Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR3300)
Drug Name
TH-302
Prodrug Info TH-302 is the prodrug of TH-302 metabolite RM12
Synonyms
TH-302; evofosfamide; 918633-87-1; TH 302; TH302; UNII-8A9RZ3HN8W; Evofosfamide(TH 302); n,n'-bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1h-imidazol-5-yl)methyl ester; 8A9RZ3HN8W; compound 3b; TH-302; Evofosfamide;HAP-302; Phosphorodiamidic acid, N,N'-bis(2-bromoethyl)-, (1-methyl-2-nitro-1H-imidazol-5-yl)methyl ester; 2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine; Evofosfamide [USAN:INN]; Evofosfamide(TH-302); C9H16Br2N5O4P; CHEMBL260046; SCHEMBL2357174
Indication Kaposi sarcoma [ICD11: 2B57] Phase 2 [1]
Melanoma [ICD11: ICD11: 2C30] Phase 1 [2]
Pancreatic cancer [ICD11: ICD11: 2C10] Phase 1 [3]
Prostate cancer [ICD11: ICD11: 2C82] Phase 1 [4]
Squamous cell carcinoma [ICD11: ICD11: 2B60-2D01] Phase 1 [5]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 449.04 Topological Polar Surface Area 114
Heavy Atom Count 21 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
11984561
CAS Number
918633-87-1
TTD Drug ID
D0H1EA
Formula
C9H16Br2N5O4P
Canonical SMILES
CN1C(=CN=C1[N+](=O)[O-])COP(=O)(NCCBr)NCCBr
InChI
InChI=1S/C9H16Br2N5O4P/c1-15-8(6-12-9(15)16(17)18)7-20-21(19,13-4-2-10)14-5-3-11/h6H,2-5,7H2,1H3,(H2,13,14,19)
InChIKey
UGJWRPJDTDGERK-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
TH-302 metabolite RM12 DM015172
132324
Hydrolysis - Hydrolysis 1 [6] , [7]
TH-302 metabolite RM3 DM016030
24194527
Hydrolysis - Hydrolysis 1 [6]
TH-302 metabolite RM9 DM017366 N. A. Conjugation - Glutathione conjugation 1 [6]
TH-302 metabolite RM10 DM017375 N. A. Hydrolysis - Hydrolysis 2 [6]
TH-302 metabolite RM5 DM017374 N. A. Hydrolysis - Hydrolysis 2 [6]
TH-302 metabolite RM6 DM017373 N. A. Oxidation - Oxidation 2 [6]
TH-302 metabolite RM7 DM017367 N. A. Hydrolysis - Hydrolysis 2 [6]
TH-302 metabolite RM8 DM017368 N. A. Hydrolysis - Hydrolysis 3 [6]
TH-302 metabolite DM3 DM017372 N. A. Hydrolysis - Hydrolysis 4 [8]
TH-302 metabolite DM4 DM017371 N. A. Hydrolysis - Hydrolysis 4 [8]
TH-302 metabolite RM13 DM017369 N. A. Conjugation - N-acetylation 4 [6]
TH-302 metabolite RM11 DM017370 N. A. Oxidation - Oxidation 5 [6]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008526 TH-302 TH-302 metabolite RM9 Conjugation - Glutathione conjugation Unclear [6]
MR008536 TH-302 TH-302 metabolite RM3 Hydrolysis - Hydrolysis Unclear [6]
MR008537 TH-302 TH-302 metabolite RM12 Hydrolysis - Hydrolysis POR [6], [7]
MR008527 TH-302 metabolite RM9 TH-302 metabolite RM7 Hydrolysis - Hydrolysis Unclear [6]
MR008533 TH-302 metabolite RM9 TH-302 metabolite RM6 Oxidation - Oxidation Unclear [6]
MR008534 TH-302 metabolite RM9 TH-302 metabolite RM5 Hydrolysis - Hydrolysis Unclear [6]
MR008535 TH-302 metabolite RM9 TH-302 metabolite RM10 Hydrolysis - Hydrolysis Unclear [6]
MR008528 TH-302 metabolite RM7 TH-302 metabolite RM8 Hydrolysis - Hydrolysis Unclear [6]
MR008529 TH-302 metabolite RM8 TH-302 metabolite RM13 Conjugation - N-acetylation Unclear [6]
MR008531 TH-302 metabolite RM8 TH-302 metabolite DM4 Hydrolysis - Hydrolysis Unclear [8]
MR008532 TH-302 metabolite RM8 TH-302 metabolite DM3 Hydrolysis - Hydrolysis Unclear [8]
MR008530 TH-302 metabolite RM13 TH-302 metabolite RM11 Oxidation - Oxidation Unclear [6]
⏷ Show the Full List of 12 MR(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 8695).
2 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
5 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
6 Metabolism, pharmacokinetics and excretion of a novel hypoxia activated cytotoxic prodrug, TH-302, in rats
7 Pharmacokinetics of TH-302: a hypoxically activated prodrug of bromo-isophosphoramide mustard in mice, rats, dogs and monkeys
8 Metabolism and excretion of TH-302 in dogs

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