathepsin BHomo sapiens (human)
lysosomeCathepsin BHomo sapiens (human)
extracellular regionCathepsin SHomo sapiens (human)
extracellular spaceCathepsin SHomo sapiens (human)
lysosomeCathepsin SHomo sapiens (human)
late endosomeCathepsin SHomo sapiens (human)
endolysosome lumenCathepsin SHomo sapiens (human)
lysosomal lumenCathepsin SHomo sapiens (human)
intracellular membrane-bounded organelleCathepsin SHomo sapiens (human)
phagocytic vesicleCathepsin SHomo sapiens (human)
collagen-containing extracellular matrixCathepsin SHomo sapiens (human)
tertiary granule lumenCathepsin SHomo sapiens (human)
ficolin-1-rich granule lumenCathepsin SHomo sapiens (human)
extracellular spaceCathepsin SHomo sapiens (human)
lysosomeCathepsin SHomo sapiens (human)
plasma membraneGastrin/cholecystokinin type B receptorHomo sapiens (human)
intracellular membrane-bounded organelleGastrin/cholecystokinin type B receptorHomo sapiens (human)
plasma membraneGastrin/cholecystokinin type B receptorHomo sapiens (human)
extracellular regionCathepsin KHomo sapiens (human)
extracellular spaceCathepsin KHomo sapiens (human)
nucleoplasmCathepsin KHomo sapiens (human)
lysosomeCathepsin KHomo sapiens (human)
external side of plasma membraneCathepsin KHomo sapiens (human)
apical plasma membraneCathepsin KHomo sapiens (human)
endolysosome lumenCathepsin KHomo sapiens (human)
lysosomal lumenCathepsin KHomo sapiens (human)
intracellular membrane-bounded organelleCathepsin KHomo sapiens (human)
extracellular spaceCathepsin KHomo sapiens (human)
lysosomeCathepsin KHomo sapiens (human)
extracellular regionDipeptidyl peptidase 1Homo sapiens (human)
extracellular spaceDipeptidyl peptidase 1Homo sapiens (human)
nucleoplasmDipeptidyl peptidase 1Homo sapiens (human)
lysosomeDipeptidyl peptidase 1Homo sapiens (human)
endoplasmic reticulum lumenDipeptidyl peptidase 1Homo sapiens (human)
centrosomeDipeptidyl peptidase 1Homo sapiens (human)
membraneDipeptidyl peptidase 1Homo sapiens (human)
COPII-coated ER to Golgi transport vesicleDipeptidyl peptidase 1Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartment membraneDipeptidyl peptidase 1Homo sapiens (human)
azurophil granule lumenDipeptidyl peptidase 1Homo sapiens (human)
intracellular membrane-bounded organelleDipeptidyl peptidase 1Homo sapiens (human)
collagen-containing extracellular matrixDipeptidyl peptidase 1Homo sapiens (human)
extracellular exosomeDipeptidyl peptidase 1Homo sapiens (human)
lysosomeDipeptidyl peptidase 1Homo sapiens (human)
extracellular spaceDipeptidyl peptidase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID48398Effect of 10 mM of GSH on the inhibitory activity of compound against Cathepsin K, at pH 5.52001Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1
Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L.
AID48405Inhibition of Cathepsin K at pH 72001Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1
Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L.
AID51224Inhibitory activity tested against Human Cathepsin L using Z-Phe-Arg-pNA as substrate2001Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1
Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L.
AID48399Effect of 10 mM of GSH on the inhibitory activity against Cathepsin K, at pH 72001Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1
Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L.
AID1553480Half life of the compound2019Journal of medicinal chemistry, 06-27, Volume: 62, Issue:12
Emerging and Re-Emerging Warheads for Targeted Covalent Inhibitors: Applications in Medicinal Chemistry and Chemical Biology.
AID48404Inhibition of Cathepsin K at pH 5.52001Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1
Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L.
AID570622Inhibition of human recombinant cathepsin C after 1 hr2011ACS medicinal chemistry letters, Feb-10, Volume: 2, Issue:2
Discovery of novel cyanamide-based inhibitors of cathepsin C.
AID241950Inhibitory concentration against human cathepsin K using 10 uM Cbz-Phe-Arg-AMC2005Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7
Novel and potent cyclic cyanamide-based cathepsin K inhibitors.
AID570624Inhibition of human recombinant cathepsin B after 1 hr2011ACS medicinal chemistry letters, Feb-10, Volume: 2, Issue:2
Discovery of novel cyanamide-based inhibitors of cathepsin C.
AID1170688GSH reactivity assessed as reaction half life through transition state modeling at pH 7.42014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Chemical and computational methods for the characterization of covalent reactive groups for the prospective design of irreversible inhibitors.
AID1170692Reactivity of covalent reactive group using GSH reaction assessed as pseudo-first-order reaction at 37 degC by nuclear magnetic resonance spectroscopy2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Chemical and computational methods for the characterization of covalent reactive groups for the prospective design of irreversible inhibitors.
AID570623Inhibition of human recombinant cathepsin K after 1 hr2011ACS medicinal chemistry letters, Feb-10, Volume: 2, Issue:2
Discovery of novel cyanamide-based inhibitors of cathepsin C.
AID570627Metabolic stability in rat plasma assessed as compound remaining after 30 mins by HPLC analysis2011ACS medicinal chemistry letters, Feb-10, Volume: 2, Issue:2
Discovery of novel cyanamide-based inhibitors of cathepsin C.
AID570626Inhibition of human recombinant cathepsin S after 1 hr2011ACS medicinal chemistry letters, Feb-10, Volume: 2, Issue:2
Discovery of novel cyanamide-based inhibitors of cathepsin C.
AID570625Inhibition of human recombinant cathepsin L after 1 hr2011ACS medicinal chemistry letters, Feb-10, Volume: 2, Issue:2
Discovery of novel cyanamide-based inhibitors of cathepsin C.
AID238235Inhibition constant against human cathepsin K2005Bioorganic & medicinal chemistry letters, Jun-15, Volume: 15, Issue:12
Acyclic cyanamide-based inhibitors of cathepsin K.
AID50270Inhibitory activity tested against Human Cathepsin B using Z-Phe-Arg-pNA as substrate2001Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1
Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L.
AID48411Inhibitory activity tested against Human Cathepsin K using Z-Phe-Arg-pNA as substrate2001Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1
Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (50.00)29.6817
2010's3 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]