Page last updated: 2024-12-07

l 692429

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Description

L 692429: stimulates release of growth hormone; RN refers to (R)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID121879
CHEMBL ID308716
SCHEMBL ID7417293
SCHEMBL ID18787567
MeSH IDM0217267

Synonyms (35)

Synonym
CHEMBL308716 ,
bdbm50049481
arg-pro-lys-pro-phe-trp-leu
3-amino-3-methyl-n-{2-oxo-1-[2''-(2h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2,3,4,5-tetrahydro-1h-benzo[b]azepin-3-yl}-butyramide
(r)-n-(1-((2''-(2h-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-oxo-2,3,4,5-tetrahydro-1h-benzo[b]azepin-3-yl)-3-amino-3-methylbutanamide
3-amino-3-methyl-n-{2-oxo-1-[2''-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2,3,4,5-tetrahydro-1h-benzo[b]azepin-3-yl}-butyramide
3-amino-3-methyl-n-{(r)-2-oxo-1-[2''-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2,3,4,5-tetrahydro-1h-benzo[b]azepin-3-yl}-butyramide
l-692429
l 692429
3-amino-3-methyl-n-[(3r)-2-oxo-1-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]-4,5-dihydro-3h-1-benzazepin-3-yl]butanamide
l-692,429
6gm6zn5s1y ,
unii-6gm6zn5s1y
145455-23-8
butanamide, 3-amino-3-methyl-n-(2,3,4,5-tetrahydro-2-oxo-1-((2'-(1h-tetrtazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1h-1-benzazepin-3-yl)-, (r)-
l 692,429
butanamide, 3-amino-3-methyl-n-(2,3,4,5-tetrahydro-2-oxo-1-((2'-(1h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1h-1-benzazepin-3-yl)-, (r)-
gtpl5868
mk 0751
SCHEMBL7417293
DTXSID20163045
SCHEMBL18787567
SBJLJOFPWOYATP-XMMPIXPASA-N ,
3-amino-3-methyl-n-((r)-2,3,4,5-tetrahydro-2-oxo-1-((2'-(1h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1h-1-benzazepin-3-yl)butanamide
butanamide, 3-amino-3-methyl-n-((3r)-2,3,4,5-tetrahydro-2-oxo-1-((2'-(2h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1h-1-benzazepin-3-yl)-
3-amino-3-methyl-n-((3r)-2,3,4,5-tetrahydro-2-oxo-1-((2'-(2h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1h-1-benzazepin-3-yl)butanamide
HY-10957
(r)-n-(1-((2'-(2h-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-oxo-2,3,4,5-tetrahydro-1h-benzo[b]azepin-3-yl)-3-amino-3-methylbutanamide
Q27078402
mk-0751
l-692429 free base
145455-23-8 (free base)
CS-0002978
MS-29463
AKOS040733563

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The identification of L-739,943 (8b), a potent, orally bioavailable benzolactam growth hormone secretagogue, is obtained from zwitterionic L-692,429 through modification of its amino acid side chain and replacement of the acidic 2'-tetrazole with the neutral and potency enhancing 2'-(N-methylaminocarbonylamino)methyl substituent."( A potent, orally bioavailable benzazepinone growth hormone secretagogue.
Bochis, R; Butler, B; Chan, WW; Chen, Z; Cheng, K; Chiu, SL; Cunningham, PK; DeVita, RJ; Feeney, WP; Fisher, MH; Frontier, AJ; Hickey, GJ; Jacks, TM; Kotliar, A; Leung, K; Schleim, KD; Schoen, WR; Smith, RG; Wyvratt, MJ, 1998
)
0.3
" Compound 37S showed a good pharmacokinetic profile in rats with 28% oral bioavailability at 10 mg/kg and excellent in vivo activity as evidenced by a significant weight gain after 4 days of oral administration at 10 mg/kg twice a day."( Oxindole derivatives as orally active potent growth hormone secretagogues.
Hourai, S; Hume, WE; Kumagai, K; Nagamine, J; Nagata, R; Noguchi, H; Okazaki, K; Seki, H; Taiji, M; Tokunaga, T; Ueki, Y; Umezome, T, 2001
)
0.31

Dosage Studied

ExcerptRelevanceReference
" At a concentration of 50 nM, L-756,867 shifted the dose-response curve of L-692,429-induced GH release to the right by about tenfold."( Inhibition of L-692,429-stimulated rat growth hormone release by a weak substance P antagonist: L-756,867.
Butler, B; Chan, WW; Chaung, LY; Cheng, K; Smith, RG; Wei, L, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Growth hormone secretagogue receptor type 1Rattus norvegicus (Norway rat)IC50 (µMol)0.06000.00520.11530.2500AID75337
Type-1 angiotensin II receptorHomo sapiens (human)IC50 (µMol)3.60000.00020.09323.6000AID39663
Growth hormone secretagogue receptor type 1Homo sapiens (human)IC50 (µMol)2.80000.00040.58926.0000AID75341
Growth hormone secretagogue receptor type 1Homo sapiens (human)Ki0.06300.00020.03360.0906AID75338
Growth hormone secretagogue receptor type 1Sus scrofa (pig)IC50 (µMol)0.06300.06300.06300.0630AID75336
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Growth hormone secretagogue receptor type 1Rattus norvegicus (Norway rat)EC50 (µMol)0.06000.00130.01540.0600AID175853
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (74)

Processvia Protein(s)Taxonomy
regulation of cell growthType-1 angiotensin II receptorHomo sapiens (human)
kidney developmentType-1 angiotensin II receptorHomo sapiens (human)
renin-angiotensin regulation of aldosterone productionType-1 angiotensin II receptorHomo sapiens (human)
maintenance of blood vessel diameter homeostasis by renin-angiotensinType-1 angiotensin II receptorHomo sapiens (human)
regulation of systemic arterial blood pressure by renin-angiotensinType-1 angiotensin II receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayType-1 angiotensin II receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationType-1 angiotensin II receptorHomo sapiens (human)
Rho protein signal transductionType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationType-1 angiotensin II receptorHomo sapiens (human)
regulation of vasoconstrictionType-1 angiotensin II receptorHomo sapiens (human)
calcium-mediated signalingType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of phospholipase A2 activityType-1 angiotensin II receptorHomo sapiens (human)
low-density lipoprotein particle remodelingType-1 angiotensin II receptorHomo sapiens (human)
regulation of renal sodium excretionType-1 angiotensin II receptorHomo sapiens (human)
angiotensin-activated signaling pathwayType-1 angiotensin II receptorHomo sapiens (human)
regulation of cell population proliferationType-1 angiotensin II receptorHomo sapiens (human)
symbiont entry into host cellType-1 angiotensin II receptorHomo sapiens (human)
regulation of inflammatory responseType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of inflammatory responseType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of protein metabolic processType-1 angiotensin II receptorHomo sapiens (human)
cell chemotaxisType-1 angiotensin II receptorHomo sapiens (human)
phospholipase C-activating angiotensin-activated signaling pathwayType-1 angiotensin II receptorHomo sapiens (human)
blood vessel diameter maintenanceType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of blood vessel endothelial cell proliferation involved in sprouting angiogenesisType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of CoA-transferase activityType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of reactive oxygen species metabolic processType-1 angiotensin II receptorHomo sapiens (human)
inflammatory responseType-1 angiotensin II receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayGrowth hormone secretagogue receptor type 1Homo sapiens (human)
spermatogenesisGrowth hormone secretagogue receptor type 1Homo sapiens (human)
learning or memoryGrowth hormone secretagogue receptor type 1Homo sapiens (human)
actin polymerization or depolymerizationGrowth hormone secretagogue receptor type 1Homo sapiens (human)
adult feeding behaviorGrowth hormone secretagogue receptor type 1Homo sapiens (human)
response to hormoneGrowth hormone secretagogue receptor type 1Homo sapiens (human)
hormone-mediated signaling pathwayGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of norepinephrine secretionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
growth hormone secretionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
response to foodGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of appetiteGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of appetiteGrowth hormone secretagogue receptor type 1Homo sapiens (human)
response to follicle-stimulating hormoneGrowth hormone secretagogue receptor type 1Homo sapiens (human)
response to estradiolGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of interleukin-1 beta productionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of interleukin-6 productionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of tumor necrosis factor productionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
cellular response to insulin stimulusGrowth hormone secretagogue receptor type 1Homo sapiens (human)
ghrelin secretionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of multicellular organism growthGrowth hormone secretagogue receptor type 1Homo sapiens (human)
regulation of hindgut contractionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of insulin-like growth factor receptor signaling pathwayGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of fatty acid metabolic processGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of insulin secretionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
decidualizationGrowth hormone secretagogue receptor type 1Homo sapiens (human)
insulin-like growth factor receptor signaling pathwayGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of inflammatory responseGrowth hormone secretagogue receptor type 1Homo sapiens (human)
regulation of synapse assemblyGrowth hormone secretagogue receptor type 1Homo sapiens (human)
regulation of transmission of nerve impulseGrowth hormone secretagogue receptor type 1Homo sapiens (human)
regulation of growth hormone secretionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
response to growth hormoneGrowth hormone secretagogue receptor type 1Homo sapiens (human)
cellular response to lipopolysaccharideGrowth hormone secretagogue receptor type 1Homo sapiens (human)
response to dexamethasoneGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of locomotion involved in locomotory behaviorGrowth hormone secretagogue receptor type 1Homo sapiens (human)
cellular response to thyroid hormone stimulusGrowth hormone secretagogue receptor type 1Homo sapiens (human)
regulation of neurotransmitter receptor localization to postsynaptic specialization membraneGrowth hormone secretagogue receptor type 1Homo sapiens (human)
postsynaptic modulation of chemical synaptic transmissionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
regulation of postsynapse organizationGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of small intestinal transitGrowth hormone secretagogue receptor type 1Homo sapiens (human)
response to L-glutamateGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of sprouting angiogenesisGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of eating behaviorGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of small intestine smooth muscle contractionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
regulation of gastric motilityGrowth hormone secretagogue receptor type 1Homo sapiens (human)
positive regulation of vascular endothelial cell proliferationGrowth hormone secretagogue receptor type 1Homo sapiens (human)
cellular response to insulin-like growth factor stimulusGrowth hormone secretagogue receptor type 1Homo sapiens (human)
negative regulation of macrophage apoptotic processGrowth hormone secretagogue receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
angiotensin type I receptor activityType-1 angiotensin II receptorHomo sapiens (human)
angiotensin type II receptor activityType-1 angiotensin II receptorHomo sapiens (human)
protein bindingType-1 angiotensin II receptorHomo sapiens (human)
bradykinin receptor bindingType-1 angiotensin II receptorHomo sapiens (human)
protein heterodimerization activityType-1 angiotensin II receptorHomo sapiens (human)
growth hormone secretagogue receptor activityGrowth hormone secretagogue receptor type 1Homo sapiens (human)
G protein-coupled receptor activityGrowth hormone secretagogue receptor type 1Homo sapiens (human)
growth hormone-releasing hormone receptor activityGrowth hormone secretagogue receptor type 1Homo sapiens (human)
peptide hormone bindingGrowth hormone secretagogue receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
plasma membraneGrowth hormone secretagogue receptor type 1Rattus norvegicus (Norway rat)
plasma membraneType-1 angiotensin II receptorHomo sapiens (human)
membraneType-1 angiotensin II receptorHomo sapiens (human)
plasma membraneType-1 angiotensin II receptorHomo sapiens (human)
plasma membraneGrowth hormone secretagogue receptor type 1Homo sapiens (human)
cell surfaceGrowth hormone secretagogue receptor type 1Homo sapiens (human)
neuron projectionGrowth hormone secretagogue receptor type 1Homo sapiens (human)
membrane raftGrowth hormone secretagogue receptor type 1Homo sapiens (human)
synaptic membraneGrowth hormone secretagogue receptor type 1Homo sapiens (human)
Schaffer collateral - CA1 synapseGrowth hormone secretagogue receptor type 1Homo sapiens (human)
postsynapseGrowth hormone secretagogue receptor type 1Homo sapiens (human)
glutamatergic synapseGrowth hormone secretagogue receptor type 1Homo sapiens (human)
plasma membraneGrowth hormone secretagogue receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID59491Compound was evaluated for Minimum effective dose in beagles1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Peptidomimetic growth hormone secretagogues. Design considerations and therapeutic potential.
AID196085Effect on stimulation of GH release from rat pituitary cells in the presence of somatostatin; inhibitory1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
A novel 3-substituted benzazepinone growth hormone secretagogue (L-692,429).
AID176604In vitro growth hormone (GH) releasing activity in rat primary pituitary cells.1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
A potent, orally bioavailable benzazepinone growth hormone secretagogue.
AID175855In vitro growth hormone releasing activity was measured in rat pituitary cells2001Journal of medicinal chemistry, Dec-20, Volume: 44, Issue:26
Oxindole derivatives as orally active potent growth hormone secretagogues.
AID196084Effect on stimulation of GH release from rat pituitary cells in the presence of His-D-Trp-D-Lys-Trp-D-Phe-Lys-NH2; antagonism1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
A novel 3-substituted benzazepinone growth hormone secretagogue (L-692,429).
AID75338Binding Affinity against Growth hormone secretagogue receptor of swine using [35S]MK-0677 as radioligand1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Development of a high specific activity sulfur-35-labeled sulfonamide radioligand that allowed the identification of a new growth hormone secretagogue receptor.
AID194528In vitro evaluation for growth hormone release from the pituitary incubates1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Peptidomimetic growth hormone secretagogues. Design considerations and therapeutic potential.
AID39663Inhibition against human angiotensin II receptor, type 1 (AG2-R)2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Recognition of privileged structures by G-protein coupled receptors.
AID75336Inhibition against pig growth hormone secretagogue (GHS) receptor2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Recognition of privileged structures by G-protein coupled receptors.
AID75341Inhibition against human growth hormone secretagogue (GHS) receptor2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Recognition of privileged structures by G-protein coupled receptors.
AID419512Volume of distribution at steady state in human at 1 mg/kg2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
In silico prediction of volume of distribution in human using linear and nonlinear models on a 669 compound data set.
AID75331Effective concentration of compound to stimulate 300% increase of growth hormone secretion2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
Angiotensin II AT1 receptor antagonists. Clinical implications of active metabolites.
AID185554Compound was tested for GH releasing from cultured rat pituitary cells (maximal increase in 15 min)1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Peptidomimetic growth hormone secretagogues. Design considerations and therapeutic potential.
AID175658Effective Concentration for GH secretion from rat pituitary cell was determined1996Journal of medicinal chemistry, Apr-26, Volume: 39, Issue:9
Development of a high specific activity sulfur-35-labeled sulfonamide radioligand that allowed the identification of a new growth hormone secretagogue receptor.
AID1859421Stimulation of growth hormone secretion in rat pituitary cells2022European journal of medicinal chemistry, May-05, Volume: 235An insight into the multifunctional role of ghrelin and structure activity relationship studies of ghrelin receptor ligands with clinical trials.
AID195901Effective concentration for their ability to release growth hormone in the rat pituitary cell assay2003Bioorganic & medicinal chemistry letters, May-19, Volume: 13, Issue:10
Substituted bridged phenyl piperidines: orally active growth hormone secretagogues.
AID175853In vitro growth hormone release was determined in rat pituitary cell assay1998Bioorganic & medicinal chemistry letters, Jan-06, Volume: 8, Issue:1
Potent 3-spiropiperidine growth hormone secretagogues.
AID176605In vitro growth hormone release in rat pituitary cells assay was determined1999Bioorganic & medicinal chemistry letters, Nov-15, Volume: 9, Issue:22
Acyclic structural variants of growth hormone secretagogue L-692,429.
AID196080In vitro dose required for stimulation of GH release from rat pituitary cells1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
A novel 3-substituted benzazepinone growth hormone secretagogue (L-692,429).
AID18150Compound was evaluated percentage of Oral bioavailability in dogs1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Peptidomimetic growth hormone secretagogues. Design considerations and therapeutic potential.
AID196083Effect on stimulation of GH release from rat pituitary cells in the presence of GRF; synergy1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
A novel 3-substituted benzazepinone growth hormone secretagogue (L-692,429).
AID228870In vivo efficacy was evaluated for growth hormone release1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Peptidomimetic growth hormone secretagogues. Design considerations and therapeutic potential.
AID75337Inhibition against rat growth hormone secretagogue (GHS) receptor2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Recognition of privileged structures by G-protein coupled receptors.
AID196082Effect on stimulation of GH release from rat pituitary cells in the presence of GHRP; no effect1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
A novel 3-substituted benzazepinone growth hormone secretagogue (L-692,429).
AID1346009Human ghrelin receptor (Ghrelin receptor)2005Molecular endocrinology (Baltimore, Md.), Sep, Volume: 19, Issue:9
Nonpeptide and peptide growth hormone secretagogues act both as ghrelin receptor agonist and as positive or negative allosteric modulators of ghrelin signaling.
AID1345930Rat ghrelin receptor (Ghrelin receptor)1993Science (New York, N.Y.), Jun-11, Volume: 260, Issue:5114
A nonpeptidyl growth hormone secretagogue.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's27 (67.50)18.2507
2000's12 (30.00)29.6817
2010's0 (0.00)24.3611
2020's1 (2.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.41

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 Index10.41 (24.57)
Research Supply Index3.83 (2.92)
Research Growth Index4.24 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (12.50%)5.53%
Reviews10 (25.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (62.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]