Page last updated: 2024-12-04

thiamine pyrophosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Occurs in Manufacturing Related Drugs Related Conditions Protein Interactions Research Growth

Description

Thiamine Pyrophosphate: 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. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

thiamine(1+) diphosphate chloride : An organic chloride salt of thiamine(1+) diphosphate. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Thiamine Triphosphate: 3-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,8,8-tetrahydroxy-3,5,7-trioxa-4,6,8-triphosphaoct-1-yl)thiazolium hydroxide, inner salt, P,P',P''-trioxide. The triphosphate ester of thiamine. In Leigh's disease, this compound is present in decreased amounts in the brain due to a metabolic block in its formation. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

thiamine(1+) triphosphate(4-) : Trianion of thiamine(1+) diphosphate arising from deprotonation of the four OH groups of the triphosphate. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID9068
CHEMBL ID2104121
CHEBI ID18290
SCHEMBL ID21111
MeSH IDM0021323
PubMed CID15938964
CHEBI ID58938
MeSH IDM0021323

Synonyms (111)

Synonym
thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)-, chloride
thiamine diphosphate chloride
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(diphosphooxy)ethyl]-4-methyl-1,3-thiazol-3-ium chloride
coenzymate
CHEBI:18290 ,
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-diphosphoethyl)-4-methyl-1,3-thiazolium chloride
cocarboxylasum
cocarboxilasa
cocarboxylase
thiamine(1+) diphosphate chloride
thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-3,5-dioxa-4,6-diphosphahex-1-yl)-, chloride, p,p'-dioxide
thiamine pyrophosphate
154-87-0
thiamine pyrophosphate, >=95%
coenzymate (tn)
cocarboxylase (jan/inn)
D01225
thiamine pyrophosphoric ester
thiaminepyrophosphate
metabolase
coxylase
bivitasi
b-neurox
cocarboxylasum [inn-latin]
einecs 205-836-1
co-carboxylase [ban]
thiamine, trihydrogen pyrophosphate (ester)
berolase
coenbione
thiaminpyrophosphate
thiamine-pp
biosyth
thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)-, chloride
nutrase
cocarboxilasa [inn-spanish]
tdp (thiamin ester)
pyrolase
pyruvodehydrase
diphosphothiamine
tpp (coenzyme)
cocarbina
thiaminediphosphate
ai3-63012
co-bi
cocarboxil
farmaneurina
diphosphothiamin
bioxylasi
cocarboxylase [inn:dcf:jan]
thiamine pyrophosphate chloride
vitamin b1 pyrophosphoric acid ester chloride
T0183
cothiamine
xmk8k8eviu ,
coenzyme-b
magnesiocarbina
thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)-, chloride (1:1)
bioxilasi
stadion
coneurina
b-carbossilasi
unii-xmk8k8eviu
vitamin b1 pyrophosphate chloride
co-carboxylase
tiaxin
cocarvit
dtxsid6046262 ,
cas-154-87-0
dtxcid4026262
tox21_111940
cocarboxylase chloride
AKOS015913954
aneurinepyrophosphoric acid
thiamine diphosphate [inci]
thiamine diphosphoric acid ester chloride
thiamine pyrophosphoric acid ester chloride
thiamine diphosphate ester chloride
thiamine diphosphate [mi]
cocarboxylase hydrochloride [who-dd]
902463-63-2
cocarboxylase [jan]
CHEMBL2104121
SCHEMBL21111
mfcd00038740
thiamine pyrophosphate, pharmaceutical secondary standard; certified reference material
J-009154
aneurinepyrophosphoric acid, cocarboxylase
FT-0753118
YXVCLPJQTZXJLH-UHFFFAOYSA-N
Q60998678
3-((4-amino-2-methylpyrimidin-5-yl)methyl)-5-(2-((hydroxy(phosphonooxy)phosphoryl)oxy)ethyl)-4-methylthiazol-3-ium chloride
3-((4-amino-2-methylpyrimidin-5-yl)methyl)-5-(2-(hydroxy(phosphonooxy)phosphoryloxy)ethyl)-4-methylthiazol-3-ium chloride
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium chloride
BCP14885
2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate;chloride
CS-0059498
HY-113076
H11938
AS-56027
A883690
SY073227
NCHEMBIO867-COMP3 ,
15666-52-1
thiamine triphosphate
thiamine(1+) triphosphate(4-)
CHEBI:58938
thiamine triphosphate trianion
thiamine triphosphate(3-)
Q27126357
[[2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1-thia-3-azoniacyclopenta-2,4-dien-5-yl]et
[[2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethoxy-oxidophosphoryl]oxy-oxidophosphoryl] phosphate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Preadministration of thiamin and especially of thiamin diphosphate decreased the toxic effect of cyclophosphamide."( [Metabolism and toxicity of various xenobiotics in vitamin B1 deficiency and after administration of thiamine and thiamine diphosphate].
Lutsiuk, NB; Lychko, AP; Pentiuk, AA,
)
0.13

Pharmacokinetics

ExcerptReferenceRelevance
" Thiamine diphosphate administered intraperitoneally in a dose of 10 mg/kg (one time a day for a week) does not change pharmacokinetic and analgesic effect of naproxene."( [The modification of the pharmacokinetics and analgesic effect of naproxen by cimetidine, phenobarbital and thiamine diphosphate].
Pentiuk, AA; Stanislavchuk, NA; Vovk, OG,
)
0.13

Bioavailability

ExcerptReferenceRelevance
" Recent evidences have shown that the administration of thiamine or lipid-soluble derivatives, such as benfotiamine (developed to improve the bioavailability of thiamine), has positive effects in the diabetic patient (after thiamine is transformed into TPP)."( Could thiamine pyrophosphate be a regulator of the nitric oxide synthesis in the endothelial cell of diabetic patients?
Alcázar-Leyva, S; Alvarado-Vásquez, N, 2011
)
0.37
" Systemic bioavailability was demonstrated through eradication of Helicobacter pylori in a mouse infection model."( Preclinical studies of amixicile, a systemic therapeutic developed for treatment of Clostridium difficile infections that also shows efficacy against Helicobacter pylori.
Bassaganya-Riera, J; Bruce, AM; Burgess, SL; Guerrant, RL; Hoffman, PS; Hontecillas, R; Macdonald, TL; Olekhnovich, I; Viladomiu, M; Warren, CA, 2014
)
0.4
" The present data suggest that thiamine precursors with high bioavailability might be useful as a complementary therapy in several neuropsychiatric disorders."( Thiamine and benfotiamine prevent stress-induced suppression of hippocampal neurogenesis in mice exposed to predation without affecting brain thiamine diphosphate levels.
Anthony, DC; Bazhenova, N; Bettendorff, L; Caron, N; Coumans, B; Gorlova, A; Lakaye, B; Malgrange, B; Markova, N; Pavlov, D; Sambon, M; Shevtsova, E; Strekalova, T; Svistunov, A; Vignisse, J; Wins, P, 2017
)
0.46
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
" Though a promising nutraceutical approach for cancer therapy, thiamine's low bioavailability may limit clinical effectiveness."( Thiamine mimetics sulbutiamine and benfotiamine as a nutraceutical approach to anticancer therapy.
Bartlett, MG; Byrnes, CC; Jonus, HC; Kim, J; Said, HM; Valle, ML; Zastre, JA, 2020
)
0.56
" Understanding the consequences of this feedback inhibition is essential for developing reliable methods for measuring TPK activity in tissue extracts and for optimizing the therapeutic use of thiamine and its prodrugs with higher bioavailability under pathological conditions."( Product inhibition of mammalian thiamine pyrophosphokinase is an important mechanism for maintaining thiamine diphosphate homeostasis.
Alhama-Riba, J; Bettendorff, L; Brans, A; Pavlova, O; Sambon, M; Wins, P, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" dosing of thiamine (0."( Protection against misonidazole-induced neuropathy in rats: a biochemical assessment.
Dewar, AJ; Rose, GP; Stratford, IJ, 1983
)
0.27
" Thiamin, given at a dosage above the requirement of the vitamin for chickens, did not reduce the anorexia or the TPP effect of furazolidone-treated birds, although it stimulated the feed intake and growth of birds on unmedicated feed."( Anorexia and antagonism of thiamin utilization in poultry treated with furazolidone.
Ali, BH; Bartlet, AL, 1982
)
0.26
" A dose-response dependence was observed in MTT assay."( Cell damage through pentose phosphate pathway in fetus fibroblast cells exposed to methyl mercury.
Amoli, JS; Barin, A; Ebrahimi-Rad, M; Sadighara, P, 2011
)
0.37
" TPP, especially at a dosage of 20 mg/kg, significantly reduced TBARS and MPO levels that increase with cisplatin administration compared with the thiamine group, while TPP significantly increases GSH and SOD levels."( An investigation of the effect of thiamine pyrophosphate on cisplatin-induced oxidative stress and DNA damage in rat brain tissue compared with thiamine: thiamine and thiamine pyrophosphate effects on cisplatin neurotoxicity.
Cayir, A; Cetin, N; Siltelioglu Turan, I; Suleyman, H; Tan, H; Turan, MI, 2014
)
0.4
" Administration of a single 200-mg dose of intravenous thiamine achieved supraphysiological concentrations of thiamine pyrophosphate, with repeated dosing sustaining this effect."( Relationship of blood thiamine pyrophosphate to plasma phosphate and the response to enteral nutrition plus co-administration of intravenous thiamine during critical illness.
Abdelhamid, YA; Ankravs, M; Bellomo, R; Byrne, KM; Clancy, A; Collie, JTB; Deane, AM; Finnis, ME; Greaves, R; Jiang, A; Tascone, B, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Occurs in Manufacturing (1 Product(s))

Product Categories

Product CategoryProducts
Vitamins & Supplements1

Products

ProductBrandCategoryCompounds Matched from IngredientsDate Retrieved
Bluebonnet Nutrition CellularActive® Coenzyme B-Complex -- 100 Vcaps®Bluebonnet NutritionVitamins & SupplementsPABA, Biotin, Choline, riboflavin 5' phosphate, inositol hexanicotinate, Inositol, Vitamin B3, niacinamide, PABA, Pantothenic Acid, pyridoxal 5' phosphate, pyridoxine HCl, Vitamin B6, Vitamin B2, cocarboxylase, Vitamin B1, Vitamin B12, Vitamin B62024-11-29 10:47:42

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metaboliteAny fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
organic chloride salt
vitamin B1Any member of the group of 1,3-thiazolium cations that exhibit biological activity against vitamin B1 deficiency in animals. Symptoms of vitamin B1 deficiency include constipation, loss of apetite, fatigue, nausea, delirium, blurry vision and muscle weakness. Severe vitamin B1 deficiency can also lead to a disease known as beriberi. Vitamin B1 consists of the vitamer thiamin and its acid, aldehyde and phosphorylated derivatives (and their corresponding ionized, salt and hydrate forms).
organophosphate oxoanionAn organic phosphoric acid derivative in which one or more oxygen atoms of the phosphate group(s) has been deprotonated.
vitamin B1Any member of the group of 1,3-thiazolium cations that exhibit biological activity against vitamin B1 deficiency in animals. Symptoms of vitamin B1 deficiency include constipation, loss of apetite, fatigue, nausea, delirium, blurry vision and muscle weakness. Severe vitamin B1 deficiency can also lead to a disease known as beriberi. Vitamin B1 consists of the vitamer thiamin and its acid, aldehyde and phosphorylated derivatives (and their corresponding ionized, salt and hydrate forms).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (3)

PathwayProteinsCompounds
Renz2020 - GEM of Human alveolar macrophage with SARS-CoV-20490
thiamine triphosphate metabolism08
thiamin triphosphate metabolism08

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
potassium voltage-gated channel subfamily H member 2 isoform dHomo sapiens (human)Potency12.58930.01789.637444.6684AID588834
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)Ki23,485.00000.00121.25638.9000AID1147919; AID1147920; AID1147921; AID1147922
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
1-deoxy-D-xylulose-5-phosphate synthaseMycobacterium tuberculosis H37RvKd3.10003.10003.10003.1000AID1163702
1-deoxy-D-xylulose-5-phosphate synthaseDeinococcus radiodurans R1 = ATCC 13939 = DSM 20539Kd0.11400.11400.11400.1140AID1163701
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1147920Noncompetitive inhibition of electric eel AChE using acetylthiocholine chloride as substrate at pH 7 by Michaelis-Menten plot analysis1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Inhibition of acetylcholinesterase by thiamine. A structure-function study.
AID1147921Competitive inhibition of electric eel AChE using acetylthiocholine chloride as substrate at pH 8.25 by Michaelis-Menten plot analysis1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Inhibition of acetylcholinesterase by thiamine. A structure-function study.
AID1147922Noncompetitive inhibition of electric eel AChE using acetylthiocholine chloride as substrate at pH 8.25 by Michaelis-Menten plot analysis1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Inhibition of acetylcholinesterase by thiamine. A structure-function study.
AID1163702Binding affinity to Mycobacterium tuberculosis DXS2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Development of inhibitors of the 2C-methyl-D-erythritol 4-phosphate (MEP) pathway enzymes as potential anti-infective agents.
AID1163701Binding affinity to Deinococcus radiodurans DXS2014Journal of medicinal chemistry, Dec-11, Volume: 57, Issue:23
Development of inhibitors of the 2C-methyl-D-erythritol 4-phosphate (MEP) pathway enzymes as potential anti-infective agents.
AID1147919Competitive inhibition of electric eel AChE using acetylthiocholine chloride as substrate at pH 7 by Michaelis-Menten plot analysis1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Inhibition of acetylcholinesterase by thiamine. A structure-function study.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (2,260)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901415 (62.61)18.7374
1990's222 (9.82)18.2507
2000's275 (12.17)29.6817
2010's258 (11.42)24.3611
2020's90 (3.98)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials29 (1.19%)5.53%
Trials0 (0.00%)5.53%
Reviews124 (5.07%)6.00%
Reviews10 (7.30%)6.00%
Case Studies33 (1.35%)4.05%
Case Studies2 (1.46%)4.05%
Observational4 (0.16%)0.25%
Observational0 (0.00%)0.25%
Other2,254 (92.23%)84.16%
Other125 (91.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Pirofosfato de Tiamina Como Coadyuvante de la Metformina en el Tratamiento de Pacientes Con Diabetes Mellitus Tipo 2 [NCT04053621]92 participants (Anticipated)Interventional2021-01-31Not yet recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]