X
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. Thyloquinone
9. Kappaxin
10. Kayklot
11. Klottone
12. Kolklot
13. Panosine
14. Kanone
15. 2-methyl-1,4-naphthalenedione
16. Menadion
17. Menaphthon
18. Kipca
19. Prokayvit
20. Aquakay
21. Aquinone
22. Hemodal
23. Kaergona
24. Mitenon
25. Mitenone
26. Karcon
27. Kareon
28. Kativ-g
29. Kaykot
30. Koaxin
31. Synkay
32. K-thrombyl
33. K-vitan
34. Kappaxan
35. Juva-k
36. Vitamin K 3
37. Menaquinone 0
38. 2-methyl-1,4-naphthochinon
39. Vitamin K2(0)
40. Vitamin K0
41. Memodol
42. Usaf Ek-5185
43. 3-methyl-1,4-naphthoquinone
44. Menaphtone
45. 2-methyl-1,4-naftochinon
46. 1,4-naphthalenedione, 2-methyl-
47. 2-methyl-1,4-dihydronaphthalene-1,4-dione
48. Menaphthene
49. Kaynone
50. 1,4-naphthoquinone, 2-methyl-
51. Menadione (vitamin K3)
52. Nsc 4170
53. Ccris 6672
54. Hsdb 3354
55. Menaquinone O
56. Nsc-4170
57. Einecs 200-372-6
58. Unii-723jx6cxy5
59. Mfcd00001681
60. Methyl-1,4-naphthoquinone
61. 723jx6cxy5
62. Dtxsid4021715
63. Mnq
64. 1,4-naphthalenedione, 2-methyl
65. Chebi:28869
66. Ai3-14700
67. Nsc4170
68. Menadione [usp:ban]
69. Chembl590
70. 2-methyl-1,4-naphthalendione
71. Mls000069420
72. Dtxcid801715
73. 1,4-dihydro-2-methylnaphthalene-1,4-dione
74. Menadionum
75. Menadione (vitamin K3) 10 Microg/ml In Acetonitrile
76. Kappaxan (van)
77. Vk3
78. Cas-58-27-5
79. Menadione Semiquinone
80. Ncgc00016258-02
81. Menadione (usp:ban)
82. Smr000059102
83. Menadione (mart.)
84. Menadione [mart.]
85. Menadione (usp-rs)
86. Menadione [usp-rs]
87. Menadione (ep Monograph)
88. Menadione [ep Monograph]
89. Menadione (usp Monograph)
90. Menadione [usp Monograph]
91. 2-methyl-1,4-naftochinon [czech]
92. Menadione (usp)
93. Kappaxin (tn)
94. 2-methyl-1,4-naphthochinon [german]
95. Phytomenadione Impurity A (ep Impurity)
96. Phytomenadione Impurity A [ep Impurity]
97. Sr-01000712386
98. 2-methyl-1,4-naphthodione
99. Methyl-1,4-naphthalenedione
100. Mendione
101. Menadione Phenolic
102. 2-methyl-1,4-naphthoquinone, 5
103. Menadione, 9
104. Menadione,(s)
105. Phytomenadione Imp. A (ep); Menadione; 2-methylnaphthalene-1,4-dione; Phytomenadione Impurity A
106. Menadione1528
107. Prestwick_313
108. Menadione, 98%
109. Menadione, Crystalline
110. Spectrum_001228
111. Specplus_000191
112. Menadione [mi]
113. Menadione [hsdb]
114. Menadione [inci]
115. Opera_id_1802
116. Prestwick0_000459
117. Prestwick1_000459
118. Prestwick2_000459
119. Prestwick3_000459
120. Spectrum2_001194
121. Spectrum4_000722
122. Spectrum5_001764
123. Menadione [vandf]
124. M0373
125. Ncimech_000105
126. Cid_4055
127. Menadione [who-dd]
128. 2-methyl-1,4-napthoquinone
129. Schembl25970
130. Bspbio_000538
131. Kbiogr_000984
132. Kbiogr_002527
133. Kbioss_001708
134. Kbioss_002535
135. 2-methyl-1,4 Naphthoquinone
136. 34524-96-4
137. Mls001148443
138. Bidd:er0556
139. Divk1c_000080
140. Divk1c_006287
141. Spectrum1502254
142. Spbio_001267
143. Spbio_002477
144. 3-methyl-1,4-naphthalenedione
145. Bpbio1_000592
146. Menadione [orange Book]
147. 2-methyl-[1,4]-naphthoquinone
148. Bdbm24778
149. Hms500d22
150. Kbio1_000080
151. Kbio1_001231
152. Kbio2_001708
153. Kbio2_002527
154. Kbio2_004276
155. Kbio2_005095
156. Kbio2_006844
157. Kbio2_007663
158. Kbio3_003005
159. Wln: L66 Bv Evj C1
160. Cmap_000077
161. Ninds_000080
162. Bio1_000471
163. Bio1_000960
164. Bio1_001449
165. Hms1569k20
166. Hms1921p06
167. Hms2092f12
168. Hms2096k20
169. Hms2232a09
170. Hms2234j16
171. Hms3371m08
172. Hms3373a12
173. Hms3655p03
174. Hms3869n03
175. Pharmakon1600-01502254
176. Amy31055
177. Bcp25699
178. Hy-b0332
179. Str01143
180. Tox21_110334
181. Tox21_301367
182. Bbl027351
183. Ccg-35354
184. Menadione (k3), Analytical Standard
185. Nsc758200
186. S1949
187. Stl377874
188. Akos004910447
189. Akos025244105
190. Tox21_110334_1
191. Db00170
192. Fs-2556
193. Nsc-758200
194. Sb17255
195. Idi1_000080
196. Qtl1_000056
197. Usepa/opp Pesticide Code: 006319
198. Ncgc00016258-01
199. Ncgc00016258-03
200. Ncgc00016258-04
201. Ncgc00016258-06
202. Ncgc00016258-07
203. Ncgc00016258-08
204. Ncgc00094978-01
205. Ncgc00094978-02
206. Ncgc00255225-01
207. Ac-34841
208. Nci60_003945
209. Smr000653532
210. Sy018303
211. Sbi-0051776.p002
212. Menadione, Meets Usp Testing Specifications
213. Ft-0612893
214. Ft-0675843
215. Sw219798-1
216. C05377
217. D02335
218. En300-125382
219. A831816
220. Q192471
221. 1,4-naphthalenedione, 2-methyl-, Radical Ion(1-)
222. Q-201350
223. Sr-01000712386-2
224. Sr-01000712386-5
225. Sr-01000712386-6
226. Vitamin K3; 2-methyl-1,4-naphthalenedione
227. Brd-k78126613-001-16-0
228. Vitamin K3; 2-methyl-1,4-naphthoquinone; Menaphthone
229. Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene
230. Z1255430959
231. Menadione, European Pharmacopoeia (ep) Reference Standard
232. 03aae1e9-b215-45af-976c-91e61894a467
233. Menadione, United States Pharmacopeia (usp) Reference Standard
234. Menadione, Pharmaceutical Secondary Standard; Certified Reference Material
235. Inchi=1/c11h8o2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6h,1h
| 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 | g/mol |
| Monoisotopic Mass | g/mol |
| Topological Polar Surface Area | 34.1 |
| 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.
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.
Hepatic
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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