Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H8O8P2.4Na.6H2O |
| Molecular Weight | 530.1747 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].CC1=C(OP([O-])([O-])=O)C2=CC=CC=C2C(OP([O-])([O-])=O)=C1
InChI
InChIKey=QIWDGSYHBCMXSI-UHFFFAOYSA-J
InChI=1S/C11H12O8P2.4Na.6H2O/c1-7-6-10(18-20(12,13)14)8-4-2-3-5-9(8)11(7)19-21(15,16)17;;;;;;;;;;/h2-6H,1H3,(H2,12,13,14)(H2,15,16,17);;;;;6*1H2/q;4*+1;;;;;;/p-4
DescriptionSources: http://www.netdoctor.co.uk/medicines/liver-kidney-and-urinary-system/a7076/menadiol-diphosphate/http://onlinelibrary.wiley.com/doi/10.1046/j.1365-2036.2000.00880.x/epdfCurator's Comment: description was created based on several sources, including:
http://www.ncbi.nlm.nih.gov/pubmed/3581100
Sources: http://www.netdoctor.co.uk/medicines/liver-kidney-and-urinary-system/a7076/menadiol-diphosphate/http://onlinelibrary.wiley.com/doi/10.1046/j.1365-2036.2000.00880.x/epdf
Curator's Comment: description was created based on several sources, including:
http://www.ncbi.nlm.nih.gov/pubmed/3581100
Menadiol is one of the forms of vitamin K4. Chemically, it is closely related to menadione. Oral menadiol appears to be an effectiv ealternative to intravenous phytomenadione in the correction of coagulopathies associated with obstructiveliver disease. This simplifies the care of patients with deranged clotting times requiring cholangeopancrea-tography, particularly those to be managed as out-patients. Menadiol should receive clinical testing as a chemosensitizing agent in human lymphatic neoplasms (HLN). This effect occurred at a concentration (2.0 micrograms/ml; 4.7 microM) of menadiol which is probably clinically achievable and which did not deplete intracellular glutathione.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.102 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8866040/ |
75 mg single, intravenous dose: 75 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MENADIOL plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
32.453 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8866040/ |
75 mg single, intravenous dose: 75 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MENADIOL plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
27.17 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8866040/ |
75 mg single, intravenous dose: 75 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MENADIOL plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, 67.5 n = 12 Health Status: unhealthy Condition: coagulopathies associated with cholestasis Age Group: 67.5 Sex: M+F Population Size: 12 Sources: |
|
1360 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 1360 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 1360 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult n = 13 Health Status: unhealthy Condition: advanced malignancy Age Group: adult Sex: M+F Population Size: 13 Sources: |
DLT: Anemia, Leukopenia... Dose limiting toxicities: Anemia (grade 1, 5 patients) Sources: Leukopenia (grade 1, 1 patient) Nausea (grade 1, 2 patients) Vomiting (grade 2, 3 patients) Hypersensitivity reaction (grade 1, 2 patients) Hypersensitivity reaction (grade 2, 7 patients) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Leukopenia | grade 1, 1 patient DLT |
1360 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 1360 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 1360 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult n = 13 Health Status: unhealthy Condition: advanced malignancy Age Group: adult Sex: M+F Population Size: 13 Sources: |
| Hypersensitivity reaction | grade 1, 2 patients DLT |
1360 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 1360 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 1360 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult n = 13 Health Status: unhealthy Condition: advanced malignancy Age Group: adult Sex: M+F Population Size: 13 Sources: |
| Nausea | grade 1, 2 patients DLT |
1360 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 1360 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 1360 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult n = 13 Health Status: unhealthy Condition: advanced malignancy Age Group: adult Sex: M+F Population Size: 13 Sources: |
| Anemia | grade 1, 5 patients DLT |
1360 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 1360 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 1360 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult n = 13 Health Status: unhealthy Condition: advanced malignancy Age Group: adult Sex: M+F Population Size: 13 Sources: |
| Vomiting | grade 2, 3 patients DLT |
1360 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 1360 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 1360 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult n = 13 Health Status: unhealthy Condition: advanced malignancy Age Group: adult Sex: M+F Population Size: 13 Sources: |
| Hypersensitivity reaction | grade 2, 7 patients DLT |
1360 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 1360 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 1360 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult n = 13 Health Status: unhealthy Condition: advanced malignancy Age Group: adult Sex: M+F Population Size: 13 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Redox changes of cytochrome b(559) in the presence of plastoquinones. | 2001 Jan 5 |
|
| A novel membrane-bound respiratory complex from Desulfovibrio desulfuricans ATCC 27774. | 2003 Aug 18 |
|
| Phase I trial of menadiol diphosphate (vitamin K3) in advanced malignancy. | 2005 Jun |
|
| A novel chimera: the "truncated hemoglobin-antibiotic monooxygenase" from Streptomyces avermitilis. | 2007 Aug 15 |
|
| 2,5-dihydroxybenzyl and (1,4-dihydroxy-2-naphthyl)methyl, novel reductively armed photocages for the hydroxyl moiety. | 2007 Nov 23 |
|
| Cooperation of NAD(P)H:quinone oxidoreductase 1 and UDP-glucuronosyltransferases reduces menadione cytotoxicity in HEK293 cells. | 2010 Apr 9 |
Sample Use Guides
Adults: Usual therapeutic dose: 10-40mg daily
Children: If, on the recommendation of a physician, a children's dosage is required, it is suggested that 5-20mg daily be given.
The elderly: Recommendations for use in the elderly do not differ from those for other adults.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: The effect of menadiol (vitamin K3) on fresh specimens of human lymphatic neoplasms (HLN) was tested by means of the differential staining cytotoxicity assay. By itself, menadiol was moderately toxic to HLN, but not to normal lymphocytes or non-small cell lung cancer. Menadiol increased the cytotoxic effects of a number of standard agents in HLN.
Unknown
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C943
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| Code System | Code | Type | Description | ||
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C66084
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6700-42-1
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2OVL75B30W
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300000040292
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5032
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Kappadione
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SUB03141MIG
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CHEMBL1201348
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197855
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DTXSID50217202
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DB09332
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
