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Alprostadil

HCID 5280723
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Grundinformationen

CAS
745-65-3
Standard-SMILES
CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O
InChIKey
GMVPRGQOIOIIMI-DWKJAMRDSA-N
Summenformel
C20H34O5
Durchschnittliche Molmasse
354,5 g/mol
Monoisotopische Masse
354,24062419

Überblick

Prostaglandin E1 is a prostaglandins E. It has a role as a vasodilator agent, an anticoagulant, a platelet aggregation inhibitor and a human metabolite. It is a conjugate acid of a prostaglandin E1(1-).

Namen und Bezeichner

Bevorzugter Name
Alprostadil
IUPAC
7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
Lokaler Name
Alprostadil
Englischer Name
Prostaglandin E1
Summenformel
C20H34O5
Molmasse
354.48

Namen und Synonyme

alprostadilProstaglandin E1745-65-3PGE1CaverjectEdexMuseAlprostadilumBefarProstin VR PediatricVitarosPrink
Weitere Namen anzeigen
Alprostadil (PGE1)Prost-13-en-1-oic acidProstaglandine E1PGElLiplePalux
PGE-1Prostavasin(11alpha,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acidCaverject ImpulsePGE1alphaDTXSID9022578Lipo PGE1Prostaglandin E1alpha

Datenbank-Bezeichner

CAS
745-65-3
PubChem CID
5280723
DTXSID
DTXSID9022578
ChEMBL
CHEMBL495
ChEBI
CHEBI:15544
UNII
F5TD010360
EC Number
212-017-2
Nikkaji
J3.319G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,2
Polarare Oberfläche (TPSA)
94,8 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
13
Schwere Atome
25
Formalladung
0
Komplexität
432

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
LogP3.20
Human Drugs · 3 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Medicines administered to the neonate [c]

Melting Point · 2 Einträge

115-116 °C

115 - 116 °C

Physical DescriptionSolid
Dissociation Constants · 2 Einträge

4.87

4.85 (at 25 °C)

Collision Cross Section · 2 Einträge

190.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

198.3 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 74 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxikologische Informationen

Adverse EffectsAdverse Effects of Intraurethral Alprostadil Suppositories (MUSE)
Toxicity Summary · 1 Eintrag

The use of alprostadil for the treatment of erectile dysfunction in males may lead to prolonged erections and, in some cases, priapism. The incidence of priapism as an adverse effect of alprostadil is more common with the intraurethral suppository. This condition can also occur when unauthorized combination therapy is used or when patients exceed the prescribed dosage.

Sicherheitsdaten

F
8-10
wgk
3
ridadr
UN 2811 6.1/PG 3
hs_code
29375000
RTECS-Nr.
GY4569800
risk_code
22-36/37/38-61
hazard_code
Xn,Xi

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 6 Einträge

G04BE01

G - Genito urinary system and sex hormones

C - Cardiovascular system

QG - Genito urinary system and sex hormones

QC - Cardiovascular system

C01EA01

Protein BindingAlprostadil is bound in plasma primarily to albumin (81% bound) and, to a lesser extent, alpha-globulin IV-4 fraction (55% bound).
Pharmacodynamics · 1 Eintrag

Prostaglandin E1 is produced endogenously to relax vascular smooth muscle and cause vasodilation. As a synthetic form of prostaglandin E1, alprostadil has the same pharmacodynamic effects. Alprostadil inhibits platelet aggregation, has anti-inflammatory effects, interferes with immune responses, and stimulates factor X, a blood coagulation enzyme. In adult males, the use of alprostadil may lead to prolonged erection and priapism, penile fibrosis, hypotension, and injection site bleeding. In patients treated up to 24 months with alprostadil, the incidence of prolonged erections (>4 hours long) was 4% of all, and the incidence of priapism (erections greater than 6 hours in duration) was <1%. Patients with preexisting cardiovascular disease treated with alprostadil may also have higher cardiac risk. Neonates with congenital heart defects treated with alprostadil may experience apnea. Apnea is experienced by 10-12% of neonates and is more common in those weighing less than 2 kg at birth. The administration of alprostadil to neonates may also result in gastric outlet obstruction secondary to antral hyperplasia.

Mechanism of Action · 1 Eintrag

Alprostadil is a smooth muscle relaxant that promotes vasodilation and platelet aggregation inhibition. In neonatal patients with ductus arteriosus patency, alprostadil relaxes the ductus arteriosus (DA) smooth muscle, preventing or reversing the functional closure of the DA that occurs shortly after birth. This results in increased pulmonary or systemic blood flow in infants. Alprostadil appears to be most effective within 96 hours after birth since the DA rapidly loses its responsiveness to alprostadil. When administered by intracavernosal injection or as an intraurethral suppository, alprostadil acts locally to relax the trabecular smooth muscle of the corpora cavernosa and the cavernosal arteries. Swelling, elongation, and rigidity of the penis result when arterial blood rapidly flows into the corpus cavernosum to expand the lacunar spaces. The entrapped blood reduces the venous blood outflow as sinusoids compress against the tunica albuginea leading to penile rigidity. This is referred to as the corporal veno-occlusive mechanism.

Zugehörige Reaktionen

18
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 26304
HRID 26304als Eduktuspto-grants-1979_04
Reaktionsgleichung von HRID 46949
HRID 46949als Eduktuspto-grants-1979_11
Reaktionsgleichung von HRID 329226
HRID 329226als Eduktuspto-grants-1977_04
Reaktionsgleichung von HRID 437096
HRID 437096als Eduktuspto-grants-1977_06
Reaktionsgleichung von HRID 462132
HRID 462132als Eduktuspto-grants-1977_12
Reaktionsgleichung von HRID 866499
HRID 866499als Eduktuspto-grants-1978_07
Reaktionsgleichung von HRID 866500
HRID 866500als Eduktuspto-grants-1978_07
Reaktionsgleichung von HRID 866665
HRID 866665als Eduktuspto-grants-1978_07
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Physikochemische Eigenschaften

Schmelzpunkt
115 · 115-116 °C
Siedepunkt
407.69 °C · 407.69°C (rough estimate)
Dichte
1.0458 · 1.0458 (rough estimate)
Brechungsindex
1.612 · 1.6120 (estimate)
storage temp.
-20 °C · -20°C
Löslichkeit
1 mg/mL · ethanol: 1 mg/mL
pka
4.85 · pKa 4.85± 0.07(H2O,t=25±0.1,I=0.1(NaCl)) (Uncertain)
Aggregatzustand
powder
Farbe
White to off-white
Biologische Quelle
synthetic (organic)
Wasserlöslichkeit
insoluble
Merck
13 · 13,7968
BRN
5294062 · 5294062
Stabilität
1 year · 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.
InChI
1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
InChIKey
GMVPRGQOIOIIMI-DWKJAMRDSA-N
SMILES
O=C1[C@H](CCCCCCC(O)=O)[C@@H](/C=C/[C@H](CCCCC)O)[C@H](O)C1
safety_code
36-26
hazard_class
6.1(b)
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 Oral
Biological Half-LifeIn healthy adults and neonates given a single intravenous dose of alprostadil, half-life goes from 5 to 10 minutes.
Metabolism/Metabolites · 1 Eintrag

Alprostadil is rapidly metabolized in the human body. Following intracavernous administration, alprostadil is metabolized in the corpus cavernosum, and a smaller portion is absorbed from the penis into systemic circulation. After intravenous or arterial administration, alprostadil is metabolized and distributed throughout the entire body except for the central nervous system. As much as 60-90% of the circulating alprostadil may be metabolized in the lungs through first-pass pulmonary elimination, in a process known as beta- and omega-oxidation. The enzymatic oxidation of the C15-hydroxy group of alprostadil leads to the formation of 15-keto-PGE<sub>1</sub>, while the reduction of the C13, 14-double bond produces 15-keto-PGE<sub>0</sub>, and 13,14-dihydro-PGE<sub>1</sub> (PGE<sub>0</sub>). The 15-keto metabolites are inactive, but the PGE<sub>0</sub> metabolite has a similar potency to alprostadil in isolated animal organs. The major metabolite of alprostadil is 15-keto-PGE<sub>0</sub>.

FDA Pharmacological Classification · 6 Einträge

F5TD010360

ALPROSTADIL

Physiologic Effects [PE] - Genitourinary Arterial Vasodilation

Established Pharmacologic Class [EPC] - Prostaglandin Analog

Established Pharmacologic Class [EPC] - Prostaglandin E1 Agonist

Mechanisms of Action [MoA] - Prostaglandin Receptor Agonists

MeSH Pharmacological Classification · 3 Einträge

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

Drugs used to cause dilation of the blood vessels.

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.

Absorption, Distribution and Excretion · 4 Einträge

In patients with erectile dysfunction given 20 μg of alprostadil intracavernously, the systemic plasma concentrations of prostaglandin E1 increased from a baseline of 0.8 pg/mL to a Cmax of 16.8 pg/mL (corrected for baseline). The tmax and AUC for this group of patients were 4.8 min and 173 pg⋅min/mL, respectively. In patients given 20 μg of alprostadil intravenously, AUC was similar to the one detected in patients that received alprostadil intracavernously (174 pg⋅min/mL); however, they had a higher tmax (25.5 min) and a lower Cmax (7.09 pg/mL). Compared to the same dose given by a short-term intravenous infusion, the absolute bioavailability of alprostadil estimated from systemic exposure was about 98%.

Following the degradation of alprostadil by beta- and omega-oxidation, metabolites are excreted primarily by the kidney, and excretion is essentially complete within 24 hours after administration (92%). Approximately 88% and 12% of alprostadil metabolites are excreted through urine and feces, respectively, over 72 hours. Alprostadil and its metabolites are not retained in tissues, and unchanged alprostadil has not been detected in urine.

The volume of distribution of alprostadil has yet to be determined.

In patients with erectile dysfunction given an intravenous infusion of alprostadil (20 μg), the total body clearance was 115 L/min.

Tissue LocationsEpidermis
Cellular LocationsCytoplasm
Anwendungen · 2 Einträge

BeschreibungProstaglandin 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).

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

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-ButoxyethylmethacrylatSilbernitratgamma-Linolenic acid methyl esterGlutathionCyclopentenWasserstoffIcosa-5,8,11,14-tetraensureDinoprostonEthyl acetate solutionNatriumperiodatEthandiolNatriummethanolatp-Toluenesulfonic acid monohydrateKalium-tert-butanolatNatriumhydridOsmiumtetraoxidProstaglandin E1 methyl ester(2R,3S)-1,2-Epoxy-3-hydroxy-4-pentene