PR-104

PR-104 is a drug from the class of hypoxia-activated prodrugs (HAPs),^[1] which is being researched as a potential anti-cancer therapeutic agent. It is a phosphate ester "pre-prodrug" that is rapidly converted to the HAP PR-104A in the body. PR-104A is in turn metabolised to reactive nitrogen mustard DNA crosslinking agents in hypoxic tissues such as found in solid tumours.^[2][3][4] Following initial clinical studies,^[5][6] it was discovered that PR-104A is also activated by the enzyme AKR1C3, independently of hypoxia.^[7] Hypoxia in the bone marrow of patients with leukaemia,^[8][9] and high activity of AKR1C3 in some leukaemia subtypes ^[10][11][12] has led to interest in clinical trials of PR-104 in relapsed refractory acute leukaemias.^[13][14]

CAS Number

• 851627-62-8 ^Y

PubChem CID

• 11455973

ChemSpider

• 9630821

UNII

• V16D2ZT7DT

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PR-104

Identifiers
IUPAC name [2-({2-[(2-Bromoethyl)[2-(methanesulfonyloxy)ethyl]amino]-3,5-dinitrophenyl}formamido)ethoxy]phosphonic acid
CAS Number	851627-62-8 Y
PubChem CID	11455973
ChemSpider	9630821
UNII	V16D2ZT7DT
CompTox Dashboard (EPA)	DTXSID001005607
Chemical and physical data
Formula	C14H20BrN4O12PS
Molar mass	579.27 g·mol−1
3D model (JSmol)	Interactive image
SMILES CS(=O)(=O)OCCN(CCBr)c1c(cc(cc1[N+](=O)[O-])[N+](=O)[O-])C(=O)NCCOP(=O)(O)O
InChI InChI=1S/C14H20BrN4O12PS/c1-33(28,29)31-7-5-17(4-2-15)13-11(14(20)16-3-6-30-32(25,26)27)8-10(18(21)22)9-12(13)19(23)24/h8-9H,2-7H2,1H3,(H,16,20)(H2,25,26,27) Key:GZSOKPMDWVRVMG-UHFFFAOYSA-N

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