| Identification | Back Directory | [Name]
Sulprostone | [CAS]
60325-46-4 | [Synonyms]
sch286
Nalador
SHB-286
ZK-57671
CP-34086
CP-34089
SULPROSTONE
Sulprostone USP/EP/BP
Sulprostone >=95% (HPLC), oil
(1r-(1-alpha(z),2-beta(1e,3r*),3-alpha))--n-(methylsulfonyl)
16-phenoxy-omega-17,18,19,20-tetranorpge-2methylsulfonylamide
16-phenoxy-17,18,19,20tetranorprostaglandine(sub2)methylsulfonylamide
16-phenoxy-omega-17,18,19,20-tetranorprostaglandine2methylsulfonylamide
5-heptenamide,7-(3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocyclopentyl)
(5Z,11alpha,13E,15R)-11,15-Dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-amide
N-(METHYLSULFONYL)-9-OXO-11ALPHA,15R-DIHYDROXY-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-AMIDE
(5Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3R)-3-hydroxy-4-buten-1-yl]-5-oxocyclopentyl]-N-(methylsulfonyl)-5-heptenamide
(5z,11α,13e,15r)-11,15-dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-5,13-dienoic acid methane sulfonamide
(5Z,11a,13E,15R)--11,15-Dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-5,13-dienoic acid methane sulfonamide
(5Z,11ALPHA,13E,15R)-11,15-DIHYDROXY-9-OXO-16-PHENOXY-17,18,19,20-TETRANORPROSTA-5,13-DIENOIC ACID METHANE SULFONAMIDE
(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(E,3R)-3-hydroxy-4-(phenoxy)but-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide
5-Heptenamide, 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5-oxocyclopentyl]-N-(methylsulfonyl)-, (5Z)-
CP-34089, SHB-286, ZK-57671, (5Z,11α,13E,15R)--11,15-Dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-5,13-dienoic acid methane sulfonamide | [EINECS(EC#)]
262-173-0 | [Molecular Formula]
C23H31NO7S | [MDL Number]
MFCD00216056 | [MOL File]
60325-46-4.mol | [Molecular Weight]
465.56 |
| Chemical Properties | Back Directory | [Melting point ]
79.25°C | [density ]
1.1918 (rough estimate) | [refractive index ]
1.5650 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMSO: >5 mg/mL
| [form ]
solid
| [color ]
white to off-white
|
| Hazard Information | Back Directory | [Description]
Sulprostone is a metabolism resistant synthetic analog of PGE2. It is a selective agonist for EP3 receptors with a Ki value of 0.35 nM at the human recombinant EP3-III receptor and an IC50 of 0.01 μM for the inhibition of PGE2 binding. Sulprostone is a potent stimulator of uterine smooth muscle contractions with high abortifacient activity. | [Originator]
Nalador,Schering,W. Germany,1981 | [Uses]
antimalarial activity | [Definition]
ChEBI: Sulprostone is a prostanoid. | [Manufacturing Process]
9α-Hydroxy-11α,15α-bis-(tetrahydropyran-2-yloxy)-16-phenoxy-cis-5-trans-
13-ω-tetranorprostadienoicacid: To a solution of 1.6 g (3.6 mmols) (4-
carbohydroxy-n-butyl)triphenylphosphonium bromide in a dry nitrogen
atmosphere in 6.0 ml dry dimethyl sulfoxide was added 3.24 ml (6.5 mmols)
of a 2.0 M solution of sodium methylsulfinylmethide in dimethyl sulfoxide. To
this red ylide solution was added dropwise a solution of 613 mg (1.29 mmols)
2-[5α-hydroxy-3α-(tetrahydropyran-2-yloxy)-2α-(3α-tetrahydropyran-2-yloxy-
4-phenoxytrans-1-buten-1-yl)cyclopent-1α-yl] acetaldehyde, γ-hemiacetal in
5.0 ml dry dimethyl sulfoxide over a period of 20 minutes.
After an additional 2 hours stirring at room temperature, the reaction mixture
was poured onto ice water. The basic aqueous solution was washed twice with
ethyl acetate (20 ml) and acidified to pH 3 with 10% aqueous hydrochloric
acid.
The acidic solution was extracted with ethyl acetate (3 x 20 ml) and the
combined organic extracts washed once with water (10 ml), dried (MgSO4)
and evaporated to a solid residue. This solid residue was triturated with ethyl
acetate and the filtrate concentrated. Yield: 754 mg of 9α-hydroxy-11α,15α-bis-(tetrahydropyran-2-yloxy)-16-phenoxy-cis-5-trans-13-
ωtetranorprostadienoic acid was collected.
9-Oxo-11α,15α-bis-(tetrahydropyran-2-yloxy)-16-phenoxy-cis-5-trans-13-ω-
tetranorprostadienoicacid: To a solution cooled to -10°C under nitrogen of 754
mg (1.3 mmols) 9α-hydroxy-11α,15α-bis-(tetrahydropyran-2-yloxy)-16-
phenoxy-cis-5-trans-13-ω-tetranorprostadienoic acid in 13 ml reagent grade
acetone was added dropwise to 0.56 ml (1.41 mmols) of Jones' reagent
(chromic anhydride). After 20 minutes at -10°C, 0.260 ml 2-propanol was
added and the reaction mixture was allowed to stir an additional 5 minutes at
which time it was combined with 75 ml ethyl acetate, washed with water (3 x
10 ml), dried (MgSO4)and concentrated to give 752 mg of 9-oxo-11α,15α-bis-
(tetrahydropyran-2-yloxy)-16-phenoxy-cis-5-trans-13-ω-tetranorprostadienoic
acid, which was chromatographed on silica gel using ethyl acetate as eluent to
afford 505 mg of pure intermediate.
N-Methanesulfonyl-9-oxo-11α,15α-dihydroxy-5-cis-13-trans-16-phenoxy-ω-
tetranorprostadienamide:To 1.0 mmols of 9-oxo-11α,15α-bis-
(tetrahydropyran-2-yloxy)-16-phenoxy-cis-5-trans-13-ω-tetranorprostadienoic
acid in 40 ml THF is added 2 ml triethylamine. After 15 minutes of stirring at
room temperature 10.0 ml of 0.1 M methanesulfonylisocyanate in THF is
added. After a further 1 hour of stirring, the reaction mixture is neutralized
with acetic acid and the solvent removed by evaporation (in vacuo). The
resultant residue is taken up in methylene chlorine and washed successively
with water and sodium bicarbonate to yield, after drying and solvent
evaporation, N-methanesulfonyl-9-oxo-11α,15α-bis-(tetrahydropyran-2-yloxy)-
16-phenoxy-cis-5-trans-13-ω-tetranorprostadienamide. This intermediate is
then hydrolyzed overnight with acetic acid/water and purified by column
chromatography to give the desired N-methanesulfonyl-9-oxo-11α,15α-
dihydroxy-5-cis-13-trans-16-phenoxy-ω-tetranorprostadienamide. | [Therapeutic Function]
Contraceptive | [World Health Organization (WHO)]
Sultopride, a neuroleptic indicated for the treatment of acute and
chronic psychoses, was introduced on the market in 1976. In the early 1990s, its
use was associated with cardiac arrhythmias, some of which were fatal. This led
the regulatory authority in France to take restrictive action on the product.
Sultopride continues to be marketed in several other countries. | [Biological Activity]
Selective EP3 prostanoid receptor agonist. | [Biochem/physiol Actions]
Sulprostone is an analog of prostaglandin E2 (PGE2)1 and antagonizes vasopressin-induced antidiuretic responses in cells from rat renal inner medullae by a mechanism that involves activation of Rho.2 | [storage]
Store at -20°C |
|
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