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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 USED.

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


For more Therapeutic Uses (Complete) data for PHYTONADIONE (22 total), please visit the HSDB record page.


4.3 Drug Warning

IN PT WHO HAVE SEVERE HEPATIC DISEASE, ADMIN OF LARGE DOSES OF MENADIONE OR PHYLLOQUINONE MAY FURTHER DEPRESS FUNCTION OF LIVER.

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


Maternal Medication usually Compatible with Breast-Feeding: K1 (vitamin): Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 141 (1994)


A rare hypersensitivity-like reaction, which has occasionally resulted in death, has been reported after intravenous administration of phytonadione, especially when administration is rapid.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2957


In newborns, especially premature infants, mendiol sodium diphosphate has been associated with hemolytic anemia, hyperbilirubinemia, and kernicterus because of immature hepatic function in these infants. There is less risk with phytonadione, unless high doses are given.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2957


For more Drug Warnings (Complete) data for PHYTONADIONE (21 total), please visit the HSDB record page.


4.4 Drug Indication

Oral phylloquinone is indicated to treat prothrombin deficiency caused by coumarin or indanedione derivatives; and hypoprothrombinemia secondary to antibacterial therapy, salicylates, or obstructive jaundice or biliary fistulas with concomitant bile salt administration. Parenteral (intravenous, intramuscular, and subcutaneous) phylloquinone is indicated to treat coagulation disorders due to faulty formation of coagulation factors II, VII, IX, and X caused by vitamin K deficiency or some interference with vitamin K activity. These indications include the above indications as well as hypoprothrombinemia secondary to sprue, ulcerative colitis, celiac disease, intestinal resection, pancreatic cystic fibrosis, or regional enteritis; or hypoprothrombinemia caused by interference with vitamin k metabolism.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Phylloquinone is a vitamin K indicated in the treatment of coagulation disorders due to faulty formation of coagulation factors II, VII, IX, and X caused by deficiency or interference in the activity of vitamin K. It has a long duration of action as vitamin K is cycled in the body, and a wide therapeutic index as large doses can be tolerated. Patients should have their prothrombin time monitored during therapy and healthcare professionals should be aware of the increased risk of hypersensitivity reactions with parenteral administration.


5.2 MeSH Pharmacological Classification

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.)


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.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Reversed Anticoagulation Activity [PE]; Vitamin K [CS]; Vitamin K [EPC]; Warfarin Reversal Agent [EPC]; Increased Prothrombin Activity [PE]
5.4 ATC Code

B02BA01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


B - Blood and blood forming organs

B02 - Antihemorrhagics

B02B - Vitamin k and other hemostatics

B02BA - Vitamin k

B02BA01 - Phytomenadione


5.5 Absorption, Distribution and Excretion

Absorption

A 4 g oral dose of phylloquinone is 13% 9% bioavailable, with a Tmax of 4.7 0.8 hours. 1.5 0.8 nmol is found in the plasma compartment, and 3.6 3.4 nmol is found in the second compartment. A 10 mg intramuscular phylloquinone dose is 89.2% 25.4% bioavailable. The same dose reaches a mean Cmax of 67 30 ng/mL, with a mean Tmax of 9.2 6.6 hours, and an AUC of 1700 500 h\*ng/mL. A 10 mg intravenous phylloquinone dose has a mean AUC of 1950 450 h\*ng/mL.


Route of Elimination

Intravenous phylloquinone is 36% eliminated in the feces in 5 days and 22% recovered in urine in 3 days.


Volume of Distribution

The steady state volume of distribution of phylloquinone is 20 6 L in subjects who are also taking phenprocoumon therapy.


Clearance

Intravenous phylloquinone is 90% cleared in 2 hours, and 99% cleared in 8 hours. A 10 mg intravenous dose of phylloquinone has a mean clearance of 91 24 mL/min.


Little is known about the excretion of vitamin K. High fecal concentrations of vitamin K probably result from bacterial synthesis in the intestine.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 3566


Although the drug may be concentrated in the liver for a short time after absorption, only small amounts of phytonadione are stored in body tissues.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 3566


Phytonadione is absorbed from the GI tract only in the presence of bile salts. Radioisotope studies show that absorption occurs via intestinal lymph. There is some evidence that absorption of phytonadione across the GI mucosa is a saturable, energy-dependent process that occurs in the proximal small intestine.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 3566


Fat-soluble vit...k...absorbed from skin... /vit 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. 139


For more Absorption, Distribution and Excretion (Complete) data for PHYTONADIONE (7 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Phylloquinone's phytyl side chain is omega hydroxylated by CYP4F2. The side chain is then cleaved to 5 or 7 carbons long, and then glucuronidated prior to elimination. Vitamin Ks in general undergo a cycle of reduction to vitamin K hydroquinone by vitamin K epoxide reductase (VKOR), oxidation to vitamin K epoxide by gamma-glutamyl carboxylase, and converted back to vitamin K by VKOR.


...In experimental animals...phylloquinone...can be converted to more potent menaquinone series. Whether this can occur in man and of what significance these transformations are to action of phylloquinone...are still unknown.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1593


In animals treated with warfarin, major fraction of phylloquinone is metabolized to phylloquinone oxide.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1593


Phytonadione is rapidly metabolized to more polar metabolites, which are excreted in the bile and urine. The major urinary metabolites result from shortening of the side chain to five or seven carbon atoms, yielding carboxylic acids that are conjugated with glucuronate prior to excretion. Treatment with a coumarin-type anticoagulant results in a marked increase in the amount of phytonadione-2,3-epoxide in the liver and blood. Such treatment also increases the urinary excretion of phytonadione metabolites, primarily degradative products of phytonadione-2,3-epoxide. The biliary metabolites of phytonadione have not been identified.

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


The liver plays an exclusive role in the metabolic transformations leading to the elimination of vitamin K from the body. After intravenous doses of 45 ug to 1 mg (3)H-phylloquinone, about 20% of the radiolabel was excreted in the urine within three days, and 35-50% was excreted as metabolites in the feces via the bile.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V76 461-2 (2000)


5.7 Biological Half-Life

Intravenous phylloquinone has an initial half life of 22 minutes, followed by a half life of 125 minutes.


5.8 Mechanism of Action

Vitamin K is a cofactor of gamma-carboxylase. Gamma carboxylase attaches carboxylic acid functional groups to glutamate, allowing precursors of factors II, VII, IX, and X to bind calcium ions. Binding of calcium ions converts these clotting factors to their active form, which are then secreted from hepatocytes into the blood, restoring normal clotting function. Vitamin K may also carboxylate matrix proteins in chondrocytes, inhibiting calcification of joints, and may increase type II collagen. The role of vitamin K in osteroarthritis, bone density, and vascular calcification is currently under investigation.


Vit k is necessary for formation of prothrombinogen & 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. /vit k/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 943


In normal animals and man, phyltonadione ... /is/ virtually devoid of pharmacodynamic activity. In Animals and man deficient in vitamin k, the pharmacological action of vitamin k is identical to its normal physiological function, that is, to promote hepatic biosynthesis of prothrombin (factor ii), proconvertin (factor vii), plasma thromboplastin component (ptc, christmas factor, factor ix), and Stuart factor (factor x).

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


On the basis of studies of microsomal metabolism in vitro and studies in rats and mice in vivo, /it was suggested/ that vitamin K may be mutagenic by affecting the mixed-function oxidase system which metabolizes benzo(a)pyrene. Phylloquinone at a high concentration (200 umol/l) inhibited the conversion of benzo(a)pyrene to its more polar metabolites, ... . Paradoxically, at a lower concentration of phylloquinone (25 umol/l), ... the metabolism of benzo(a)pyrene was increased. In this system, therefore, .... phylloquinone could either potentiate or inhibit it, depending on the concentration. This overall weaker inhibitory effect of phylloquinone could be due to the low solubility of this lipophilic compound, but it is difficult to explain the mechanism of the enhanced metabolism of benzo(a)pyrene at lower concentrations of phylloquinone.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V76 472 (2000)


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Virtual BoothTransoPharm USA works in the Sourcing and Management of Active Pharmaceutical Ingredients.

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Transo-Pharm, a fully licensed and certified distributor, specializes in pharmaceutical components for the health and veterinary industries. It offers support to clients throughout the entire API life cycle, from product development through sales. Transo-Pharm serves as a sourcing and regulatory marketing agent for API manufacturers. It aids clients in establishing DMFs and provides GMP consulting. With a dedicated regulatory department, a warehouse, proprietary IPs for API processes, and partnerships with laboratories, Transo-Pharm offers a wide range of services. It operates from its offices in Shanghai, Hong Kong, Singapore, and the US.
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Virtual BoothBiophore is a research-driven global pharmaceutical company focused on niche APIs for the generic industry.

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About the Company : Biophore, founded in 2007, has established itself as a reliable partner in the development and manufacturing of niche and complex pharmaceutical products. With 4 USFDA and EU-appro...

Biophore, founded in 2007, has established itself as a reliable partner in the development and manufacturing of niche and complex pharmaceutical products. With 4 USFDA and EU-approved API manufacturing facilities, a dedicated intermediate facility, and a R&D laboratory housing 400 scientists, Biophore has positioned itself as a global leader among API companies. It consistently ranks among the top 10 US DMF filers and has obtained over 150 patents worldwide in process and polymorph areas. Biophore's facilities have an impressive track record of successful audits by regulatory bodies such as USFDA, EMEA, ANVISA, COFEPRIS, and WHO GMP.
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Virtual BoothFaran Shimi: Leading producer of high-quality APIs & alkaloid opiates, serving major pharmaceutical companies across the Middle East.

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Virtual BoothShanghai Minbiotech is the leading producer of biopharmaceuticals and a variety of high-end generic & innovative drugs.

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About the Company : HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years of business experiences on the marketi...

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About the Company : Nhwa is specialized in manufacturing APIs and dosages in the field of Central Nervous System. With 40 years of experience and excellent reputation, Nhwa has become the leader of ma...

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Phytonadione

About the Company : MENADIONA is an independent privately-owned company, founded in 1970. Ever since, the company has been involved in manufacturing active ingredients (APIs) and key intermediates for...

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RELIANCE"},{"dataSource":"API Import","activeIngredients":"","year":"2025","qtr":"Q2","strtotime":1745001000,"product":"5013224264 VITAMIN K1 API, 1 KG ALU BOTTLE (QTY 1 NOS X1KG 5013224264 VITAMIN K1 API, 1 KG ALU BOTTLE (QTY 1 NOS X1KG","address":"882\/1-871, NEAR KANKAVATI ,VILLAGE-","city":"AHMEDABAD, GUJARAT","supplier":"DSM NUTRITIONAL PRODUCTS ASIA PACIFIC","supplierCountry":"SWITZERLAND","foreign_port":"AMSTERDAM, SCHIPHOL","customer":"AMNEAL PHARMACEUTICALS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"1.00","actualQuantity":"1","unit":"KGS","unitRateFc":"33787.4","totalValueFC":"34102.4","currency":"USD","unitRateINR":"2919228.6","date":"19-Apr-2025","totalValueINR":"2919228.63","totalValueInUsd":"34102.4","indian_port":"Ahmedabad Air","hs_no":"29362930","bill_no":"9581598","productDescription":"API","marketType":"REGULATED MARKET","country":"SWITZERLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"AMSTERDAM, SCHIPHOL","supplierAddress":"30 PASIR PANJANG ROAD MAPLETREE BUS INESS CITY#13-31, SINGAPORE Singapo re, , SINGAPORE SINGAPORE","customerAddress":"882\/1-871, NEAR KANKAVATI ,VILLAGE-"},{"dataSource":"API Import","activeIngredients":"","year":"2025","qtr":"Q2","strtotime":1745001000,"product":"5013224264 VITAMIN K1 API,1 KG ALU BOTTLE 1 NOS X1 KGS 5013224264 VITAMIN K1 API,1 KG ALU BOTTLE 1 NOS X1 KGS","address":"882\/1-871, NEAR KANKAVATI ,VILLAGE-","city":"AHMEDABAD, GUJARAT","supplier":"DSM NUTRITIONAL PRODUCTS ASIA PACIFIC","supplierCountry":"SWITZERLAND","foreign_port":"AMSTERDAM, SCHIPHOL","customer":"AMNEAL PHARMACEUTICALS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"1.00","actualQuantity":"1","unit":"KGS","unitRateFc":"33787.4","totalValueFC":"34102.4","currency":"USD","unitRateINR":"2919228.6","date":"19-Apr-2025","totalValueINR":"2919228.63","totalValueInUsd":"34102.4","indian_port":"Ahmedabad Air","hs_no":"29362930","bill_no":"9581598","productDescription":"API","marketType":"REGULATED MARKET","country":"SWITZERLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"AMSTERDAM, SCHIPHOL","supplierAddress":"30 PASIR PANJANG ROAD MAPLETREE BUS INESS CITY#13-31, SINGAPORE Singapo re, , SINGAPORE SINGAPORE","customerAddress":"882\/1-871, NEAR KANKAVATI ,VILLAGE-"}]
13-Jan-2022
19-Apr-2025
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DOSAGE - TABLET;ORAL - 5MG **Federal Register...DOSAGE - TABLET;ORAL - 5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 10104

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DOSAGE - INJECTABLE;INJECTION - 10MG/ML ***Fe...DOSAGE - INJECTABLE;INJECTION - 10MG/ML ***Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 12223

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DOSAGE - INJECTABLE;INJECTION - 1MG/0.5ML **F...DOSAGE - INJECTABLE;INJECTION - 1MG/0.5ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 12223

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DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL...DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL;0.02MG/VIAL;0.001MG/VIAL;5MG/VIAL;0.01MG/VIAL;0.14MG/VIAL;17MG/VIAL;0.2MG/VIAL;1MG/VIAL;1.4MG/VIAL;EQ 1.2MG BASE/VIAL;0.7MG/VIAL;7MG/VIAL

USFDA APPLICATION NUMBER - 18920

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DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/...DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/ML;12MCG/ML;40 IU/ML;1MCG/ML;3MG/ML;120MCG/ML;8MG/ML;1.2MG/ML;0.72MG/ML;1.2MG/ML;660 IU/ML;0.03MG/ML

USFDA APPLICATION NUMBER - 21163

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DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/...DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/ML;12MCG/ML;40 IU/ML;1MCG/ML;3MG/ML;120MCG/ML;8MG/ML;1.2MG/ML;0.72MG/ML;1.2MG/ML;660 IU/ML;30MCG/ML

USFDA APPLICATION NUMBER - 21163

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DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;...DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;0.06MG/VIAL;0.005MG/VIAL;15MG/VIAL;0.005MG/VIAL;0.6MG/VIAL;40MG/VIAL;6MG/VIAL;3.6MG/VIAL;6MG/VIAL;1MG/VIAL;10MG/VIAL;0.15MG/VIAL

USFDA APPLICATION NUMBER - 21625

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DOSAGE - INJECTABLE;INJECTION - 1MG/0.5ML

USFDA APPLICATION NUMBER - 83722

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DOSAGE - INJECTABLE;INJECTION - 1MG/0.5ML

USFDA APPLICATION NUMBER - 87954

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DOSAGE - INJECTABLE;INJECTION - 10MG/ML

USFDA APPLICATION NUMBER - 87955

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ABOUT THIS PAGE

Looking for 84-80-0 / Vitamin K1 API manufacturers, exporters & distributors?

Vitamin K1 manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Vitamin K1 API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Vitamin K1 manufacturer or Vitamin K1 supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Vitamin K1 manufacturer or Vitamin K1 supplier.

PharmaCompass also assists you with knowing the Vitamin K1 API Price utilized in the formulation of products. Vitamin K1 API Price is not always fixed or binding as the Vitamin K1 Price is obtained through a variety of data sources. The Vitamin K1 Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Vitamin K1

Synonyms

Phylloquinone, Phytonadione, 84-80-0, Phytomenadione, Phytylmenadione, 3-phytylmenadione

Cas Number

84-80-0

Unique Ingredient Identifier (UNII)

MLF3D1712D

About 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.

Alpha-Phylloquinone Manufacturers

A Alpha-Phylloquinone manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Alpha-Phylloquinone, including repackagers and relabelers. The FDA regulates Alpha-Phylloquinone manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Alpha-Phylloquinone API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Alpha-Phylloquinone manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Alpha-Phylloquinone Suppliers

A Alpha-Phylloquinone supplier is an individual or a company that provides Alpha-Phylloquinone active pharmaceutical ingredient (API) or Alpha-Phylloquinone finished formulations upon request. The Alpha-Phylloquinone suppliers may include Alpha-Phylloquinone API manufacturers, exporters, distributors and traders.

click here to find a list of Alpha-Phylloquinone suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Alpha-Phylloquinone USDMF

A Alpha-Phylloquinone DMF (Drug Master File) is a document detailing the whole manufacturing process of Alpha-Phylloquinone active pharmaceutical ingredient (API) in detail. Different forms of Alpha-Phylloquinone DMFs exist exist since differing nations have different regulations, such as Alpha-Phylloquinone USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Alpha-Phylloquinone DMF submitted to regulatory agencies in the US is known as a USDMF. Alpha-Phylloquinone USDMF includes data on Alpha-Phylloquinone's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Alpha-Phylloquinone USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Alpha-Phylloquinone suppliers with USDMF on PharmaCompass.

Alpha-Phylloquinone JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Alpha-Phylloquinone Drug Master File in Japan (Alpha-Phylloquinone JDMF) empowers Alpha-Phylloquinone API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Alpha-Phylloquinone JDMF during the approval evaluation for pharmaceutical products. At the time of Alpha-Phylloquinone JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Alpha-Phylloquinone suppliers with JDMF on PharmaCompass.

Alpha-Phylloquinone CEP

A Alpha-Phylloquinone CEP of the European Pharmacopoeia monograph is often referred to as a Alpha-Phylloquinone Certificate of Suitability (COS). The purpose of a Alpha-Phylloquinone CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Alpha-Phylloquinone EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Alpha-Phylloquinone to their clients by showing that a Alpha-Phylloquinone CEP has been issued for it. The manufacturer submits a Alpha-Phylloquinone CEP (COS) as part of the market authorization procedure, and it takes on the role of a Alpha-Phylloquinone CEP holder for the record. Additionally, the data presented in the Alpha-Phylloquinone CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Alpha-Phylloquinone DMF.

A Alpha-Phylloquinone CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Alpha-Phylloquinone CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Alpha-Phylloquinone suppliers with CEP (COS) on PharmaCompass.

Alpha-Phylloquinone WC

A Alpha-Phylloquinone written confirmation (Alpha-Phylloquinone WC) is an official document issued by a regulatory agency to a Alpha-Phylloquinone manufacturer, verifying that the manufacturing facility of a Alpha-Phylloquinone active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Alpha-Phylloquinone APIs or Alpha-Phylloquinone finished pharmaceutical products to another nation, regulatory agencies frequently require a Alpha-Phylloquinone WC (written confirmation) as part of the regulatory process.

click here to find a list of Alpha-Phylloquinone suppliers with Written Confirmation (WC) on PharmaCompass.

Alpha-Phylloquinone NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Alpha-Phylloquinone as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Alpha-Phylloquinone API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Alpha-Phylloquinone as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Alpha-Phylloquinone and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Alpha-Phylloquinone NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Alpha-Phylloquinone suppliers with NDC on PharmaCompass.

Alpha-Phylloquinone GMP

Alpha-Phylloquinone Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Alpha-Phylloquinone GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Alpha-Phylloquinone GMP manufacturer or Alpha-Phylloquinone GMP API supplier for your needs.

Alpha-Phylloquinone CoA

A Alpha-Phylloquinone CoA (Certificate of Analysis) is a formal document that attests to Alpha-Phylloquinone's compliance with Alpha-Phylloquinone specifications and serves as a tool for batch-level quality control.

Alpha-Phylloquinone CoA mostly includes findings from lab analyses of a specific batch. For each Alpha-Phylloquinone CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Alpha-Phylloquinone may be tested according to a variety of international standards, such as European Pharmacopoeia (Alpha-Phylloquinone EP), Alpha-Phylloquinone JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Alpha-Phylloquinone USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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