35121-78-9

Basic information

• Product Name: Epoprostenol
• Synonyms: 5-[7-hydroxy-8-(3-hydroxyoct-1-enyl)-4-oxabicyclo[3.3.0]oct-3-ylidene]pentanoic acid;6(9)-Oxy-11,15-dihydroxyprosta-5,13-dienoic acid;PGX;Prostaglandin X;U 53217;Vasocyclin;(5Z，9α，11α，13E，15S)-6，9-Epoxy-11，15-dihydroxyprosta-5，13-dien-1-oicacid;Cyclo-Prostin
• CAS NO: 35121-78-9
• Molecular Formula: C20H31O5.Na
• Molecular Weight: 374.45
• Product Categories: API
• Mol File: 35121-78-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 530.2°Cat760mmHg
• Flash Point: 182.1°C
• Appearance: /
• Density: 1.221
• Vapor Pressure: 1.86E-13mmHg at 25°C
• Refractive Index: 1.611
• PKA: 4.70±0.10(Predicted)
• CAS DataBase Reference: Epoprostenol(CAS DataBase Reference)
• NIST Chemistry Reference: Epoprostenol(35121-78-9)
• EPA Substance Registry System: Epoprostenol(35121-78-9)

Safety Data

• Hazardous Substances Data: 35121-78-9(Hazardous Substances Data)

Usage

Originator

Prostacyclin,ZYF Pharm Chemical

Uses

Inhibitor (platelet). [Names previously used: Prostacyclin, PGI2, Prostagland in I2, Prostaglandin X, PGX].

Manufacturing Process

Preparation of prostacyclin:Pig aortas were stripped of adventitia, snap frozen in liquid nitrogen, crushed into a fine powder, resuspended in 0.05 M Tris buffer (pH 7.5) (1:4, w:v) andhomogenised at high speed in a Polytron (KIMENATIC, LUCERNE, SWITZERLAND) homogenizer. The homogenate was centrifuged for 15 min and the resulting supernatant centrifuged again for 5 min. The pellet was discarded, while the pellet obtained after centrifugation of the supernatant was resuspended in deionized water and lyophilized. An average yield of 150 mg of aortic microsomal powder (51% protein) per 100 g of aortic tissue was obtained.

Brand name

Flolan (GlaxoSmithKline).

Therapeutic Function

Platelet aggregation inhibitor, Antimetastatic

InChI:InChI=1/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17?,18+,19?/m0/s1

Upstream product

• 61799-74-4 PGI₂ methyl ester 
• 42935-17-1 9,11-Epidioxy-15-hydroxy-5,13-icosadiensaeure 
• 149-73-5 trimethyl orthoformate 
• 78824-82-5 11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester 
• 59926-53-3 5,6-didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGF_2α methyl ester 

Downstream Products

• 58962-34-8 7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-6-oxo-heptanoic acid 

Relevant articles and documents

A SHORT WAY TO PROSTACYCLIN

A facile, stereospecific preparation of prostacyclin has been accomplished starting from a 5,6-dehydroprostaglandin F2α derivative.

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

Prodrug derivatives of carboxylic acid drugs

Novel ester derivatives of carboxylic acid medicaments of formula (I), wherein R--COO--represents the acyloxy residue of a carboxylic acid drug or medicament, n is an integrer from 1 to 3, and R1 and R2 are the same or different and are selected from a group consisting of an alkyl, an alkenyl, an aryl, an aralkyl, a cycloalkyl and which group may be unsubstituted or substituted, or R1 and R2 together with the N forms a 4-, 5-, 6- or 7-membered heterocyclic ring, which in addition to the nitrogen atom may contain one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which heterocyclic group may be substituted. These compounds are highly biolabile prodrug forms of the corresponding carboxylic acid compounds and are highly susceptible to undergoing enzymatic hydrolysis in vivo whereas they are highly stable in aqueous solution. The novel derivatives are less irritating to mucosa than the parent carboxylic acids and may provide an improved bio-availability of the drugs.