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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
Structure of MENADIOL SODIUM DIPHOSPHATE

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

HIDE SMILES / InChI

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
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
Transient kinetic studies of heme reduction in Escherichia coli nitrate reductase A (NarGHI) by menaquinol.
2003 May 13
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
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
Characterization of the Desulfovibrio desulfuricans ATCC 27774 DsrMKJOP complex--a membrane-bound redox complex involved in the sulfate respiratory pathway.
2006 Jan 10
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
Cooperation of NAD(P)H:quinone oxidoreductase 1 and UDP-glucuronosyltransferases reduces menadione cytotoxicity in HEK293 cells.
2010 Apr 9
Measurement of menadione in urine by HPLC.
2010 Sep 15
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
Name Type Language
MENADIOL SODIUM DIPHOSPHATE
ORANGE BOOK   USP   VANDF  
Common Name English
2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate) tetrasodium salt, hexahydrate
Common Name English
PROCOAGULO
Brand Name English
KAPPADIONE
Brand Name English
MENADIOL SODIUM DIPHOSPHATE HEXAHYDRATE
Common Name English
MENADIOL SODIUM DIPHOSPHATE [USP IMPURITY]
Common Name English
SYNKA-VIT
Brand Name English
THYLOKAY
Brand Name English
SYNKAYVITE
Brand Name English
1,4-NAPHTHALENEDIOL, 2-METHYL-, BIS(DIHYDROGEN PHOSPHATE), TETRASODIUM SALT, HEXAHYDRATE
Common Name English
MENADIOL SODIUM DIPHOSPHATE [VANDF]
Common Name English
CAIDRINE
Brand Name English
MENADIOL SODIUM DIPHOSPHATE [ORANGE BOOK]
Common Name English
SYNKAVITE
Brand Name English
MENADIOL SODIUM PHOSPHATE HEXAHYDRATE
Common Name English
KATIV
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C943
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C66084
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
CAS
6700-42-1
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
FDA UNII
2OVL75B30W
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
SMS_ID
300000040292
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
DRUG CENTRAL
5032
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
WIKIPEDIA
Kappadione
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
EVMPD
SUB03141MIG
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201348
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
PUBCHEM
197855
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID50217202
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
DRUG BANK
DB09332
Created by admin on Fri Dec 15 15:16:14 GMT 2023 , Edited by admin on Fri Dec 15 15:16:14 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of MENADIOL
PARENT (SALT/SOLVATE)
Structure of MENADIOL DIPHOSPHATE
NIH
NCATS
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