METADOXINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H11NO3.C5H7NO3
Molecular Weight	298.2918
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@@H]1CCC(=O)N1.CC2=NC=C(CO)C(CO)=C2O

InChI

InChIKey=RYKKQQUKJJGFMN-HVDRVSQOSA-N

InChI=1S/C8H11NO3.C5H7NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5;7-4-2-1-3(6-4)5(8)9/h2,10-12H,3-4H2,1H3;3H,1-2H2,(H,6,7)(H,8,9)/t;3-/m.0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14611722
Curator's Comment: description was created based on several sources, including https://www.drugs.com/nda/metadoxine_170109.html | http://www.alcobra-pharma.com/products.cfm?productID=142229 | https://www.ncbi.nlm.nih.gov/pubmed/1870355

Metadoxine is an ion pair salt of pyridoxine and pyrrolidon carboxilate (PCA). Metadoxine is predominantly used in developing nations for acute alcohol intoxication. The positive effect of metadoxine on ethanol metabolism can be explained by the maintenance of normal levels of alcohol dehydrogenase during chronic ethanol intake. Metadoxine was investigated against ADHD, but FDA put hold on phase III clinical trials. Metadoxine is also investigated as a treatment for fragile X synsdome.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alcohol dehydrogenase 6 Target ID: CHEMBL2096668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1870355	Modulator 828
5-hydroxytryptamine receptor 2B 12 Target ID: P41595 Gene ID: 3357.0 Gene Symbol: HTR2B Target Organism: Homo sapiens (Human) Sources: http://files.shareholder.com/downloads/AMDA-1SVKDP/4348079336x0x783719/B3794860-4B8C-41EF-9273-41E23ADFD8AD/44310-AA-1438_USPMH_2014_310_v14.pdf	Antagonist 2778
GABA-B receptor 32 Target ID: CHEMBL2111463 Sources: http://files.shareholder.com/downloads/AMDA-1SVKDP/4348079336x0x783719/B3794860-4B8C-41EF-9273-41E23ADFD8AD/44310-AA-1438_USPMH_2014_310_v14.pdf	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Alcoholic hepatitis 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14611722	Primary	Approved 8429	VIBOLIV Approved Use The medication is a hepatoprotective agent, prescribed for the treatment of fatty liver due to alcoholism.
Attention deficit hyperactivity disorder 68 Sources: https://clinicaltrials.gov/ct2/show/NCT02059642	Primary	Phase III 656	Unknown Approved Use Unknown
Fragile X syndrome 7 Sources: https://clinicaltrials.gov/ct2/show/NCT02126995	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of pyridoxine-pyrrolidon-carboxylate on hepatic and cerebral ATP levels in ethanol treated rats.	1980 Jun	7192694
Action of metadoxine on isolated human and rat alcohol and aldehyde dehydrogenases. Effect on enzymes in chronic ethanol-fed rats.	1991 Jan-Feb	1870355
Metadoxine in the treatment of acute and chronic alcoholism: a review.	2003 Sep-Dec	14611722

Patents

Sample Use Guides

In Vivo Use Guide

For treatment of fatty liver due to alcoholism, metadoxine could be administered orally, intravenously or intramuscularly. The recommended dose for oral administration is 0.5-1 g/day. The recommended dose for intravenous or intramuscular administration is 300-600 mg/day.

Route of Administration: Other

In Vitro Use Guide

The rat stomach fundus bioassay was used to assess the functional activity of metadoxine at the 5-HT2B receptor. For the antagonist assay, ex vivo tissues were repeatedly exposed to a submaximal concentration of the reference agonist 5-carboxamidotryptamine (5-CT, 0.3 μM) to obtain a control contraction, then tissues were washed. This sequence was reproduced at 40-minute intervals in the presence of increasing concentrations of metadoxine (1, 5, 10, and 20 mg/mL) added 30 minutes before the addition of 5-CT

Name

Type

Language

METADOXINE

Common Name

English

METADOXINE [MART.]

Common Name

English

METASIN

Common Name

English

5-OXO-L-PROLINE COMPOUND WITH 5-HYDROXY-6-METHYLPYRIDINE-3,4-DIMETHANOL (1:1)

Systematic Name

English

PYRIDOXINE PYROGLUTAMATE

Common Name

English

Metadoxine [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

414513