Darodipine | CAS#72803-02-2 | a calcium antagonist

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

MedKoo CAT#: 326891

CAS#: 72803-02-2

Description: Darodipine, also known as PY-108068, is a potent a calcium antagonist. Darodipine dose-depentently blocks I(Ca,L) in rat isolated cardiomyocytes. Darodipine exerts protective effects against free-radical-induced electrophysiological alterations independently of its calcium antagonistic properties; this effect is possibly due to trapping of specific radical species. .

Chemical Structure

Darodipine

CAS# 72803-02-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326891
Name: Darodipine
CAS#: 72803-02-2
Chemical Formula: C19H21N3O5
Exact Mass: 371.15
Molecular Weight: 371.393
Elemental Analysis: C, 61.45; H, 5.70; N, 11.31; O, 21.54

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 315
50mg	USD 550
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: PY-108068; PY108068; PY108068; PY108-068; PY-108-068; PY 108-068; Darodipine

IUPAC/Chemical Name: diethyl 4-(benzo[c][1,2,5]oxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

InChi Key: QERUYFVNIOLCHV-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H21N3O5/c1-5-25-18(23)14-10(3)20-11(4)15(19(24)26-6-2)16(14)12-8-7-9-13-17(12)22-27-21-13/h7-9,16,20H,5-6H2,1-4H3

SMILES Code: O=C(C1=C(C)NC(C)=C(C(OCC)=O)C1C2=CC=CC3=NON=C23)OCC

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: >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:	Darodipine (PY 108-068, PY-108068) is a potent calcium channel antagonist.
In vitro activity:	Electrophysiological and electron spin resonance (e.s.r.) techniques were used to study the mechanism of the protective effect of darodipine on rat isolated cardiomyocytes exposed to an exogenous source of oxygen free radicals (OFR). ICa,L blockade by darodipine was concentration-dependent, peak current being reduced by 20% with 50 nm and by 58% with 100 nm darodipine. A 2 min pretreatment with 50 nm darodipine significantly reduced the incidence of these arrhythmogenic events following a 5 min exposure to OFR (36% of cells, n=14; P<0.05 vs nonpretreated cells). Pretreatment with darodipine also prevented APD prolongation caused by OFR (137±12 ms after DHF vs 117±6 ms before DHF n=14, not significant) but not the decrease of MDP (−63.4±2.5 mV after DHF vs −70.9±1.0 mV before DHF, P<0.05). The e.s.r. spectra obtained from the DHF-DMPO solution in the absence of darodipine demonstrated the presence of two components corresponding to two DMPO adducts. The addition of darodipine (50– 500 nm) led to a concentration-dependent decrease in intensity of the signals, the intensity of the DMPO-COO.− adduct being decreased more than that of the DMPO-OH. adduct. Reference: Br J Pharmacol. 1997 Dec; 122(7): 1353–1360. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1565083/
In vivo activity:	To investigate the mechanisms of the serotonergic pathways, the selective 5-HT1A receptor agonist 8-OHDPAT was injected S.C. to rats pretreated I.P. with darodipine (0.3-5.0 mg/kg). A low dose of darodipine (0.3 mg/kg) antagonized the presynaptic, but enhanced the postsynaptic effects of 8-OHDPAT, suggesting relief of the autoreceptor-mediated inhibition of the 5-HT release. Thus, the amine released could stimulate postsynaptic receptors, adding its action to that of 8-OHDPAT. A high dose of darodipine (5.0 mg/kg) left unchanged, or also enhanced, the signs of inhibition of serotonergic neurotransmission displayed by 8-OHDPAT, reducing but not suppressing the increase in the behavioral response to the stimulation of postsynaptic 5-HT1A receptors. It was speculated that the effects of darodipine on scrotonergic pathways of rat brain could be due to changes in the back-regulation of the neurotransmission, mediated by 5-HT1A autoreceptors. Reference: Pharmacol Biochem Behav. 1997 Oct;58(2):299-303. https://pubmed.ncbi.nlm.nih.gov/9300583/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	H2O	0.3	0.69

Preparing Stock Solutions

The following data is based on the product molecular weight 371.39 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. Matucci R, Ottaviani MF, Barbieri M, Cerbai E, Mugelli A. Protective effect of darodipine, a calcium antagonist, on rat cardiomyocytes against oxygen radical-mediated injury. Br J Pharmacol. 1997 Dec;122(7):1353-60. doi: 10.1038/sj.bjp.0701525. PMID: 9421282; PMCID: PMC1565083. 2. Amenta F, Cavallotti D, Del Valle M, Mancini M, Naves FJ, Vega JA, Zeng YC. Age-related changes in brain microanatomy: sensitivity to treatment with the dihydropyridine calcium channel blocker darodipine (PY 108-068). Brain Res Bull. 1995;36(5):45360. doi: 10.1016/0361-9230(94)00210-r. PMID: 7712207. 3. Gaggi R, D'Allolio R, Santangelo M, Roncada P. Interactions between darodipine or isradipine and the 5-HT1A receptor agonist 8OHDPAT in rat brain. Pharmacol Biochem Behav. 1997 Oct;58(2):299-303. doi: 10.1016/s0091-3057(97)00238-4. PMID: 9300583 4. Amenta F, Mancini M, Naves FJ, Vega JA, Zaccheo D. Effect of treatment with the dihydropyridine-type calcium antagonist darodipine (PY 108-068) on the expression of calbindin D-28K immunoreactivity in the cerebellar cortex of aged rats. Mech Ageing Dev. 1995 Jan 13;77(3):149-57. doi: 10.1016/0047-6374(94)01512-k. PMID: 7739263.
In vitro protocol:	1. Matucci R, Ottaviani MF, Barbieri M, Cerbai E, Mugelli A. Protective effect of darodipine, a calcium antagonist, on rat cardiomyocytes against oxygen radical-mediated injury. Br J Pharmacol. 1997 Dec;122(7):1353-60. doi: 10.1038/sj.bjp.0701525. PMID: 9421282; PMCID: PMC1565083. 2. Amenta F, Cavallotti D, Del Valle M, Mancini M, Naves FJ, Vega JA, Zeng YC. Age-related changes in brain microanatomy: sensitivity to treatment with the dihydropyridine calcium channel blocker darodipine (PY 108-068). Brain Res Bull. 1995;36(5):45360. doi: 10.1016/0361-9230(94)00210-r. PMID: 7712207.
In vivo protocol:	1. Gaggi R, D'Allolio R, Santangelo M, Roncada P. Interactions between darodipine or isradipine and the 5-HT1A receptor agonist 8OHDPAT in rat brain. Pharmacol Biochem Behav. 1997 Oct;58(2):299-303. doi: 10.1016/s0091-3057(97)00238-4. PMID: 9300583. 2. Amenta F, Mancini M, Naves FJ, Vega JA, Zaccheo D. Effect of treatment with the dihydropyridine-type calcium antagonist darodipine (PY 108-068) on the expression of calbindin D-28K immunoreactivity in the cerebellar cortex of aged rats. Mech Ageing Dev. 1995 Jan 13;77(3):149-57. doi: 10.1016/0047-6374(94)01512-k. PMID: 7739263.

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1: Sannita WG, Garbarino S, Gesino D, Massimilla S, Ogliastro C. Plasma concentration and CNS effects of Ca antagonists darodipine and nimodipine after single-dose oral administration to healthy volunteers. Neuropsychobiology. 1999 Sep;40(3):158-70. PubMed PMID: 10494052.

2: Matucci R, Ottaviani MF, Barbieri M, Cerbai E, Mugelli A. Protective effect of darodipine, a calcium antagonist, on rat cardiomyocytes against oxygen radical-mediated injury. Br J Pharmacol. 1997 Dec;122(7):1353-60. PubMed PMID: 9421282; PubMed Central PMCID: PMC1565083.

3: Gaggi R, D'Allolio R, Santangelo M, Roncada P. Interactions between darodipine or isradipine and the 5-HT1A receptor agonist 8-OHDPAT in rat brain. Pharmacol Biochem Behav. 1997 Oct;58(2):299-303. PubMed PMID: 9300583.

4: Gaggi R, Dall'Olio R, Roncada P, Gianni AM. Effects of isradipine and darodipine on serotonergic system of the rat brain. Pharmacol Biochem Behav. 1995 Jun-Jul;51(2-3):183-7. PubMed PMID: 7545305.

5: Gaggi R, Dall'Olio R, Roncada P, Gianni AM. Peculiar effects of isradipine and darodipine on the rat brain dopaminergic system. Gen Pharmacol. 1995 Mar;26(2):303-8. PubMed PMID: 7590078.

6: Amenta F, Ferrante F, Mancini M, Sabbatini M, Vega JA, Zaccheo D. Effect of long-term treatment with the dihydropyridine-type calcium channel blocker darodipine (PY 108-068) on the cerebral capillary network in aged rats. Mech Ageing Dev. 1995 Jan 31;78(1):27-37. PubMed PMID: 7603088.

7: Amenta F, Mancini M, Naves FJ, Vega JA, Zaccheo D. Effect of treatment with the dihydropyridine-type calcium antagonist darodipine (PY 108-068) on the expression of calbindin D-28K immunoreactivity in the cerebellar cortex of aged rats. Mech Ageing Dev. 1995 Jan 13;77(3):149-57. PubMed PMID: 7739263.

8: Colombo G, Agabio R, Lobina C, Reali R, Melis F, Fadda F, Gessa GL. Effects of the calcium channel antagonist darodipine on ethanol withdrawal in rats. Alcohol Alcohol. 1995 Jan;30(1):125-31. PubMed PMID: 7748269.

9: Amenta F, Cavallotti D, Del Valle M, Mancini M, Naves FJ, Vega JA, Zeng YC. Age-related changes in brain microanatomy: sensitivity to treatment with the dihydropyridine calcium channel blocker darodipine (PY 108-068). Brain Res Bull. 1995;36(5):453-60. PubMed PMID: 7712207.

10: Vega JA, Sabbatini M, Del Valle ME, Amenta F. Effect of treatment with the dihydropyridine-type calcium antagonist darodipine (PY 108-068) on the expression of neurofilament protein immunoreactivity in the cerebellar cortex of aged rats. Mech Ageing Dev. 1994 Aug;75(2):169-77. PubMed PMID: 7823639.

11: Ferrante F, Ricci A, Rossodivita I, Amenta F. Influence of treatment with the calcium channel blocker darodipine (PY 108-068) on the morphology of pial and coronary arteries in spontaneously hypertensive rats. Clin Exp Hypertens. 1994 May;16(3):341-57. PubMed PMID: 8038759.

12: Sannita WG, Busico S, Di Bon G, Ferrari A, Riela S. Pharmacokinetics and electroencephalographic effects of darodipine 50-200 mg modified release (MR) acute oral administration: dose-finding study in healthy volunteers. Int J Clin Pharmacol Res. 1993;13(5):281-91. PubMed PMID: 8200723.

13: Hubert B, Atkinson J, Guerret M, Hoffman M, Devissaguet JP, Maincent P. The preparation and acute antihypertensive effects of a nanocapsular form of darodipine, a dihydropyridine calcium entry blocker. Pharm Res. 1991 Jun;8(6):734-8. PubMed PMID: 2062803.

14: Pinquier JL, Urien S, Chaumet-Riffaud P, Tillement JP. Differences in the serum binding determinants of isradipine and darodipine--consequences for serum protein binding in various diseases. Br J Clin Pharmacol. 1989 Nov;28(5):587-92. PubMed PMID: 2531607; PubMed Central PMCID: PMC1380020.

15: Chrysant SG, Chrysant C, Trus J, Hitchcock A. Monotherapy of hypertension with darodipine: a new calcium-channel blocker. Clin Cardiol. 1988 Jul;11(7):467-72. PubMed PMID: 3046791.

16: Pinquier JL, Urien S, Lemaire M, Chaumet-Riffaud P, Tillement JP. Comparative binding of two closely related dihydropyridines (isradipine and darodipine) to serum proteins and erythrocytes. Pharmacology. 1988;36(5):305-12. PubMed PMID: 2457222.

17: Urien S, Pinquier JL, Paquette B, Chaumet-Riffaud P, Kiechel JR, Tillement JP. Effect of the binding of isradipine and darodipine to different plasma proteins on their transfer through the rat blood-brain barrier. Drug binding to lipoproteins does not limit the transfer of drug. J Pharmacol Exp Ther. 1987 Jul;242(1):349-53. PubMed PMID: 2956411.

18: Ginsburg R, Carey B, Zera P. Effect of calcium antagonist darodipine on the isolated human heart. Eur J Pharmacol. 1986 Jun 17;125(2):287-91. PubMed PMID: 3743638.

19: Al-Mahmood HA, el-Khatim MS, Gumaa KA, Thulesius O. The effect of calcium-blockers nicardipine, darodipine, PN-200-110 and nifedipine on insulin release from isolated rat pancreatic islets. Acta Physiol Scand. 1986 Feb;126(2):295-8. PubMed PMID: 2939690.

20: Hof RP, Hof A. Mutual inhibition and synergistic effects of ergotamine and the calcium antagonist darodipine. Gen Pharmacol. 1986;17(3):309-14. PubMed PMID: 3721185.

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