CAS 60325-46-4|Sulprostone

Introduction：Basic information about CAS 60325-46-4|Sulprostone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Sulprostone BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles48
7. Synonyms

Common Name	Sulprostone
CAS Number	60325-46-4	Molecular Weight	465.560
Density	1.3±0.1 g/cm3	Boiling Point	/
Molecular Formula	C₂₃H₃₁NO₇S	Melting Point	78.5-80ºC
MSDS	ChineseUSA	Flash Point	/
Symbol	GHS07, GHS08	Signal Word	Danger

Names

Name	(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide
Synonym	More Synonyms

Sulprostone BiologicalActivity

Description	Sulprostone (SHB 286), a prostaglandin E2 (PGE2) analogue, is a potent and selective EP3 receptor agonist. Sulprostone has potential antiulcer and nonsteroidal abortifacient effects used for the research of pregnancy termination and hemorrhages during delivery[1][2][3].
Related Catalog	Research Areas >>Cardiovascular DiseaseSignaling Pathways >>GPCR/G Protein >>Prostaglandin ReceptorResearch Areas >>Inflammation/Immunology
Target	EP3 Receptor
In Vitro	Sulprostone (SHB 286) has Ki values of 21 nM and 0.6 nM for EP1 and EP3 in cultured Chinese hamster ovary cells[1]. Sulprostone (1, 1.5 or 2 mg/mL) does not significantly modify the viability and the purity of Dendritic cells (DCs). Sulprostone impairs spontaneous and directed DC migration independently from its concentration. Sulprostone reduces the expression of CCR7 and impairs migration of DCs[2].
In Vivo	Sulprostone (0.5 mg/kg; IV) has a T1/2 of 0.451 hours, a CL of 56 mL/min•kg, a Vss of 0.583 L/kg and an AUC of 149 ng•h/mL[3]. Animal Model: Male cynomolgus monkey[3] Dosage: 0.5 mg/kg (Pharmacokinetic Analysis) Administration: IV Result: Had a T1/2 of 0.451 hours, a CL of 56 mL/min•kg, a Vss of 0.583 L/kg and an AUC of 149 ng•h/mL.
References	[1]. S Narumiya, et al. Prostanoid receptors: structures, properties, and functions. Physiol Rev. 1999 Oct;79(4):1193-226. [2]. Jenny Bulgarelli, et al. Skewing effect of sulprostone on dendritic cell maturation compared with dinoprostone. Cytotherapy. 2018 Jun;20(6):851-860. [3]. Yifan Shi, et al. Bioanalysis of sulprostone, a prostaglandin E 2 analogue and selective EP 3 agonist, in monkey plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Aug 15;1092:51-57.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Melting Point	78.5-80ºC
Molecular Formula	C₂₃H₃₁NO₇S
Molecular Weight	465.560
Exact Mass	465.182129
PSA	138.38000
LogP	0.26
Index of Refraction	1.589
InChIKey	UQZVCDCIMBLVNR-TWYODKAFSA-N
SMILES	CS(=O)(=O)NC(=O)CCCC=CCC1C(=O)CC(O)C1C=CC(O)COc1ccccc1
Storage condition	−20°C
Water Solubility	DMSO: >5 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MJ8810000

CHEMICAL NAME :: 5-Heptenamide, 7-(3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxoc yclopentyl)- N-(methylsulfonyl)-, (1R-(1-alpha(Z),2-beta(1E,3R*),3-alpha))-

CAS REGISTRY NUMBER :: 60325-46-4

LAST UPDATED :: 199803

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C23-H31-N-O7-S

MOLECULAR WEIGHT :: 465.61

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EKFAE9 Eksperimental'naya i Klinicheskaya Farmakologiya. Experimental and Clinical Pharmacology. (Mezhdunarodnaya Kniga, ul. B. Yakimanka, 39, 117049 Moscow, Russia) V.55- 1992- Volume(issue)/page/year: 56(4),37,1993

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 18 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EKFAE9 Eksperimental'naya i Klinicheskaya Farmakologiya. Experimental and Clinical Pharmacology. (Mezhdunarodnaya Kniga, ul. B. Yakimanka, 39, 117049 Moscow, Russia) V.55- 1992- Volume(issue)/page/year: 56(4),37,1993

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EKFAE9 Eksperimental'naya i Klinicheskaya Farmakologiya. Experimental and Clinical Pharmacology. (Mezhdunarodnaya Kniga, ul. B. Yakimanka, 39, 117049 Moscow, Russia) V.55- 1992- Volume(issue)/page/year: 56(4),37,1993 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 17 ug/kg

SEX/DURATION :: female 23 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 137,8,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 10 ug/kg

SEX/DURATION :: female 9 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 19,29,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 20 ug/kg

SEX/DURATION :: female 49 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 22,471,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 30 ug/kg

SEX/DURATION :: female 15 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,279,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 15 ug/kg

SEX/DURATION :: female 7 week(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - abortion

REFERENCE :: GOBIDS Gynecologic and Obstetric Investigation. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.9- 1978- Volume(issue)/page/year: 29,10,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 5 ug/kg

SEX/DURATION :: female 10 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 27,51,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraplacental

DOSE :: 500 ng/kg

SEX/DURATION :: female 15 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 26,279,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intracervical

DOSE :: 1 ug/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 16,377,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 550 mg/kg

SEX/DURATION :: female 6-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: EKFAE9 Eksperimental'naya i Klinicheskaya Farmakologiya. Experimental and Clinical Pharmacology. (Mezhdunarodnaya Kniga, ul. B. Yakimanka, 39, 117049 Moscow, Russia) V.55- 1992- Volume(issue)/page/year: 56(4),37,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 900 ug/kg

SEX/DURATION :: female 21-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: 44LQAF "International Sulprostone Symposium, Papers, Vienna, 1978," Friebel, K., et al., eds., Berlin, Fed. Rep. Ger., Schering AG, 1979 Volume(issue)/page/year: -,39,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 120 ug/kg

SEX/DURATION :: female 63-64 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: ACEDAB Acta Endocrinologica, Supplementum (Copenhagen). (Periodica, Skolegade 12 E, DK-2500 Valby, Denmark) No.1- 1948- Volume(issue)/page/year: 253,148,1983

Safety Information

Symbol	GHS07, GHS08
Signal Word	Danger
Hazard Statements	H315-H319-H335-H360
Precautionary Statements	P201-P261-P305 + P351 + P338-P308 + P313
Personal Protective Equipment	Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes	T:Toxic
Risk Phrases	R60;R36/37/38
Safety Phrases	53-22-36/37-45
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	MJ8810000

Articles48

Quantitative phosphoproteomic analysis of signaling downstream of the prostaglandin e2/g-protein coupled receptor in human synovial fibroblasts: potential antifibrotic networks.

J. Proteome Res. 13(11) , 5262-80, (2014)

The Prostaglandin E2 (PGE2) signaling mechanism within fibroblasts is of growing interest as it has been shown to prevent numerous fibrotic features of fibroblast activation with limited evidence of d...

Angiogenesis in the primate ovulatory follicle is stimulated by luteinizing hormone via prostaglandin E2.

Biol. Reprod. 92(1) , 15, (2015)

Rapid angiogenesis occurs as the ovulatory follicle is transformed into the corpus luteum. To determine if luteinizing hormone (LH)-stimulated prostaglandin E2 (PGE2) regulates angiogenesis in the ovu...

PGE2 reduces MMP-14 and increases plasminogen activator inhibitor-1 in cardiac fibroblasts.

Prostaglandins Other Lipid Mediat. 113-115 , 62-8, (2014)

Prostaglandin E2 (PGE2) is elevated during cardiac injury and we have previously shown that mice lacking the PGE2 EP4 receptor display dilated cardiomyopathy (DCM) with increased expression of the mem...

Synonyms

Sulprostonum

N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide

Nalador

[1R-[1a(Z),2b(1E,3R*),3a]]-7-[3-Hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocyclopentyl]-N-(methylsulfonyl)-5-heptenamide

Sulprostone

SHB-286

Sulprostona

(5Z)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxybut-1-en-1-yl]-5-oxocyclopentyl}-N-(methylsulfonyl)hept-5-enamide

(5Z)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5-oxocyclopentyl}-N-(methylsulfonyl)-5-heptenamide

5-Heptenamide, 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5-oxocyclopentyl]-N-(methylsulfonyl)-, (5Z)-

SHB 286

EINECS 262-173-0

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