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Details

Stereochemistry ACHIRAL
Molecular Formula C11H8O8P2.4Na
Molecular Weight 422.083
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MENADIOL SODIUM DIPHOSPHATE ANHYDROUS

SMILES

[Na+].[Na+].[Na+].[Na+].CC1=C(OP([O-])([O-])=O)C2=CC=CC=C2C(OP([O-])([O-])=O)=C1

InChI

InChIKey=GZBACHSOZNEZOG-UHFFFAOYSA-J
InChI=1S/C11H12O8P2.4Na/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);;;;/q;4*+1/p-4

HIDE SMILES / InChI
Molecular Formula C11H8O8P2
Molecular Weight 330.1239
Charge -4
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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: 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

1941
158
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Basic research
Unknown

Approved Use

Unknown
Preventive
Approved
8429
Kappadione

Approved Use

Unknown

Launch Date

1981
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/11121919/
unhealthy, 67.5
n = 12
Health Status: unhealthy
Condition: coagulopathies associated with cholestasis
Age Group: 67.5
Sex: M+F
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/11121919/
Sources:
https://pubmed.ncbi.nlm.nih.gov/11121919/
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:
https://pubmed.ncbi.nlm.nih.gov/15868379/
unhealthy, adult
n = 13
Health Status: unhealthy
Condition: advanced malignancy
Age Group: adult
Sex: M+F
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/15868379/
DLT: Anemia, Leukopenia...
Dose limiting toxicities:
Anemia (grade 1, 5 patients)
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)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15868379/
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/15868379/
unhealthy, adult
n = 13
Health Status: unhealthy
Condition: advanced malignancy
Age Group: adult
Sex: M+F
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/15868379/
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:
https://pubmed.ncbi.nlm.nih.gov/15868379/
unhealthy, adult
n = 13
Health Status: unhealthy
Condition: advanced malignancy
Age Group: adult
Sex: M+F
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/15868379/
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:
https://pubmed.ncbi.nlm.nih.gov/15868379/
unhealthy, adult
n = 13
Health Status: unhealthy
Condition: advanced malignancy
Age Group: adult
Sex: M+F
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/15868379/
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:
https://pubmed.ncbi.nlm.nih.gov/15868379/
unhealthy, adult
n = 13
Health Status: unhealthy
Condition: advanced malignancy
Age Group: adult
Sex: M+F
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/15868379/
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:
https://pubmed.ncbi.nlm.nih.gov/15868379/
unhealthy, adult
n = 13
Health Status: unhealthy
Condition: advanced malignancy
Age Group: adult
Sex: M+F
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/15868379/
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:
https://pubmed.ncbi.nlm.nih.gov/15868379/
unhealthy, adult
n = 13
Health Status: unhealthy
Condition: advanced malignancy
Age Group: adult
Sex: M+F
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/15868379/
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:6746
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6746
ChemicalBook
CB2678939
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2678939
MolPort
MolPort-006-111-404
https://www.molport.com/shop/molecule-link/MolPort-006-111-404
ZINC
ZINC000018120050
http://zinc15.docking.org/substances/ZINC000018120050
eMolecules
36553897
https://www.emolecules.com/cgi-bin/more?vid=36553897
PubMed

PubMed

TitleDatePubMed
Investigations of tritiated menadiol sodium diphosphate (T-MNDP) as a radioactive drug.
1974 May
Transient kinetic studies of heme reduction in Escherichia coli nitrate reductase A (NarGHI) by menaquinol.
2003 May 13
Phase I trial of menadiol diphosphate (vitamin K3) in advanced malignancy.
2005 Jun
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
Patents

Patents

003718-004
4
003718-006
4
003718-010
4
005725-001
4
20080118544
5

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:38:43 GMT 2023
Edited
by admin
on Fri Dec 15 16:38:43 GMT 2023
Record UNII
R2L46WE615
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MENADIOL SODIUM DIPHOSPHATE ANHYDROUS
Common Name English
2-METHYL-1,4-NAPHTHALENEDIOL BIS(DIHYDROGEN PHOSPHATE) TETRASODIUM SALT
Common Name English
MENADIOL SODIUM PHOSPHATE
Common Name English
MENADIOL SODIUM DIPHOSPHATE [MI]
Common Name English
1,4-NAPHTHALENEDIOL, 2-METHYL-, 1,4-BIS(DIHYDROGEN PHOSPHATE), SODIUM SALT (1:4)
Common Name English
1,4-NAPHTHALENEDIOL, 2-METHYL-, BIS(DIHYDROGEN PHOSPHATE), TETRASODIUM SALT
Common Name English
Menadiol sodium diphosphate [WHO-DD]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
205-012-1
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY
CAS
131-13-5
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY
FDA UNII
R2L46WE615
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY
PUBCHEM
8555
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY
RXCUI
52549
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID80156832
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY
SMS_ID
100000086418
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY
MERCK INDEX
m7168
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB09332
Created by admin on Fri Dec 15 16:38:43 GMT 2023 , Edited by admin on Fri Dec 15 16:38:43 GMT 2023
PRIMARY
Related Record Type Details
Structure of MENADIOL DIPHOSPHATE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of MENADIOL
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