Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0033)
Name
Vitamin K1
Synonyms
Phylloquinone; Vitamin K1; phytonadione; 84-80-0; Phytomenadione; Phytylmenadione; 3-Phytylmenadione; Aquamephyton; Konakion; Phyllochinon; Mephyton; Monodion; Synthex P; Kinadion; Kephton; 2-Methyl-3-phytyl-1,4-naphthoquinone; Mono-Kay; Combinal K1; Kativ N; alpha-Phylloquinone; Fitomenadiona; K-Ject; Phyllochinonum; Phytomenadionum; Phytonadionum; trans-Phylloquinone; Aqua mephyton; VitaminK1; Antihemorrhagic vitamin; Fitomenadione; Vitamin K 1; 79083-00-4; 2',3'-trans-Vitamin K1; 2-Methyl-3-phytyl-1,4-naphthochinon; 11104-38-4; CHEBI:18067; Vitamin K1(20); UNII-S5Z3U87QHF; NSC 270681; Phylloquinone e-form; Aqua-Mephytin; Phythyl-menadion; VITAMIN K; 1,4-Naphthoquinone, 2-methyl-3-phytyl-; DTXSID8023472; HSDB 3162; 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione; 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione; EINECS 201-564-2; NSC-270681; S5Z3U87QHF; 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione; DTXCID003472; MLF3D1712D; Phytonadione, (E)-(+/-)-; 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-, (R-(R*,R*-(E)))-; 1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-; 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-; 2-Methyl-3-((7R,11R,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione; Orakay; 2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone; 2-Methyl-3-phythyl-1,4-naphthochinon; 1,4-Naphthalenedione, 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl)-; CAS-84-80-0; rel-2-Methyl-3-((7R,11R,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione; Phytonadione, K1; 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-, [R-[R*,R*-(E)]]-; 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione; Vitamin K-1; Phytonadione [USP:JAN]; Kanavit; Neokay; a-Phylloquinone; Konakion mm; NSC270681; vitaminum k1; 2-Methyl-3-((2E)-3,7,11,15-tetramethyl-2-hexadecenyl)naphthoquinone; Konakion mm paed; (E)-phytonadione; 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione; 2-methyl-3-((7R,11R,E)-3,7,11,15-tetramethylhexadec-2-enyl)naphthalene-1,4-dione; NCGC00159423-02; EINECS 234-330-3; EINECS 279-052-3; MFCD00214063; vitamin K1, 11; Vitamin K1 ,(S); VEDA-K1; VETA-K1; PHYTONADIONE [JAN]; phylloquinone;2-METHYL-3-PHYTYL-1,4-NAPHTHOQUINONE; Phylloquinone;Phytomenadione; SCHEMBL3882; 2',3'-trans-phylloquinone; Phythyl-menadion (GERMAN); Vitamin K1 (Phylloquinone); Vitamin K1, viscous liquid; CHEMBL1550; UNII-MLF3D1712D; PHYTONADIONE, (E)-; PHYLLOQUINONE, (E)-; MLS001074732; BIDD:GT0793; PHYTOMENADIONE, (E)-; PHYTONADIONE (USP-RS); SCHEMBL351365; 2', 3'-trans-Vitamin K1; PHYTOMENADIONE (MART.); 2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone #; -2-enyl)naphthalene-1,4-dione; BDBM24782; B02BA01; [r-[r*,R*-(E)]]-2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-napthalenedione; [r-[r*,R*-(E)]]-2-Methyl-3-(3-7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione; PHYLLOQUINONE E-FORM [MI]; HMS2094G09; HMS2270J10; Pharmakon1600-01505485; HY-N0684; PHYTOMENADIONE (EP IMPURITY); PHYTONADIONE (USP MONOGRAPH); Tox21_111655; BDBM50553259; LMPR02030028; NSC760373; s4698; 2-Methyl-3-phytyl-1,4-napthoquinone; AKOS015841892; Tox21_111655_1; A034SE7857; CCG-213568; CS-6376; DB01022; NSC-760373; (R*,R*-(E))-(1)-2-Methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone; NCGC00159423-03; Phylloquinone (K1), analytical standard; AC-34846; AS-13734; SMR000112043; SBI-0206926.P001; trans-Phytomenadione 100 microg/mL in Ethanol; AB00698065_04; A840928; EN300-22411510; Q186093; SR-05000001941; C31H46O2 (2-methyl-3-phytyl-1,4-naphthoquinone); Q-201934; SR-05000001941-1; W-108488; Z2568644345; 2-methyl-3-((7R,11R,E)-3,7,11,15-tetramethylhexadec; 84C51B31-3CE2-476B-BE66-A84BDD46A513; VITAMIN K1; 2-METHYL-3-PHYTYL-1,4-NAPHTHOQUINONE; Phytomenadione, European Pharmacopoeia (EP) Reference Standard; Phytonadione, United States Pharmacopeia (USP) Reference Standard; 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalened- ione; Vitamin K1, BioXtra, >=99.0% (sum of isomers, HPLC), mixtur of isomers; 1,4-Naphthalenedione, 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl)-; 2-Methyl-3-((2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl)-1,4-naphthoquinone; Phytonadione, Pharmaceutical Secondary Standard; Certified Reference Material; 1,4-NAPHTHALENEDIONE, 2-METHYL-3-((2E,7R,11R)-3,7,11,15-TETRAMETHYL-2-HEXADECEN-1-YL)-, REL-; 2-METHYL-3-((2E,7R,11R)-3,7,11,15-TETRAMETHYL-2-HEXADECENYL)-1,4-NAPHTHALENEDIONE; 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione;Vitamin K1; MIXTURE OF THE TRANS (E) AND CIS (Z) ISOMERS CONTAINING NOT LESS THAN 75% OF TRANS-PHYTOMENADIONE

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Status
Approved
Drug Type
Small molecular drug
Structure
Formula
C31H46O2
IUPAC Name
2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
Canonical SMILES
CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C
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
InChIKey
MBWXNTAXLNYFJB-NKFFZRIASA-N
PubChem CID
5284607
TTD Drug ID
D00FSV
Full List of Ferroptosis Target Related to This Drug
Long-chain-fatty-acid--CoA ligase 4 (ACSL4)
 Target Info 
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Target for Ferroptosis Driver
Responsed Disease Acute kidney failure ICD-11: GB60
 Disease Info 
Pathway Response Fatty acid metabolism hsa01212
Cell Process Cell ferroptosis
In Vitro Model NIH3T3 cells Normal Mus musculus CVCL_0594
HT-1080 cells Fibrosarcoma Homo sapiens CVCL_0317
MCT (Murine proximal tubular epithelial cells)
In Vivo Model
All mice used in our in vivo studies were 8-week-old males of the C57BL/6J background. Kidneys were exposed via a midline abdominal incision and bilateral renal pedicle clamping for 35 min using microaneurysm clamps (Aesculap Inc., Center Valley, PA, USA). Throughout the surgical procedure, the mice were kept under isoflurane narcosis, and their body temperature was maintained at 36-37 by continuous monitoring using a temperature-controlled, self-regulated heating system (Fine Science Tools, Heidelberg, Germany). After clamps were removed, kidney reperfusion was confirmed visually before the abdomen was closed in two layers using standard 6-0 sutures. To maintain fluid balance, all mice were supplemented with 1 ml of prewarmed PBS administered intraperitoneally directly after surgery. After 48 h of reperfusion, the mice were sacrificed, blood samples were obtained by retrobulbar puncture, and kidneys were collected for analysis.

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Response regulation Renal expression of ACSL4 was markedly enhanced by IRI and reduced by vitamin K1. Vitamin K1 as a potent inhibitor of ferroptosis, and hence, it represents a potential drug for the treatment of pathological cell death processes during acute kidney injury in humans.
References
Ref 1 Vitamin K1 inhibits ferroptosis and counteracts a detrimental effect of phenprocoumon in experimental acute kidney injury. Cell Mol Life Sci. 2022 Jun 28;79(7):387. doi: 10.1007/s00018-022-04416-w.