Calcium threonate

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Calcium threonate
Accession Number
DB11168
Type
Small Molecule
Groups
Approved
Description

Calcium threonate is a calcium salt of threnoic acid and a novel drug developed for the treatment of osteoporosis and as a calcium supplement 1. It is found in dietary supplements as a source of L-threonate used in the treatment of calcium deficiency and prevention of osteoporosis. The most common form is calcium L-threonate, or (2R,3S)-2,3,4-trihydroxy butyric acid calcium 1. L-threonate is an active metabolite of vitamin C that mediates a stimulatory action on vitamin C uptake 1. Therapeutic efficacy of calcium threonate in reducing was studied and investigated due to the hypothesis that it may play a role in the mineralization process through its positive action on vitamin C.

Structure
Thumb
Synonyms
  • Calcium L-threonate
  • Threonine, calcium salt
Active Moieties
NameKindUNIICASInChI Key
Calcium cationionic2M83C4R6ZB14127-61-8BHPQYMZQTOCNFJ-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Soin Solaire Complete SPF30Calcium threonate (.001 mg/1mL) + Calcium ascorbate dihydrate (.17 mg/1mL) + Panthenol (7.5 mg/1mL) + Titanium dioxide (70 mg/1mL) + Tocopherol (1 mg/1mL) + alpha-Tocopherol acetate (5 mg/1mL)EmulsionTopicalElemis Limited2012-03-272012-12-31Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ferrex 150 Forte PlusCalcium threonate (0.8 mg/1) + Calcium ascorbate dihydrate (60 mg/1) + Cyanocobalamin (25 ug/1) + Folic Acid (1 mg/1) + Iron (150 mg/1) + Succinic acid (50 mg/1)CapsuleOralBreckenridge Pharmaceutical, Inc.2008-08-012012-09-30Us
Folcaps Care OneCalcium threonate (1 mg/1) + Alpha-Linolenic Acid (50 mg/1) + Biotin (300 mg/1) + Calcium Carbonate (100 mg/1) + Calcium ascorbate dihydrate (24 mg/1) + Cholecalciferol (800 [iU]/1) + Doconexent (350 mg/1) + Docusate sodium (50 mg/1) + Folic Acid (1 mg/1) + Icosapent (100 mg/1) + Iodine (150 ug/1) + Iron (27 mg/1) + Magnesium (50 mg/1) + Nicotinamide (10 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (1.5 mg/1) + Zinc (5 mg/1) + alpha-Tocopherol acetate (15 [iU]/1)Capsule, gelatin coatedOralMayne Pharma2009-05-012016-12-31Us
Folcaps Omega-3Calcium threonate (1 mg/1) + Alpha-Linolenic Acid (30 mg/1) + Calcium (150 mg/1) + Calcium ascorbate dihydrate (24 mg/1) + Cholecalciferol (170 [iU]/1) + Doconexent (260 mg/1) + Ferrous asparto glycinate (7 mg/1) + Folic Acid (1 mg/1) + Icosapent (40 mg/1) + Iron (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)Capsule, gelatin coatedOralMayne Pharma2011-01-032016-12-31Us
Se-Care ChewableCalcium threonate (50 mg/1) + Calcium Carbonate (250 mg/1) + Calcium ascorbate dihydrate (50 mg/1) + Cholecalciferol (6 ug/1) + Cupric oxide (2 mg/1) + DL-alpha tocopheryl acetate (3.5 [iU]/1) + Ferrous fumarate (40 mg/1) + Folic Acid (1 mg/1) + Magnesium oxide (50 mg/1) + Pyridoxine hydrochloride (2 mg/1) + Zinc oxide (15 mg/1)Tablet, chewableOralSeton Pharmaceuticals2009-05-012011-08-31Us
Se-Care ConceiveCalcium threonate (30 mg/1) + Calcium Carbonate (200 mg/1) + Calcium ascorbate dihydrate (30 mg/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + Ferrous fumarate (30 mg/1) + Folic Acid (1 mg/1) + Magnesium oxide (100 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (3.4 mg/1) + Thiamine mononitrate (3 mg/1) + Zinc oxide (15 mg/1)Tablet, film coatedOralSeton Pharmaceuticals2009-05-052011-04-15Us
Se-Vate 21/7Calcium threonate (0.8 mg/1) + Ascorbic acid (140 mg/1) + Calcium ascorbate dihydrate (60 mg/1) + Cyanocobalamin (10 ug/1) + Ferrous asparto glycinate (70 mg/1) + Ferrous fumarate (81 mg/1) + Folic Acid (1 mg/1) + Succinic acid (150 mg/1)KitSeton Pharmaceuticals2009-05-122011-05-30Us
UltimateCare ONE NFCalcium threonate (1 mg/1) + Alpha-Linolenic Acid (50 mg/1) + Biotin (300 [iU]/1) + Calcium (100 mg/1) + Calcium ascorbate dihydrate (24 mg/1) + Cholecalciferol (800 [iU]/1) + DL-alpha tocopheryl acetate (15 [iU]/1) + Doconexent (350 mg/1) + Docusate sodium (50 mg/1) + Ferrous asparto glycinate (7 mg/1) + Folic Acid (1 mg/1) + Icosapent (100 mg/1) + Iodine (150 [iU]/1) + Iron (20 mg/1) + Magnesium oxide (50 mg/1) + Nicotinamide (10 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (1.5 mg/1) + Zinc oxide (5 mg/1)CapsuleOralTrigen Laboratories, Inc.2009-12-042014-02-11Us
Categories
UNII
HBB4YPO93U
CAS number
70753-61-6
Weight
Average: 310.268
Monoisotopic: 310.0212876
Chemical Formula
C8H14CaO10
InChI Key
ZJXGOFZGZFVRHK-BALCVSAKSA-L
InChI
InChI=1S/2C4H8O5.Ca/c2*5-1-2(6)3(7)4(8)9;/h2*2-3,5-7H,1H2,(H,8,9);/q;;+2/p-2/t2*2-,3+;/m00./s1
IUPAC Name
calcium bis((2R,3S)-2,3,4-trihydroxybutanoate)
SMILES
[Ca++].OC[C@H](O)[C@@H](O)C([O-])=O.OC[C@H](O)[C@@H](O)C([O-])=O

Pharmacology

Indication

No approved therapeutic indications.

Pharmacodynamics

In a preclinical study, calcium L-theronate inhibited the bone resorption of osteoclasts in vitro 1.

Mechanism of action

Once dissociated to calcium and L-theronic acid, L-threonic acid exhibits significant stimulatory action on vitamin C uptake and prolongs the retention of vitamin C in human T-lymphoma cells 1. Vitamin C is a marker for osteoblast formation and has been shown to stimulate procollagen and enhance collagen synthesis 1. Via stimulation of vitamin C uptake, L-threonic acid acts as a metabolite that influences the mineralization process 1.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

Learn more
Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

Learn more
Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

Learn more
Absorption

Human studies demonstrate that calcium from calcium L-threonate is absorbed 2. In an open-label, single- and multiple-dose study of healthy adult Chinese subjects receiving a single oral dose of 2025 mg calcium theronate, the peak plasma concentration (Cmax) was 32.3 mg/L 1. The time to reach peak plasma concentration (Tmax) was approximately 2 hours 1.

Volume of distribution

The apparent total volume of distribution following a single oral dose of 2025 mg calcium theronate in healthy adult Chinese subjects was approximately 53.6 L 1.

Protein binding
Not Available
Metabolism
Not Available
Route of elimination

The presence of threonic acid in human urine has been identified 2. In a pharmacokinetic study of rats receiving 200 mg/kg bw of calcium threonate orally, approximately 30% of the calcium was excreted in the urine, around 40% was eliminated in the faeces, and about 10 -20% remained in the blood and bone, and about 10% was stored in organs after 24 hours of administration 2.

Half life

The terminal-phase elimination half-life following a single oral dose of 2025 mg calcium theronate in healthy adult Chinese subjects was approximately 2.7 hours 1.

Clearance

Apparent total clearance following a single oral dose of 2025 mg calcium theronate in healthy adult Chinese subjects was approximately 14.5 L/h 1.

Toxicity

Calcium L-threonate has low oral acute toxicity, with no adverse effects observed at doses as high as 40 g/kg bw in mice or 32 g/kg bw in rats 2. In a subchronic study of rats, the NOAEL of 4 g/kg bw/day was reported with the occurrence of reversible effects on blood coagulation and accretion of the thyroid gland 2. Studies in vitro and in vivo suggest that calcium L-threonate is unlikely to have genotoxic, carcinogenic, or mutagenic potential as L-threonate is an endogenous compound in the body 2. Reproductive and developmental toxicity studies in mice indicated that calcium L-threonate in doses up to 6 g/kg bw/day has no adverse effect on the fertility and the developing fetus, and did not cause maternal toxicity 2.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of Calcium threonate can be decreased when used in combination with (R)-warfarin.
(S)-WarfarinThe therapeutic efficacy of Calcium threonate can be decreased when used in combination with (S)-Warfarin.
4-hydroxycoumarinThe therapeutic efficacy of Calcium threonate can be decreased when used in combination with 4-hydroxycoumarin.
AbciximabThe therapeutic efficacy of Calcium threonate can be decreased when used in combination with Abciximab.
AcenocoumarolThe therapeutic efficacy of Calcium threonate can be decreased when used in combination with Acenocoumarol.
Acetylsalicylic acidThe therapeutic efficacy of Calcium threonate can be decreased when used in combination with Acetylsalicylic acid.
Alpha-1-proteinase inhibitorAlpha-1-proteinase inhibitor may increase the thrombogenic activities of Calcium threonate.
AlteplaseThe therapeutic efficacy of Calcium threonate can be decreased when used in combination with Alteplase.
AmediplaseThe therapeutic efficacy of Calcium threonate can be decreased when used in combination with Amediplase.
Aminocaproic AcidThe risk or severity of adverse effects can be increased when Aminocaproic Acid is combined with Calcium threonate.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

References

General References
  1. Wang HY, Hu P, Jiang J: Pharmacokinetics and safety of calcium L-threonate in healthy volunteers after single and multiple oral administrations. Acta Pharmacol Sin. 2011 Dec;32(12):1555-60. doi: 10.1038/aps.2011.138. Epub 2011 Oct 10. [PubMed:21986570]
  2. European Food Safety Authority (EFSA): Opinion on Calcium L-threonate for use as a source of calcium in food supplements [Link]
External Links
PubChem Compound
13388558
PubChem Substance
347827930
ChemSpider
9337769
MSDS
Download (196 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Tablet, coatedOral
CapsuleOral
Capsule, gelatin coatedOral
TabletOral
Capsule, liquid filledOral
Tablet, chewableOral
Tablet, film coatedOral
Kit
EmulsionTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>300MSDS
water solubilitySolubleAustralian Government Department of Health Therapeutic Goods Administration: Compositional guideline for Calcium L-threonate
Predicted Properties
PropertyValueSource
Water Solubility86.1 mg/mLALOGPS
logP-1.7ALOGPS
logP-2.1ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.82 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity37.18 m3·mol-1ChemAxon
Polarizability11.18 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Sugar acids and derivatives
Alternative Parents
Short-chain hydroxy acids and derivatives / Beta hydroxy acids and derivatives / Monosaccharides / Fatty acids and conjugates / Secondary alcohols / Carboxylic acid salts / Polyols / Organic calcium salts / Monocarboxylic acids and derivatives / Carboxylic acids
show 5 more
Substituents
Beta-hydroxy acid / Sugar acid / Short-chain hydroxy acid / Hydroxy acid / Fatty acid / Monosaccharide / Carboxylic acid salt / Secondary alcohol / Organic calcium salt / Carboxylic acid derivative
show 11 more
Molecular Framework
Not Available
External Descriptors
Not Available

Drug created on December 03, 2015 09:51 / Updated on June 04, 2019 07:17