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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 of METADOXINE

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
Molecular Formula C8H11NO3
Molecular Weight 169.1778
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C5H7NO3
Molecular Weight 129.114
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Unknown
127998
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
817
Antagonist
2737
Agonist
2637
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
VIBOLIV

Approved Use

The medication is a hepatoprotective agent, prescribed for the treatment of fatty liver due to alcoholism.
Primary
Phase III
651
Unknown

Approved Use

Unknown
Primary
Phase II
1133
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Metadoxine in the treatment of acute and chronic alcoholism: a review.
2003 Sep-Dec
Patents

Patents

FR 2485372 A1
1
JP 55049306
1

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
Substance Class Chemical
Created
by admin
on Sat Dec 17 02:34:10 UTC 2022
Edited
by admin
on Sat Dec 17 02:34:10 UTC 2022
Record UNII
EJQ7M98H5J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METADOXINE
MART.   WHO-DD  
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
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
Code System Code Type Description
EPA CompTox
DTXSID80996053
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
PRIMARY
MESH
C037845
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
PRIMARY
PUBCHEM
115198
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
PRIMARY
EVMPD
SUB14531MIG
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
PRIMARY
ECHA (EC/EINECS)
277-913-8
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
PRIMARY
WIKIPEDIA
Metadoxine
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
PRIMARY
CAS
74536-44-0
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
PRIMARY
FDA UNII
EJQ7M98H5J
Created by admin on Sat Dec 17 02:34:10 UTC 2022 , Edited by admin on Sat Dec 17 02:34:10 UTC 2022
PRIMARY
Related Record Type Details
Structure of PYRIDOXINE
PARENT -> SALT/SOLVATE
Structure of PIDOLIC ACID
PARENT -> SALT/SOLVATE
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