Cocarboxylase

Identification

Brand Names
EnBrace HR, EnLyte
Generic Name
Cocarboxylase
DrugBank Accession Number
DB01987
Background

The coenzyme form of Vitamin B1 present in many animal tissues. It is a required intermediate in the pyruvate dehydrogenase complex and the ketoglutarate dehydrogenase complex.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 424.306
Monoisotopic: 424.037142664
Chemical Formula
C12H18N4O7P2S
Synonyms
  • Cocarboxylase
  • Thiamine diphosphate
  • Thiamine pyrophosphate

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPyruvate dehydrogenase E1 componentNot AvailableEscherichia coli (strain K12)
UPyruvate-flavodoxin oxidoreductaseNot AvailableDesulfovibrio africanus
UIndole-3-pyruvate decarboxylaseNot AvailableEnterobacter cloacae
UCarboxyethylarginine synthaseNot AvailableStreptomyces clavuligerus
UTransketolase 1Not AvailableEscherichia coli (strain K12)
UAcetolactate synthase, catabolic
cofactor
product of
Klebsiella pneumoniae
ARNA
binder
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
Adverseeffects
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Toxicity

Not Available

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.
Not Available
Food Interactions
  • Take with or without food. Many different products contain cocarboxylase; refer to the product monograph for more specific instruction. EnBrace HR and EnLyte products should be taken on an empty stomach.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cocarboxylase chlorideXMK8K8EVIU154-87-0YXVCLPJQTZXJLH-UHFFFAOYSA-N
Cocarboxylase tetrahydrate749XRF8JS668684-55-9KLOLNRGPRQYTIW-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
PramLyteCocarboxylase (25 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Betaine (500 ug/1) + Citric acid monohydrate (1.83 mg/1) + Cobamamide (50 ug/1) + Escitalopram oxalate (10 mg/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic acid (1 mg/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (7 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal phosphate (25 ug/1) + Sodium citrate (3.67 mg/1) + Zinc ascorbate (1 mg/1)KitOralAllegis Pharmaceuticals, LLC2015-09-112016-01-04US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EnBrace HRCocarboxylase (25 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Betaine (500 ug/1) + Cobamamide (50 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic acid (1 mg/1) + Magnesium L-threonate (1 mg/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (5.23 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal phosphate (25 ug/1) + Zinc ascorbate (1 mg/1)Capsule, delayed release pelletsOralJaymac Pharmaceuticals, Llc2011-08-12Not applicableUS flag
EnLyteCocarboxylase (25 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Betaine (500 ug/1) + Citric acid monohydrate (1.83 mg/1) + Cobamamide (50 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic acid (1 mg/1) + Magnesium L-threonate (1 mg/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (7 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal phosphate (25 ug/1) + Sodium citrate (3.67 mg/1) + Zinc ascorbate (1 mg/1)Capsule, delayed release pelletsOralJaymac Pharmaceuticals Llc2011-08-12Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Thiamine phosphates
Alternative Parents
Organic pyrophosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives / 4,5-disubstituted thiazoles / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organooxygen compounds
show 3 more
Substituents
4,5-disubstituted 1,3-thiazole / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiamine phosphate (CHEBI:45931)
Affected organisms
Not Available

Chemical Identifiers

UNII
Q57971654Y
CAS number
136-08-3
InChI Key
AYEKOFBPNLCAJY-UHFFFAOYSA-N
InChI
InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)
IUPAC Name
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(hydrogen phosphonatooxy)(hydroxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
SMILES
CC1=C(CCO[P@](O)(=O)O[P@](O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N

References

General References
Not Available
Human Metabolome Database
HMDB0062636
KEGG Compound
C00068
PubChem Compound
5431
PubChem Substance
46504577
ChemSpider
5238
RxNav
10459
ChEBI
45931
ChEMBL
CHEMBL1236235
Wikipedia
Thiamine_pyrophosphate
PDB Entries
1umb / 1umc / 1umd / 3ey9 / 3eya / 5z2r / 5z2u

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4WithdrawnTreatmentMenstrual Related Mood Disorder / Premenstrual Dysphoric Disorder ( PMDD) / Premenstrual Syndrome (PMS) / Premenstrual tension with edema1
3RecruitingTreatmentAcute Decompensated Heart Failure (ADHF)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Powder, for solutionIntramuscular
Granule, effervescentOral
Injection, solutionIntramuscular
SuppositoryRectal
Tablet, effervescentOral
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionParenteral
Injection, powder, for solutionIntravenous
Capsule, delayed release pelletsOral
InjectionIntramuscular
Injection, powder, for solutionIntramuscular
KitOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.372 mg/mLALOGPS
logP-1.2ALOGPS
logP-5.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area171.8 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.02 m3·mol-1ChemAxon
Polarizability35.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9991
Blood Brain Barrier+0.9185
Caco-2 permeable-0.5574
P-glycoprotein substrateNon-substrate0.5425
P-glycoprotein inhibitor INon-inhibitor0.9236
P-glycoprotein inhibitor IINon-inhibitor0.9453
Renal organic cation transporterNon-inhibitor0.8564
CYP450 2C9 substrateNon-substrate0.8308
CYP450 2D6 substrateNon-substrate0.8148
CYP450 3A4 substrateNon-substrate0.6365
CYP450 1A2 substrateNon-inhibitor0.7333
CYP450 2C9 inhibitorNon-inhibitor0.7484
CYP450 2D6 inhibitorNon-inhibitor0.8677
CYP450 2C19 inhibitorNon-inhibitor0.7037
CYP450 3A4 inhibitorNon-inhibitor0.9729
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8603
Ames testNon AMES toxic0.6085
CarcinogenicityNon-carcinogens0.908
BiodegradationNot ready biodegradable0.7694
Rat acute toxicity2.6182 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8781
hERG inhibition (predictor II)Non-inhibitor0.5906
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , negativeLC-MS/MSsplash10-03di-2590000000-3b56b15f83f1eb31bbd6

Targets

Drugtargets2
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pyruvate dehydrogenase activity
Specific Function
Component of the pyruvate dehydrogenase (PDH) complex, that catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2).
Gene Name
aceE
Uniprot ID
P0AFG8
Uniprot Name
Pyruvate dehydrogenase E1 component
Molecular Weight
99667.78 Da
References
  1. Ali MS, Shenoy BC, Eswaran D, Andersson LA, Roche TE, Patel MS: Identification of the tryptophan residue in the thiamin pyrophosphate binding site of mammalian pyruvate dehydrogenase. J Biol Chem. 1995 Mar 3;270(9):4570-4. doi: 10.1074/jbc.270.9.4570. [Article]
  2. Jacobia SJ, Korotchkina LG, Patel MS: Characterization of a missense mutation at histidine-44 in a pyruvate dehydrogenase-deficient patient. Biochim Biophys Acta. 2002 Jan 2;1586(1):32-42. doi: 10.1016/s0925-4439(01)00083-7. [Article]
  3. Patel MS, Korotchkina LG: Regulation of mammalian pyruvate dehydrogenase complex by phosphorylation: complexity of multiple phosphorylation sites and kinases. Exp Mol Med. 2001 Dec 31;33(4):191-7. doi: 10.1038/emm.2001.32. [Article]
Kind
Protein
Organism
Desulfovibrio africanus
Pharmacological action
Unknown
General Function
Thiamine pyrophosphate binding
Specific Function
Catalyzes the ferredoxin-dependent oxidative decarboxylation of pyruvate. Required for the transfer of electrons from pyruvate to ferredoxin (PubMed:9294422, PubMed:7612653). Ferredoxin I and ferre...
Gene Name
por
Uniprot ID
P94692
Uniprot Name
Pyruvate synthase
Molecular Weight
133679.405 Da
Kind
Protein
Organism
Enterobacter cloacae
Pharmacological action
Unknown
General Function
Thiamine pyrophosphate binding
Specific Function
Not Available
Gene Name
ipdC
Uniprot ID
P23234
Uniprot Name
Indole-3-pyruvate decarboxylase
Molecular Weight
60022.965 Da
Kind
Protein
Organism
Streptomyces clavuligerus
Pharmacological action
Unknown
General Function
Thiamine pyrophosphate binding
Specific Function
Involved in the biosynthesis of the beta-lactamase inhibitor, clavulanic acid. Catalyzes the thiamine diphosphate (ThDP) dependent condensation of D-glyceraldehyde-3-phosphate (D-G3P) with L-argini...
Gene Name
ceaS
Uniprot ID
Q9LCV9
Uniprot Name
N(2)-(2-carboxyethyl)arginine synthase
Molecular Weight
60906.59 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Transketolase activity
Specific Function
Catalyzes the reversible transfer of a two-carbon ketol group from sedoheptulose-7-phosphate to glyceraldehyde-3-phosphate, producing xylulose-5-phosphate and ribose-5-phosphate. Catalyzes the tran...
Gene Name
tktA
Uniprot ID
P27302
Uniprot Name
Transketolase 1
Molecular Weight
72211.14 Da
Kind
Protein
Organism
Klebsiella pneumoniae
Pharmacological action
Unknown
Actions
Cofactor
Product of
General Function
Thiamine pyrophosphate binding
Specific Function
Not Available
Gene Name
budB
Uniprot ID
P27696
Uniprot Name
Acetolactate synthase, catabolic
Molecular Weight
60337.52 Da
References
  1. Wang JG, Lee PK, Dong YH, Pang SS, Duggleby RG, Li ZM, Guddat LW: Crystal structures of two novel sulfonylurea herbicides in complex with Arabidopsis thaliana acetohydroxyacid synthase. FEBS J. 2009 Mar;276(5):1282-90. doi: 10.1111/j.1742-4658.2009.06863.x. [Article]
  2. Sommer B, von Moeller H, Haack M, Qoura F, Langner C, Bourenkov G, Garbe D, Loll B, Bruck T: Detailed structure-function correlations of Bacillus subtilis acetolactate synthase. Chembiochem. 2015 Jan 2;16(1):110-8. doi: 10.1002/cbic.201402541. Epub 2014 Nov 13. [Article]
Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Binder
References
  1. Furniss S, Grover N: Thermodynamic examination of the pyrophosphate sensor helix in the thiamine pyrophosphate riboswitch. RNA. 2011 Apr;17(4):710-7. doi: 10.1261/rna.2263211. Epub 2011 Mar 2. [Article]

Enzymes

Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Thiamine pyrophosphate binding
Specific Function
Not Available
Gene Name
mdlC
Uniprot ID
P20906
Uniprot Name
Benzoylformate decarboxylase
Molecular Weight
56354.475 Da
References
  1. Weiss PM, Garcia GA, Kenyon GL, Cleland WW, Cook PF: Kinetics and mechanism of benzoylformate decarboxylase using 13C and solvent deuterium isotope effects on benzoylformate and benzoylformate analogues. Biochemistry. 1988 Mar 22;27(6):2197-205. doi: 10.1021/bi00406a058. [Article]
Kind
Protein
Organism
Lactobacillus plantarum (strain ATCC BAA-793 / NCIMB 8826 / WCFS1)
Pharmacological action
Unknown
General Function
Thiamine pyrophosphate binding
Specific Function
Important for the aerobic growth. Decarboxylates pyruvate in four steps. The energy released is partially stored in acetyl phosphate.
Gene Name
pox5
Uniprot ID
P37063
Uniprot Name
Pyruvate oxidase
Molecular Weight
66110.5 Da
References
  1. Muller YA, Schulz GE: Structure of the thiamine- and flavin-dependent enzyme pyruvate oxidase. Science. 1993 Feb 12;259(5097):965-7. doi: 10.1126/science.8438155. [Article]
  2. Sedewitz B, Schleifer KH, Gotz F: Purification and biochemical characterization of pyruvate oxidase from Lactobacillus plantarum. J Bacteriol. 1984 Oct;160(1):273-8. [Article]

Drug created on June 13, 2005 13:24 / Updated on February 21, 2021 18:51