General Information of Drug (ID: DM8HDOL)

Drug Name
Phytonadione Drug Info
Synonyms
Phyllochinon; Phyllohydroquinone; Phytomenadione; Fitomenadione [DCIT]; Phyllochinon [German]; LT00452032; Fitomenadiona [INN-Spanish]; Mephyton (TN); Phylloquinone (8CI); Phytomenadione (INN); Phytomenadionum [INN-Latin]; Phytonadione [USAN:JAN]; Vitamin K1 (TN); Vitamin K1 (VAN); Vitamin K1 (generic); Phythyl-menadion (GERMAN); Phytonadione (JP15/USP); 1,4-Naphthalenedione, 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl)-, radical ion(1-); 2-(3,7,11,15-Tetramethylhexadec-2-enyl)-3-methylnaphthalene-1,4-dione; 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalened-ione; 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione; 2-Methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone; 2-Methyl-3-phythyl-1,4-naphthochinon; 2-Methyl-3-phytyl-1,4-naphthochinon; 2-Methyl-3-phytyl-1,4-naphthochinon [German]; 2-methyl-3-(3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione; 2-methyl-3-[(E)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione; 3-Phytylmenadione
Indication
Disease Entry ICD 11 Status REF
Bleeding disorder GA20-GA21 Approved [1]
Osteoporosis FB83.0 Approved [2]
Vitamin K deficiency 5B59 Approved [1]
Autosomal dominant hypocalcemia 5A50.0Y Investigative [2]
Therapeutic Class
Vitamins
Cross-matching ID
PubChem CID
5284607
ChEBI ID
CHEBI:18067
CAS Number
CAS 79083-00-4
TTD Drug ID
DM8HDOL

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Drug(s) Affected By Prothrombin (F2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Colchicine DM2POTE Acute gout flare FA25.0 Approved [9]
Methotrexate DM2TEOL Anterior urethra cancer Approved [10]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [11]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [12]
Chlorpromazine DMBGZI3 Acute intermittent hepatic porphyria 5C58.11 Approved [13]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [14]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [15]
Testosterone enanthate DMB6871 N. A. N. A. Approved [16]
Atorvastatin DMF28YC Acute coronary syndrome BA41 Approved [17]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [18]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Protein c-Fos (FOS)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [19]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [20]
Verapamil DMA7PEW Angina pectoris BA40 Approved [21]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [22]
Acebutolol DM0TI4U Hypertension BA00-BA04 Approved [21]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [23]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [24]
Methotrexate DM2TEOL Anterior urethra cancer Approved [25]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [26]
Quercetin DM3NC4M Obesity 5B81 Approved [27]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Matrix Gla protein (MGP)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [28]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [29]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [30]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [31]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [15]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [32]
Dasatinib DMJV2EK Blast phase chronic myelogenous leukemia, BCR-ABL1 positive Approved [33]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [34]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [35]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [36]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 4F2 (CYP4F2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Warfarin DMJYCVW Atrial fibrillation BC81.3 Approved [37]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [29]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [38]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [39]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [15]
Demecolcine DMCZQGK Solid tumour/cancer 2A00-2F9Z Approved [40]
Ethanol DMDRQZU Chronic pain MG30 Approved [41]
Rosiglitazone DMILWZR Chronic kidney disease GB61 Approved [29]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [42]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [15]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Vitamin K-dependent gamma-carboxylase (GGCX) TT76OLR VKGC_HUMAN Cofactor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 4F2 (CYP4F2) OTKILAER CP4F2_HUMAN Regulation of Drug Effects [4]
Matrix Gla protein (MGP) OTZWU3FU MGP_HUMAN Gene/Protein Processing [5]
Protein c-Fos (FOS) OTJBUVWS FOS_HUMAN Gene/Protein Processing [6]
Prothrombin (F2) OTNFSM49 THRB_HUMAN Gene/Protein Processing [7]
Vitamin K epoxide reductase complex subunit 1 OTOJNJRD VKOR1_HUMAN Biotransformations [8]
Vitamin K epoxide reductase complex subunit 1-like protein 1 OT7QSEWT VKORL_HUMAN Biotransformations [8]

References

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2 Phytonadione FDA Label
3 Quinone oxidoreductases and vitamin K metabolism. Vitam Horm. 2008;78:85-101.
4 Effects of CYP4F2 polymorphism on response to warfarin during induction phase: a prospective, open-label, observational cohort study. Clin Ther. 2012 Apr;34(4):811-23. doi: 10.1016/j.clinthera.2012.02.009. Epub 2012 Mar 13.
5 Vitamin K1 Inhibition of Renal Crystal Formation through Matrix Gla Protein in the Kidney. Kidney Blood Press Res. 2019;44(6):1392-1403. doi: 10.1159/000503300. Epub 2019 Oct 22.
6 Effect of cell differentiation for neuroblastoma by vitamin k analogs. Jpn J Clin Oncol. 2009 Apr;39(4):251-9. doi: 10.1093/jjco/hyp011. Epub 2009 Mar 8.
7 Specificity of increased des-gamma-carboxyprothrombin in hepatocellular carcinoma after vitamin K1 injection. J Hepatol. 1987 Aug;5(1):27-9. doi: 10.1016/s0168-8278(87)80057-0.
8 VKORC1 and VKORC1L1 have distinctly different oral anticoagulant dose-response characteristics and binding sites. Blood Adv. 2018 Mar 27;2(6):691-702.
9 [Colchicine in chronic liver disease of alcoholic etiology. Double-blind, randomized study of its effects on blood levels of plasma proteins and clinical course in patients]. Rev Assoc Med Bras (1992). 1995 May-Jun;41(3):207-12.
10 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
11 Cytoskeletal activation and altered gene expression in endothelial barrier regulation by simvastatin. Am J Respir Cell Mol Biol. 2004 May;30(5):662-70. doi: 10.1165/rcmb.2003-0267OC. Epub 2003 Nov 20.
12 Molecular characterization of a toxicological tipping point during human stem cell differentiation. Reprod Toxicol. 2020 Jan;91:1-13. doi: 10.1016/j.reprotox.2019.10.001. Epub 2019 Oct 7.
13 Effects of chlorpromazine with and without UV irradiation on gene expression of HepG2 cells. Mutat Res. 2005 Aug 4;575(1-2):47-60. doi: 10.1016/j.mrfmmm.2005.03.002. Epub 2005 Apr 26.
14 Antithrombotic effects of aspirin based on PLA1/A2 glycoprotein IIIa polymorphism in patients with coronary artery disease. Thromb Res. 2007;119(3):301-3. doi: 10.1016/j.thromres.2006.03.005. Epub 2006 May 3.
15 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
16 Haemostatic effects of supraphysiological levels of testosterone in normal men. Thromb Haemost. 1995 Aug;74(2):693-7.
17 Atorvastatin and quinapril inhibit blood coagulation in patients with coronary artery disease following 28 days of therapy. J Thromb Haemost. 2006 Nov;4(11):2397-404. doi: 10.1111/j.1538-7836.2006.02165.x. Epub 2006 Aug 14.
18 Gene Expression Regulation and Pathway Analysis After Valproic Acid and Carbamazepine Exposure in a Human Embryonic Stem Cell-Based Neurodevelopmental Toxicity Assay. Toxicol Sci. 2015 Aug;146(2):311-20. doi: 10.1093/toxsci/kfv094. Epub 2015 May 15.
19 Essential role of cell cycle regulatory genes p21 and p27 expression in inhibition of breast cancer cells by arsenic trioxide. Med Oncol. 2011 Dec;28(4):1225-54.
20 Cannabidiol Activates Neuronal Precursor Genes in Human Gingival Mesenchymal Stromal Cells. J Cell Biochem. 2017 Jun;118(6):1531-1546. doi: 10.1002/jcb.25815. Epub 2016 Dec 29.
21 Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro. Toxicol Sci. 2003 Aug;74(2):260-70. doi: 10.1093/toxsci/kfg113. Epub 2003 May 2.
22 Sertraline induces endoplasmic reticulum stress in hepatic cells. Toxicology. 2014 Aug 1;322:78-88. doi: 10.1016/j.tox.2014.05.007. Epub 2014 May 24.
23 Estrogen regulation in human breast cancer cells of new downstream gene targets involved in estrogen metabolism, cell proliferation and cell transformation. J Mol Endocrinol. 2004 Apr;32(2):397-414.
24 Microarray analysis of H2O2-, HNE-, or tBH-treated ARPE-19 cells. Free Radic Biol Med. 2002 Nov 15;33(10):1419-32.
25 Methotrexate induces production of IL-1 and IL-6 in the monocytic cell line U937. Arthritis Res Ther. 2014 Jan 20;16(1):R17. doi: 10.1186/ar4444.
26 Simvastatin inhibits NOR-1 expression induced by hyperlipemia by interfering with CREB activation. Cardiovasc Res. 2005 Aug 1;67(2):333-41. doi: 10.1016/j.cardiores.2005.03.016. Epub 2005 Apr 21.
27 The G protein-coupled receptor GPR30 mediates c-fos up-regulation by 17beta-estradiol and phytoestrogens in breast cancer cells. J Biol Chem. 2004 Jun 25;279(26):27008-16. doi: 10.1074/jbc.M403588200. Epub 2004 Apr 16.
28 Comparative gene expression profiling reveals partially overlapping but distinct genomic actions of different antiestrogens in human breast cancer cells. J Cell Biochem. 2006 Aug 1;98(5):1163-84.
29 Transcriptomic analysis of untreated and drug-treated differentiated HepaRG cells over a 2-week period. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):27-35.
30 Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
31 Identification of transcriptome signatures and biomarkers specific for potential developmental toxicants inhibiting human neural crest cell migration. Arch Toxicol. 2016 Jan;90(1):159-80.
32 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
33 Dasatinib reverses cancer-associated fibroblasts (CAFs) from primary lung carcinomas to a phenotype comparable to that of normal fibroblasts. Mol Cancer. 2010 Jun 27;9:168.
34 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
35 Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
36 Analysis of estrogen agonism and antagonism of tamoxifen, raloxifene, and ICI182780 in endometrial cancer cells: a putative role for the epidermal growth factor receptor ligand amphiregulin. J Soc Gynecol Investig. 2005 Oct;12(7):e55-67.
37 CYP4F2 genetic variant alters required warfarin dose. Blood. 2008 Apr 15;111(8):4106-12. doi: 10.1182/blood-2007-11-122010. Epub 2008 Feb 4.
38 Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.
39 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
40 Characterization of formaldehyde's genotoxic mode of action by gene expression analysis in TK6 cells. Arch Toxicol. 2013 Nov;87(11):1999-2012.
41 CYP4F2 repression and a modified alpha-tocopherol (vitamin E) metabolism are two independent consequences of ethanol toxicity in human hepatocytes. Toxicol In Vitro. 2017 Apr;40:124-133.
42 Blood transcript immune signatures distinguish a subset of people with elevated serum ALT from others given acetaminophen. Clin Pharmacol Ther. 2016 Apr;99(4):432-41.