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
Structure for Cocarboxylase (DB01987)
- Weight
- Average: 424.306
Monoisotopic: 424.037142664 - Chemical Formula
- C12H18N4O7P2S
- Synonyms
- Cocarboxylase
- Thiamine diphosphate
- Thiamine pyrophosphate
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Diabetic coma Combination Product in combination with: Pyridoxal phosphate (DB00114), Flavin mononucleotide (DB03247), Nicotinamide (DB02701) •••••••••••• ••••••••• Treatment of Diabetic coma •••••••••••• •••••••••• •••••••• Used in combination to treat Eclampsia Combination Product in combination with: Pyridoxal phosphate (DB00114), Flavin mononucleotide (DB03247), Nicotinamide (DB02701) •••••••••••• ••••••••• Treatment of Hyperemesis gravidarum •••••••••••• •••••••••• •••••••• Used in combination to treat Neuritis Combination Product in combination with: Flavin mononucleotide (DB03247), Pyridoxal phosphate (DB00114), Nicotinamide (DB02701) •••••••••••• ••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ARNA binderHumans UAcetolactate synthase, catabolic cofactorproduct ofKlebsiella pneumoniae UPyruvate dehydrogenase E1 component Not Available Escherichia coli (strain K12) UPyruvate-flavodoxin oxidoreductase Not Available Desulfovibrio africanus UIndole-3-pyruvate decarboxylase Not Available Enterobacter cloacae UCarboxyethylarginine synthase Not Available Streptomyces clavuligerus UTransketolase 1 Not Available Escherichia coli (strain K12) - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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
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 Cocarboxylase chloride XMK8K8EVIU 154-87-0 YXVCLPJQTZXJLH-UHFFFAOYSA-N Cocarboxylase tetrahydrate 749XRF8JS6 68684-55-9 KLOLNRGPRQYTIW-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ADENOPLEX RICHTER Cocarboxylase (38.3 mg) + Cyanocobalamin (0.5 mg) + Pyridoxine hydrochloride (300 mg) Powder, for solution Intramuscular Italian Devices Srl 2014-07-08 Not applicable Italy 
BIOCHETASI Cocarboxylase (47 mg) + Riboflavin-5'-phosphate sodium salt dihydrate (28 mg) + Potassium citrate (1.06 mg) + Pyridoxine hydrochloride (15 mg) + Sodium citrate (56 mg) Injection, solution Intramuscular Alfasigma s.p.a. 2014-07-08 2020-10-13 Italy BIOCHETASI Cocarboxylase (50 mg) + Citric acid (100 mg) + Riboflavin-5'-phosphate sodium salt dihydrate (25 mg) + Potassium citrate (50 mg) + Pyridoxine hydrochloride (12.5 mg) + Sodium citrate (425 mg) Granule, effervescent Oral Alfasigma s.p.a. 2019-10-31 Not applicable Italy BIOCHETASI Cocarboxylase (50 mg) + Citric acid (70 mg) + Riboflavin 5'-phosphate sodium anhydrous (25 mg) + Potassium citrate (50 mg) + Pyridoxine hydrochloride (12.5 mg) + Sodium citrate (425 mg) Tablet, effervescent Oral Alfasigma s.p.a. 2014-07-08 Not applicable Italy BIOCHETASI Cocarboxylase (150 mg) + Riboflavin-5'-phosphate sodium salt dihydrate (50 mg) + Potassium citrate (10 mg) + Pyridoxine hydrochloride (30 mg) + Sodium citrate (250 mg) Suppository Rectal Alfasigma s.p.a. 2014-07-08 Not applicable Italy - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image EnBrace HR Cocarboxylase (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 pellets Oral Jaymac Pharma 2011-08-12 Not applicable US 
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
- External Links
- Human Metabolome Database
- HMDB0062636
- KEGG Compound
- C00068
- PubChem Compound
- 5431
- PubChem Substance
- 46504577
- ChemSpider
- 5238
- 10459
- ChEBI
- 45931
- ChEMBL
- CHEMBL1236235
- Wikipedia
- Thiamine_pyrophosphate
- PDB Entries
- 1umb / 1umc / 1umd / 3ey9 / 3eya / 5z2r / 5z2u
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Withdrawn Treatment Menstrual Related Mood Disorder / Premenstrual Dysphoric Disorder (PMDD) / Premenstrual Syndrome (PMS) / Premenstrual tension with edema 1 3 Recruiting Treatment Acute Decompensated Heart Failure (ADHF) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder, for solution Intramuscular Granule, effervescent Oral Injection, solution Intramuscular Suppository Rectal Tablet, effervescent Oral Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for solution Parenteral Injection, powder, for solution Intravenous Capsule, liquid filled Oral Capsule, delayed release pellets Oral Injection Intramuscular Injection, powder, for solution Intramuscular Kit Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.372 mg/mL ALOGPS logP -1.2 ALOGPS logP -5.9 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 1.78 Chemaxon pKa (Strongest Basic) 6.48 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 171.8 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 94.02 m3·mol-1 Chemaxon Polarizability 36.75 Å3 Chemaxon Number of Rings 2 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
Property Value Probability Human Intestinal Absorption - 0.9991 Blood Brain Barrier + 0.9185 Caco-2 permeable - 0.5574 P-glycoprotein substrate Non-substrate 0.5425 P-glycoprotein inhibitor I Non-inhibitor 0.9236 P-glycoprotein inhibitor II Non-inhibitor 0.9453 Renal organic cation transporter Non-inhibitor 0.8564 CYP450 2C9 substrate Non-substrate 0.8308 CYP450 2D6 substrate Non-substrate 0.8148 CYP450 3A4 substrate Non-substrate 0.6365 CYP450 1A2 substrate Non-inhibitor 0.7333 CYP450 2C9 inhibitor Non-inhibitor 0.7484 CYP450 2D6 inhibitor Non-inhibitor 0.8677 CYP450 2C19 inhibitor Non-inhibitor 0.7037 CYP450 3A4 inhibitor Non-inhibitor 0.9729 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8603 Ames test Non AMES toxic 0.6085 Carcinogenicity Non-carcinogens 0.908 Biodegradation Not ready biodegradable 0.7694 Rat acute toxicity 2.6182 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8781 hERG inhibition (predictor II) Non-inhibitor 0.5906
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-002b-8936000000-119f14d7b717fad84f6b MS/MS Spectrum - , negative LC-MS/MS splash10-03di-2590000000-3b56b15f83f1eb31bbd6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.1411142 predictedDarkChem Lite v0.1.0 [M-H]- 173.08577 predictedDeepCCS 1.0 (2019) [M+H]+ 195.7649142 predictedDarkChem Lite v0.1.0 [M+H]+ 175.54982 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.0736142 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.81786 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Yes
Binder
References
- 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]
- Kind
- Protein
- Organism
- Klebsiella pneumoniae
- Pharmacological action
- Unknown
- Actions
- CofactorProduct 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
- 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]
- 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
- 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
- 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]
- 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]
- 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
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
- 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
- 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]
- 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 at June 13, 2005 13:24 / Updated at February 21, 2021 18:51