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745-65-3

Basic Information
CAS No.: 745-65-3
Name: Prostaglandin E1
Article Data: 30
Molecular Structure:
Molecular Structure of 745-65-3 (Prostaglandin E1)
Formula: C20H34O5
Molecular Weight: 354.487
Synonyms: Cyclopentaneheptanoicacid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, (-)- (8CI);Cyclopentaneheptanoicacid, 3a-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-(7CI);(-)-Prostaglandin E1;11a,15(S)-Dihydroxy-9-oxo-13-trans-prostenoic acid;11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid;Alprox TD;Caveject;Caverject;Eglandin;Liple;Lipoprost;Liprostin;Minprog;NSC 165559;ONO 1608;Palux;Prostandin 500;Prostin VR Pediatric;Prostivas;SEPA-PGE1;SEPA-alprostadil;Topiglan;Vasaprostan;l-PGE1;l-Prostaglandin E1;Prostaglandin E1;
EINECS: 212-017-2
Density: 1.131 g/cm3
Melting Point: 115-116 °C
Boiling Point: 529.3 °C at 760 mmHg
Flash Point: 288 °C
Solubility: insoluble in water
Appearance: Crystalline solid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38
Safety: 36-26
Transport Information: UN 2811 6.1/PG 3
PSA: 94.83000
LogP: 3.47510
Synthetic route
1251949-12-8

C32H64O5Si2

745-65-3

ALPROSTADIL

Conditions
ConditionsYield
With hydrogen fluoride; water In acetonitrile at 20℃; for 6h; stereoselective reaction;90%
3434-33-1

prostaglandin E1 methyl ester

745-65-3

ALPROSTADIL

Conditions
ConditionsYield
With porcine pancreatic lipase; sodium chloride; calcium chloride In tetrahydrofuran; water for 0.5h; Hydrolysis; Enzymatic reaction; pH 7.1;89%
With pig liver esterase In water for 4h; Ambient temperature;86%
With porcine liver esterase; phosphate buffer solution In acetone for 4h; Ambient temperature;86%
With phosphate buffer Baker's yeast, pH 7.0;72%
(microbiological transformation);
87007-31-6

7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid

745-65-3

ALPROSTADIL

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile Yield given;
1012104-26-5

(8R,11R,12R,15S)-11,15-Bis-(2-trimethylsilylethoxymethoxy)-9-oxo-prost-13-en-1-oic acid 2-trimethylsilylethoxymethyl ester

745-65-3

ALPROSTADIL

Conditions
ConditionsYield
With nitromethane; n-butanethiol; magnesium bromide In diethyl ether at 20℃; for 1h;
1012104-24-3

(S)-E-3-(2-trimethylsilylethoxymethoxy)-1-tributylstannyl-1-octene

745-65-3

ALPROSTADIL

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
1.2: 2-thienyl(cyano)copper lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
1.3: 67 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.1: magnesium bromide; nitromethane; n-butanethiol / diethyl ether / 1 h / 20 °C
View Scheme
1012104-25-4

2-trimethylsilylethoxymethyl-(R)-3-(2-trimethylsilylethoxymethoxy)-5-oxo-1-cyclopentene-1-heptenoate

745-65-3

ALPROSTADIL

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
1.2: 2-thienyl(cyano)copper lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
1.3: 67 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.1: magnesium bromide; nitromethane; n-butanethiol / diethyl ether / 1 h / 20 °C
View Scheme
54996-33-7

7-(3R-hydroxy-5-oxo-cyclopent-1-enyl)heptanoic acid

745-65-3

ALPROSTADIL

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 31 percent / 4-(dimethylamino)pyridine; lithium carbonate / dimethylformamide / 20 h / 20 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 2-thienyl(cyano)copper lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.3: 67 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.1: magnesium bromide; nitromethane; n-butanethiol / diethyl ether / 1 h / 20 °C
View Scheme
39178-64-8

(E)-1-iodo-1-octen-3-one

745-65-3

ALPROSTADIL

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 95 percent / n-butylboronic complex of diphenyl D-prolinol; catecholborane / toluene / 36 h / -78 °C
2.1: 97 percent / Et3N; imidazole / dimethylformamide / 20 °C
3.1: n-BuLi; CuCN; MeLi / diethyl ether / 3.08 h / -78 - 0 °C
3.2: diethyl ether; hexane / 0.33 h / -78 °C
4.1: pyridinium p-toluenesulfonate / acetone; H2O / 4 h / 20 °C
5.1: 89 percent / porcine pancreatic lipase; NaCl; CaCl2 / H2O; tetrahydrofuran / 0.5 h / Enzymatic reaction; pH 7.1
View Scheme
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Specification

1. Introduction of Prostaglandin E1
Prostaglandin E1 is one kind of white powder. The IUPAC Name of this chemical is 7-[(1R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid. Besides, Prostaglandin E1 belogns to Miscellaneous Biochemicals; Prostaglandins; Prostaglandin; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Prostanoid receptor and related. In addition, Prostaglandin E1 is reported soluble in ethanol at >100 mg/ml. It is insoluble in water.

2. Properties of Prostaglandin E1
Physical properties about Prostaglandin E1 are:
(1)Melting Point: 115-116 °C; (2)Boiling point: 529.3 °C at 760 mmHg; (3)Storage Temperature: -20°C; (4)Flash Point: 288 °C; (5)Density: 1.131 g/cm3; (6)Surface Tension: 52.3 dyne/cm; (7)Enthalpy of Vaporization: 92.52 kJ/mol; (8)Vapour Pressure: 2.06E-13 mmHg at 25°C; (9)XLogP3-AA: 3.2; (10)H-Bond Donor: 3; (11)H-Bond Acceptor: 5; (12)Rotatable Bond Count: 13; (13)Tautomer Count: 3; (14)Exact Mass: 354.240624; (15)MonoIsotopic Mass: 354.240624; (16)Topological Polar Surface Area: 94.8; (17)Heavy Atom Count: 25; (18)Formal Charge: 0; (19)Complexity: 432; (20)Isotope Atom Count: 0; (21)Defined Atom Stereocenter Count: 0; (22)Undefined Atom Stereocenter Count: 4; (23)Defined Bond Stereocenter Count: 0; (24)Undefined Bond Stereocenter Count: 1; (25)Covalently-Bonded Unit Count: 1; (26)Feature 3D Acceptor Count: 5; (27)Feature 3D Donor Count: 2; (28)Feature 3D Anion Count: 1; (29)Feature 3D Hydrophobe Count: 4; (30)Feature 3D Ring Count: 1; (31)Effective Rotor Count: 13.8; (32)Conformer Sampling RMSD: 1.6; (33)CID Conformer Count: 88.

3. Structure Descriptors of Prostaglandin E1
(1)Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
(2)Isomeric SMILES: CCCCC[C@@H](/C=C/C1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O
(3)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)/b13-12+/t15-,16+,17?,19+/m0/s1  
(4)InChIKey: GMVPRGQOIOIIMI-ZWLIRFKBSA-N

4. Toxicity information of Prostaglandin E1

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 19800ug/kg (19.8mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
mouse LD50 intravenous 21mg/kg (21mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
mouse LD50 oral 186mg/kg (186mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
mouse LD50 subcutaneous 26400ug/kg (26.4mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
rat LD50 intraarterial 21mg/kg (21mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 499, 1983.
rat LD50 intraperitoneal 24900ug/kg (24.9mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
rat LD50 intravenous 19200ug/kg (19.2mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
rat LD50 oral 228mg/kg (228mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
rat LD50 subcutaneous 18600ug/kg (18.6mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.

5. Safety Information of Prostaglandin E1
Hazard Codes: XnHarmful,XiIrritant
Risk Statements: 22-36/37/38
22:  Harmful if swallowed 
36:  Irritating to the eyes 
37:  Irritating to the respiratory system 
38:  Irritating to the skin 
Safety Statements: 36-26
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing

6. Uses of Prostaglandin E1
Prostaglandin E1 (CAS NO.745-65-3) is used as a drug in the treatment of erectile dysfunction and has vasodilatory properties. Aprostadil is also used in maintaining a patent ductus arteriosus in the newborn. This is primarily useful when there is threat of premature closure of the ductus arteriosus in an infant with ductal-dependent congenital heart disease, including cyanotic lesions (e.g., pulmonary atresia/stenosis, tricuspid atresia/stenosis, transposition of the great arteries) and acyanotic lesions (e.g., coarctation of the aorta, hypoplastic left heart syndrome, critical aortic stenosis, interrupted aortic arch).

7. Production of Prostaglandin E1 
Prostaglandin E1 can be got from Methyl g-linolenate which is showed as follows:

Production of Prostaglandin E1