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745-65-3 molecular structure
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7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

ChemBase ID: 650
Molecular Formular: C20H34O5
Molecular Mass: 354.48096
Monoisotopic Mass: 354.24062419
SMILES and InChIs

SMILES:
O[C@H]1[C@@H]([C@@H](CCCCCCC(=O)O)C(=O)C1)C=C[C@@H](O)CCCCC
Canonical SMILES:
CCCCC[C@@H](C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O)O
InChI:
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)/t15-,16+,17+,19+/m0/s1
InChIKey:
GMVPRGQOIOIIMI-DODZYUBVSA-N

Cite this record

CBID:650 http://www.chembase.cn/molecule-650.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
IUPAC Traditional name
alprostadil
Brand Name
Alprostadil Prostoglandin E1
Befar
Caverject
Edex
Muse
PGE1
Prink
Prostaglandin E1
Prostin VR
Prostin VR Pediatric
l-Prostaglandin E1
Alprox-TD
Femprox
Topiglan
Alista
Synonyms
alprostadil
Alprostadil
PGE1
(11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid
Prostaglandin E1
Prostaglandin E1
Alprostadil
(11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-oic Acid
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic Acid
Alprox TD
Caveject
Liprostin
ONO 1608
Palux
Prostandin
Minprog
NSC 165559
Topiglan
U 10136
Vasaprostan
l-PGE1
l-Prostaglandin E1
Prostaglandin E1
(11α,13E,15S)-11,15-二羟基-9-氧代前列-13-烯-1-酸
前列地尔
前列腺素 E1
前列腺素 E1
前列地尔
CAS Number
745-65-3
EC Number
212-017-2
MDL Number
MFCD00077860
Beilstein Number
5294062
PubChem SID
24898661
46508029
24890439
24898994
24887977
160964113
24898855
PubChem CID
149351
5280723

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.353232  H Acceptors
H Donor LogD (pH = 5.5) 2.4122984 
LogD (pH = 7.4) 0.6635846  Log P 3.5871918 
Molar Refractivity 98.3185 cm3 Polarizability 38.432873 Å3
Polar Surface Area 94.83 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five true 
Log P 3.04  LOG S -3.65 
Solubility (Water) 7.88e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
26.7 mg/L expand Show data source
acetone: soluble50 mg/mL, clear, colorless to faintly yellow expand Show data source
DMSO expand Show data source
Ethanol expand Show data source
ethanol: soluble1 mg/mL expand Show data source
ethanol: soluble5 mg/mL expand Show data source
THF expand Show data source
Water expand Show data source
Apperance
powder expand Show data source
White to Off-White Solid expand Show data source
Melting Point
115-116°C expand Show data source
Hydrophobicity(logP)
3.3 expand Show data source
Storage Condition
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
GY4569800 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
61-22 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H361 expand Show data source
GHS Precautionary statements
P281-P301 + P310 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... PTGIR(5739)mouse ... Ptger1(19216), Ptger2(19217), Ptger3(19218), Ptger4(19219) expand Show data source
Purity
≥98% (HPLC) expand Show data source
≥99.0% (TLC) expand Show data source
Potency
0.25-100 ng/mL expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
suitable for cell culture expand Show data source
Biological Source
synthetic expand Show data source
Sterility
γ-irradiated expand Show data source
Product Line
BioReagent expand Show data source
BioXtra expand Show data source
Empirical Formula (Hill Notation)
C20H34O5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00770 external link
Item Information
Drug Groups approved; investigational
Description Alprostadil is produced endogenously and causes vasodilation by means of a direct effect on vascular and 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. In infants, it is used for palliative, not definitive, therapy to temporarily maintain the patency of the ductus arteriosus until corrective or palliative surgery can be performed in neonates who have congenital heart defects and who depend upon the patent ductus for survival. In adults, it is used for the treatment of erectile dysfunction due to neurogenic, vasculogenic, psychogenic, or mixed etiology.
Indication For palliative, not definitive, therapy to temporarily maintain the patency of the ductus arteriosus until corrective or palliative surgery can be performed in neonates who have congenital heart defects and who depend upon the patent ductus for survival. Also for the treatment of erectile dysfunction due to neurogenic, vasculogenic, psychogenic, or mixed etiology.
Pharmacology Alprostadil (prostaglandin E1) is produced endogenously to relax vascular smooth muscle and cause vasodilation. In adult males, the vasodilatory effects of alprostadil on the cavernosal arteries and the trabecular smooth muscle of the corpora cavernosa result in rapid arteriolar inflow and expansion of the lacunar spaces within the corpora. As the expanded corporal sinusoids are compressed against the tunica albuginea, venous outflow through the subtunical vessels is impeded and penile rigidity develops. This is referred to as the corporal veno-occlusive mechanism. In infants, the vasodilatory effects of alprostadil increase pulmonary or systemic blood flow.
Toxicity Oral, mouse: LD50 = 186 mg/kg; Oral, rat: LD50 = 228 mg/kg. Apnea, bradycardia, pyrexia, hypotension, and flushing may be signs of drug overdosage.
Affected Organisms
Humans and other mammals
Biotransformation Alprostadil must be infused continuously because it is very rapidly metabolized. As much as 80% of the circulating alprostadil may be metabolized in one pass through the lungs, primarily by beta- and omega-oxidation.
Absorption The absolute bioavailability of alprostadil has not been determined.
Half Life 5 to 10 minutes (after a single dose), in healthy adults and neonates.
Protein Binding Bound in plasma primarily to albumin (81% bound) and to a lesser extent alpha-globulin IV-4 fraction (55% bound).
Elimination Alprostadil must be infused continuously because it is very rapidly metabolized. As much as 80% of the circulating alprostadil may be metabolized in one pass through the lungs, primarily by β- and ω-oxidation. The metabolites are excreted primarily by the kidney, and excretion is essentially complete within 24 hours after administration.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - P5515 external link
Biochem/physiol Actions
Vasodilator; activates adenylate cyclase.
Sigma Aldrich - P7527 external link
Application
For use in cell culture applications for the study of prostaglandin regulated cell signaling and gene regulation.
Sigma Aldrich - P8908 external link
Physical form
powder-0 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw
Application
Prostaglandin E1 may be used in cell culture to protect human umbilical vein endothelial cells (HUVEC) from injury induced by hydrogen peroxide.
Sigma Aldrich - 82474 external link
Other Notes
Enhancement of cAMP responses by protein kinase C activation.1
Toronto Research Chemicals - P838600 external link
A primary Prostaglandin; easily crystallized from purified biological extracts. Vasodilator (peripheral).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Anggard, S., et al.: J. Biol. Chem., 239, 4097 (1964)
  • • Wooster, D.L., et al.: J. Am. Med. Assoc., 245, 1846 (1964)
  • • Linet, O.I., et al.: N. Engl. J. Med., 334, 873 (1964)
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PATENTS

PATENTS

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