Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0039)
Name
Orlistat
Synonyms
orlistat; 96829-58-2; Tetrahydrolipstatin; Xenical; Alli; Orlipastat; (-)-Tetrahydrolipstatin; Orlipastatum [INN-Latin]; Ro-18-0647; C29H53NO5; Ro 18-0647/002; Orlistat (Alli, Xenical); (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate; [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate; N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; MLS002207022; N-Formyl-L-leucine, ester with (3S,4S)-3-hexyl-4-((2S)-2-hydroxytridecyl)-2-oxetanone; CHEMBL175247; DTXSID8023395; 95M8R751W8; NSC-758881; Orlipastatum; SMR000466339; THLP; Ro-180647002; Ro-180647-002; Ro-18-0647/002; (S)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)tridecan-2-yl formyl-L-leucinate; tetrahydrolipastatin; DTXCID40820067; MFCD05662360; (S)-((S)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)tridecan-2-yl) 2-formamido-4-methylpentanoate; Xenical (TN); CAS-96829-58-2; L-Leucine, N-formyl-, (1S)-1-(((2S,3S)-3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester; SR-01000759417; orlistatum; Orlistat [USAN:INN:BAN]; UNII-95M8R751W8; HSDB 7556; N-formyl-L-leucine (1S)-1-{[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl}dodecyl ester; L-Leucine, N-formyl-, (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; NCGC00095128-01; (-)-Tetrahydrolipstatin; Orlistat; Ro 18-0647/002; Tetrahydrolipstatin; Xenical; L-Leucine, N-formyl-, 1-[(3-hexyl-4-oxo-2-oxetanyl)methyl]dodecyl ester, [2S-[2alpha(R*),3beta]]-; THL; KS-1183; Lipase Inhibitor, THL; ORLISTAT [HSDB]; ORLISTAT [USAN]; ORLISTAT [INN]; ORLISTAT [JAN]; ORLISTAT [MI]; (-)-tetrahydrolipostatin; ORLISTAT [VANDF]; R-212; ORLISTAT [MART.]; ORLISTAT [USP-RS]; ORLISTAT [WHO-DD]; Orlistat (JAN/USP/INN); ORLISTAT [EMA EPAR]; Orlistat, >=98%, solid; SCHEMBL16408; L-Leucine, N-formyl-, 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester, (2S-(2alpha(R*),3beta))-; MLS000759448; MLS001423955; BIDD:GT0853; ORLISTAT [ORANGE BOOK]; GTPL5277; ORLISTAT [USP MONOGRAPH]; BDBM24567; CHEBI:94686; AHLBNYSZXLDEJQ-FWEHEUNISA-N; Tetrahydrolipstatin;Ro-18-0647; HMS2051I08; HMS3413P06; HMS3677P06; HY-B0218; Tox21_111437; HB4009; s1629; AKOS015894875; Tox21_111437_1; BCP9001031; CCG-100851; DB01083; NC00101; NSC 758881; Ro18-0647; NCGC00165856-01; NCGC00165856-02; NCGC00165856-03; NCGC00165856-15; [(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate; BO164179; R212; BCP0726000044; O0381; SW197481-2; D04028; EN300-268136; AB00639987-09; AB00639987_10; Q424163; Q-201519; SR-01000759417-5; SR-01000759417-7; Z2379810072; Orlistat, United States Pharmacopeia (USP) Reference Standard; Orlistat, Pharmaceutical Secondary Standard; Certified Reference Material; (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl N-formyl-L-leucinate; 2-formamido-3-[(3-hexyl-4-oxo-oxetan-2-yl)methyl]-2-isobutyl-tetradecanoate; N-formyl-L-leucine (S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; N-formyl-L-leucine-(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]-dodecyl ester; (2S)-2-formamido-4-methylpentanoic acid [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] ester; [(2S)-1-[(2R,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2R)-2-formamido-4-methylpentanoate; 104872-04-0; L-LEUCINE, N-FORMYL-, 1-((3-HEXYL-4-OXO-2-OXETANYL)METHYL)DODECYL ESTER, (2S-(2.ALPHA.(R*),3.BETA.))-

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Status
Approved
Drug Type
Small molecular drug
Structure
3D MOL
2D MOL
Formula
C29H53NO5
IUPAC Name
[(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate
Canonical SMILES
CCCCCCCCCCCC(CC1C(C(=O)O1)CCCCCC)OC(=O)C(CC(C)C)NC=O
InChI
InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1
InChIKey
AHLBNYSZXLDEJQ-FWEHEUNISA-N
PubChem CID
3034010
TTD Drug ID
D0T9TJ
Full List of Ferroptosis Target Related to This Drug
Phospholipid hydroperoxide glutathione peroxidase (GPX4)
 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 Suppressor
Responsed Disease Lung cancer ICD-11: 2C25
 Disease Info 
Pathway Response Fatty acid metabolism hsa01212
AMPK signaling pathway hsa04152
Cell Process Cell ferroptosis
Cell proliferation
In Vitro Model NCI-H1299 cells Lung large cell carcinoma Homo sapiens CVCL_0060
A-549 cells Lung adenocarcinoma Homo sapiens CVCL_0023
LL/2 (LLC1) cells Lung cancer Mus musculus CVCL_4358
In Vivo Model
C57BL/6 mice were anesthetized, and 5 x 105 LLC cells were implanted subcutaneously into the right flank. Five days post-implant, mice were randomized and assigned into two groups and treated with orlistat (10 mg/kg, intraperitoneal injection) or PBS daily for 14 days. The tumor volume was measured twice a week with a caliper, and the tumor volume was calculated according to the formula ((length x width2 )/2).

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Response regulation Orlistat, as a single agent, inhibited the proliferation and viabilities of lung cancer cells and induced ferroptosis-like cell death in vitro. Mechanistically, we found that orlistat reduced the expression of GPX4, a central ferroptosis regulator, and induced lipid peroxidation.
References
Ref 1 Orlistat induces ferroptosis-like cell death of lung cancer cells. Front Med. 2021 Dec;15(6):922-932. doi: 10.1007/s11684-020-0804-7. Epub 2021 Jun 4.