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

MedKoo CAT#: 202460

CAS#: 221635-42-3

Description: RH1 is a new bioreductive agent that is an excellent substrate for the two-electron reducing enzyme, NAD(P)H quinone oxidoreductase 1 (NQO1). In phase trials, RH1 was well tolerated with predictable and manageable toxicity. The MTD of 1430 μg/m(2)/day is the dose recommended for phase II trials. The biomarkers of DNA cross linking, DTD activity and NQO1 status have been validated and clinically developed.

Chemical Structure

CAS# 221635-42-3

Theoretical Analysis

MedKoo Cat#: 202460
Name: RH1
CAS#: 221635-42-3
Chemical Formula: C12H14N2O3
Exact Mass: 234.10044
Molecular Weight: 234.25
Elemental Analysis: C, 61.53; H, 6.02; N, 11.96; O, 20.49

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 @medkoo.com or click below button.
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Synonym: NSC697726; NSC697726; NSC 697726; RH 1; RH-1; RH1.

IUPAC/Chemical Name: 2,5-di(aziridin-1-yl)-3-(hydroxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione


InChi Code: InChI=1S/C12H14N2O3/c1-7-9(13-2-3-13)12(17)8(6-15)10(11(7)16)14-4-5-14/h15H,2-6H2,1H3

SMILES Code: O=C1C(N2CC2)=C(CO)C(C(N3CC3)=C1C)=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 234.25 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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1: Danson SJ, Johnson P, Ward TH, Dawson M, Denneny O, Dickinson G, Aarons L, Watson A, Jowle D, Cummings J, Robson L, Halbert G, Dive C, Ranson M. Phase I pharmacokinetic and pharmacodynamic study of the bioreductive drug RH1. Ann Oncol. 2011 Jul;22(7):1653-60. doi: 10.1093/annonc/mdq638. Epub 2011 Mar 4. PubMed PMID: 21378203.

2: Park MT, Song MJ, Oh ET, Lee H, Choi BH, Jeong SY, Choi EK, Park HJ. The anti-tumour compound, RH1, causes mitochondria-mediated apoptosis by activating c-Jun N-terminal kinase. Br J Pharmacol. 2011 Jun;163(3):567-85. doi: 10.1111/j.1476-5381.2011.01233.x. PubMed PMID: 21250978; PubMed Central PMCID: PMC3101619.

3: Hussein D, Holt SV, Brookes KE, Klymenko T, Adamski JK, Hogg A, Estlin EJ, Ward T, Dive C, Makin GW. Preclinical efficacy of the bioreductive alkylating agent RH1 against paediatric tumours. Br J Cancer. 2009 Jul 7;101(1):55-63. doi: 10.1038/sj.bjc.6605100. Epub 2009 Jun 2. PubMed PMID: 19491903; PubMed Central PMCID: PMC2713707.

4: Begleiter A, Leith MK, Patel D, Hasinoff BB. Role of NADPH cytochrome P450 reductase in activation of RH1. Cancer Chemother Pharmacol. 2007 Oct;60(5):713-23. Epub 2007 Jan 26. PubMed PMID: 17256129.

5: Hasinoff BB, Begleiter A. The reductive activation of the antitumor drug RH1 to its semiquinone free radical by NADPH cytochrome P450 reductase and by HCT116 human colon cancer cells. Free Radic Res. 2006 Sep;40(9):974-8. PubMed PMID: 17015278.

6: Digby T, Leith MK, Thliveris JA, Begleiter A. Effect of NQO1 induction on the antitumor activity of RH1 in human tumors in vitro and in vivo. Cancer Chemother Pharmacol. 2005 Sep;56(3):307-16. Epub 2005 May 5. PubMed PMID: 15877230.

7: Kim JY, West CM, Valentine H, Ward TH, Patterson AV, Stratford IJ, Roberts SA, Hendry JH. Cytotoxicity of the bioreductive agent RH1 and its lack of interaction with radiation. Radiother Oncol. 2004 Mar;70(3):311-7. PubMed PMID: 15064018.

8: Kim JY, Kim CH, Stratford IJ, Patterson AV, Hendry JH. The bioreductive agent RH1 and gamma-irradiation both cause G2/M cell cycle phase arrest and polyploidy in a p53-mutated human breast cancer cell line. Int J Radiat Oncol Biol Phys. 2004 Feb 1;58(2):376-85. PubMed PMID: 14751506.

9: Nemeikaite-Ceniene A, Sarlauskas J, Anusevicius Z, Nivinskas H, Cenas N. Cytotoxicity of RH1 and related aziridinylbenzoquinones: involvement of activation by NAD(P)H:quinone oxidoreductase (NQO1) and oxidative stress. Arch Biochem Biophys. 2003 Aug 1;416(1):110-8. PubMed PMID: 12859987.

Additional Information

RH1 may be an effective NQO1-directed antitumor agent for treatment of cancer cells having elevated NQO1 activity. As some studies have indicated that RH1 may also be a substrate for the one-electron reducing enzyme, NADPH cytochrome P 450 reductase (P 450 Red), P 450 Red may contribute to the activation of RH1 where NQO1 activities are low and P 450 Red activities are high. The mean P 450 Red activity in the human tumor cell line panel used by NCI for evaluation of new anticancer agents is 14.8 nmol min-1 mg prot-1, while the mean NQO1 activity in these cell lines is 199.5 nmol min-1 mg prot-1. see:  Begleiter, Asher; Leith, Marsha K.; Patel, Daywin; Hasinoff, Brian B. Cancer Chemotherapy and Pharmacology (2007), 60(5), 713-723.