Derenofylline | SLV320 | CAS#251945-92-3 | adenosine A(1) antagonist

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

MedKoo CAT#: 319809

CAS#: 251945-92-3

Description: Derenofylline, also known as SLV320, is a selective and potent adenosine A(1) antagonist in vitro (Ki=1 nM) with a selectivity factor of at least 200 versus other adenosine receptor subtypes. SLV320 significantly decreased albuminuria by about 50%, but did not alter glomerular filtration rate (GFR). SLV320 prevented nephrectomy-dependent rise in plasma levels of creatinine kinase (CK), ALT and AST. SLV320 suppresses cardiac fibrosis and attenuates albuminuria without affecting blood pressure in rats with 5/6 nephrectomy.

Chemical Structure

Derenofylline

CAS# 251945-92-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319809
Name: Derenofylline
CAS#: 251945-92-3
Chemical Formula: C18H20N4O
Exact Mass: 308.16
Molecular Weight: 308.385
Elemental Analysis: C, 70.11; H, 6.54; N, 18.17; O, 5.19

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 380
50mg	USD 650
100mg	USD 1040
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: SLV320; SLV-320; SLV 320; Derenofylline

IUPAC/Chemical Name: (1r,4r)-4-((2-phenyl-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexan-1-ol

InChi Key: RBZNJGHIKXAKQE-HDJSIYSDSA-N

InChi Code: InChI=1S/C18H20N4O/c23-14-8-6-13(7-9-14)20-18-15-10-11-19-17(15)21-16(22-18)12-4-2-1-3-5-12/h1-5,10-11,13-14,23H,6-9H2,(H2,19,20,21,22)/t13-,14-

SMILES Code: O[C@H]1CC[C@H](NC2=C3C(NC(C4=CC=CC=C4)=N2)=NC=C3)CC1

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, not in water

Shelf Life: >2 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

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Product Data:

Product Data

Instruction:

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Biological target:	Derenofylline (SLV 320) is an adenosine A1 receptor antagonist, with Ki values of 1 nM, 200 nM and 398 nM for human A1, A3 and A2A receptors respectively. In addition, the receptor-binding affinities as well as enzyme inhibitory properties of SLV320 were evaluated in a series of 94 receptors and 6 phosphodiesterases (PDE1–PDE6).
In vitro activity:	In receptor binding experiments using cloned human receptors, SLV320 (for chemical structure see Figure 1) behaved as a potent and selective A1 receptor ligand with selectivity factors of 200–4000 versus other adenosine receptor subtypes (see Table 1a). The selectivity factors are higher than those of the reference A1 antagonist DPCPX (8-cyclopentyl-1,3-dipropylxanthine; see Table 1b). A significant binding was measured only for the high-affinity rolipram-binding site on PDE4 (from mouse brain). SLV320 caused rolipram displacement from its binding site with a Ki of 79 nm, which was 79-fold less potent compared to its binding at the A1 receptor site. Reference: Br J Pharmacol. 2007 Aug;151(7):1025-32. https://pubmed.ncbi.nlm.nih.gov/17558436/
In vivo activity:	Therefore, the novel selective adenosine A(1) receptor antagonist SLV320 was investigated, focusing on its potential in preventing cardiomyopathy in rats with 5/6 nephrectomy. Male Sprague-Dawley rats were allocated to 4 groups of 12 rats each: 5/6 nephrectomy (5/6 NX), 5/6 NX plus SLV320 (10 mg kg(-1) d(-1) mixed with food), sham and sham plus SLV320. In rats with 5/6 NX SLV320 significantly decreased albuminuria by about 50%, but did not alter glomerular filtration rate (GFR). SLV320 normalized cardiac collagen I+III contents in 5/6 NX rats. SLV320 prevented nephrectomy-dependent rise in plasma levels of creatinine kinase (CK), ALT and AST. Blood pressure did not differ between study groups. SLV320 suppresses cardiac fibrosis and attenuates albuminuria without affecting blood pressure in rats with 5/6 nephrectomy, indicating that selective A(1) receptor antagonists may be beneficial in uraemic cardiomyopathy. Reference: Br J Pharmacol. 2007 Aug;151(7):1025-32. https://pubmed.ncbi.nlm.nih.gov/17558436/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	250.0	810.69

Preparing Stock Solutions

The following data is based on the product molecular weight 308.39 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.

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

Formulation protocol:	1. Sureechatchaiyan P, Hamacher A, Brockmann N, Stork B, Kassack MU. Adenosine enhances cisplatin sensitivity in human ovarian cancer cells. Purinergic Signal. 2018 Dec;14(4):395-408. doi: 10.1007/s11302-018-9622-7. Epub 2018 Aug 4. PMID: 30078088; PMCID: PMC6298929. 2. Kalk P, Eggert B, Relle K, Godes M, Heiden S, Sharkovska Y, Fischer Y, Ziegler D, Bielenberg GW, Hocher B. The adenosine A1 receptor antagonist SLV320 reduces myocardial fibrosis in rats with 5/6 nephrectomy without affecting blood pressure. Br J Pharmacol. 2007 Aug;151(7):1025-32. doi: 10.1038/sj.bjp.0707319. Epub 2007 Jun 11. PMID: 17558436; PMCID: PMC2042943.
In vitro protocol:	1. Sureechatchaiyan P, Hamacher A, Brockmann N, Stork B, Kassack MU. Adenosine enhances cisplatin sensitivity in human ovarian cancer cells. Purinergic Signal. 2018 Dec;14(4):395-408. doi: 10.1007/s11302-018-9622-7. Epub 2018 Aug 4. PMID: 30078088; PMCID: PMC6298929. 2. Kalk P, Eggert B, Relle K, Godes M, Heiden S, Sharkovska Y, Fischer Y, Ziegler D, Bielenberg GW, Hocher B. The adenosine A1 receptor antagonist SLV320 reduces myocardial fibrosis in rats with 5/6 nephrectomy without affecting blood pressure. Br J Pharmacol. 2007 Aug;151(7):1025-32. doi: 10.1038/sj.bjp.0707319. Epub 2007 Jun 11. PMID: 17558436; PMCID: PMC2042943.
In vivo protocol:	1. Kalk P, Eggert B, Relle K, Godes M, Heiden S, Sharkovska Y, Fischer Y, Ziegler D, Bielenberg GW, Hocher B. The adenosine A1 receptor antagonist SLV320 reduces myocardial fibrosis in rats with 5/6 nephrectomy without affecting blood pressure. Br J Pharmacol. 2007 Aug;151(7):1025-32. doi: 10.1038/sj.bjp.0707319. Epub 2007 Jun 11. PMID: 17558436; PMCID: PMC2042943.

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1: Pang PS, Mehra M, Maggioni AP, Filippatos G, Middlebrooks J, Turlapaty P, Kazei D, Gheorghiade M; RENO-DEFEND Investigators. Rationale, design, and results from RENO-DEFEND 1: a randomized, dose-finding study of the selective A1 adenosine antagonist SLV320 in patients hospitalized with acute heart failure. Am Heart J. 2011 Jun;161(6):1012-23.e3. doi: 10.1016/j.ahj.2011.03.004. PubMed PMID: 21641345.

2: Mitrovic V, Seferovic P, Dodic S, Krotin M, Neskovic A, Dickstein K, de Voogd H, Böcker C, Ziegler D, Godes M, Nakov R, Essers H, Verboom C, Hocher B. Cardio-renal effects of the A1 adenosine receptor antagonist SLV320 in patients with heart failure. Circ Heart Fail. 2009 Nov;2(6):523-31. doi: 10.1161/CIRCHEARTFAILURE.108.798389. Epub 2009 Sep 24. PubMed PMID: 19919976.

3: Givertz MM. Adenosine A1 receptor antagonists at a fork in the road. Circ Heart Fail. 2009 Nov;2(6):519-22. doi: 10.1161/CIRCHEARTFAILURE.109.916072. PubMed PMID: 19919975.

4: Kiesman WF, Elzein E, Zablocki J. A1 adenosine receptor antagonists, agonists, and allosteric enhancers. Handb Exp Pharmacol. 2009;(193):25-58. doi: 10.1007/978-3-540-89615-9_2. Review. PubMed PMID: 19639278.

5: Kalk P, Eggert B, Relle K, Godes M, Heiden S, Sharkovska Y, Fischer Y, Ziegler D, Bielenberg GW, Hocher B. The adenosine A1 receptor antagonist SLV320 reduces myocardial fibrosis in rats with 5/6 nephrectomy without affecting blood pressure. Br J Pharmacol. 2007 Aug;151(7):1025-32. Epub 2007 Jun 11. PubMed PMID: 17558436; PubMed Central PMCID: PMC2042943.

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