Taprostene (CG-4203) is a synthetic, chemically stable analog of prostacyclin (PGI2). Taprostene displays endothelial and cardioprotective effects after acute myocardial ischemia-reperfusion in cats. Taprostene enhances cytoprotective effects while minimizing unwanted hemodynamic effects.

Physicochemical Properties

Molecular Formula	C24H30O5
Molecular Weight	398.49
Exact Mass	398.209
CAS #	108945-35-3
PubChem CID	5311243
Appearance	Typically exists as solid at room temperature
Density	1.3±0.1 g/cm3
Boiling Point	609.4±55.0 °C at 760 mmHg
Flash Point	209.2±25.0 °C
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.670
LogP	3.78
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Heavy Atom Count	29
Complexity	635
Defined Atom Stereocenter Count	5
SMILES	C1CCC(CC1)[C@@H](/C=C/[C@@H]2[C@H]3C/C(=C/C4=CC(=CC=C4)C(=O)O)/O[C@H]3C[C@H]2O)O
InChi Key	ZLJOKYGJNOQXDP-OZUBPDBUSA-N
InChi Code	InChI=1S/C24H30O5/c25-21(16-6-2-1-3-7-16)10-9-19-20-13-18(29-23(20)14-22(19)26)12-15-5-4-8-17(11-15)24(27)28/h4-5,8-12,16,19-23,25-26H,1-3,6-7,13-14H2,(H,27,28)/b10-9+,18-12-/t19-,20-,21-,22-,23+/m1/s1
Chemical Name	3-[(Z)-[(3aR,4R,5R,6aS)-4-[(E,3S)-3-cyclohexyl-3-hydroxyprop-1-enyl]-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]methyl]benzoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Prostaglandin Receptor[1]
ln Vivo	In a 6-hour model of myocardial ischemia (MI) with reperfusion in anesthetized cats, tappestene (100 ng/kg/min) is administered intravenously starting 30 minutes postocclusion of the left anterior descending coronary artery and followed by reperfusion 1 hour later. Taprostene has a profile of activity that includes preventing aggregation in cat platelets15 at concentrations that are much lower than that required to produce significant vasodilator activity in rabbit aortic rings. Taprostene infusion results in significantly lower plasma creatine phosphokinase activities for the MI + Taprostene group compared with the MI + vehicle group. Taprostene is effective not just in circulatory shock but also in acute inflammatory states and in rat models of myocardial hypoxia and chronic ischemia. It also has cytoprotective and antiaggregatory properties. Initially, a range of Taprostene infusion rates, ranging from 50 to 200 ng/kg/min, were employed to achieve an infusion rate that exhibited minimal hemodynamic (i.e., vasodilator) effects while maintaining cardioprotective properties. After ischemia and reperfusion, taprostene therapy prevents neutrophils from sticking to the myocardial endothelium in both compromised and necrotic cardiac tissue[1].
Animal Protocol	Animal/Disease Models: Adult male cats (2.5-3.5 kg)[1] Doses: 100 ng/kg Route of Administration: Infused intravenously (iv) at a rate of 100 ng/kg/min until the end of the experiment (ie, for 5.5 hrs (hours)). Experimental Results: In six cat aortic rings, 1-100 ng/mL failed to exert any vasorelaxant effect. Relaxed the vascular rings 34% at 300 ng/mL. The EC50 was 520 ng/mL, a value 26 times that of its antiplatelet aggregatory effect in cat platelet -rich plasma.
References	[1]. Endothelium and myocardial protecting actions of Taprostene, a stable prostacyclin analogue, after acute myocardial ischemia and reperfusion in cats. Circ Res. 1990 May;66(5):1362-70.
Additional Infomation	Taprostene is a member of benzoic acids.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.5095 mL	12.5474 mL	25.0947 mL
	5 mM	0.5019 mL	2.5095 mL	5.0189 mL
	10 mM	0.2509 mL	1.2547 mL	2.5095 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.