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 |
|---|---|---|
| Investigations of tritiated menadiol sodium diphosphate (T-MNDP) as a radioactive drug. | 1974 May |
|
| Concerted action of DT-diaphorase and superoxide dismutase in preventing redox cycling of naphthoquinones: an evaluation. | 2001 Aug |
|
| Redox changes of cytochrome b(559) in the presence of plastoquinones. | 2001 Jan 5 |
|
| Roles of NapF, NapG and NapH, subunits of the Escherichia coli periplasmic nitrate reductase, in ubiquinol oxidation. | 2002 Apr |
|
| Oxygen control of nif gene expression in Klebsiella pneumoniae depends on NifL reduction at the cytoplasmic membrane by electrons derived from the reduced quinone pool. | 2003 Apr |
|
| Effects of site-directed mutations on heme reduction in Escherichia coli nitrate reductase A by menaquinol: a stopped-flow study. | 2003 Dec 9 |
|
| Elimination of the disulfide bridge in the Rieske iron-sulfur protein allows assembly of the [2Fe-2S] cluster into the Rieske protein but damages the ubiquinol oxidation site in the cytochrome bc1 complex. | 2003 Nov 25 |
|
| NapGH components of the periplasmic nitrate reductase of Escherichia coli K-12: location, topology and physiological roles in quinol oxidation and redox balancing. | 2004 Apr 1 |
|
| Role of NAD(P)H:quinone oxidoreductase encoded by drgA gene in reduction of exogenous quinones in cyanobacterium Synechocystis sp. PCC 6803 cells. | 2004 Feb |
|
| Evidence for two different electron transfer pathways in the same enzyme, nitrate reductase A from Escherichia coli. | 2004 Jun |
|
| Menadione kills trophozoites and cysts of Giardia intestinalis. | 2004 May |
|
| Phase I trial of menadiol diphosphate (vitamin K3) in advanced malignancy. | 2005 Jun |
|
| Structural and biochemical evidence for an enzymatic quinone redox cycle in Escherichia coli: identification of a novel quinol monooxygenase. | 2005 Mar 4 |
|
| An unbiased cell morphology-based screen for new, biologically active small molecules. | 2005 May |
|
| Characterization of the Desulfovibrio desulfuricans ATCC 27774 DsrMKJOP complex--a membrane-bound redox complex involved in the sulfate respiratory pathway. | 2006 Jan 10 |
|
| 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 |
|
| UDP-glucuronosyltransferases 1A6 and 1A10 catalyze reduced menadione glucuronidation. | 2008 Jun 27 |
|
| The structure of the leukemia drug imatinib bound to human quinone reductase 2 (NQO2). | 2009 Feb 24 |
|
| Cooperation of NAD(P)H:quinone oxidoreductase 1 and UDP-glucuronosyltransferases reduces menadione cytotoxicity in HEK293 cells. | 2010 Apr 9 |
|
| The alternative complex III of Rhodothermus marinus and its structural and functional association with caa3 oxygen reductase. | 2010 Aug |
|
| Proteogenomic and functional analysis of chromate reduction in Acidiphilium cryptum JF-5, an Fe(III)-respiring acidophile. | 2010 Dec |
|
| Measurement of menadione in urine by HPLC. | 2010 Sep 15 |
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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C943
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
C66084
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
6700-42-1
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
2OVL75B30W
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
300000040292
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
5032
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
Kappadione
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
SUB03141MIG
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
CHEMBL1201348
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
197855
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
DTXSID50217202
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY | |||
|
DB09332
Created by
admin on Fri Dec 15 15:16:14 UTC 2023 , Edited by admin on Fri Dec 15 15:16:14 UTC 2023
|
PRIMARY |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
