Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H36O2 |
Molecular Weight | 284.4772 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCCCC(O)=O
InChI
InChIKey=QIQXTHQIDYTFRH-UHFFFAOYSA-N
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)
Molecular Formula | C18H36O2 |
Molecular Weight | 284.4772 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Stearic Acid is a typical example of a fatty acid, which are essentially long hydrocarbon chains containing a carboxyl group at one end and a methyl group at the other. The chain lengths can vary from 3 (propionic acid) to 24 (lignoceric acid) but the majority of fatty acids found in hydrogenated vegetable or animal oils are around C16-C20 in length. Stearic acid is a saturated acid, since there are no double bonds between neighbouring carbon atoms. Stearic acid is found in various animal and plant fats, and is a major component of cocoa butter and shea butter. Stearic acid is a very common amino acid is used in the manufacturing of more than 3,200 skin and hair care products sold in the United States. On product labels, it is sometimes listed under other names, including Century 1240, cetylacetic acid, Emersol 120, Emersol 132, Emersol 150, Formula 300 and Glycon DP. Stearic Acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products. Stearic acid is used along with castor oil for preparing softeners in textile sizing. Being inexpensively available and chemically benign, stearic acid finds many niche applications It is used in the manufacture of candles, and as a hardener in candies when mixed with simple sugar and corn syrup. It is also used to produce dietary supplements. In fireworks, stearic acid is often used to coat metal powders such as aluminum and iron. This prevents oxidation, allowing compositions to be stored for a longer period of time.
Stearic acid is a common lubricant during injection molding and pressing of ceramic powders. It is also used as a mold release for foam latex that is baked in stone molds. Stearic acid is known antidiabetic and antioxidant agent.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5586 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28450226 |
9.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | CELLBN First care cleanser Approved UseUnknown Launch Date2017 |
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Preventing | MARY KAY TIMEWISE REPAIR VOLU-FIRM THE GO SET Approved UseUses:
helps prevent sunburn
if used as directed with other sun protection measures (see Directions), decreases the risk of skin cancer and early skin aging caused by the sun Launch Date2017 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16978661/ Page: 4.0 |
no |
PubMed
Title | Date | PubMed |
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Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions. | 2000 Jun 20 |
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Final report on the safety assessment of PEG-25 propylene glycol stearate, PEG-75 propylene glycol stearate, PEG-120 propylene glycol stearate, PEG-10 propylene glycol, PEG-8 propylene glycol cocoate, and PEG-55 propylene glycol oleate. | 2001 |
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Characterisation of myogenic cell membrane: II. Dynamic changes in membrane lipids during the differentiation of mouse C2 myoblast cells. | 2001 |
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A comparison of reflectance and transmittance near-infrared spectroscopic techniques in determining drug content in intact tablets. | 2001 |
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Prediction of drug content and hardness of intact tablets using artificial neural network and near-infrared spectroscopy. | 2001 Aug |
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Heterogeneous fatty acylation of Src family kinases with polyunsaturated fatty acids regulates raft localization and signal transduction. | 2001 Aug 17 |
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Palmitate decreases proton pumping of liver-type cytochrome c oxidase. | 2001 Dec |
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Long-term stability characterization of a controlled release gastrointestinal therapeutic system coated with a cellulose acetate pseudolatex. | 2001 Jan |
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Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation. | 2001 Jan-Feb |
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DC calcium lactate, a new filler-binder for direct compaction of tablets. | 2001 Jun 19 |
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Effect of polymer molecular weight and addition of calcium stearate on response of MG63 osteoblast-like cells to UHMWPE particles. | 2001 Mar |
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[The firmness of Avicel PH 102 and Avicel PH 301 compression and the effect of magnesium stearate] ]. | 2001 Mar |
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Formulation and process optimization to eliminate picking from market image tablets. | 2001 Mar 14 |
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Effect of magnesium stearate or calcium stearate as additives on dissolution profiles of diltiazem hydrochloride from press-coated tablets with hydroxypropylmethylcellulose acetate succinate in the outer shell. | 2001 Mar 23 |
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Saturated non-esterified fatty acids stimulate de novo diacylglycerol synthesis and protein kinase c activity in cultured aortic smooth muscle cells. | 2001 May |
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Identification and total synthesis of novel fatty acids from the Siphonarid limpet Siphonaria denticulata. | 2001 Nov |
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X-ray structure of the orphan nuclear receptor RORbeta ligand-binding domain in the active conformation. | 2001 Nov 1 |
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The cytotoxicity and chemical constituents of the hexane fraction of Typhonium flagelliforme (Araceace). | 2001 Sep |
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[Extracellular metabolites of hydrocarbon-oxidizing bacteria as a substrate for sulfate reduction]. | 2001 Sep-Oct |
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Food-drug interactions. | 2002 |
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Computerized posturography with sway frequency analysis: application in occupational and environmental health. | 2002 Jan |
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[Effect of magnesium stearate on the tensile strength of tablets made with the binder Prosolv SMCC 90]. | 2002 Jan |
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The effect of formulation on reduced radioiodide thyroid uptake. | 2002 Jan |
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The impact of low levels of amorphous material (<5%) on the blending characteristics of a direct compression formulation. | 2002 Jan 14 |
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The effects of some physico-chemical factors and pharmaceutical excipients on the bioavailability of nitrofurantoin oily and aqueous suspensions in rats. | 2002 Mar |
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Loss of regulation of lipogenesis in the Zucker diabetic rat. II. Changes in stearate and oleate synthesis. | 2002 Mar |
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Investigation of excipient type and level on drug release from controlled release tablets containing HPMC. | 2002 May |
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The apoplastic oxidative burst in response to biotic stress in plants: a three-component system. | 2002 May |
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Buccoadhesive erodible disk for treatment of oro-dental infections: design and characterisation. | 2002 May 15 |
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Fatty acid mobilized by the vascular endothelial growth factor in human endothelial cells. | 2002 Nov |
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Roller compaction and tabletting of St. John's wort plant dry extract using a gap width and force controlled roller compactor. II. Study of roller compaction variables on granule and tablet properties by a 3(3) factorial design. | 2002 Nov |
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Development of polymer film dosage forms of lidocaine for buccal administration: II. Comparison of preparation methods. | 2002 Nov |
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Characterization of a surface modified dry powder inhalation carrier prepared by "particle smoothing". | 2002 Oct |
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Design of controlled release system with multi-layers of powder. | 2002 Sep |
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Influence of physical parameters and lubricants on the compaction properties of granulated and non-granulated cross-linked high amylose starch. | 2002 Sep |
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Inverse gas chromatography study on partially esterified paper fiber. | 2002 Sep 6 |
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Duration of coffee- and exercise-induced changes in the fatty acid profile of human serum. | 2003 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: When these
same investigators used a lower amount of dietary stearic
acid (i.e., an increase of 3 g/day using milk chocolate) in
a similar study, no differences in platelet aggregation or
platelet activation activity were found
A stearic acid-rich diet (~ 7% of
calories or 19 g/day) had beneficial effects on several
measures of thrombosis (e.g., platelet volume, platelet
aggregation, coagulation factor VII activity) in healthy
males. Stearic acid was increased by 12
g/day using stearic acid-enriched margarine.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16524362
Inhibition of EDR (endothelium-dependent relaxation) induced by acetylcholine was dose-dependent (0.5-2 mmol/l NEFA), and the greatest inhibition (51%) was observed with stearic acid (2 mmol/l).
Substance Class |
Chemical
Created
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on
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Record UNII |
4ELV7Z65AP
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Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68388
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CFR |
21 CFR 184.1090
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JECFA EVALUATION |
STEARIC ACID
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CFR |
21 CFR 357.210
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CFR |
21 CFR 172.860
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EPA PESTICIDE CODE |
79082
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NCI_THESAURUS |
C68421
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DSLD |
7 (Number of products:123)
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261168
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4611
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57-11-4
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m10200
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PRIMARY | Merck Index | ||
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25956
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C68426
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25629
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2000
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4ELV7Z65AP
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200-313-4
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28842
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1092
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1310551
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5281
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CHEMBL46403
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1368706
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SUB12597MIG
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1621008
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4ELV7Z65AP
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STEARIC ACID
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C031183
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DTXSID8021642
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DB03193
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
Values are % of weight of fatty acid composition.
O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range)
Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for US corn oil w/std. deviation of 0.25%
LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value).
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
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LIPID -> FATTY ACID |
JB Rossell and co-workers; JAOCS62(2), 221-230(1985).
Range weight is a mean.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID |
MAY BE PRESENT
USP
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for international corn oil w/std. deviation of 0.6%
LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID | |||
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LIPID -> FATTY ACID | |||
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID |
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ACTIVE MOIETY |
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