Page last updated: 2024-12-05

stearylamine

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

Description

Stearylamine is a long-chain aliphatic amine with the chemical formula CH3(CH2)16NH2. It is a white, waxy solid that is insoluble in water but soluble in organic solvents. Stearylamine is a common ingredient in cosmetics, pharmaceuticals, and other industrial products. It is used as an emulsifier, surfactant, and antistatic agent. Stearylamine is also used in the synthesis of other chemicals, such as stearamide and stearic acid. Stearylamine is produced by the reaction of stearic acid with ammonia. The reaction is typically carried out in the presence of a catalyst, such as nickel or cobalt. Stearylamine is a relatively stable compound and can be stored for long periods of time. However, it is important to keep stearylamine away from oxidizing agents, as it can be oxidized to form stearylamine oxide. Stearylamine has a wide range of applications in different industries, including cosmetics, pharmaceuticals, and textiles. In cosmetics, it is used as an emulsifier, surfactant, and antistatic agent. It is also used in the production of shampoos, conditioners, and other hair care products. In pharmaceuticals, stearylamine is used as an excipient in tablets and capsules. It is also used in the production of creams, lotions, and other topical formulations. In textiles, stearylamine is used as a softener and antistatic agent. It is also used in the production of fabrics with water-repellent properties. Stearylamine is studied due to its various industrial applications and its potential toxicity. The effects of stearylamine on human health are not fully understood, but it is known to be an irritant and can cause skin and eye irritation. Studies are ongoing to investigate the potential health effects of stearylamine.'

stearylamine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

octadecan-1-amine : An 18-carbon primary aliphatic amine. [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]

Cross-References

ID SourceID
PubMed CID15793
CHEMBL ID55860
CHEBI ID63866
SCHEMBL ID2159903
SCHEMBL ID12291
SCHEMBL ID3868686
SCHEMBL ID6253291
MeSH IDM0053912

Synonyms (87)

Synonym
bdbm50147579
c18h39n
stearylamine
oktadecylamin
n-octadecylamine
n-stearylamine
armofilm
adogenen 142
alamine 7
1-aminooctadecane
1-octadecanamine
armeen 18d
nsc9857
octadecylamine
nsc-9857
noram sh
wln: z18
kemamine p 990
alamine 7d
124-30-1
nissan amine ab
armeen 118d
stearamine
inchi=1/c18h39n/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h2-19h2,1h
octadecane,1-amino
octadecan-1-amine
einecs 204-695-3
crodamine 1.18d
amine ab
oktadecylamin [czech]
brn 0636111
stearyl amine
kemamine p990
hsdb 1194
armeen 18
1-octadecylamine
farmin 80
nsc 9857
ai3-14661
ccris 4688
monooctadecylamine
octadecylamine, technical grade, 90%
octadecylamine, 97%
NCGC00164134-01
NCIOPEN2_007744
61788-45-2
octadecylamine, >=99.0% (gc)
STK062786
AKOS000269090
CHEMBL55860 ,
chebi:63866 ,
FT-0659903
O0014
A833419
octadecanamine
SCHEMBL2159903
ec 262-976-6
einecs 262-976-6
unii-ffv58uny7o
ec 204-695-3
ffv58uny7o ,
4-04-00-00825 (beilstein handbook reference)
FT-0608174
octadecylamine [hsdb]
stearamine [inci]
SCHEMBL12291
SCHEMBL3868686
1-octadecyl amine
octadecyl amine
SCHEMBL6253291
armeen 1180
amine 18-90
armid htd
octadecylamineadogenen 142
F3145-0795
DTXSID1025801
mfcd00008159
J-005064
steamfilm fg
kemamine p-990, p-990d
1-octadecanamine, 9ci
Q2013790
EN300-18141
STR09001
D70506
CS-W012394
Z57204689

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Stearylamine- and cardiolipin-containing liposomes were toxic (ID50) at 200 microM liposomal lipid concentrations or less, whereas phosphatidylglycerol- and phosphatidylserine-containing liposomes were toxic in the range 130-3000 microM."( Toxicity of non-drug-containing liposomes for cultured human cells.
Ito, M; Lazo, R; Mayhew, E, 1987
)
1.18
" The present study was initiated to determine whether chronically administered liposome-encapsulated doxorubicin would be less toxic than the free drug."( Prevention of chronic doxorubicin cardiotoxicity in beagles by liposomal encapsulation.
Ferrans, VJ; Herman, EH; Rahman, A; Schein, PS; Vick, JA, 1983
)
0.27
" The results of the ocular tolerance study in rabbit eye indicate that hourly administration of a positively-charged emulsion vehicle was well tolerated without any toxic or inflammatory response to the ocular surface during the five days of the study."( Physicochemical characterization and acute toxicity evaluation of a positively-charged submicron emulsion vehicle.
Benita, S; Frucht-Pery, J; Hoffman, A; Klang, SH, 1994
)
0.29
" Complexes containing DSPC and DSPE phospholipids, which have high phase transition temperatures, were less toxic in comparison with the formulations obtained with lecithin, DOPC, and DOPE."( Influence of phospholipid composition on cationic emulsions/DNA complexes: physicochemical properties, cytotoxicity, and transfection on Hep G2 cells.
Bruxel, F; Fraga, M; Lagranha, VL; Matte, U; Teixeira, HF, 2011
)
0.37

Pharmacokinetics

ExcerptReferenceRelevance
"The purpose of this study was to estimate the pharmacokinetic parameters and tissue distribution of positively charged stearylamine (LN-P-SA) and pegylated lipid nanospheres (LN-P-PEG) of piperine in BALB/c mice."( Pharmacokinetics and tissue distribution of piperine lipid nanospheres.
Veerareddy, PR; Vobalaboina, V, 2008
)
0.55
" The in vivo pharmacokinetic and tissue distribution were conducted in mice."( Brain delivery of transferrin coupled indinavir submicron lipid emulsions--pharmacokinetics and tissue distribution.
Afzal, SM; Kishan, V; Kumar, PU; Prabhakar, K; Rajanna, A, 2011
)
0.37
" The monodisperse, (~50 nm), positively charged Fp-cLNCs with high drug loadings demonstrated linear pharmacokinetic profiles of the drug with an increased oral absolute bioavailability (up to ~21%) compatible with therapeutic anticoagulant effect (>0."( Oral fondaparinux: use of lipid nanocapsules as nanocarriers and in vivo pharmacokinetic study.
Benoit, JP; Lagarce, F; Legras, P; Macchi, L; Ramadan, A; Saulnier, P; Tessier-Marteau, A; Thomas, O, 2011
)
0.37

Compound-Compound Interactions

ExcerptReferenceRelevance
" Monensin in long-circulating liposomes of stearylamine with 5 mol% DSPE-mPEG 2000 in combination with free artemisinin resulted in enhanced killing of parasites, prevented parasite recrudescence, and improved survival."( Stearylamine Liposomal Delivery of Monensin in Combination with Free Artemisinin Eliminates Blood Stages of Plasmodium falciparum in Culture and P. berghei Infection in Murine Malaria.
Dutt, S; Ghosh, PC; Hasan, GM; Rajendran, V; Raza, M; Rohra, S, 2015
)
2.12

Bioavailability

ExcerptReferenceRelevance
" It has been demonstrated that unless the corneal epithelium is damaged, DSP is poorly absorbed by the cornea (Kupferman et al."( In-vivo studies on dexamethasone sodium phosphate liposomes.
Al-Muhammed, J; Ercan, MT; Hincal, AA; Ozer, AY,
)
0.13
"Design of a liposome delivery system for vaginal administration of acyclovir, able to provide sustained release and improved bioavailability of the encapsulated drug for the local treatment of genital herpes was investigated."( Development and in vitro evaluation of a liposomal vaginal delivery system for acyclovir.
Filipović-Grcić, J; Jalsenjak, I; Martinac, A; Pavelić, Z; Skalko-Basnet, N, 2005
)
0.33
"Silymarin is a natural lipotropic agent of low bioavailability from oral products."( Increasing bioavailability of silymarin using a buccal liposomal delivery system: preparation and experimental design investigation.
Afifi, NN; El-Samaligy, MS; Mahmoud, EA, 2006
)
0.33
" Aiming at improving its poor bioavailability from oral products, silymarin hybrid liposomes are introduced in this work for buccal administration after investigating their stability and in vivo hepatoprotective efficiency."( Evaluation of hybrid liposomes-encapsulated silymarin regarding physical stability and in vivo performance.
Afifi, NN; El-Samaligy, MS; Mahmoud, EA, 2006
)
0.33
" In conclusion, gatifloxacin liposomal hydrogel is a suitable delivery system for the improvement of the ocular bioavailability of gatifloxacin."( Optimization of gatifloxacin liposomal hydrogel for enhanced transcorneal permeation.
Hosny, KM, 2010
)
0.36
" In conclusion, ciprofloxacin liposomal hydrogel is a suitable delivery system for improving the ocular bioavailability of ciprofloxacin."( Ciprofloxacin as ocular liposomal hydrogel.
Hosny, KM, 2010
)
0.36
"Nitrendipine, a dihydropyridine calcium channel blocker, has very poor oral bioavailability (10-20%) due to first pass effect."( Preparation and characterization of nitrendipine solid lipid nanoparticles.
Hussain, A; Manjunath, K; Venkateswarlu, V, 2011
)
0.37
" The monodisperse, (~50 nm), positively charged Fp-cLNCs with high drug loadings demonstrated linear pharmacokinetic profiles of the drug with an increased oral absolute bioavailability (up to ~21%) compatible with therapeutic anticoagulant effect (>0."( Oral fondaparinux: use of lipid nanocapsules as nanocarriers and in vivo pharmacokinetic study.
Benoit, JP; Lagarce, F; Legras, P; Macchi, L; Ramadan, A; Saulnier, P; Tessier-Marteau, A; Thomas, O, 2011
)
0.37
"59-fold increase in relative bioavailability as compared to TMX suspension."( Alpha-lipoic acid-stearylamine conjugate-based solid lipid nanoparticles for tamoxifen delivery: formulation, optimization, in-vivo pharmacokinetic and hepatotoxicity study.
Chand, M; Dhaundiyal, A; Jena, SK; Samal, SK; Sangamwar, AT; Sonvane, B, 2016
)
0.77
"α-lipoic acid-stearylamine conjugate-based SLNs have a great potential in enhancing the oral bioavailability of poorly soluble drugs like TMX."( Alpha-lipoic acid-stearylamine conjugate-based solid lipid nanoparticles for tamoxifen delivery: formulation, optimization, in-vivo pharmacokinetic and hepatotoxicity study.
Chand, M; Dhaundiyal, A; Jena, SK; Samal, SK; Sangamwar, AT; Sonvane, B, 2016
)
1.13

Dosage Studied

ExcerptRelevanceReference
" At the dosage regimen utilized, liposomal doxorubicin and free doxorubicin exerted comparable degrees of bone marrow suppression."( Prevention of chronic doxorubicin cardiotoxicity in beagles by liposomal encapsulation.
Ferrans, VJ; Herman, EH; Rahman, A; Schein, PS; Vick, JA, 1983
)
0.27
" In this study, two sphingosine-activated protein kinases were distinguished by their substrate specificity, their dose-response to sphingosine and the specificity of their activation by sphingosine and dihydrosphingosine stereoisomers."( Regulation of sphingosine-activated protein kinases: selectivity of activation by sphingoid bases and inhibition by non-esterified fatty acids.
Bielawska, A; Hannun, YA; Liotta, D; Menaldiv, D, 1993
)
0.29
"3% (w/w) stearylamine could only be obtained when lecithins dosing up to 80% (w/w) phosphatidylcholine (PC) were employed, but they did not resist to long term storage up to 90 days."( Influence of stearylamine and dicetylphosphate on the physical properties of submicron O/W emulsions.
Ludwig, A; Mbela, N; Verschueren, E,
)
0.92
" Dose-response of intraventricular injection of liposomal NGF showed significant reduction in infarct volume at the dose of 5 and 10 microg/rat of NGF."( Treatment of focal cerebral ischemia with liposomal nerve growth factor.
Chen, WY; Chern, CM; Hsu, LC; Hu, HH; Huang, KJ; Law, SL; Luk, YO; Wong, WJ,
)
0.13
" These results demonstrated that the submicron emulsion preparation of ZT was a relatively safe dosage form for rapid and effective intranasal delivery of ZT."( Preparation and evaluation of zolmitriptan submicron emulsion for rapid and effective nasal absorption in beagle dogs.
Cai, C; Gu, P; He, H; Qi, N; Tang, X; Yu, C; Zhang, W, 2011
)
0.37
"To reduce the problems of poor solubility, high in vivo dosage requirement, and weak targeting ability of paclitaxel (PTX), a hyaluronic acid-octadecylamine (HA-ODA)-modified nano-structured lipid carrier (HA-NLC) was constructed."( Hyaluronic acid derivative-modified nano-structured lipid carrier for cancer targeting and therapy.
Liu, H; Liu, JW; Liu, X; Wang, SL, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
film-forming compoundAny compound that leaves a pliable, cohesive, and continuous covering over a surface when applied to it.
[role 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]

Drug Classes (1)

ClassDescription
primary aliphatic amine
[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 (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
retinoid X nuclear receptor alphaHomo sapiens (human)Potency15.84890.000817.505159.3239AID588544
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dynamin-1Homo sapiens (human)IC50 (µMol)28.15003.15004.17335.0000AID63727
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
endocytosisDynamin-1Homo sapiens (human)
receptor-mediated endocytosisDynamin-1Homo sapiens (human)
endosome organizationDynamin-1Homo sapiens (human)
modulation of chemical synaptic transmissionDynamin-1Homo sapiens (human)
protein homooligomerizationDynamin-1Homo sapiens (human)
protein homotetramerizationDynamin-1Homo sapiens (human)
regulation of vesicle sizeDynamin-1Homo sapiens (human)
clathrin coat assembly involved in endocytosisDynamin-1Homo sapiens (human)
vesicle scissionDynamin-1Homo sapiens (human)
receptor internalizationDynamin-1Homo sapiens (human)
synaptic vesicle budding from presynaptic endocytic zone membraneDynamin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
RNA bindingDynamin-1Homo sapiens (human)
GTPase activityDynamin-1Homo sapiens (human)
protein bindingDynamin-1Homo sapiens (human)
GTP bindingDynamin-1Homo sapiens (human)
phosphatidylinositol-4,5-bisphosphate bindingDynamin-1Homo sapiens (human)
phosphatidylinositol-3,4,5-trisphosphate bindingDynamin-1Homo sapiens (human)
GDP bindingDynamin-1Homo sapiens (human)
protein kinase bindingDynamin-1Homo sapiens (human)
identical protein bindingDynamin-1Homo sapiens (human)
protein homodimerization activityDynamin-1Homo sapiens (human)
microtubule bindingDynamin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
photoreceptor inner segmentDynamin-1Homo sapiens (human)
plasma membraneDynamin-1Homo sapiens (human)
clathrin-coated pitDynamin-1Homo sapiens (human)
endocytic vesicleDynamin-1Homo sapiens (human)
chromaffin granuleDynamin-1Homo sapiens (human)
cell projectionDynamin-1Homo sapiens (human)
extracellular exosomeDynamin-1Homo sapiens (human)
photoreceptor ribbon synapseDynamin-1Homo sapiens (human)
presynapseDynamin-1Homo sapiens (human)
presynaptic endocytic zone membraneDynamin-1Homo sapiens (human)
glutamatergic synapseDynamin-1Homo sapiens (human)
membrane coatDynamin-1Homo sapiens (human)
plasma membraneDynamin-1Homo sapiens (human)
synapseDynamin-1Homo sapiens (human)
microtubuleDynamin-1Homo sapiens (human)
cytoplasmDynamin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1069924Antiviral activity against HCV infected in human Huh7 cells assessed as reduction in RNA level by luciferase reporter gene assay relative to control2014Bioorganic & medicinal chemistry letters, Feb-15, Volume: 24, Issue:4
Dual inhibition of HCV and HIV by ring-expanded nucleosides containing the 5:7-fused imidazo[4,5-e][1,3]diazepine ring system. In vitro results and implications.
AID63727Concentration required against dynamin-1 GTPase activity of sheep brain.2004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
Long chain amines and long chain ammonium salts as novel inhibitors of dynamin GTPase activity.
AID1069917Antiviral activity against HIV2014Bioorganic & medicinal chemistry letters, Feb-15, Volume: 24, Issue:4
Dual inhibition of HCV and HIV by ring-expanded nucleosides containing the 5:7-fused imidazo[4,5-e][1,3]diazepine ring system. In vitro results and implications.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (310)

TimeframeStudies, This Drug (%)All Drugs %
pre-199041 (13.23)18.7374
1990's39 (12.58)18.2507
2000's90 (29.03)29.6817
2010's119 (38.39)24.3611
2020's21 (6.77)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.56

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index37.56 (24.57)
Research Supply Index5.77 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index54.93 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (0.93%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other318 (99.07%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]