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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=C(O)C(CO)=C(CO)C=N2

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 C5H7NO3
Molecular Weight 129.114
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIBOLIV

Approved Use

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

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.61 mg/L
900 mg single, intravenous
dose: 900 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.61 mg/L
900 mg single, intravenous
dose: 900 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
26.22 mg × h/L
900 mg single, intravenous
dose: 900 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
23.43 mg × h/L
900 mg single, intravenous
dose: 900 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.85 h
900 mg single, intravenous
dose: 900 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.77 h
900 mg single, intravenous
dose: 900 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1800 mg 2 times / day multiple, intravenous
Highest studied dose
Dose: 1800 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 1800 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
2000 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2000 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2000 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Effects of pyridoxine-pyrrolidon-carboxylate on hepatic and cerebral ATP levels in ethanol treated rats.
1980 Jun
Metadoxine in the treatment of acute and chronic alcoholism: a review.
2003 Sep-Dec
Patents

Sample Use Guides

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
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 Mon Mar 31 19:43:11 GMT 2025
Edited
by admin
on Mon Mar 31 19:43:11 GMT 2025
Record UNII
EJQ7M98H5J
Record Status Validated (UNII)
Record Version
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Name Type Language
METADOXINE
MART.   WHO-DD  
Common Name English
METADOXINE [MART.]
Preferred 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 Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
Code System Code Type Description
SMS_ID
100000091630
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID80996053
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
MESH
C037845
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
PUBCHEM
115198
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
EVMPD
SUB14531MIG
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
ECHA (EC/EINECS)
277-913-8
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
WIKIPEDIA
Metadoxine
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
CAS
74536-44-0
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
FDA UNII
EJQ7M98H5J
Created by admin on Mon Mar 31 19:43:11 GMT 2025 , Edited by admin on Mon Mar 31 19:43:11 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE