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Product Name: Sulprostone
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60325-46-4

60325-46-4 structure

Name: Sulprostone
Chemical Name: (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide
CAS Number: 60325-46-4
Molecular Formula: C₂₃H₃₁NO₇S
Molecular Weight: 465.560
Catalog: API Hormone and endocrine-regulating drugs Prostaglandins
Create Date: 2018-03-10 08:00:00
Modify Date: 2024-01-06 04:30:31
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].

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

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 Disease Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor Research 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.

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
Storage condition	−20°C
Water Solubility	DMSO: >5 mg/mL

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

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

Precursor 10
64282-82-2 51638-93-8 286840-19-5 54347-99-8
64282-81-1 32233-40-2 62961-72-2 122517-79-7
118457-23-1 871669-32-8
DownStream 0

60325-46-4	142326-59-8
2228438-44-4	2229399-80-6
2228438-59-1	2229504-97-4
2228923-01-9	2229396-91-0
2228438-64-8	2228353-62-4
2228235-73-0	2229264-60-0