CAS 69552-46-1|Carbacyclin

Introduction：Basic information about CAS 69552-46-1|Carbacyclin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Carbacyclin BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Synonyms

Common Name	Carbacyclin
CAS Number	69552-46-1	Molecular Weight	350.492
Density	1.2±0.1 g/cm3	Boiling Point	514.8±50.0 °C at 760 mmHg
Molecular Formula	C₂₁H₃₄O₄	Melting Point	65-67 °C
MSDS	/	Flash Point	279.2±26.6 °C

Names

Name	(5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid
Synonym	More Synonyms

Carbacyclin BiologicalActivity

Description	Carbacyclin is a PGI2 analogue, acts as a prostacyclin (PGI2) receptor agonist and vasodilator, and potently inhibits platelet aggregation.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>Prostaglandin ReceptorResearch Areas >>Cardiovascular Disease
Target	PGI2 Receptor
In Vitro	Carbacyclin is an agonist of prostacyclin (PGI2) receptor[1]. Carbacyclin acts as an inhibitor of platelet aggregation induced by ADP or collagen in vitro[2]. Carbacyclin is a PGI2 analogue, activates CPT-1 mRNA expression through PPARδ, independent of the IP receptor signaling pathway. Carbacyclin (0.02 μM to 20 μM) activates the IP receptor signaling pathway via PKA, and such an effect is inhibited by H-89, a PKA inhibitor. Carbacyclin (0.02-80 μM) increases PPRE promoter activity via PPARδ independent of the IP receptor signaling pathway in cardiomyocytes[3].
In Vivo	Carbacyclin is 0.03 times as active as prostacyclin on inhibiting platelet aggregation in human, dog or rabbit plasma[2]. Carbacyclin (100 μg, i.p.) induces CPT-1 mRNA expression in murine heart[3].
Cell Assay	Primary cultures of neonatal rat cardiomyocytes are prepared from the ventricles of 1-day-old Wistar rats, and are seeded at a density of 4 × 105/6-well plastic plates, 9 × 105/60 mm dishes, or 3 × 106/100 mm dishes with Dulbecco's modified Eagle's medium (DMEM) containing 10% fetal calf serum (FCS). After 40 h of incubation, cultured cardiomyocytes are serum-starved for 8 h before Carbacyclin stimulation.
Animal Admin	Mice[3] Ten to twelve week-old male C57BL/6 mice (20-25 g) are used in the experiment. Mice (n = 4) are injected intraperitoneally with 100 μg of Carbacyclin, and are sacrificed at the times indicated. The hearts are excised, and the ventricles are then homogenized with 3 mL of Isogen for the following total RNA extraction procedure[3].
References	[1]. Takasuka M, et al. FTIR spectral study of intramolecular hydrogen bonding in thromboxane A2 receptor agonist (U-46619), prostaglandin (PG)E2, PGD2, PGF2 alpha, prostacyclin receptor agonist (carbacyclin), and their related compounds in dilute CCl4 solution: structure-activity relationships. J Med Chem. 1994 Jan 7;37(1):47-56. [2]. Whittle BJ, et al. Carbacyclin--a potent stable prostacyclin analogue for the inhibition of platelet aggregation. Prostaglandins. 1980 Apr;19(4):605-27. [3]. Kuroda T, et al. Carbacyclin induces carnitine palmitoyltransferase-1 in cardiomyocytes via peroxisome proliferator-activated receptor (PPAR) delta independent of the IP receptor signaling pathway. J Mol Cell Cardiol. 2007 Jul;43(1):54-62.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	514.8±50.0 °C at 760 mmHg
Melting Point	65-67 °C
Molecular Formula	C₂₁H₃₄O₄
Molecular Weight	350.492
Flash Point	279.2±26.6 °C
Exact Mass	350.245697
PSA	77.76000
LogP	3.65
Vapour Pressure	0.0±3.0 mmHg at 25°C
Index of Refraction	1.611
InChIKey	XZFRIPGNUQRGPI-WBQKLGIQSA-N
SMILES	CCCCCC(O)C=CC1C(O)CC2CC(=CCCCC(=O)O)CC21

Safety Information

Hazard Codes	Xn: Harmful;
Risk Phrases	R20/21/22
Safety Phrases	22-36

Synonyms

Carboprostacyclin

carbaprostacyclin

carbacyclin

Pentanoic acid, 5-[(3aS,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2(1H)-pentalenylidene]-, (5Z)-

6a-Carba-pgi2

Carba pgx

6,9-Methano pgi2

6,9-Methanoprostaglandin I2

Carbacycline

(5Z)-5-[(3aS,4R,5R,6aS)-5-Hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]hexahydro-2(1H)-pentalenylidene]pentanoic acid

(5Z)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]hexahydropentalen-2(1H)-ylidene]pentanoic acid

MFCD00210824

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