WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202331

CAS#: 851627-62-8

Description: PR-104 is a non-toxic, small-molecule, hypoxia-activated, 3,5-dinitrobenzamide nitrogen mustard pre-prodrug with potential antitumor activity. Upon intravenous administration, PR-104 is converted by systemic phosphatases to the alcohol intermediate PR-104A, which is reduced to form the active DNA-crosslinking mustard species hydroxylamine PR-104H intracellularly under hypoxic conditions. PR-104H specifically crosslinks hypoxic tumor cell DNA, resulting in the inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis in susceptible hypoxic tumor cell populations while sparing normoxic tissues.

Chemical Structure

CAS# 851627-62-8

Theoretical Analysis

MedKoo Cat#: 202331
Name: PR-104
CAS#: 851627-62-8
Chemical Formula: C14H20BrN4O12PS
Exact Mass: 577.97194
Molecular Weight: 579.27
Elemental Analysis: C, 29.03; H, 3.48; Br, 13.79; N, 9.67; O, 33.14; P, 5.35; S, 5.54

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: PR 104; PR-104; PR104.

IUPAC/Chemical Name: 2-((2-bromoethyl)(2,4-dinitro-6-((2-(phosphonooxy)ethyl)carbamoyl)phenyl)amino)ethyl methanesulfonate


InChi Code: 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)

SMILES Code: CS(=O)(OCCN(CCBr)C1=C(C(NCCOP(O)(O)=O)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 579.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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2. Gu, Yongchuan; Atwell, Graham J.; Wilson, William R. Metabolism and excretion of the novel bioreductive prodrug PR-104 in mice, rats, dogs, and humans. Drug Metabolism and Disposition (2010), 38(3), 498-508. CODEN: DMDSAI ISSN:0090-9556. CAN 152:540913 AN 2010:327864

3. Guise, Christopher P.; Abbattista, Maria R.; Singleton, Rachelle S.; Holford, Samuel D.; Connolly, Joanna; Dachs, Gabi U.; Fox, Stephen B.; Pollock, Robert; Harvey, Justin; Guilford, Parry; Donate, Fernando; Wilson, William R.; Patterson, Adam V. The Bioreductive Prodrug PR-104A Is Activated under Aerobic Conditions by Human Aldo-Keto Reductase 1C3. Cancer Research (2010), 70(4), 1573-1584. CODEN: CNREA8 ISSN:0008-5472. CAN 152:469295 AN 2010:192736

4. Jameson, Michael B.; Rischin, Danny; Pegram, Mark; Gutheil, John; Patterson, Adam V.; Denny, William A.; Wilson, William R. A phase I trial of PR-104, a nitrogen mustard prodrug activated by both hypoxia and aldo-keto reductase 1C3, in patients with solid tumors. Cancer Chemotherapy and Pharmacology (2010), 65(4), 791-801. CODEN: CCPHDZ ISSN:0344-5704. AN 2010:80563

5. Cairns, Rob A.; Bennewith, Kevin L.; Graves, Edward E.; Giaccia, Amato J.; Chang, Daniel T.; Denko, Nicholas C. Pharmacologically Increased Tumor Hypoxia can be Measured by 18F-Fluoroazomycin Arabinoside Positron Emission Tomography and Enhances Tumor Response to Hypoxic Cytotoxin PR-104. Clinical Cancer Research (2009), 15(23), 7170-7174. CODEN: CCREF4 ISSN:1078-0432. AN 2009:1504923

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8. Gu, Yongchuan; Wilson, William R. Rapid and sensitive ultra-high-pressure liquid chromatography-tandem mass spectrometry analysis of the novel anticancer agent PR-104 and its major metabolites in human plasma: Application to a pharmacokinetic study. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2009), 877(27), 3181-3186. CODEN: JCBAAI ISSN:1570-0232. CAN 151:417407 AN 2009:1125172

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10. Singleton, Rachelle S.; Guise, Christopher P.; Ferry, Dianne M.; Pullen, Susan M.; Dorie, Mary J.; Brown, J. Martin; Patterson, Adam V.; Wilson, William R. DNA Cross-Links in Human Tumor Cells Exposed to the Prodrug PR-104A: Relationships to Hypoxia, Bioreductive Metabolism, and Cytotoxicity. Cancer Research (2009), 69(9), 3884-3891. CODEN: CNREA8 ISSN:0008-5472. CAN 151:48754 AN 2009:517726

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13. Patterson, Adam Vorn; Wilson, William Robert. Use of PR-104 or a related nitrobenzene derivative in combination with gemcitabine for cancer treatment. PCT Int. Appl. (2008), 31pp. CODEN: PIXXD2 WO 2008033039 A1 20080320 CAN 148:347331 AN 2008:353264

14. Patterson, Adam Vorn; Cossum, Paul Adrian. PR-104 or related compound combination with bevacizumab for cancer treatment. PCT Int. Appl. (2008), 37pp. CODEN: PIXXD2 WO 2008033041 A1 20080320 CAN 148:347326 AN 2008:352906

15. Patterson, Adam Vorn; Wilson, William Robert. Nitrobenzene derivative combination with docetaxel for the treatment of cancer. U.S. Pat. Appl. Publ. (2008), 26 pp. CODEN: USXXCO US 2008064665 A1 20080313 CAN 148:347317 AN 2008:321951

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17. Hicks, Kevin O.; Myint, Hilary; Patterson, Adam V.; Pruijn, Frederik B.; Siim, Bronwyn G.; Patel, Kashyap; Wilson, William. R. Oxygen Dependence and Extravascular Transport of Hypoxia-Activated Prodrugs: Comparison of the Dinitrobenzamide Mustard PR-104A and Tirapazamine. International Journal of Radiation Oncology, Biology, Physics (2007), 69(2), 560-571. CODEN: IOBPD3 ISSN:0360-3016. CAN 148:112416 AN 2007:1039164

18. Patel, Kashyap; Lewiston, David; Gu, Yongchuan; Hicks, Kevin O.; Wilson, William R. Analysis of the hypoxia-activated dinitrobenzamide mustard phosphate pre-prodrug PR-104 and its alcohol metabolite PR-104A in plasma and tissues by liquid chromatography-mass spectrometry. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2007), 856(1-2), 302-311. CODEN: JCBAAI ISSN:1570-0232. CAN 147:461512 AN 2007:996381

19. Guise, Chris P.; Wang, Anderson T.; Theil, Anke; Bridewell, David J.; Wilson, William R.; Patterson, Adam V. Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: A role for NADPH:cytochrome P450 oxidoreductase under hypoxia. Biochemical Pharmacology (2007), 74(6), 810-820. CODEN: BCPCA6 ISSN:0006-2952. CAN 147:439451 AN 2007:897047

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21. Yang, Shangjin; Atwell, Graham J.; Denny, William A. Synthesis of asymmetric halomesylate mustards with aziridineethanol/alkali metal halides: application to an improved synthesis of the hypoxia prodrug PR-104. Tetrahedron (2007), 63(25), 5470-5476. CODEN: TETRAB ISSN:0040-4020. CAN 147:166022 AN 2007:556217

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