Enprostil

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Names

[ Name ]:
Enprostil

[Synonym ]:
Enprostil (JAN/USAN/INN)
4,5-Heptadienoic acid, 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5-oxocyclopentyl]-, methyl ester
Syngard
Enprostil
(dl)-9-Keto-11a,15a-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic Acid Methyl Ester
Camleed (TN)
methyl (4,5,6S)-7-<(1R,2R,3R)-3-hydroxy-2-<(E)-(3R)-3-hydroxy-4-phenoxy-1-butenyl>-5-oxocyclopentyl>-4,5-heptadienoate
Gardrine
Methyl 7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5-oxocyclopentyl}-4,5-heptadienoate
[1a,2b(1E,3R*),3a]-7-[3-Hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocyclopentyl]-4,5-heptadienoic Acid Methyl Ester
methyl (4,5,6R)-7-<(1R,2R,3R)-3-hydroxy-2-<(E)-(3R)-3-hydroxy-4-phenoxy-1-butenyl>-5-oxocyclopentyl>-4,5-heptadienoate
Camleed
Gardrin
Methyl 7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxybut-1-en-1-yl]-5-oxocyclopentyl}hepta-4,5-dienoate

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
552.9±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₂₈O₆

[ Molecular Weight ]:
400.46

[ Flash Point ]:
185.7±23.6 °C

[ Exact Mass ]:
400.188599

[ PSA ]:
93.06000

[ LogP ]:
1.45

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.586

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MI5433000

CHEMICAL NAME :: 4,5-Heptadienoic acid, 7-(3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxoc yclopentyl)-, methyl ester, (1-alpha,2-beta(1E,3R*),3-alpha)-

CAS REGISTRY NUMBER :: 73121-56-9

LAST UPDATED :: 199504

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C23-H28-O6

MOLECULAR WEIGHT :: 400.51

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1600 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - cyanosis Musculoskeletal - other changes Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >160 ug/kg

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

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1600 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 80 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - tremor Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: >320 ug/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(3aR,4R,5R,6aS)-4-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol
(3aR,4R,5R,6aS)-Hexahydro-4-[(E)-(3R)-4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-2-one
1-[5α-hydroxy-2β-[(E)-4-phenoxy-3α-tetrahydropyran-2-yloxy-1-butenyl]-3α-tetrahydropyran-2-yloxycyclopent-1α-yl]but-3-yn-2-ol