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Prostaglandin E1

Prostaglandin E1 Structure
CAS No.
745-65-3
Chemical Name:
Prostaglandin E1
Synonyms
ALPROSTADIL;PGE1;Prost-13-en-1-oic acid;Caverject;Prostaglandine E1;Alprostadil (PGE1);Prostin VR Pediatric;PGEl;Liple;Palux
CBNumber:
CB6141459
Molecular Formula:
C20H34O5
Molecular Weight:
354.49
MOL File:
745-65-3.mol
MSDS File:
SDS
Modify Date:
2024/11/16 15:32:52

Prostaglandin E1 Properties

Melting point 115-116 °C
alpha -64 º (c=1.0, C2H5OH)
Boiling point 407.69°C (rough estimate)
Density 1.0458 (rough estimate)
refractive index 1.6120 (estimate)
storage temp. -20°C
solubility ethanol: 1 mg/mL
form powder
pka pKa 4.85± 0.07(H2O,t=25±0.1,I=0.1(NaCl)) (Uncertain)
color White to off-white
Water Solubility insoluble
Merck 13,7968
BRN 5294062
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey GMVPRGQOIOIIMI-DWKJAMRDSA-N

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P301+P310+P330
Hazard Codes  Xn,Xi
Risk Statements  22-36/37/38-61
Safety Statements  36-26
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  GY4569800
8-10
HazardClass  6.1(b)
PackingGroup  III
HS Code  29375000
NFPA 704
0
2 0

Prostaglandin E1 price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) P7527 Prostaglandin E1 powder, γ-irradiated, BioXtra, suitable for cell culture 745-65-3 1MG ₹29822.88 2022-06-14 Buy
Sigma-Aldrich(India) P8908 Prostaglandin E1 synthetic, powder, BioReagent, suitable for cell culture 745-65-3 10MG ₹100488.48 2022-06-14 Buy
Sigma-Aldrich(India) P5515 Prostaglandin E1 ≥98% (HPLC), synthetic 745-65-3 1MG ₹17114.33 2022-06-14 Buy
Sigma-Aldrich(India) P7527 Prostaglandin E1 powder, γ-irradiated, BioXtra, suitable for cell culture 745-65-3 10MG ₹50769.25 2022-06-14 Buy
Sigma-Aldrich(India) P5515 Prostaglandin E1 ≥98% (HPLC), synthetic 745-65-3 5MG ₹49199.63 2022-06-14 Buy
Product number Packaging Price Buy
P7527 1MG ₹29822.88 Buy
P8908 10MG ₹100488.48 Buy
P5515 1MG ₹17114.33 Buy
P7527 10MG ₹50769.25 Buy
P5515 5MG ₹49199.63 Buy

Prostaglandin E1 Chemical Properties,Uses,Production

Description

Prostaglandin E1 is an endogenous prostaglandin with vasodilatory, anti-platelet, and anti-hypertensive activities. It is in clinical use for the treatment of erectile dysfunction and the emergency management of infants with patent ductus arteriosus. It has also been used in the treatment of peripheral arterial occlusive disease (PAD).

Chemical Properties

Crystalline Solid

Uses

A primary Prostaglandin; easily crystallized from purified biological extracts. Vasodilator (peripheral)

Indications

Alprostadil (prostaglandin E1 [PGE1]; Edex, Topiglan) exerts a number of effects, including systemic vasodilation, inhibition of platelet aggregation, and stimulation of intestinal motility. PGE1 relaxes isolated smooth muscle cells contracted by norepinephrine. It has become widely used in the treatment of ED. Alprostadil binds with PGE receptors and results in a cyclic adenosine monophosphate (cAMP) mediated smooth muscle relaxation. Little is known about the pharmacokinetics of PGE1, but it is believed that as much as 80% is metabolized in one pass through the lungs. Such rapid degradation probably accounts for its lack of significant cardiovascular side effects when administered intracavernosally. PGE1 can also be metabolized in the penis.

World Health Organization (WHO)

Alprostadil, a prostaglandin with vasodilating and platelet antiaggregatory activity, was introduced in 1984 for the treatment of chronic arterial obstruction. Intravenous administration of the drug has been associated with adverse effects that have sometimes been severe. These include allergic reactions, pulmonary oedema and cardiac insufficiency. Interactions with antihypertensive agents, vasodilators, anticoagulants and inhibitors of platelet aggregation have also occurred. This has led the German agency to modify the approved product information of alprostadil preparations to warn against these adverse effects.

Biological Functions

Prostaglandin E1 is produced endogenously to relax vascular smooth muscle and cause vasodilation by activating the adenylate cyclase/cAMP pathway. Recent studies show that the cAMP is important in the PGE1 relaxation of penile erectile tissue and vasodilation of penile resistance arteries. Moreover, agents that stimulate the release of cAMP also crossactivate the NO/cGMP cascade.

General Description

PGE1, Alprostadil (Prostin VR Pediatric), is a naturally occurring prostaglandin that has found particular use in maintaining a patent (opened) ductus arteriosus in infants with congenital defects that restrict pulmonary or systemic blood flow.
Alprostadil must be administered intravenously continually at a rate of approximately 0.1 μg/kg/min to maintain the patency of the ductus arteriosus until corrective surgery can be performed. Up to 80% of circulating alprostadil may be metabolized in a single pass through the lungs. Because apnea has been observed in 10% to 12% of neonates with congenital heart defects, this product should be administered only when ventilatory assistance is immediately available. Other commonly observed side effects include decreased arterial blood pressure, which should be monitored during infusion; inhibited platelet aggregation, which might aggravate bleeding tendencies; and diarrhea.

Biological Activity

Prostaglandin with some selectivity for EP 3 and EP 4 receptors (K i values are 1.1, 2.1, 36, 10? and 33 nM for mouse EP 3 , EP 4 , EP 1 , EP 2 and IP receptors respectively). Inhibits platelet aggregation and is a vasodilator in vivo .

Mechanism of action

PGE1 is not orally effective. Its therapeutic success depends on its being injected intracavernosally or administered transurethrally or intraurethrally. PGE1 has also been used in combination with other agents, such as papaverine. The injection does not appear to produce any long-term side effects on penile smooth muscle. Transurethral therapy with alprostadil, such as MUSE (alprostadil urethral suppository or medicated urethral system for erection) is also an effective therapeutic technique, and there may be a role for this form of administration in selected patients with ED.The intracavernosal injection of alprostadil (e.g., alprostadil alfadex; Edex, Viridal) is safe and effective in patients with ED when sildenafil is ineffective. Both of these delivery systems have been used in the treatment of ED. MUSE can also be used in conjunction with a penile constrictor device (e.g., ACTIS).

Clinical Use

Prostaglandin E1 (PGE1; Alprostadil) is approved for the intracavernosal (Caverject, Edex)or intraurethral suppository (Muse) treatment of ED. A three-drug combination of PGE1, papaverine, and phentolamine sometimes is used as an intracavernosal injection to achieve a synergistic action. Erectile dysfunction that is medication-induced or caused by endocrine problems, such as hypogonadism or hyper- or hypothyroidism, should be evaluated and appropriately treated before PGE1 treatment is considered.

Metabolism

The major route of excretion of PGE1 metabolites is via the kidney. Its elimination half-life is 5 to 10 minutes. If any alprostadil is systemically absorbed, it is metabolized by a single pass through the lungs. The onset of action is within 10 minutes, and the time to peak effect is less than 20 minutes. The duration of action is 1 to 3 hours for the intracavernosal injection and 30 to 60 minutes for the intraurethral suppository.

Global( 454)Suppliers
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Prostaglandin E1 Spectrum

Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11a,13E,15S)- (8S,11S,12S,13E,15R)-11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid ent-PGE1 Alprostadil (PGE1)/Prostaglandin E1 Prostaglandin E1 or AIPROSTADIL l-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoicacid l-cyclopentaneheptanoicaci l-pge1 l-protaglandine1 (1R,2R,3R)-3-Hydroxy-2-((E)-(3S)-3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid 3-HYDROXY-2-(3-HYDROXY-1-OCTENYL)-5-OXO-CYCLOPENTANEHEPTANOIC ACID 9-OXO-11ALPHA,15S-DIHYDROXY-PROST-13E-EN-1-OIC ACID 11,15-DIHYDROXY-9-OXOPROST-13-EN-1-OIC ACID [11ALPHA,13E,15S]-11,15-DIHYDROXY-9-OXOPROST-13-EN-1-OIC ACID (11ALPHA,13E,15S)-11,15-DIHYDROXY-9-OXOPROST-13-ENOIC ACID [11ALPHA,13E,15S]-11,15-DIHYDROXY-9-OXOPROSTA-13-EN-1-OIC ACID Caveject Liprostin (11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid, Alprostadil, PGE1 (11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid, Alprostadil, PGE1, Prostaglandin E1 (11α, 13E, 15S)-11, 15-dihydroxy-9-oxyprosta-13-en-1-oic acid prostine VR PGEl Cyclopentaneheptanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, l Alprostadil lyophilized liposoMal Prostaglandin E1 (PGE1) (11α,13E,15S)-11,15-Dihydroxy-9-oxo-prost-13-en-1-oicacid Alprostadil (25 mg) Alprostadil (prostandin E1) Alprostadil(Caverject) cGMP Alprostadil Prostaglandin E1 Analytical Reference Standard Alprostadil(Prostaglandin E1) 11,15-dihydroxy-9-oxo-, (11α,13E,15S)-prost-13-en-1-oic acid 7-((1R,2R,3R)-3-Hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)heptanoic acid (-)-protaglandine1 11,15-dihydroxy-9-oxo-,(11-alpha,13e,15s)-prost-13-en-1-oicaci (11A,13E,15S)-11,15-DIHYDROXY-9-OXO-PROST-13-EN-1-OIC ACID Prostaglandin E1 Prostandin Prostaglandin E1, 98+% l-Cyclopentaneheptanoic (11α,13e,15s)-11,15-dihydroxy-9-oxoprost-13-enoic acid 7-[3-hydroxy-2-(3-hydroxyoct-1-enyl)-5-oxo-cyclopentyl]heptanoic acid 11α,15(S)-Dihydroxy-9-oxo-13-trans-prostenoic acid 11α,15α-Dihydroxy-9-oxo-13-trans-prostenoic acid Alprox TD Cyclopentaneheptanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, (-)- (8CI) Cyclopentaneheptanoic acid, 3α-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo- (7CI) Liple Lipoprost l-Prostaglandin E1 Minprog NSC 165559 ONO 1608 Palux Prostandin 500 Prostivas