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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/14611722Curator'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
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 |
---|---|---|---|
Target ID: CHEMBL2096668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1870355 |
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Target ID: P41595 Gene ID: 3357.0 Gene Symbol: HTR2B Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL2111463 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VIBOLIV Approved UseThe medication is a hepatoprotective agent, prescribed for the treatment of fatty liver due to alcoholism. |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.61 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17335665/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17335665/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26.22 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17335665/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17335665/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17335665/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17335665/ |
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
Dose | Population | Adverse 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: |
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
Edited
Mon Mar 31 19:43:11 GMT 2025
by
admin
on
Mon Mar 31 19:43:11 GMT 2025
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Record UNII |
EJQ7M98H5J
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
414513
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100000091630
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DTXSID80996053
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C037845
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115198
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SUB14531MIG
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277-913-8
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Metadoxine
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74536-44-0
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EJQ7M98H5J
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |