CUPRIC GLYCINATE

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C2H4NO2.Cu
Molecular Weight	211.663
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cu++].NCC([O-])=O.NCC([O-])=O

InChI

InChIKey=VVYPIVJZLVJPGU-UHFFFAOYSA-L

InChI=1S/2C2H5NO2.Cu/c2*3-1-2(4)5;/h2*1,3H2,(H,4,5);/q;;+2/p-2

HIDE SMILES / InChI

Molecular Formula	C2H4NO2
Molecular Weight	74.0587
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Cu
Molecular Weight	63.546
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a84d61a4-8e7f-4be1-aba6-f633b334aafc | http://www.sciencedirect.com/science/article/pii/S0167488912000158http://www.drugfuture.com/chemdata/schweizer-s-reagent.html | http://pubs.acs.org/doi/abs/10.1021/ed062p878?journalCode=jceda8 | http://pubs.acs.org/doi/abs/10.1021/ed019p356http://www.emdmillipore.com/US/en/product/Copper-di-ammonium-Titriplex-solution,MDA_CHEM-105217https://www.ncbi.nlm.nih.gov/pubmed/15704330 | https://www.ncbi.nlm.nih.gov/pubmed/12425037 | https://www.ncbi.nlm.nih.gov/pubmed/1599240 | http://www.certisusa.com/pdf-labels/Kocide3000_label.pdf | http://www.pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33524https://www.ncbi.nlm.nih.gov/pubmed/8556785 | https://www.ncbi.nlm.nih.gov/pubmed/2135524https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=522.518 | http://www.worldofchemicals.com/chemicals/chemical-properties/cupric-glycinate.htmlDOI: 10.1107/s0567740869001725 Retrived from http://scripts.iucr.org/cgi-bin/paper?S0567740869001725https://www.ncbi.nlm.nih.gov/pubmed/16971307https://www3.epa.gov/pesticides/chem_search/ppls/019713-00509-20110705.pdfhttp://www.drugfuture.com/chemdata/tetraamminecopper-sulfate.html | https://cameochemicals.noaa.gov/chemical/3026https://www.ncbi.nlm.nih.gov/pubmed/6526221http://fs1.agrian.com/pdfs/CORE_7.5_Copper_EDTA_Label.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/24106015 | https://www.ncbi.nlm.nih.gov/pubmed/20942456http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500013010.pdf
Curator's Comment: description was created based on several sources, including https://www.copper.org/resources/properties/compounds/other_compounds.html | http://www.vitamins-supplements.org/dietary-minerals/copper.php | https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=bea888b4-9cc6-49da-89e6-5c273b974ed1

Cupric oxide is the oxide of the copper with the chemical formula of CuO. It is used in the ceramic industry for imparting blue, green or red tints in glasses, glazes and enamels. Cupric oxide is also used as a source for copper in food supplements. Copper is an essential nutrient and a normal constituent of the diet in man and animals. The average daily dietary requirement for copper in humans has been estimated at 0.03 mg/kg body weight. Although rare, copper deficiency has been induced by supplemental zinc therapy.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Xanthine dehydrogenase/oxidase 41 Target ID: CHEMBL1075246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3861140	Inhibitor 8146	3.42 µM [Ki]
Ceruloplasmin 35 Target ID: P00450 Gene ID: 1356.0 Gene Symbol: CP Target Organism: Homo sapiens (Human) Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a84d61a4-8e7f-4be1-aba6-f633b334aafc	Binding Agent 1037
Target ID: Glutathione S-transferase, rat, liver Sources: https://www.ncbi.nlm.nih.gov/pubmed/3008276	Binding Agent 1037
reactive oxygen species metabolic process 68 Target ID: GO:0072593 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8503093	Modulator 817
Escherichia coli 80 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22098250	Inhibitor 8146

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2554
Root caries 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8556785 https://www.ncbi.nlm.nih.gov/pubmed/3201109	Preventing	Preclinical	Unknown Approved Use Unknown
Copper deficiency 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22444781 https://www.ncbi.nlm.nih.gov/pubmed/20569928	Preventing	Preclinical	Unknown Approved Use Unknown
Copper deficiency 35 Sources: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=522.518	Preventing	Approved 8307	Cupric glycinate Approved Use Indications for use. For beef calves and beef cattle for the prevention of copper deficiency, or when labeled for veterinary prescription use, for the prevention and/or treatment of copper deficiency alone or in association with molybdenum toxicity.
Unknown 2554
Copper deficiency 35 Sources: http://www.bayeranimal.co.nz/en/product-detail.php?p=%203030	Primary	Approved 8307	COPPER•MAX Approved Use Unknown
Unknown 2554
Menkes' kinky hair disease 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6520571 https://www.ncbi.nlm.nih.gov/pubmed/4042823 https://www.ncbi.nlm.nih.gov/pubmed/189959	Primary	Not Provided 505	Unknown Approved Use Unknown
Liver cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6526221 https://www.ncbi.nlm.nih.gov/pubmed/7326825	Preventing	Preclinical	Unknown Approved Use Unknown
Unknown 2554
Cancer 581 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21039194	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 581 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22812694	Diagnostic	Preclinical	Unknown Approved Use Unknown
Unknown 2554
Copper deficiency 35 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a84d61a4-8e7f-4be1-aba6-f633b334aafc	Preventing	Approved 8307	COPPER Approved Use Copper 0.4 mg/mL (Cupric Chloride Injection, USP) is indicated for use as a supplement to intravenous solutions given for total parenteral nutrition (TPN). Administration helps to maintain copper serum levels and to prevent depletion of endogenous stores and subsequent deficiency symptoms.
Unknown 2554
Unknown 2554
Copper deficiency 35 Sources: http://www.noahcompendium.co.uk/?id=-446109	Preventing	Approved 8307	COPINOX Approved Use Copinox 4g is indicated for the prevention and treatment of copper deficiency in cattle and sheep.

PubMed

Title	Date	PubMed
Determination of protein by the biuret reaction using cupric hydroxide suspension reagent.	1960	14446699
Efficacy of burning, tillage, and biocides in controlling bacteria released at field sites and effects on indigenous bacteria and fungi.	1992 Apr	1599240
The effect of various fluoride compounds on the development of experimental root surface caries in hamsters.	1995 Dec	8556785
The genetics of tasting in mice. VII. Glycine revisited, and the chromosomal location of Sac and Soa.	1995 Oct	8522158
Copper Fluoride Luminescence during UV Photofragmentation of Bis(1,1,1,5,5,5-hexafluoro-2,4-pentanedionato)copper(II) in the Gas Phase.	1996 Aug 14	11666713
Cardiopulmonary events during hemodialysis: effects of dialysis membranes and dialysate buffers.	2000 Jul	10873882
The effectiveness of ecologically acceptable ways of protection of field-grown tomato (Lycopersicon lycopersicum (L.) Karsten) from tomato late blight (Phytophthora infestans (Mont.) de Bary) in extreme weather conditions.	2001	12425037
Direct catalytic aldol-type reactions using RCH2CN.	2003 Aug 21	12917003
Antioxidant activity of olive pulp and olive oil phenolic compounds of the arbequina cultivar.	2005 Mar 23	15769127
Cu(II) acetate- and Mn(III) acetate-mediated radical reactions of [60]fullerene with ketonic compounds.	2005 Mar 7	15731864
X-ray absorption spectroscopy study of a copper-containing material after thermal treatment.	2006 Apr 17	16257485
Acute copper toxicity following copper glycinate injection.	2006 Nov	17040362
A spectroscopic and thermoanalytical study of the mineral hoganite.	2007 May	17321784
Enhanced copper release from pipes by alternating stagnation and flow events.	2007 Nov 1	18044522
Bioavailability of copper from copper glycinate in steers fed high dietary sulfur and molybdenum.	2008 Jan	17911232
Synthesis and structural investigation of mono- and polynuclear copper complexes of 4-ethyl-1-(pyridin-2-yl) thiosemicarbazide.	2008 Nov 1	18164649
Copper(II) acetate-catalyzed addition of arylboronic acids to aromatic aldehydes.	2009 Jan 16	19067580
Insight in the transport behavior of copper glycinate complexes through the porcine gastrointestinal membrane using an Ussing chamber assisted by mass spectrometry analysis.	2010 Apr	20413071
Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers.	2010 Feb 3	20067245
A chelator-free multifunctional [64Cu]CuS nanoparticle platform for simultaneous micro-PET/CT imaging and photothermal ablation therapy.	2010 Nov 3	20942456
Copper sulfide nanoparticles for photothermal ablation of tumor cells.	2010 Oct	21039194
Anti-ovulatory activity of H2 receptor blockers in albino rabbits--a preliminary study.	2011 Apr	21281096
Rapid free chlorine decay in the presence of Cu(OH)2: chemistry and practical implications.	2011 Oct 15	21868051
Expeditious synthesis of phenanthrenes via CuBr2-catalyzed coupling of terminal alkynes and N-tosylhydrazones derived from o-formyl biphenyls.	2011 Oct 7	21875127
Zeta potential and solubility to toxic ions as mechanisms of lung inflammation caused by metal/metal oxide nanoparticles.	2012 Apr	22240982
Protective effect of sulphoraphane against oxidative stress mediated toxicity induced by CuO nanoparticles in mouse embryonic fibroblasts BALB 3T3.	2012 Feb	22293418
CuBr2--a new multiferroic material with high critical temperature.	2012 May 8	22488570
Evaluation of topically applied copper(II) oxide nanoparticle cytotoxicity in human skin organ culture.	2013 Feb	22954531
Probing the chemical nature of dihydrogen complexation to transition metals, a gas phase case study: H2-CuF.	2013 Jan 18	23301994
Design, synthesis, antioxidant, and anti-breast cancer activities of novel diethyl(alkyl/aryl/heteroarylamino)(4-(pyridin-2-yl)phenyl)methylphosphonates.	2013 May	23589377
Molecular responses of mouse macrophages to copper and copper oxide nanoparticles inferred from proteomic analyses.	2013 Nov	23882024
Cytotoxicity in the age of nano: the role of fourth period transition metal oxide nanoparticle physicochemical properties.	2013 Nov 25	24120544
The modality of cell-particle interactions drives the toxicity of nanosized CuO and TiO₂ in human alveolar epithelial cells.	2013 Oct 24	23906720
SILAC-based quantitative proteomic analysis of human lung cell response to copper oxide nanoparticles.	2014	25470785
Activation of Erk and p53 regulates copper oxide nanoparticle-induced cytotoxicity in keratinocytes and fibroblasts.	2014	25336953
Interference of CuO nanoparticles with metal homeostasis in hepatocytes under sub-toxic conditions.	2014	24343273
Synthesis and biomedical applications of copper sulfide nanoparticles: from sensors to theranostics.	2014 Feb 26	24106015
Effects of different sources of copper on Ctr1, ATP7A, ATP7B, MT and DMT1 protein and gene expression in Caco-2 cells.	2014 Jul	24815816
Electron induced surface reactions of organometallic metal(hfac)₂ precursors and deposit purification.	2014 Jun 11	24784352
CuO nanoparticles induce apoptosis by impairing the antioxidant defense and detoxification systems in the mouse hippocampal HT22 cell line: protective effect of crocetin.	2015 Jun	25701151
A Facile Strategy for Catalyst Separation and Recycling Suitable for ATRP of Hydrophilic Monomers Using a Macroligand.	2016 Jan	26506506
Dissecting copper homeostasis in diabetes mellitus.	2017 Apr	28276155
Unusual 4-arsonoanilinium cationic species in the hydrochloride salt of (4-aminophenyl)arsonic acid and formed in the reaction of the acid with copper(II) sulfate, copper(II) chloride and cadmium chloride.	2017 Apr 1	28378716
Roles of Copper-Binding Proteins in Breast Cancer.	2017 Apr 20	28425924
Supplementation with copper edetate in control of Haemonchus contortus of sheep, and its effect on cholinesterase's and superoxide dismutase activities.	2017 Feb	28007539
Ultrasonic energy enhanced the efficiency of advance extraction methodology for enrichment of trace level of copper in serum samples of patients having neurological disorders.	2017 Jul	28427628
Comparison of the efficacy of a commercial footbath product with copper sulfate for the control of digital dermatitis.	2017 Jul	28478000
Folic acid-modified and functionalized CuS nanocrystal-based nanoparticles for combined tumor chemo- and photothermal therapy.	2017 Jun	27899044
Amino acid-mediated 'turn-off/turn-on' nanozyme activity of gold nanoclusters for sensitive and selective detection of copper ions and histidine.	2017 Jun 15	28213326
Effects of Excess Copper Ions on Decidualization of Human Endometrial Stromal Cells.	2017 May	27726061

Patents

Sample Use Guides

In Vivo Use Guide

Copper 0.4 mg/mL (Cupric Chloride Injection) contains 0.4 mg copper/mL and is administered intravenously only after dilution. The additive should be diluted in a volume of fluid not less than 100 mL. For the adult receiving total parenteral nutrition, the suggested additive dosage is 0.5 to 1.5 mg copper/day (1.25 to 3.75 mL/day). For pediatric patients, the suggested additive dosage is 20 mcg copper/kg/day (0.05 mL/kg/day). Infants weighing less than 1500 gm may have increased requirements because of their low body reserves and increased requirements for growth.

Route of Administration: Intravenous

In Vitro Use Guide

Human Endometrial Stromal Cells were treated with non-toxic concentrations of copper ions (0-250 uM). mRNA expressions of insulin-like growth factor binding protein (IGFBP-1), prolactin (PRL), Mn-SOD, and FOXO1 were down-regulated during decidualization following the treatments with 100 or 250 uM copper ions. Meanwhile, the amount of malonaldehyde in the supernatant of cells was increased.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 16:41:37 UTC 2022` Edited by `admin` on `Fri Dec 16 16:41:37 UTC 2022`
Record UNII	68VAV8QID7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CUPRIC GLYCINATE

Common Name

English

COPPER(II) GLYCINATE

Systematic Name

English

BIS(GLYCINATO-N,O)COPPER

Common Name

English

Copper glycinate [WHO-DD]

Common Name

English

CUPRIC BISGLYCINATE

Common Name

English

CUPRIC BISGLYCINATE [MI]

Common Name

English

COPPER GLYCINATE [INCI]

Common Name

English

COPPER GLYCINATE

Official Name

English

CUPRIC GLYCINATE [GREEN BOOK]

Common Name

English

NSC-162736

Code

English

COPPER(II) BISGLYCINATE

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 522.518