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    Chemistry

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    Also known as: Phylloquinone, Phytonadione, 84-80-0, Phytomenadione, Phytylmenadione, 3-phytylmenadione
    Molecular Formula
    C31H46O2
    Molecular Weight
    450.7  g/mol
    InChI Key
    MBWXNTAXLNYFJB-NKFFZRIASA-N
    FDA UNII
    MLF3D1712D
    Vitamin K1
    A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.
    1 2D Structure

    Vitamin K1

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
    2.1.2 InChI
    InChI=1S/C31H46O2/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/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1
    2.1.3 InChI Key
    MBWXNTAXLNYFJB-NKFFZRIASA-N
    2.1.4 Canonical SMILES
    CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C
    2.1.5 Isomeric SMILES
    CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    MLF3D1712D
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aquamephyton

    2. Konakion

    3. Phyllohydroquinone

    4. Phylloquinone

    5. Phytomenadione

    6. Phytonadione

    7. Vitamin K 1

    2.3.2 Depositor-Supplied Synonyms

    1. Phylloquinone

    2. Phytonadione

    3. 84-80-0

    4. Phytomenadione

    5. Phytylmenadione

    6. 3-phytylmenadione

    7. Aquamephyton

    8. Konakion

    9. Mephyton

    10. Monodion

    11. Phyllochinon

    12. Synthex P

    13. 2-methyl-3-phytyl-1,4-naphthoquinone

    14. Kinadion

    15. Vitamink1

    16. Mono-kay

    17. Combinal K1

    18. Kativ N

    19. Alpha-phylloquinone

    20. Trans-phylloquinone

    21. K-ject

    22. Fitomenadiona

    23. Phyllochinonum

    24. Phytomenadionum

    25. Phytonadionum

    26. Aqua Mephyton

    27. Antihemorrhagic Vitamin

    28. Vitamin K 1

    29. Fitomenadione

    30. Aqua-mephytin

    31. Kephton

    32. 79083-00-4

    33. 2',3'-trans-vitamin K1

    34. 2-methyl-3-phytyl-1,4-naphthochinon

    35. 11104-38-4

    36. Vitamin K

    37. Phylloquinone E-form

    38. 2-methyl-3-[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione

    39. Chebi:18067

    40. 2-methyl-3-[(e,7r,11r)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione

    41. Nsc 270681

    42. Nsc-270681

    43. S5z3u87qhf

    44. 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione

    45. 1,4-naphthoquinone, 2-methyl-3-phytyl-

    46. Phythyl-menadion

    47. Mlf3d1712d

    48. Phytonadione, (e)-(+/-)-

    49. 1,4-naphthalenedione,2-methyl-3-[(2e,7r,11r)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-

    50. Dsstox_cid_3472

    51. 1,4-naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-, (r-(r*,r*-(e)))-

    52. 2-methyl-3-((7r,11r,e)-3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione

    53. Dsstox_rid_77041

    54. Dsstox_gsid_23472

    55. Vitamin K1-18o(mixture Of 1-18o And 4-18o)

    56. Orakay

    57. 1,4-naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-

    58. 2-methyl-3-[(2e)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone

    59. 2-methyl-3-phythyl-1,4-naphthochinon

    60. Cas-84-80-0

    61. Rel-2-methyl-3-((7r,11r,e)-3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione

    62. Phytonadione, K1

    63. 1,4-naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-, [r-[r*,r*-(e)]]-

    64. Phyllochinon [german]

    65. Fitomenadione [dcit]

    66. Vitamin K1 (van)

    67. Phytonadione [usp:jan]

    68. Unii-s5z3u87qhf

    69. Fitomenadiona [inn-spanish]

    70. Phytomenadionum [inn-latin]

    71. Kanavit

    72. Neokay

    73. A-phylloquinone

    74. Konakion Mm

    75. Konakion Mm Paed

    76. Hsdb 3162

    77. Vitamin K1 Oil

    78. (e)-phytonadione

    79. 2-methyl-3-((7r,11r,e)-3,7,11,15-tetramethylhexadec-2-enyl)naphthalene-1,4-dione

    80. Ncgc00159423-02

    81. Trans-phytomenadione

    82. Einecs 201-564-2

    83. Einecs 234-330-3

    84. Einecs 279-052-3

    85. Mfcd00214063

    86. Vitamin K1, 11

    87. Vitamin K1 (generic)

    88. Vitamin K1 ,(s)

    89. Phytonadione [jan]

    90. 2-methyl-3-phytyl-1,4-naphthochinon [german]

    91. Schembl3882

    92. Vitamin K1 (phylloquinone)

    93. Vitamin K1, Viscous Liquid

    94. Chembl1550

    95. Unii-mlf3d1712d

    96. Phytonadione, (e)-

    97. Phylloquinone, (e)-

    98. Mls001074732

    99. Bidd:gt0793

    100. Phytomenadione, (e)-

    101. Schembl351365

    102. Vitamin K1 (e-phytonadione)

    103. 2-methyl-3-[(2e)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone #

    104. Dtxsid8023472

    105. Bdbm24782

    106. [r-[r*,r*-(e)]]-2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-napthalenedione

    107. [r-[r*,r*-(e)]]-2-methyl-3-(3-7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione

    108. Phylloquinone E-form [mi]

    109. Hms2094g09

    110. Hms2270j10

    111. Pharmakon1600-01505485

    112. 10485-69-5

    113. Hy-n0684

    114. Zinc3831332

    115. Tox21_111655

    116. Bdbm50553259

    117. Lmpr02030028

    118. Nsc760373

    119. S4698

    120. 2-methyl-3-phytyl-1,4-napthoquinone

    121. Akos015841892

    122. Tox21_111655_1

    123. Ccg-213568

    124. Cs-6376

    125. Db01022

    126. Nsc-760373

    127. (r*,r*-(e))-(1)-2-methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone

    128. Ncgc00159423-03

    129. Phylloquinone (k1), Analytical Standard

    130. Ac-34846

    131. As-13734

    132. Smr000112043

    133. Sbi-0206926.p001

    134. Trans-phytomenadione 100 Microg/ml In Ethanol

    135. Ab00698065_04

    136. 214v063

    137. A840928

    138. Q186093

    139. Sr-05000001941

    140. C31h46o2 (2-methyl-3-phytyl-1,4-naphthoquinone)

    141. Q-201934

    142. Sr-05000001941-1

    143. W-108488

    144. 2-methyl-3-((7r,11r,e)-3,7,11,15-tetramethylhexadec

    145. 84c51b31-3ce2-476b-be66-a84bdd46a513

    146. Vitamin K1; 2-methyl-3-phytyl-1,4-naphthoquinone

    147. Phytomenadione, European Pharmacopoeia (ep) Reference Standard

    148. Phytonadione, United States Pharmacopeia (usp) Reference Standard

    149. 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalened- Ione

    150. Vitamin K1 Solution, 10 Mug/ml In Ethanol, Certified Reference Material

    151. Vitamin K1, Bioxtra, >=99.0% (sum Of Isomers, Hplc), Mixtur Of Isomers

    152. 1,4-naphthalenedione, 2-methyl-3-((2e,7r,11r)-3,7,11,15-tetramethyl-2-hexadecen-1-yl)-

    153. 1,4-naphthalenedione, 2-methyl-3-((2e,7r,11r)-3,7,11,15-tetramethyl-2-hexadecenyl)-

    154. Phytonadione, Pharmaceutical Secondary Standard; Certified Reference Material

    155. 1,4-naphthalenedione, 2-methyl-3-((2e,7r,11r)-3,7,11,15-tetramethyl-2-hexadecen-1-yl)-, Rel-

    156. 2-methyl-3-((2e,7r,11r)-3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione

    157. 2-methyl-3-[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione

    158. 2-methyl-3-[(e,7r,11r)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione;vitamin K1

    159. Vitamin K1-13c6 Solution, 5 Mug/ml In Ethanol, Certified Reference Material, Ampule Of 1 Ml

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 450.7 g/mol
    Molecular Formula C31H46O2
    XLogP310.9
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count14
    Exact Mass450.349780706 g/mol
    Monoisotopic Mass450.349780706 g/mol
    Topological Polar Surface Area34.1 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity696
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NamePhytonadione
    Drug LabelPhytonadione is a vitamin, which is a clear, yellow to amber, viscous, odorless or nearly odorless liquid. It is insoluble in water, soluble in chloroform and slightly soluble in ethanol. It has a molecular weight of 450.70.Phytonadione is 2-methyl-3...
    Active IngredientPhytonadione
    Dosage FormInjectable
    RouteInjection
    Strength1mg/0.5ml
    Market StatusPrescription
    CompanyIntl Medication

    2 of 4  
    Drug NameVitamin k1
    PubMed HealthPhytonadione
    Drug ClassesNutriceutical, Nutritive Agent
    Drug LabelPhytonadione is a vitamin, which is a clear, yellow to amber, viscous, odorless or nearly odorless liquid. It is insoluble in water, soluble in chloroform and slightly soluble in ethanol. It has a molecular weight of 450.70.Phytonadione is 2-methyl-3...
    Active IngredientPhytonadione
    Dosage FormInjectable
    RouteInjection
    Strength1mg/0.5ml; 10mg/ml
    Market StatusPrescription
    CompanyHospira

    3 of 4  
    Drug NamePhytonadione
    Drug LabelPhytonadione is a vitamin, which is a clear, yellow to amber, viscous, odorless or nearly odorless liquid. It is insoluble in water, soluble in chloroform and slightly soluble in ethanol. It has a molecular weight of 450.70.Phytonadione is 2-methyl-3...
    Active IngredientPhytonadione
    Dosage FormInjectable
    RouteInjection
    Strength1mg/0.5ml
    Market StatusPrescription
    CompanyIntl Medication

    4 of 4  
    Drug NameVitamin k1
    PubMed HealthPhytonadione
    Drug ClassesNutriceutical, Nutritive Agent
    Drug LabelPhytonadione is a vitamin, which is a clear, yellow to amber, viscous, odorless or nearly odorless liquid. It is insoluble in water, soluble in chloroform and slightly soluble in ethanol. It has a molecular weight of 450.70.Phytonadione is 2-methyl-3...
    Active IngredientPhytonadione
    Dosage FormInjectable
    RouteInjection
    Strength1mg/0.5ml; 10mg/ml
    Market StatusPrescription
    CompanyHospira

    4.2 Therapeutic Uses

    Antifibrinolytic Agents

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    THE RATIONAL THERAPEUTIC USE OF VITAMIN K IS BASED ON ITS ABILITY TO CORRECT BLEEDING TENDENCY OR HEMORRHAGE ASSOC WITH ITS DEFICIENCY. A DEFICIENCY OF VITAMIN K & ITS ATTENDANT DEFICIENCY OF PROTHROMBIN & RELATED CLOTTING FACTORS CAN RESULT FROM INADEQUATE INTAKE, ABSORPTION, OR UTILIZATION OF VITAMIN, OR AS A CONSEQUENCE OF ACTION OF THE ACTION OF A VITAMIN K ANTAGONIST. /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. 1785

    BLEEDING THAT ACCOMPANIES OBSTRUCTIVE JAUNDICE OR BILIARY FISTULA RESPONDS PROMPTLY TO ADMINISTRATION OF VITAMIN K. ORAL PHYTONADIONE ADMIN WITH BILE SALTS IS BOTH SAFE AND EFFECTIVE AND SHOULD BE USED IN THE CARE OF THE JAUNDICED PATIENT, BOTH PREOPERATIVELY & POSTOPERATIVELY.

    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. 1785

    IF FOR SOME REASON ORAL ADMIN IS NOT FEASIBLE /IN TREATMENT OF OBSTRUCTIVE JAUNDICE OR BILIARY FISTULA/, A PARENTERAL PREPN SHOULD BE