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1. 2-methyl-1,4-naphthalenedione
2. 2-methyl-1,4-naphthoquinone
3. 2-methylnaphthoquinone
4. Bisulfite, Menadione
5. Bisulfite, Menadione Sodium
6. Menadione Bisulfite
7. Menadione Sodium Bisulfite
8. Menadione Sodium Bisulfite, Trihydrate
9. Sodium Bisulfite, Menadione
10. Vicasol
11. Vikasol
12. Vitamin K 3
13. Vitamin K3
14. Vitamin K3 Sodium Bisulfite
1. 58-27-5
2. Vitamin K3
3. 2-methyl-1,4-naphthoquinone
4. 2-methylnaphthalene-1,4-dione
5. Menaphthone
6. Kayquinone
7. 2-methylnaphthoquinone
8. 2-methyl-1,4-naphthalenedione
9. Thyloquinone
10. Kappaxin
11. Klottone
12. Panosine
13. Kayklot
14. Kolklot
15. Menaphthon
16. Aquakay
17. Menadion
18. Kanone
19. Kipca
20. Aquinone
21. Kaergona
22. Kativ-g
23. Mitenone
24. Prokayvit
25. Hemodal
26. Karcon
27. Kareon
28. Kaykot
29. Koaxin
30. Mitenon
31. Synkay
32. Vitamin K 3
33. K-thrombyl
34. K-vitan
35. Kipca-oil Soluble
36. Juva-k
37. Vitamin K2(0)
38. Vitamin K0
39. 2-methyl-1,4-naphthochinon
40. Menaquinone 0
41. Menaphtone
42. Usaf Ek-5185
43. 3-methyl-1,4-naphthoquinone
44. 1,4-naphthalenedione, 2-methyl-
45. Menaphthene
46. Kaynone
47. 2-methyl-1,4-naftochinon
48. Menadione (vitamin K3)
49. 2-methyl-1,4-dihydronaphthalene-1,4-dione
50. 1,4-naphthoquinone, 2-methyl-
51. Menaquinone O
52. Nsc 4170
53. Mfcd00001681
54. Methyl-1,4-naphthoquinone
55. Nsc4170
56. Nsc-4170
57. Mnq
58. Chembl590
59. 2-methyl-1,4-naphthalendione
60. Mls000069420
61. 723jx6cxy5
62. 1,4-dihydro-2-methylnaphthalene-1,4-dione
63. Menadionum
64. Memodol
65. 1,4-naphthalenedione, 2-methyl
66. Chebi:28869
67. Menadione (vitamin K3) 10 Microg/ml In Acetonitrile
68. Kappaxan (van)
69. Vk3
70. Cas-58-27-5
71. Menadione Semiquinone
72. Ncgc00016258-02
73. Smr000059102
74. Dsstox_cid_1715
75. Dsstox_rid_76289
76. Dsstox_gsid_21715
77. 2-methyl-1,4-naftochinon [czech]
78. Menadione (usp)
79. Kappaxin (tn)
80. Kipca, Oil Soluble
81. 2-methyl-1,4-naphthochinon [german]
82. Ccris 6672
83. Hsdb 3354
84. Menadione [usp:ban]
85. Sr-01000712386
86. Einecs 200-372-6
87. 2-methyl-1,4-naphthodione
88. Methyl-1,4-naphthalenedione
89. Unii-723jx6cxy5
90. Mendione
91. Ai3-14700
92. 2-methyl-1,4-naphthoquinone, 5
93. Menadione, 9
94. Menadione,(s)
95. Prestwick_313
96. Menadione, 98%
97. Menadione, Crystalline
98. Spectrum_001228
99. Specplus_000191
100. Menadione [mi]
101. Menadione [hsdb]
102. Menadione [inci]
103. Opera_id_1802
104. Prestwick0_000459
105. Prestwick1_000459
106. Prestwick2_000459
107. Prestwick3_000459
108. Spectrum2_001194
109. Spectrum4_000722
110. Spectrum5_001764
111. Menadione [vandf]
112. M0373
113. Menadione [mart.]
114. Ncimech_000105
115. Cid_4055
116. Menadione [usp-rs]
117. Menadione [who-dd]
118. 2-methyl-1,4-napthoquinone
119. Schembl25970
120. Bspbio_000538
121. Kbiogr_000984
122. Kbiogr_002527
123. Kbioss_001708
124. Kbioss_002535
125. 2-methyl-1,4 Naphthoquinone
126. 34524-96-4
127. Mls001148443
128. Bidd:er0556
129. Divk1c_000080
130. Divk1c_006287
131. Spectrum1502254
132. Spbio_001267
133. Spbio_002477
134. 3-methyl-1,4-naphthalenedione
135. Bpbio1_000592
136. Zinc1677
137. Menadione [orange Book]
138. Dtxsid4021715
139. Menadione [ep Monograph]
140. 2-methyl-[1,4]-naphthoquinone
141. Bdbm24778
142. Hms500d22
143. Kbio1_000080
144. Kbio1_001231
145. Kbio2_001708
146. Kbio2_002527
147. Kbio2_004276
148. Kbio2_005095
149. Kbio2_006844
150. Kbio2_007663
151. Kbio3_003005
152. Wln: L66 Bv Evj C1
153. Menadione [usp Monograph]
154. Cmap_000077
155. Ninds_000080
156. Bio1_000471
157. Bio1_000960
158. Bio1_001449
159. Hms1569k20
160. Hms1921p06
161. Hms2092f12
162. Hms2096k20
163. Hms2232a09
164. Hms2234j16
165. Hms3371m08
166. Hms3373a12
167. Hms3655p03
168. Hms3869n03
169. Pharmakon1600-01502254
170. Amy31055
171. Bcp25699
172. Hy-b0332
173. Str01143
174. Tox21_110334
175. Tox21_301367
176. Bbl027351
177. Ccg-35354
178. Menadione (k3), Analytical Standard
179. Nsc758200
180. S1949
181. Stl377874
182. Akos004910447
183. Akos025244105
184. Tox21_110334_1
185. Db00170
186. Fs-2556
187. Nsc-758200
188. Sb17255
189. Idi1_000080
190. Qtl1_000056
191. Ncgc00016258-01
192. Ncgc00016258-03
193. Ncgc00016258-04
194. Ncgc00016258-06
195. Ncgc00016258-07
196. Ncgc00016258-08
197. Ncgc00094978-01
198. Ncgc00094978-02
199. Ncgc00255225-01
200. Ac-34841
201. Nci60_003945
202. Smr000653532
203. Sy018303
204. Sbi-0051776.p002
205. Menadione, Meets Usp Testing Specifications
206. Ft-0612893
207. Ft-0675843
208. Sw219798-1
209. C05377
210. D02335
211. Phytomenadione Impurity A [ep Impurity]
212. 001m681
213. A831816
214. Q192471
215. 1,4-naphthalenedione, 2-methyl-, Radical Ion(1-)
216. Q-201350
217. Sr-01000712386-2
218. Sr-01000712386-5
219. Sr-01000712386-6
220. Vitamin K3; 2-methyl-1,4-naphthalenedione
221. Brd-k78126613-001-16-0
222. Vitamin K3; 2-methyl-1,4-naphthoquinone; Menaphthone
223. Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene
224. Menadione, European Pharmacopoeia (ep) Reference Standard
225. 03aae1e9-b215-45af-976c-91e61894a467
226. Menadione, United States Pharmacopeia (usp) Reference Standard
227. Menadione, Pharmaceutical Secondary Standard; Certified Reference Material
| Molecular Weight | 172.18 g/mol |
|---|---|
| Molecular Formula | C11H8O2 |
| XLogP3 | 2.2 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Exact Mass | 172.052429494 g/mol |
| Monoisotopic Mass | 172.052429494 g/mol |
| Topological Polar Surface Area | 34.1 Ų |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Complexity | 289 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
The synthetic water soluble forms of vitamin K (menadione, menadiol) have long since been considered inferior to vitamin K1 (phytonadione) in the treatment of drug-induced hypoprothrombinemia.
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1783
Menadione (vitamin K3) a redox cycling quinone, is a clinically important chemotherapeutic agent. ...
PMID:11726226 Laux I, Nel A; Clin Immunol 101 (3): 335-44 (2001)
Menadione, or vitamin K3 (VK3), a potent oxidative stress inducer, has been recently used as an effective and remarkably safe cytotoxic drug for treatment of several human tumors. ...
PMID:10497012 Caricchio R et al; Clinical Immunology 93 (1): 65-74 (1999)
... Probably should not be given to newborn infants or women during last few wk of pregnancy.
American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 795
Menadione is ineffective for the treatment of warfarin and superwarfarin toxicity. It elicits a poor response and should not be used.
Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 459
Vitamin K /SRP: phytonadione preferred/ must be administered with great care to patients to whom anticoagulants have been given to combat intravascular clotting. ... The vitamin must be "titrated" against the anticoagulant, lest the patient be re-exposed to the same threat of clotting that led to anticoagulants therapy in the first place. No such problem exists in treating persons poisoned accidentally or suicidally by anticoagulant rodenticides. There is no evidence that vitamin K produces in normal persons any excessive tendency of the blood to clot. /vitamin K/
Hayes, W.J., Jr., E.R. Laws Jr., (eds.). Handbook of Pesticide Toxicology Volume 1. General Principles. New York, NY: Academic Press, Inc., 1991., p. 398
Menadione...can induce hemolysis in individuals who are genetically deficient in glucose-6-phosphate dehydrogenase.
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1564
For more Drug Warnings (Complete) data for MENADIONE (6 total), please visit the HSDB record page.
3. 3= Moderately toxic: probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz & 1 pint (or 1 lb) for 70 kg person (150 lb).
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-403
The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.
Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin K. Also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times.
Vitamins
Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body. (See all compounds classified as Vitamins.)
Antifibrinolytic Agents
Agents that prevent fibrinolysis or lysis of a blood clot or thrombus. Several endogenous antiplasmins are known. The drugs are used to control massive hemorrhage and in other coagulation disorders. (See all compounds classified as Antifibrinolytic Agents.)
B - Blood and blood forming organs
B02 - Antihemorrhagics
B02B - Vitamin k and other hemostatics
B02BA - Vitamin k
B02BA02 - Menadione
Absorption
Variable and ranges from 10% to 80%
Menadione and its water soluble derivatives ... are absorbed even in the absence of bile ... /and/ enter the bloodstream directly.
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1565
Eighteen hr after intracardiac admin of (3)H-menadione ... to rats fed diet deficient in vit k, 78% of (3)H had been excreted in urine, 3% in feces, and 29% remained in animals. Biliary excretion ... observed in dogs, & 5-10% of (14)c had been excreted by this route 12 hr after oral dose of (14)C-menadione.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 43
Vit k accum in liver, spleen, and lungs. /however/ significant amounts are not stored in body for long periods.
American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 783
VET: ... Menadione or vit k3 absorbed is converted to k2 for utilization, otherwise it is rapidly eliminated via urine.
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 659
The pharmacokinetics of menadione (vitamin K3)... were studied in rabbits after iv injection of 75 mg menadiol sodium diphosphate (Synkayvite). ... Plasma clearance was 0.822 L/min. Systemic clearance in RBCs was 0.407 L/min. Apparent volume of distribution was 30.833 L in plasma and 20.488 L in RBCs. Area under the concn-time curve was 32.453 ug min/ml for plasma and 67.219 ug min/ml for RBCs. /Menadiol sodium diphosphate/
PMID:8866040 Hu OY et al; Biopharm. Drug Dispos. 17: 493-499 (1996)
Hepatic
Distribution studies with menadione tritiated in 6,7-position, ((3)H(6,7))-2-methyl-1,4-naphthaquinone, in rats showed that lipophilic metabolite of menadione, menaquinone-4, 2-methyl-3-geranylgeranyl-1,4-naphthaquinone was present in all tissues examined.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 231
2-methyl-1,4-naphthoquinone yields in rat vit k2(20); yields vit k2(45), and vit k2(50) probably in man. /from table/
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. M-33
...Xenobiotics that are reduced by carbonyl reductases include... menadione... .
Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 145
Menadione is excreted in part as glucuronide and competes with bilirubin for detoxification mechanism of limited capacity in newborn.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1594
For more Metabolism/Metabolites (Complete) data for MENADIONE (6 total), please visit the HSDB record page.
The pharmacokinetics of menadione (vitamin K3)... were studied in rabbits after iv injection of 75 mg menadiol sodium diphosphate (Synkayvite). Mean elimination half-life of menadione was 27.17 min in plasma and 35.22 min in red blood cells... . /Menadiol sodium diphosphate/
PMID:8866040 Hu OY et al; Biopharm. Drug Dispos. 17: 493-499 (1996)
Menadione (vitamin K3) is involved as a cofactor in the posttranslational gamma-carboxylation of glutamic acid residues of certain proteins in the body. These proteins include the vitamin K-dependent coagulation factors II (prothrombin), VII (proconvertin), IX (Christmas factor), X (Stuart factor), protein C, protein S, protein Zv and a growth-arrest-specific factor (Gas6). In contrast to the other vitamin K-dependent proteins in the blood coagulation cascade, protein C and protein S serve anticoagulant roles. The two vitamin K-dependent proteins found in bone are osteocalcin, also known as bone G1a (gamma-carboxyglutamate) protein or BGP, and the matrix G1a protein or MGP. Gamma-carboxylation is catalyzed by the vitamin K-dependent gamma-carboxylases. The reduced form of vitamin K, vitamin K hydroquinone, is the actual cofactor for the gamma-carboxylases. Proteins containing gamma-carboxyglutamate are called G1a proteins.
The vitamin K-dependent blood clotting factors, in the absence of vitamin K (or in the presence of the coumarin type of anticoagulant), are biologically inactive precursor proteins in the liver. Vitamin K functions as an essential cofactor for a microsomal enzyme system that activates these precursors by the conversion of multiple residues of glutamic acid near the amino terminus of each precursor to gamma-carboxyglutamyl residues in the completed protein. The formation of this new amino acid, gamma-carboxyglutamic acid, allows the protein to bind Ca+2 and in turn to be bound to a phospholipid surface, both of which are necessary in the cascade of events that lead to clot formation. /Vitamin K/
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1783
Vitamin k is necessary for formation of prothrombinogen and other blood clotting factors in liver. During clotting, circulating prothrombin is required for production of thrombin; in turn, thrombin converts fibrinogen to fibrin, network of which constitutes clot. /vitamin k/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 943
The active form of vitamin K appears to be the reduced vitamin K hydroquinone, which, in the presence of oxygen, carbon dioxide, and the microsomal carboxylase enzyme, is converted to its 2,3-epoxide at the same time gamma-carboxylation takes place. The hydroquinone form of vitamin K is regenerated from the 2,3-epoxide by a coumarin sensitive epoxide reductase ... . /Vitamin K/
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1784
Menadione is a potent inhibitor of aldehyde oxidase (Ki ~0.1 uM) and can be used together with allopurinol to discriminate between aldehyde oxidase- and xanthine oxidase-catalyzed reactions.
Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 160
For more Mechanism of Action (Complete) data for MENADIONE (6 total), please visit the HSDB record page.
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