evofosfamide   Click here for help

GtoPdb Ligand ID: 8695

Synonyms: compound 3b [2] | TH-302
Compound class: Synthetic organic
Comment: Evofosfamide is a hypoxia-activated prodrug being investigated as an antineoplastic therapeutic (compound 3b in [2]). This compound is related to ifosfamide. Being developed by Threshold Pharmaceuticals.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 121.13
Molecular weight 446.93
XLogP 1.15
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES BrCCNP(=O)(NCCBr)OCc1cnc(n1C)[N+](=O)[O-]
Isomeric SMILES BrCCNP(=O)(NCCBr)OCc1cnc(n1C)[N+](=O)[O-]
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)
InChI Key UGJWRPJDTDGERK-UHFFFAOYSA-N
References
1. Borad MJ, Reddy SG, Bahary N, Uronis HE, Sigal D, Cohn AL, Schelman WR, Stephenson Jr J, Chiorean EG, Rosen PJ et al.. (2015)
Randomized Phase II Trial of Gemcitabine Plus TH-302 Versus Gemcitabine in Patients With Advanced Pancreatic Cancer.
J Clin Oncol, 33 (13): 1475-81. [PMID:25512461]
2. Duan JX, Jiao H, Kaizerman J, Stanton T, Evans JW, Lan L, Lorente G, Banica M, Jung D, Wang J et al.. (2008)
Potent and highly selective hypoxia-activated achiral phosphoramidate mustards as anticancer drugs.
J Med Chem, 51 (8): 2412-20. [PMID:18257544]
3. Hu J, Handisides DR, Van Valckenborgh E, De Raeve H, Menu E, Vande Broek I, Liu Q, Sun JD, Van Camp B, Hart CP et al.. (2010)
Targeting the multiple myeloma hypoxic niche with TH-302, a hypoxia-activated prodrug.
Blood, 116 (9): 1524-7. [PMID:20530289]
4. Sun JD, Liu Q, Wang J, Ahluwalia D, Ferraro D, Wang Y, Duan JX, Ammons WS, Curd JG, Matteucci MD et al.. (2012)
Selective tumor hypoxia targeting by hypoxia-activated prodrug TH-302 inhibits tumor growth in preclinical models of cancer.
Clin Cancer Res, 18 (3): 758-70. [PMID:22184053]
5. Weiss GJ, Infante JR, Chiorean EG, Borad MJ, Bendell JC, Molina JR, Tibes R, Ramanathan RK, Lewandowski K, Jones SF et al.. (2011)
Phase 1 study of the safety, tolerability, and pharmacokinetics of TH-302, a hypoxia-activated prodrug, in patients with advanced solid malignancies.
Clin Cancer Res, 17 (9): 2997-3004. [PMID:21415214]