Calcium levulinate
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Overview
- DrugBank ID
- DB13800
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
Identification
- Generic Name
- Calcium levulinate
- DrugBank Accession Number
- DB13800
- Background
The relatively new calcium levulinate is produced from a direct reaction between L- or levulinic acid levulose and calcium hydroxide 3. The resultant calcium levulinate formulation, when used as a calcium supplement, possesses a high calcium content that is observed to be 14.8% higher than the content typically found in calcium lactate 3. This formulation is considered a low molecular weight organic calcium ion type that is easily absorbed through the intestinal wall 3.
This new application of calcium is intended for use as a food fortifier, to fortify foods like sauces, condiments, beer, beverages, soft drinks, milk and milk products, soy milk and soy products with calcium nutrition 3. Calcium levulinate can be used alone, or with calcium lactate, calcium chloride, and other compounds, either for pharmaceutical tablets, capsules, or injections preparation 3.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
- Weight
- Average: 270.294
Monoisotopic: 270.0416291 - Chemical Formula
- C10H14CaO6
- Synonyms
- Calcium laevulate
- Calcium levulinate anhydrous
Pharmacology
- Indication
This new application of calcium is intended for use as a food fortifier, to fortify foods like sauces, condiments, beer, beverages, soft drinks, milk and milk products, soy milk and soy products with calcium nutrition 3. Calcium levulinate can be used alone, or with calcium lactate, calcium chloride, and other compounds, either for pharmaceutical tablets, capsules, or injections preparation 3. In essence, calcium levulinate is ultimately a relatively new calcium supplementation option 5.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Hypocalcemia Combination Product in combination with: Calcium gluconate (DB11126) •••••••••••• •••••••••• •••••••••• ••••••••• •••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
The relatively new calcium levulinate is produced from a direct reaction between L- or levulinic acid levulose and calcium hydroxide 3. The resultant calcium levulinate formulation, when used as a calcium supplement, possesses a high calcium content that is observed to be 14.8% higher than the content typically found in calcium lactate 3. Moreover, this formulation also demonstrates a high solubility of more than 30% at 25℃ 3. Furthermore, the calcium levulinate is believed to be non-toxic and non-allergic, making it especially suitable for injection or infusion administrations 3. Additionally, this levulinate formulation is reported as having a good taste, little irritation with a pH value of 7, and good stability such that no precipitation or deterioration occurs during use 3. Finally, this calcium levulinate formulation is also believed to have good compatibility with calcium lactate, calcium chloride, and other material complexes which allows the formulation to also complex effectively with a diverse variety of foodstuffs and pharmaceutical dosage forms 3.
- Mechanism of action
Much like most calcium supplements, once calcium levulinate dissociates in the body after administration, absorption of the supplemental calcium ions across the intestinal wall serves to enhance calcium stores in the body 3,5,1.
Regardless, levulinic acid (LA) is a commonly used chemical with one carbonyl group, one carboxyl group, and alpha-H comprised in its inner structure, which belongs to short-chain and non-volatile fatty acids 5. Moreover, the carbon-oxygen double bond from LA's carbonyl group possesses a strong polarity, where the oxygen atom has a stronger electron attracting ability compared to the carbon atom, such that the pi electron will ultimately transfer into the greater electronegative oxygen, therefore resulting in the formation of a positive charge center in the carbon atom 5. The electrophilic center of the carbon atom subsequently plays a critical role when the carbonyl group performs chemical reactions 5. Owing to the relatively strong electron receptor effect of the oxygen atom of the carbonyl group, LA has higher dissociation constants than a common saturated acid, which allows it to possess a stronger corresponding acidity 5. Furthermore, LA can be isomerized into the enol-isomer, owing to the presence of the carbonyl group 5. The chemical structure of LA consequently has several highly active sites, which facilitates it being used as a chemical platform for preparing many other chemical products 5. For example, the special structure of LA allows various kinds of products to be generated by way of esterification, halogenation, hydrogenation, oxy-dehydrogenation, and/or condensation, among many other methods 5.
Target Actions Organism UCalsequestrin-1 agonistHumans UCalretinin agonistHumans UCalmodulin agonistHumans - Absorption
General calcium absorption occurs primarily in the duodenum by an active transcellular and saturable system, which is stimulated and regulated by 1,25(OH)2D,25 and through a passive and vitamin D-independent paracellular transport in the jejunum and ileum, and even in the colon - where absorption is only about 4% even when the intake is high 1. Ultimately, calcium absorption depends mainly on the amount of intake - in general, absorption increases at lower intakes and decreases at high intakes 1.
Readily accessible data regarding the specific absorption of calcium levulinate is not available although the formulation is considered a low molecular weight organic calcium ion type that is easily absorbed through the intestinal wall 3.
- Volume of distribution
99% of the body's calcium supply is stored in the bones and teeth where it supports their structure and function 6. Elsewhere, 1% or less of this calcium supply is used for essential metabolic functions like vascular contraction and vasodilation, muscle function, nerve transmission, intracellular signaling, and hormonal secretion, among other activities 6.
- Protein binding
Readily accessible data regarding the protein binding of calcium levulinate is not available, although many different calcium-binding proteins exist, with different cellular and tissue distribution and involvement in specific biological function 2. Some of these proteins include calmodulin, calsequestrin, calretinin, and calcineurin, among others 2.
- Metabolism
Although calcium levulinate dissociates into absorbable calcium ion once it is administered into the body, there have been studies to suggest that the levulinate component is metabolized to 4-hydroxypentanoate - a compound that has similar pharmacologic effects as but at a lower level of potency than the 'date rape' drug gamma-hydroxybutyrate 8.
- Route of elimination
Calcium leaves the body mainly in urine and feces, but also in other body tissues and fluids, like sweat 7. Overall, a typical daily calcium loss for a healthy adult man or woman via renal excretion is approximately 5 mmol/day 7 while endogenous fecal calcium losses are about 2.1 mg/kg per day in adults and about 1.4 mg/kg per day in children 7.
- Half-life
Readily accessible data regarding the half-life of calcium levulinate is not available.
- Clearance
Despite inter-individual differences, general clinical lab tests list some reference calcium clearance values as being considered a 'normal range', like urine calcium as approximately < 250 mg/24 h 9.
- Adverse Effects
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- Toxicity
Overdosage with calcium resulting in excessively high levels of calcium in the blood known as hypercalcemia can cause renal insufficiency, vascular and soft tissue calcification, hypercalciuria, and kidney stones 6.
- Pathways
- Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Acebutolol can be decreased when used in combination with Calcium levulinate. Acetyldigitoxin Calcium levulinate may increase the arrhythmogenic and cardiotoxic activities of Acetyldigitoxin. Alendronic acid The serum concentration of Alendronic acid can be decreased when it is combined with Calcium levulinate. Alfacalcidol The risk or severity of adverse effects can be increased when Alfacalcidol is combined with Calcium levulinate. Amiodarone The therapeutic efficacy of Amiodarone can be decreased when used in combination with Calcium levulinate. - 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.
- Product Ingredients
Ingredient UNII CAS InChI Key Calcium levulinate dihydrate T6133SO781 5743-49-7 WQFDRFDIWAMOPA-UHFFFAOYSA-L - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CALCİLES 225 MG+572 MG/10 ML ENJEKSİYONLUK ÇÖZELTİ, 5 ADET Calcium levulinate (572 mg/10mL) + Calcium gluconate monohydrate (225 mg/10mL) Injection, solution Parenteral VEM İLAÇ SAN. VE TİC. A.Ş. 2018-03-14 Not applicable Turkey CALCIO AL 10% AMPOLLAS Calcium levulinate (400 mg) + Calcium gluconate monohydrate (600 mg) Solution Intravenous LABORATORIOS RYAN DE COLOMBIA S.A.S 2008-10-07 Not applicable Colombia CALCİOSEL 225 mg + 572 mg / 10 mL ENJEKSIYONLUK ÇÖZELTI Calcium levulinate dihydrate (572 mg/10ml) + Calcium gluconate monohydrate (225 mg/10ml) Injection Intramuscular HAVER FARMA İLAÇ A.Ş. 2016-04-20 Not applicable Turkey Calcium Inj Calcium levulinate (15 mg) + Calcium glycerophosphate (10 mg) Liquid Intramuscular; Intravenous; Subcutaneous Kripps Pharmacy Ltd. 1981-12-31 Not applicable Canada CALCIUM PICKEN %10 ENJEKSİYONLUK ÇÖZELTİ 100 AMPUL Calcium levulinate dihydrate (572 mg) + Calcium gluconate monohydrate (225 mg) Injection Intramuscular ADEKA İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey
Categories
- ATC Codes
- A12AA30 — Calcium laevulate
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Keto acids and derivatives
- Sub Class
- Gamma-keto acids and derivatives
- Direct Parent
- Gamma-keto acids and derivatives
- Alternative Parents
- Short-chain keto acids and derivatives / Ketones / Carboxylic acid salts / Organic calcium salts / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid salt / Gamma-keto acid / Hydrocarbon derivative / Ketone / Monocarboxylic acid or derivatives / Organic calcium salt
- Molecular Framework
- Not Available
- External Descriptors
- organic molecular entity (CHEBI:81717)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- LLQ966USIL
- CAS number
- 591-64-0
- InChI Key
- APKDPOQXVKRLEP-UHFFFAOYSA-L
- InChI
- InChI=1S/2C5H8O3.Ca/c2*1-4(6)2-3-5(7)8;/h2*2-3H2,1H3,(H,7,8);/q;;+2/p-2
- IUPAC Name
- calcium bis(4-oxopentanoate)
- SMILES
- [Ca++].CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O
References
- General References
- Burckhardt P: Calcium revisited: part I. Bonekey Rep. 2013 Oct 16;2:433. doi: 10.1038/bonekey.2013.167. [Article]
- Yanez M, Gil-Longo J, Campos-Toimil M: Calcium binding proteins. Adv Exp Med Biol. 2012;740:461-82. doi: 10.1007/978-94-007-2888-2_19. [Article]
- Preparing process and application of calcium lévulinate [Link]
- Energy densification of levulinic acid by thermal deoxygenation [Link]
- Advances in the Catalytic Production of Valuable Levulinic Acid Derivatives [Link]
- National Institutes of Health: Calcium Fact Sheet [Link]
- Dietary Reference Intakes for Calcium and Vitamin D [Link]
- Chemical Research in Toxicology: Levulinate - Potentially Toxic Pro-Drug of Abuse [File]
- Clinical Laboratory Tests Reference Values (from http://www.royalcollege.ca/rcsite/documents/credential-exams/clinical-lab-tests-reference-values-e.pdf) [File]
- External Links
- MSDS
- Download (47.1 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Parenteral Solution Intravenous Liquid Intramuscular; Intravenous; Subcutaneous Injection Intramuscular - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.82 mg/mL ALOGPS logP 0.76 ALOGPS logP -0.069 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 4.32 Chemaxon pKa (Strongest Basic) -7.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 57.2 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 37.93 m3·mol-1 Chemaxon Polarizability 10.8 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 144.71559 predictedDeepCCS 1.0 (2019) [M+H]+ 147.0772 predictedDeepCCS 1.0 (2019) [M+Na]+ 153.16689 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Calsequestrin is a high-capacity, moderate affinity, calcium-binding protein and thus acts as an internal calcium store in muscle (PubMed:28895244). Calcium ions are bound by clusters of acidic residues at the protein surface, often at the interface between subunits. Can bind around 80 Ca(2+) ions (PubMed:28895244). Regulates the release of lumenal Ca(2+) via the calcium release channel RYR1; this plays an important role in triggering muscle contraction. Negatively regulates store-operated Ca(2+) entry (SOCE) activity (PubMed:27185316)
- Specific Function
- calcium ion binding
- Gene Name
- CASQ1
- Uniprot ID
- P31415
- Uniprot Name
- Calsequestrin-1
- Molecular Weight
- 45159.635 Da
References
- Yanez M, Gil-Longo J, Campos-Toimil M: Calcium binding proteins. Adv Exp Med Biol. 2012;740:461-82. doi: 10.1007/978-94-007-2888-2_19. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Calretinin is a calcium-binding protein which is abundant in auditory neurons
- Specific Function
- calcium ion binding
- Gene Name
- CALB2
- Uniprot ID
- P22676
- Uniprot Name
- Calretinin
- Molecular Weight
- 31539.62 Da
References
- Yanez M, Gil-Longo J, Campos-Toimil M: Calcium binding proteins. Adv Exp Med Biol. 2012;740:461-82. doi: 10.1007/978-94-007-2888-2_19. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Calmodulin acts as part of a calcium signal transduction pathway by mediating the control of a large number of enzymes, ion channels, aquaporins and other proteins through calcium-binding (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Calcium-binding is required for the activation of calmodulin (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Among the enzymes to be stimulated by the calmodulin-calcium complex are a number of protein kinases, such as myosin light-chain kinases and calmodulin-dependent protein kinase type II (CaMK2), and phosphatases (PubMed:16760425, PubMed:23893133, PubMed:26969752, PubMed:27165696, PubMed:28890335, PubMed:31454269, PubMed:35568036). Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis (PubMed:16760425). Is a regulator of voltage-dependent L-type calcium channels (PubMed:31454269). Mediates calcium-dependent inactivation of CACNA1C (PubMed:26969752). Positively regulates calcium-activated potassium channel activity of KCNN2 (PubMed:27165696). Forms a potassium channel complex with KCNQ1 and regulates electrophysiological activity of the channel via calcium-binding (PubMed:25441029). Acts as a sensor to modulate the endoplasmic reticulum contacts with other organelles mediated by VMP1:ATP2A2 (PubMed:28890335)
- Specific Function
- adenylate cyclase activator activity
Components:
Name | UniProt ID |
---|---|
Calmodulin-1 | P0DP23 |
Calmodulin-2 | P0DP24 |
Calmodulin-3 | P0DP25 |
References
- Yanez M, Gil-Longo J, Campos-Toimil M: Calcium binding proteins. Adv Exp Med Biol. 2012;740:461-82. doi: 10.1007/978-94-007-2888-2_19. [Article]
Drug created at June 23, 2017 20:48 / Updated at November 05, 2024 05:15