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Sulprostone

Product Name
Sulprostone
CAS No.
60325-46-4
Chemical Name
Sulprostone
Synonyms
sch286;SHB-286;Nalador;ZK-57671;CP-34089;CP-34086;SULPROSTONE;Sulprostone USP/EP/BP;Sulprostone >=95% (HPLC), oil;Sulprostone in 5mg/ml Methyl Acetate
CBNumber
CB3224098
Molecular Formula
C23H31NO7S
Formula Weight
465.56
MOL File
60325-46-4.mol
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Sulprostone Property

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
pka
4.63±0.40(Predicted)
color 
white to off-white
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Safety

Hazard Codes 
T
Risk Statements 
60-36/37/38
Safety Statements 
53-22-36/37-45
WGK Germany 
3
RTECS 
MJ8810000
Toxicity
LD50 intraperitoneal in mouse: 18mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S8692
Product name
Sulprostone
Purity
≥95% (HPLC), oil
Packaging
1mg
Price
$223
Updated
2024/03/01
Sigma-Aldrich
Product number
S8692
Product name
Sulprostone
Purity
≥95% (HPLC), oil
Packaging
5mg
Price
$783
Updated
2024/03/01
Cayman Chemical
Product number
14765
Product name
Sulprostone
Purity
≥98%
Packaging
500μg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
14765
Product name
Sulprostone
Purity
≥98%
Packaging
1mg
Price
$107
Updated
2024/03/01
Cayman Chemical
Product number
14765
Product name
Sulprostone
Purity
≥98%
Packaging
5mg
Price
$437
Updated
2024/03/01
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Sulprostone Chemical Properties,Usage,Production

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

Uses

Human chondrocytes3 and mouse adrenal chromaffin cells4 were treated with sulprostone to study the biological effects of PGE2.

Uses

Sulprostone is a selective agonist of the PGE2 receptor.

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.

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

Sulprostone Preparation Products And Raw materials

Raw materials

Preparation Products

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Sulprostone Suppliers

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60325-46-4, SulprostoneRelated Search:

Prostaglandin E2 CHLOROPHOSPHONAZO III CIS-BUTENEDIOIC ANHYDRIDE TERT-AMYL METHYL ETHER Fumaric acid Zinc pyrithione Diltiazem hydrochloride Polybutene Misoprostol Acid Phloroglucinol Aprepitant Tranexamic acid Mifepristone Maleic acid 2-Chlorophenyl cyclopentyl ketone 3-HEXENE-1 6-DIOLE Sulprostone

  • (1r-(1-alpha(z),2-beta(1e,3r*),3-alpha))--n-(methylsulfonyl)
  • 16-phenoxy-17,18,19,20tetranorprostaglandine(sub2)methylsulfonylamide
  • 16-phenoxy-omega-17,18,19,20-tetranorpge-2methylsulfonylamide
  • 16-phenoxy-omega-17,18,19,20-tetranorprostaglandine2methylsulfonylamide
  • N-(METHYLSULFONYL)-9-OXO-11ALPHA,15R-DIHYDROXY-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-AMIDE
  • SHB-286
  • SULPROSTONE
  • ZK-57671
  • 5-heptenamide,7-(3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocyclopentyl)
  • sch286
  • (5Z,11ALPHA,13E,15R)-11,15-DIHYDROXY-9-OXO-16-PHENOXY-17,18,19,20-TETRANORPROSTA-5,13-DIENOIC ACID METHANE SULFONAMIDE
  • CP-34089
  • (5Z,11alpha,13E,15R)-11,15-Dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-amide
  • 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
  • (5Z,11a,13E,15R)--11,15-Dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-5,13-dienoic acid methane sulfonamide
  • Nalador
  • CP-34086
  • (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
  • (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)-
  • Sulprostone >=95% (HPLC), oil
  • Sulprostone USP/EP/BP
  • Sulprostone in 5mg/ml Methyl Acetate
  • 60325-46-4
  • C23H31NO7S
  • Analytical Chromatography Product Catalog
  • Analytical Standards
  • Chromatography
  • Drug Standards
  • Forensic and Veterinary Standards