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Chemistry

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Also known as: Menaquinone-4, Vitamin k2, 863-61-6, Menaquinone 4, 11032-49-8, Kaytwo
Molecular Formula
C31H40O2
Molecular Weight
444.6  g/mol
InChI Key
DKHGMERMDICWDU-GHDNBGIDSA-N
FDA UNII
27Y876D139

Vitamin K2
Menatetrenone is a menaquinone compound and form of vitamin K2 with potential antineoplastic activity. Menatetrenone may act by modulating the signalling of certain tyrosine kinases, thereby affecting several transcription factors including c-myc and c-fos. This agent inhibits tumor cell growth by inducing apoptosis and cell cycle arrest.
1 2D Structure

Vitamin K2

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione
2.1.2 InChI
InChI=1S/C31H40O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+
2.1.3 InChI Key
DKHGMERMDICWDU-GHDNBGIDSA-N
2.1.4 Canonical SMILES
CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C
2.1.5 Isomeric SMILES
CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
2.2 Other Identifiers
2.2.1 UNII
27Y876D139
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (e,e,e)-isomer Of Menatetrenone

2. 2-methyl-3-all-trans-tetraprenyl-1,4-naphthoquinone

3. 2-methyl-3-trans-tetraprenyl-1,4-naphthoquinone

4. Kefton-2

5. Menaquinone 4

6. Menaquinone-4

7. Vitamin K2(20)

8. Vitamin Mk-4

2.3.2 Depositor-Supplied Synonyms

1. Menaquinone-4

2. Vitamin K2

3. 863-61-6

4. Menaquinone 4

5. 11032-49-8

6. Kaytwo

7. Kefton-2

8. Menaquinone K4

9. Vitamin Mk 4

10. Vitamin K2(20)

11. Menatetrenona

12. Menatetrenonum

13. Menatetranone

14. Mk-4

15. Kaytwo N

16. 2-methyl-3-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione

17. 6041-00-5

18. 2-methyl-3-trans-tetraprenyl-1,4-naphthoquinone

19. 2-methyl-3-geranylgeranyl-1,4-naphthoquinone

20. Mls000028742

21. 2-methyl-3-((2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)naphthalene-1,4-dione

22. Chebi:78277

23. 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthoquinone

24. Smr000058955

25. 27y876d139

26. 1,4-naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-

27. Dsstox_cid_28895

28. 1,4-naphthalenedione, 2-methyl-3-((2e,6e,10e)3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-

29. Vitamin K2(sub 20)

30. Menatetrenone [inn:jan]

31. Mk4

32. Menatetrenonum [inn-latin]

33. K2(sub 20)

34. Menatetrenona [inn-spanish]

35. Glakay

36. E3100

37. Menaquinone(4)

38. Unii-27y876d139

39. Ncgc00183125-01

40. 2-methyl-3-((2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)naphthalene-1,4-dione

41. Mfcd00079646

42. Vitamin K2 (tn)

43. Opera_id_148

44. 2-methyl-3-tetraprenyl-1,4-naphthoquinone

45. Menatetrenone [inn]

46. Menatetrenone [jan]

47. 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthochinon

48. Dsstox_rid_80857

49. Dsstox_rid_83163

50. Menatetrenone (jp17/inn)

51. Dsstox_gsid_45406

52. Dsstox_gsid_48969

53. Menaquinone 4 [mi]

54. 1,4-naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-, (e,e,e)-

55. Menaquinone;vitamin K2

56. Menatetrenone [mart.]

57. Schembl434553

58. Schembl571912

59. Menatetrenone [who-dd]

60. Vitamin K2 (mk-4) Solution

61. Chembl259223

62. Mq-4

63. Dtxsid6048969

64. Menaquinone-4 [usp-rs]

65. Hms2230j06

66. Ea-0167

67. Amy22672

68. Hy-b2156

69. Zinc3874199

70. Tox21_110567

71. Tox21_113413

72. Bdbm50423776

73. S5082

74. Akos025311021

75. Akos037645019

76. Menaquinone (k2), Analytical Standard

77. Ccg-269176

78. Db12148

79. 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthalenedione

80. 2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetrenyl)-1,4-naphthoquinone

81. Ncgc00181325-01

82. Ncgc00181325-03

83. As-17910

84. As-56161

85. Cas-863-61-6

86. Cs-0020307

87. M2398

88. A17083

89. D00100

90. E-0167

91. 863v616

92. A935204

93. Q192354

94. 1,4-naphthalenedione, 2-methyl-3-[(2e,6e,10e)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-

95. 2-methyl-3-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-1,4-naphthoquinone

96. Vitamin K2 (mk-4) Solution, 100 Mug/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 444.6 g/mol
Molecular Formula C31H40O2
XLogP38.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count11
Exact Mass444.302830514 g/mol
Monoisotopic Mass444.302830514 g/mol
Topological Polar Surface Area34.1 Ų
Heavy Atom Count33
Formal Charge0
Complexity855
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

There is no typical dosage for vitamin K. Some multivitamin preparations contain vitamin K as vitamin K1 (phylloquinone or phytonadione) or vitamin K2 (menaquinones) at doses of 25 to 100 ug.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 711


Vitamin K is used to treat anticoagulant-induced prothrombin deficiency caused by warfarin, hyporprothrombinemia secondary to antibiotic therapy and hypoprothrombinemia secondary to vitamin C deficiency from various causes, including malabsorption syndromes. /Vitamin K/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 709


Because hemorrhagic disease of the newborn can be effectively prevented by administrating vitamin K, infants born in the US and Canada routinely receive 0.5-1 mg pf phylloquinone intramuscularly or 2.0 mg orally within 6 hours of birth. This practice is supported by both US and Canadian pediatric societies. /Phylloquinone/

National Academies of Sciences Institute of Medicine; Vitamin K. In: Dietary Reference Intakes. p.255-61 (2006) National Academies Press, Washington, DC


The current recommendations of the American Academy of Pediatrics advise that "vitamin K (phylloquinone) should be given to all newborns as a single, intramuscular dose of 0.5-1 mg" and if this advice is followed, the disease /Vitamin K deficiency bleeding/ is effectively prevented. /Vitamin K/

Suttie JW; Vitamin K. In: Encyclopedia of Dietary Supplements, ed. Coates PM et al; Marcel Dekker, New York, NY pp. 771-82 (2005)


For more Therapeutic Uses (Complete) data for Vitamin K2 (8 total), please visit the HSDB record page.


4.2 Drug Warning

... MK-7 induced more complete carboxylation of osteocalcin, and hematologists should be aware that preparations supplying 50 ug/d or more of MK-7 may interfere with oral anticoagulant treatment in a clinically relevant way.

PMID:17158229 Schurgers LJ et al; Blood 109 (8): 3279-83 (2007)


It has been suggested that vitamin K may have roles in osteoporosis and vascular health. However, this is difficult to establish on the basis of the studies performed thus far. /Vitamin K/

National Academies of Sciences Institute of Medicine; Vitamin K. In: Dietary Reference Intakes. p.255-61 (2006) National Academies Press, Washington, DC


Pregnant women and nursing mothers should avoid supplemental intakes of vitamin K greater than RDA amounts (65 ug daily) unless higher amounts are prescribed by their physicians. /Vitamin K/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 711


Individuals on chronic warfarin therapy may require dietary counseling on how to maintain steady vitamin K intake levels. Because habitual vitamin K intake may modulate warfarin dosage in patients using this anticoagulant, these individuals should maintain their normal dietary and supplementation patterns once an effective dose of warfarin has been established. /Vitamin K/

National Academies of Sciences Institute of Medicine; Vitamin K. In: Dietary Reference Intakes. p.255-61 (2006) National Academies Press, Washington, DC


For more Drug Warnings (Complete) data for Vitamin K2 (6 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Hemostatics

Agents acting to arrest the flow of blood. Absorbable hemostatics arrest bleeding either by the formation of an artificial clot or by providing a mechanical matrix that facilitates clotting when applied directly to the bleeding surface. These agents function more at the capillary level and are not effective at stemming arterial or venous bleeding under any significant intravascular pressure. (See all compounds classified as Hemostatics.)


5.2 Absorption, Distribution and Excretion

Vitamin K, mainly in the form of vitamin K1, is principally absorbed from the jejunum and ileum. ... Vitamin K is delivered to the enterocytes in micelles formed from bile salts and other substances. Vitamin K is secreted by enterocytes into the lymphatics in the form of chylomicrons. It enters the circulation via the thoracic duct and is carried in the circulation to various tissues including hepatic, bone and spleen, in the form of chylomicron remnants. In the liver, some vitamin K is stored, some is oxidized to inactive end products and some is secreted with VLDL (very low density lipoprotein). Approximately 50% of vitamin K is carried in the plasma in the form of VLDL, about 25% in LDL (low-density lopoprotein) and about 25% in HDL (high-density lipoprotein). /Vitamin K/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 709


Excretion of vitamin K and its metabolites is mainly via the feces. Some urinary excretion of vitamin K also occurs. /Vitamin K/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 710


...Menaquinones are adequately absorbed from the GI tract only if bile salts are present. Menaquinones and its water-soluble derivatives, however, are absorbed even in the absence of bile. ... Menaquinones are absorbed almost entirely by way of the lymph. /Menaquinones/

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


Menaquinone forms of vitamin K are produced by bacteria in the lower bowel, where the forms appear in large amounts. However, their contributuion to the maintenance of vitamin K status has been difficult to assess. Although the content is extremely variable, the human liver contains about 10 times as much vitamin K as a mixture of menaquinones than as phylloquinone. /Menaquinones/

National Academies of Sciences Institute of Medicine; Vitamin K. In: Dietary Reference Intakes. p.255-61 (2006) National Academies Press, Washington, DC


5.3 Metabolism/Metabolites

A major pathway of vitamin K metabolism is that which is involved in the reduction and recycling of the epoxide formed by the carboxylase. /Vitamin K/

Suttie JW; Vitamin K. In: Encyclopedia of Dietary Supplements, ed. Coates PM et al; Marcel Dekker, New York, NY pp. 771-82 (2005)


Vitamin K undergoes some oxidative metabolism. /Vitamin K/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 710


5.4 Mechanism of Action

In vivo and in vitro studies have shown that vitamin K may directly act on bone metabolism. In vitro studies have demonstrated that vitamin K2 inhibits bone resorption by, in part, inhibiting the production of bone resorbing substances such as prostaglandin E2 and interleukin-6. Vitamin K2 has been reported to enhance human osteoblast-induced mineralization in vitro and to inhibit bone loss in steroid-treated rats and ovariectomized rats.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 709


Certain naphthoquinones, in particular the synthetic vitamin K menadione, have been found to have antitumor activity in vitro and in vivo. Vitamin K2 has been found to induce the in vitro differentiation of myeloid leukemic cell lines. The mechanism of the possible anticarcinogenic activity of vitamin K is not well understood. Menadione is an oxidative stress inducer and its possible anticarcinogenic activity may, in part, be explained by induction of apoptotic cell death. One study suggested that the induction of apoptosis by menadione is mediated by the Fas/Fas ligand system. Another study reported that menadione induces cell cycle arrest and cell death by inhibiting Cda 25 phosphatase.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 709


Vitamin K 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 X 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. /Vitamin K/

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 708


The primary gene product of the vitamin K-dependent proteins contains a very homologous domain between the amino terminus of the mature protein and the signal sequence that targets the polypeptide for the secretory pathway. This "propeptide" region appears to be both a "docking" or "recognition " site for the enzyme and a modulator of the activity of the enzyme by decreasing the apparent Km of the Glu site substrate. ... A key finding essential to a complete understanding of the detailed mechanism of action of this enzyme has been the identification of an intermediate chemical form of vitamin K, which could be sufficiently basic to abstract the gamma-hydrogen of the glutamyl residue. It has been proposed that the initial attack of O(2) at the naphthoquinone carbonyl carbon adjacent to the methyl group results in the formation of a dioxetane ring, which generates an alkoxide intermediate. /Vitamin K/

Suttie JW; Vitamin K. In: Encyclopedia of Dietary Supplements, ed. Coates PM et al; Marcel Dekker, New York, NY pp. 771-82 (2005)


For more Mechanism of Action (Complete) data for Vitamin K2 (8 total), please visit the HSDB record page.


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Faran Shimi Pharmaceutical

Iran

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Kappa Bioscience

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GF Fermentech

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