Stearic acid
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Identification
- Summary
Stearic acid is an ingredient found in topical products as a skin protectant.
- Generic Name
- Stearic acid
- DrugBank Accession Number
- DB03193
- Background
Stearic acid (IUPAC systematic name: octadecanoic acid) is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. It is a waxy solid.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
- Weight
- Average: 284.4772
Monoisotopic: 284.271530396 - Chemical Formula
- C18H36O2
- Synonyms
- Acide octadécanoïque
- Acide stéarique
- C18:0
- n-octadecanoic acid
- Octadecanoic acid
- Octadecansäure
- Octadecoic acid
- Oktadekansäure
- Stearic acid
- Stearinsäure
- External IDs
- Caswell No. 801D
- FEMA No. 3035
- NSC-25956
- NSC-261168
Pharmacology
- Indication
Not Available
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- Contraindications & Blackbox Warnings
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPeroxisome proliferator-activated receptor alpha Not Available Humans UGroup IID secretory phospholipase A2 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
Acute oral toxicity (LD50): 4640 mg/kg [Rat]. Acute dermal toxicity (LD50): >5000 mg/kg Rabbit.
- Pathways
Pathway Category Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids Metabolic Plasmalogen Synthesis Metabolic - 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
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cellbn First Care Cleanser Cream 16 g/100mL Topical Worldcostec.co.,ltd 2017-05-26 Not applicable US Doctor Plus Cream 1.5 g/100mL Topical Powerful X 2018-01-09 Not applicable US Dr. G Pore Deep Clearing Foam Cream 15 g/10mL Topical GOWOONSESANG COSMETICS CO., LTD. 2016-03-01 2018-01-09 US Dr.g A-clear Foam Cream 20 g/100mL Topical GOWOONSESANG COSMETICS CO., LTD. 2015-07-05 2018-03-23 US Dr.g Hyper Brightening Cleansing Foam Cream 8 g/100mL Topical GOWOONSESANG COSMETICS CO., LTD. 2015-07-05 2018-01-09 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image For Sope Stearic acid (1.5 %) + Sodium lauryl sulfate (97 %) Liquid Topical Rougier Pharma Division Of Ratiopharm Inc 1960-12-31 1999-09-27 Canada Huile D'onagre Vitamin E Stearic acid (1 %) + Linoleic acid (72 %) + Oleic Acid (9 %) + Palmitic Acid (7 %) + Vitamin E (15 %) + alpha-Linolenic acid (11 %) Capsule Oral Le Naturiste J.M.B. Inc. 1987-12-31 2000-08-23 Canada Isa Knox Ageless Serum Makeup Base 10 Stearic acid (0.18 mL/100mL) + Aluminum hydroxide (0.18 mL/100mL) + Dimethicone (0.08 mL/100mL) + Hydroxyproline (0.53 mL/100mL) + Octinoxate (3 mL/100mL) + Titanium dioxide (3.38 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-07-04 Not applicable US Isaknox Ageless Serum Moist Pearl Base Stearic acid (0.18 mL/100mL) + Aluminum hydroxide (0.18 mL/100mL) + Dimethicone (0.08 mL/100mL) + Hydroxyproline (0.53 mL/100mL) + Octinoxate (3 mL/100mL) + Titanium dioxide (3.38 mL/100mL) Liquid Topical Lg Household & Health Care Ltd. 2010-08-31 Not applicable US Jayjun Anti Dust Fresh Foam Cleanser Stearic acid (6.84 g/90mL) + Lauric acid (6.30 g/90mL) + Palmitic Acid (11.16 g/90mL) Liquid Topical Jayjun Cosmetic Co.,ltd. 2018-12-01 2019-11-01 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cellbn First Care Cleanser Stearic acid (16 g/100mL) Cream Topical Worldcostec.co.,ltd 2017-05-26 Not applicable US Doctor Plus Stearic acid (1.5 g/100mL) Cream Topical Powerful X 2018-01-09 Not applicable US Dr. G Pore Deep Clearing Foam Stearic acid (15 g/10mL) Cream Topical GOWOONSESANG COSMETICS CO., LTD. 2016-03-01 2018-01-09 US Dr.g A-clear Foam Stearic acid (20 g/100mL) Cream Topical GOWOONSESANG COSMETICS CO., LTD. 2015-07-05 2018-03-23 US Dr.g Hyper Brightening Cleansing Foam Stearic acid (8 g/100mL) Cream Topical GOWOONSESANG COSMETICS CO., LTD. 2015-07-05 2018-01-09 US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acids and conjugates
- Direct Parent
- Long-chain fatty acids
- Alternative Parents
- Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Long-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- long-chain fatty acid, saturated fatty acid, straight-chain saturated fatty acid (CHEBI:28842) / Straight chain fatty acids, Saturated fatty acids (C01530) / Straight chain fatty acids (LMFA01010018)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 4ELV7Z65AP
- CAS number
- 57-11-4
- InChI Key
- QIQXTHQIDYTFRH-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
- IUPAC Name
- octadecanoic acid
- SMILES
- CCCCCCCCCCCCCCCCCC(O)=O
References
- Synthesis Reference
Arnold W. Fogel, "12-hydroxy stearic acid esters, compositions based upon same and methods of using and making such compositions." U.S. Patent US5993861, issued July, 1998.
US5993861- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000827
- KEGG Drug
- D00119
- KEGG Compound
- C01530
- PubChem Compound
- 5281
- PubChem Substance
- 46508522
- ChemSpider
- 5091
- BindingDB
- 50240485
- 1310551
- ChEBI
- 28842
- ChEMBL
- CHEMBL46403
- ZINC
- ZINC000004978673
- PDBe Ligand
- STE
- Wikipedia
- Stearic_acid
- PDB Entries
- 1e7i / 1fk4 / 1hmt / 1k4w / 1lif / 1uvc / 1xxs / 2fva / 2wh5 / 2zyi … show 73 more
- MSDS
- Download (73.6 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 16 g/100mL Cream Topical 15 g/10mL Cream Topical 20 g/100mL Cream Topical 8 g/100mL Cream Topical 25 g/100mL Capsule Oral Liquid Topical Injectable foam Topical Soap Topical 120 mg/1g Soap Topical 12 g/100g Cream Topical 1 g/100mL Cream Topical 1.5 g/100mL Ointment Topical Cream Topical Gel Topical 0.4 g/20mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 68.8 °C PhysProp boiling point (°C) 383 °C PhysProp water solubility 0.597 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 8.23 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 6.61e-05 mg/mL ALOGPS logP 8.02 ALOGPS logP 7.15 Chemaxon logS -6.6 ALOGPS pKa (Strongest Acidic) 4.95 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 86.29 m3·mol-1 Chemaxon Polarizability 38.64 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9888 Blood Brain Barrier + 0.9488 Caco-2 permeable + 0.8326 P-glycoprotein substrate Non-substrate 0.6321 P-glycoprotein inhibitor I Non-inhibitor 0.9598 P-glycoprotein inhibitor II Non-inhibitor 0.9277 Renal organic cation transporter Non-inhibitor 0.9266 CYP450 2C9 substrate Non-substrate 0.7886 CYP450 2D6 substrate Non-substrate 0.8956 CYP450 3A4 substrate Non-substrate 0.6982 CYP450 1A2 substrate Inhibitor 0.8326 CYP450 2C9 inhibitor Non-inhibitor 0.8808 CYP450 2D6 inhibitor Non-inhibitor 0.9554 CYP450 2C19 inhibitor Non-inhibitor 0.9578 CYP450 3A4 inhibitor Non-inhibitor 0.9484 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9647 Ames test Non AMES toxic 0.9865 Carcinogenicity Non-carcinogens 0.6452 Biodegradation Ready biodegradable 0.8795 Rat acute toxicity 1.3275 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9322 hERG inhibition (predictor II) Non-inhibitor 0.8868
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 205.6826617 predictedDarkChem Lite v0.1.0 [M-H]- 176.5943516 predictedDarkChem Standard v0.1.0 [M-H]- 206.7843617 predictedDarkChem Lite v0.1.0 [M-H]- 206.1106617 predictedDarkChem Lite v0.1.0 [M-H]- 170.31721 predictedDeepCCS 1.0 (2019) [M+H]+ 174.33687 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.43562 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as a transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2
- Specific Function
- DNA binding
- Gene Name
- PPARA
- Uniprot ID
- Q07869
- Uniprot Name
- Peroxisome proliferator-activated receptor alpha
- Molecular Weight
- 52224.595 Da
References
- Murakami K, Ide T, Suzuki M, Mochizuki T, Kadowaki T: Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. Biochem Biophys Res Commun. 1999 Jul 14;260(3):609-13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Secretory calcium-dependent phospholipase A2 that primarily targets extracellular lipids, exerting anti-inflammatory and immunosuppressive functions (PubMed:10455175, PubMed:10681567). Hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity) with preference for phosphatidylethanolamines and phosphatidylglycerols over phosphatidylcholines (PubMed:10455175). In draining lymph nodes, selectively hydrolyzes diacyl and alkenyl forms of phosphatidylethanolamines, releasing omega-3 polyunsaturated fatty acids (PUFAs) such as eicosapentaenoate and docosahexaenoate that are precursors of the anti-inflammatory lipid mediators, resolvins (By similarity). During the resolution phase of acute inflammation drives docosahexaenoate-derived resolvin D1 synthesis, which suppresses dendritic cell activation and T-helper 1 immune response (By similarity). May act in an autocrine and paracrine manner (By similarity). Via a mechanism independent of its catalytic activity, promotes differentiation of regulatory T cells (Tregs) and participates in the maintenance of immune tolerance (By similarity). May contribute to lipid remodeling of cellular membranes and generation of lipid mediators involved in pathogen clearance. Displays bactericidal activity against Gram-positive bacteria by directly hydrolyzing phospholipids of the bacterial membrane (By similarity)
- Specific Function
- calcium ion binding
- Gene Name
- PLA2G2D
- Uniprot ID
- Q9UNK4
- Uniprot Name
- Group IID secretory phospholipase A2
- Molecular Weight
- 16546.1 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]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- FABPs are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters
- Specific Function
- cytoskeletal protein binding
- Gene Name
- FABP3
- Uniprot ID
- P05413
- Uniprot Name
- Fatty acid-binding protein, heart
- Molecular Weight
- 14857.93 Da
References
- Fournier NC, Rahim M: Control of energy production in the heart: a new function for fatty acid binding protein. Biochemistry. 1985 Apr 23;24(9):2387-96. doi: 10.1021/bi00330a039. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 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]
- Spector AA, John K, Fletcher JE: Binding of long-chain fatty acids to bovine serum albumin. J Lipid Res. 1969 Jan;10(1):56-67. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 28, 2021 21:54