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Details

Stereochemistry ACHIRAL
Molecular Formula C11H12O8P2
Molecular Weight 334.1557
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MENADIOL DIPHOSPHATE

SMILES

CC1=C(OP(O)(O)=O)C2=CC=CC=C2C(OP(O)(O)=O)=C1

InChI

InChIKey=JTNHOVZOOVVGHI-UHFFFAOYSA-N
InChI=1S/C11H12O8P2/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)

HIDE SMILES / InChI
Molecular Formula C11H12O8P2
Molecular Weight 334.1557
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: 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
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
A novel membrane-bound respiratory complex from Desulfovibrio desulfuricans ATCC 27774.
2003 Aug 18
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
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
The structure of the leukemia drug imatinib bound to human quinone reductase 2 (NQO2).
2009 Feb 24
The alternative complex III of Rhodothermus marinus and its structural and functional association with caa3 oxygen reductase.
2010 Aug
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 16:15:39 GMT 2023
Edited
by admin
on Fri Dec 15 16:15:39 GMT 2023
Record UNII
GRL65FEU3T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MENADIOL DIPHOSPHATE
Common Name English
2-METHYL-1,4-NAPHTHALENEDIOL DIPHOSPHATE
Systematic Name English
1,4-NAPHTHALENEDIOL, 2-METHYL-, DIPHOSPHATE
Systematic Name English
1,4-NAPHTHALENEDIOL, 2-METHYL-, BIS(DIHYDROGEN PHOSPHATE)
Common Name English
MENADIOL BIS(DIHYDROGEN PHOSPHATE)
Common Name English
MENADIOL PHOSPHATE
Common Name English
1,4-NAPHTHALENEDIOL, 2-METHYL-, 1,4-BIS(DIHYDROGEN PHOSPHATE)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C943
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
Code System Code Type Description
CAS
84-98-0
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID10861785
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
PUBCHEM
8556
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
MESH
C023885
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
RXCUI
360777
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C80887
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
EVMPD
SUB194848
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
SMS_ID
100000181285
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
DRUG BANK
DB14650
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
FDA UNII
GRL65FEU3T
Created by admin on Fri Dec 15 16:15:39 GMT 2023 , Edited by admin on Fri Dec 15 16:15:39 GMT 2023
PRIMARY
Related Record Type Details
Structure of MENADIOL SODIUM DIPHOSPHATE ANHYDROUS
SALT/SOLVATE -> PARENT
Structure of MENADIOL SODIUM DIPHOSPHATE
SALT/SOLVATE -> PARENT
NIH
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