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Details

Stereochemistry ACHIRAL
Molecular Formula C8H10NO6P
Molecular Weight 247.1422
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRIDOXAL PHOSPHATE ANHYDROUS

SMILES

Cc1c(c(C=O)c(cn1)COP(=O)(O)O)O

InChI

InChIKey=NGVDGCNFYWLIFO-UHFFFAOYSA-N
InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20532028 | https://clinicaltrials.gov/ct2/show/NCT00157729 | https://clinicaltrials.gov/ct2/show/NCT00917293 | https://www.ncbi.nlm.nih.gov/pubmed/12213051 | https://www.ncbi.nlm.nih.gov/pubmed/23510563

Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P) is a coenzyme, the active form of vitamin B6. Pyridoxal 5′-phosphate (PLP) is used as a cofactor for a wide range of enzymes including mitochondrial cysteine desulfurase, cystathionine γ-synthase (CGS), ornithine 4,5-aminomutase (OAM), and d-serine dehydratase. The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates. PLP acts as a coenzyme in all transamination reactions, in various beta-elimination reactions, in the condensation reaction in heme synthesis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3000.0 nM [EC50]
39500.0 nM [EC50]
10.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Correlation of MRI and CT findings with histopathology in hepatic angiomyolipoma.
2001
Testing the tyrosine/catecholamine hypothesis of oral contraceptive-induced psychological side-effects: a controlled study on triphasil.
2001
The positive inotropic and chronotropic effects of evodiamine and rutaecarpine, indoloquinazoline alkaloids isolated from the fruits of Evodia rutaecarpa, on the guinea-pig isolated right atria: possible involvement of vanilloid receptors.
2001 Apr
Determination of mangafodipir trisodium and related impurities in bulk substance and pharmaceutical formulation by ion-pair high-performance liquid chromatography.
2001 Apr
Lack of catalytic activity of a murine mRNA cytoplasmic serine hydroxymethyltransferase splice variant: evidence against alternative splicing as a regulatory mechanism.
2001 Apr 24
Crystal structure of maltose phosphorylase from Lactobacillus brevis: unexpected evolutionary relationship with glucoamylases.
2001 Aug
Production of pyridoxal phosphate by a mutant strain of Schizosaccharomyces pombe.
2001 Aug
Clinical and cost effectiveness of a new hepatocellular MRI contrast agent, mangafodipir trisodium, in the preoperative assessment of liver resectability.
2001 Aug
A bioinformatical approach suggests the function of the autoimmune hepatitis target antigen soluble liver antigen/liver pancreas.
2001 Aug
P2X3 knock-out mice reveal a major sensory role for urothelially released ATP.
2001 Aug 1
Crystal structure of histidinol phosphate aminotransferase (HisC) from Escherichia coli, and its covalent complex with pyridoxal-5'-phosphate and l-histidinol phosphate.
2001 Aug 24
Inhibitory effect of glycation on catalytic activity of alanine aminotransferase.
2001 Feb
Structure-activity relationships of pyridoxal phosphate derivatives as potent and selective antagonists of P2X1 receptors.
2001 Feb 1
Metal ion inhibition of nonenzymatic pyridoxal phosphate catalyzed decarboxylation and transamination.
2001 Jan 17
Serum cystatin C is an independent predictor of total homocysteine levels in stable Korean renal transplant recipients with normal serum creatinine.
2001 Jul
Influence of pyridoxal 5'-phosphate alone and in combination with vigabatrin on brain GABA measured by 1H-NMR-spectroscopy.
2001 Jul 1
The human cDNA for a homologue of the plant enzyme 1-aminocyclopropane-1-carboxylate synthase encodes a protein lacking that activity.
2001 Jul 11
X-ray structure of Escherichia coli pyridoxine 5'-phosphate oxidase complexed with pyridoxal 5'-phosphate at 2.0 A resolution.
2001 Jul 20
Effect of vitamin B6 deficiency on the synthesis and accumulation of S-adenosylhomocysteine and S-adenosylmethionine in rat tissues.
2001 Jun
Stimulation of P2 receptors in the ventral tegmental area enhances dopaminergic mechanisms in vivo.
2001 Jun
Cassette mutagenesis of lysine 130 of human glutamate dehydrogenase. An essential residue in catalysis.
2001 Jun
Sensitivity to meat protein intake and hyperoxaluria in idiopathic calcium stone formers.
2001 Jun
PPADS, an ATP antagonist, attenuates the effects of a moderately intense sound on cochlear mechanics.
2001 Jun
Dephosphorylation of MnDPDP and related compounds by acid and alkaline phosphatase.
2001 Jun
ATP affects both axons and Schwann cells of unmyelinated C fibres.
2001 Jun
Low circulating vitamin B(6) is associated with elevation of the inflammation marker C-reactive protein independently of plasma homocysteine levels.
2001 Jun 12
Role of endogenous ATP at the incision area in a rat model of postoperative pain.
2001 Jun 13
Nucleotide-evoked relaxation of rat vas deferens--a possible role for endogenous ATP released upon alpha(1)-adrenoceptor stimulation.
2001 Jun 22
Homocyst(e)ine metabolism in hemodialysis patients treated with vitamins B6, B12 and folate.
2001 Mar
Crystal structure of threonine synthase from Arabidopsis thaliana.
2001 Mar
Adult hypophosphatasia. Current aspects.
2001 Mar
A placebo-controlled, double-blind, randomised trial of magnesium-pyridoxal-5'-phosphate-glutamate for hypercholesterolaemia and other clinical-chemical risk factors of cardiovascular disease in a primary care setting.
2001 Mar
Effect of phosphate on stability of pyridoxal in the presence of lysine.
2001 Mar
[Comparison of biphasic spiral CT and MnDPDP-enhanced MRI in the detection and characterization of liver lesions].
2001 Mar
Characterisation of P2Y(1)-like receptor in cultured rat pineal glands.
2001 Mar
Resuscitation with a blood substitute abrogates pathologic postinjury neutrophil cytotoxic function.
2001 Mar
Molecular cloning and characterization of the mouse P2Y4 nucleotide receptor.
2001 Mar 30
Structural basis for the function of pyridoxine 5'-phosphate synthase.
2001 Mar 7
Intracellular signaling pathways involved in acetaldehyde-induced collagen and fibronectin gene expression in human hepatic stellate cells.
2001 May
Three-dimensional structure of 2-amino-3-ketobutyrate CoA ligase from Escherichia coli complexed with a PLP-substrate intermediate: inferred reaction mechanism.
2001 May 1
Accelerated functional recovery after neuronal injury by P2 receptor blockade.
2001 May 25
ABA3 is a molybdenum cofactor sulfurase required for activation of aldehyde oxidase and xanthine dehydrogenase in Arabidopsis thaliana.
2001 Nov 2
Cloning, sequencing, heterologous expression, purification, and characterization of adenosylcobalamin-dependent D-ornithine aminomutase from Clostridium sticklandii.
2001 Nov 30
COMT genotype, micronutrients in the folate metabolic pathway and breast cancer risk.
2001 Oct
Crystal structures of 1-aminocyclopropane-1-carboxylate (ACC) synthase in complex with aminoethoxyvinylglycine and pyridoxal-5'-phosphate provide new insight into catalytic mechanisms.
2001 Oct 12
P2Y(AC)(-)-receptor agonists enhance the proliferation of rat C6 glioma cells through activation of the p42/44 mitogen-activated protein kinase.
2001 Sep
ATP P2X receptor-mediated enhancement of glutamate release and evoked EPSCs in dorsal horn neurons of the rat spinal cord.
2001 Sep 1
Properties and interaction of heterologously expressed glutamate decarboxylase isoenzymes GAD(65kDa) and GAD(67kDa) from human brain with ginkgotoxin and its 5'-phosphate.
2001 Sep 13
Smooth muscle does not have a common P2x receptor phenotype: expression, ontogeny and function of P2x1 receptors in mouse ileum, bladder and reproductive systems.
2001 Sep 17
Plants synthesize ethanolamine by direct decarboxylation of serine using a pyridoxal phosphate enzyme.
2001 Sep 21
Patents

Sample Use Guides

500 mgs po bid for 12 weeks.
Route of Administration: Oral
Male Wistar rat (body weight -200 g) was sacrificed by bleeding from the right femoral artery under diethyl ether anesthesia. A thoracic aorta was removed and washed with RPMI 1640 medium to avoid contamination with blood. It was then turned inside out, and cut into short segments of about 1-1.5 mm. Each aortic segment was placed in the center of a well on a 6-well culture plate and covered with 0.5 ml of gel matrix solution reconstituted as described. The solution was allowed to gel at 37°C for 20 min, and then overlaid with 2 ml of RPMI 1640 medium (Gibco, New York, USA) containing 1% of ITS+ (Becton Dickinson Labware, MA, USA). PLP (Pyridoxal phosphate ) was reconstituted in phosphate buffered saline and added on day 1. Incubation was carried out for 10 days in a fully humidified system of 5% C02 in the air at 37°C. The medium was changed on day 7 of the culture.
Name Type Language
PYRIDOXAL PHOSPHATE ANHYDROUS
Common Name English
NSC-82388
Code English
PYRIDOXAL 5-MONOPHOSPHORIC ACID ESTER
Common Name English
3-HYDROXY-5-(HYDROXYMETHYL)-2-METHYLISONICOTINALDEHYDE 5-PHOSPHATE
Common Name English
PYRIDOXAL PHOSPHATE [WHO-DD]
Common Name English
VITAMIN B6 (PYRIDOXAL 5-PHOSPHATE)
Common Name English
PYRIDOXAL 5-PHOSPHATE [MI]
Common Name English
PYRIDOXAL 5-PHOSPHATE
INCI   MI  
INCI  
Official Name English
PYRIDOXAL 5-PHOSPHATE [INCI]
Common Name English
3-HYDROXY-2-METHYL-5-((PHOSPHONOOXY)METHYL)-4-PYRIDINECARBOXALDEHYDE
Systematic Name English
PYRIDOXAL 5'-PHOSPHATE [VANDF]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/18/1983
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
WHO-ATC C10AX07
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
DSLD 2529 (Number of products:1084)
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
Code System Code Type Description
MERCK INDEX
M9362
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB05315
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY
RXCUI
1599827
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY RxNorm
PUBCHEM
1051
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY
EPA CompTox
54-47-7
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY
EVMPD
SUB04137MIG
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY
FDA UNII
F06SGE49M6
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-208-3
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY
CAS
54-47-7
Created by admin on Sat Jun 26 07:27:01 UTC 2021 , Edited by admin on Sat Jun 26 07:27:01 UTC 2021
PRIMARY