Drug Information

General Information
Drug ID
DR00039
Drug Name
Glutathione
Synonyms
5-L-Glutamyl-L-cysteinylglycine; 70-18-8; Agifutol S; Copren; Deltathione; GSH; Glutathion; Glutathione; Glutathione (reduced); Glutathione SH; Glutathione [JAN]; Glutathione-SH; Glutatiol; Glutatione; Glutide; Glutinal; Isethion; L-Glutathione reduced; L-Glutatione; L-gamma-glutamyl-L-cysteinylglycine; Ledac; Neuthion; Panaron; Tathion; Tathione; Triptide; gamma-L-Glutamyl-L-cysteinylglycine; gamma-L-Glutamylcysteinylglycine; gamma-L-glutamyl-L-cysteinyl-glycine; glutathione red; red. glutathione; reduced glutathione
Drug Type
Small molecular drug
Indication Human immunodeficiency virus infection [ICD11:1C62.Z] Approved [1]
Structure
3D MOL 2D MOL
Formula
C10H17N3O6S
Canonical SMILES
C(CC(=O)NC(CS)C(=O)NCC(=O)O)C(C(=O)O)N
InChI
InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1
InChIKey
RWSXRVCMGQZWBV-WDSKDSINSA-N
CAS Number
CAS 70-18-8
Pharmaceutical Properties Molecular Weight 307.33 Topological Polar Surface Area 160
Heavy Atom Count 20 Rotatable Bond Count 9
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 8
XLogP
-4.5
PubChem CID
124886
PubChem SID
3133343 ,3353 ,5486 ,584925 ,585393 ,585424 ,585868 ,597405 ,6435995 ,7847082 ,7887988 ,8011661 ,8019868 ,8022090 ,818762 ,820159 ,820986 ,821009 ,821976 ,821977 ,823584 ,823921 ,823937 ,823938 ,823940 ,823941 ,823951 ,824192 ,824837 ,825748 ,828541 ,828542 ,829059 ,829900 ,831498 ,833160 ,834720 ,835369 ,836320 ,836434 ,836436 ,836441 ,836516 ,837543 ,838218 ,838751 ,838765 ,841095 ,854378 ,855260
ChEBI ID
ChEBI:16856
TTD Drug ID
D02HFD
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [4]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [5]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [6]
P-GP Transporter Info P-glycoprotein 1 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data MRP1 Transporter Info Km =5000 microM Human cervical cancer cell line (Hela)-MRP1 [8]
References
1 Glutathione was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Glutathione transport is a unique function of the ATP-binding cassette protein ABCG2. J Biol Chem. 2010 May 28;285(22):16582-7.
3 Structural determinants of substrate specificity differences between human multidrug resistance protein (MRP) 1 (ABCC1) and MRP3 (ABCC3). Drug Metab Dispos. 2008 Dec;36(12):2571-81.
4 Oxidative and electrophilic stress induces multidrug resistance-associated protein transporters via the nuclear factor-E2-related factor-2 transcriptional pathway. Hepatology. 2007 Nov;46(5):1597-610.
5 Role of glutathione in the multidrug resistance protein 4 (MRP4/ABCC4)-mediated efflux of cAMP and resistance to purine analogues. Biochem J. 2002 Feb 1;361(Pt 3):497-503.
6 Regulation of Organic Anion Transporting Polypeptides (OATP) 1B1- and OATP1B3-Mediated Transport: An Updated Review in the Context of OATP-Mediated Drug-Drug Interactions. Int J Mol Sci. 2018 Mar 14;19(3). pii: E855.
7 Upregulation of cellular glutathione levels in human ABCB5- and murine Abcb5-transfected cells. BMC Pharmacol Toxicol. 2015 Dec 15;16:37.
8 Topological polar surface area defines substrate transport by multidrug resistance associated protein 1 (MRP1/ABCC1). J Med Chem. 2009 Feb 26;52(4):1214-8.

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