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Merck
CN

L6538

Sigma-Aldrich

Limaprost

≥99%, crystalline

Synonym(s):

11α,15S-Dihydroxy-17S,20-dimethyl-9-oxo-prosta-2E,13E-dien-1-oic acid, 17α,20-dimethyl-δ2-PGE1

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About This Item

Empirical Formula (Hill Notation):
C22H36O5
CAS Number:
Molecular Weight:
380.52
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
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Quality Level

Assay

≥99%

form

crystalline

solubility

DMF: soluble
DMSO: soluble
ethanol: soluble

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCC[C@H](C)C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCC\C=C\C(O)=O

InChI

1S/C22H36O5/c1-3-4-9-16(2)14-17(23)12-13-19-18(20(24)15-21(19)25)10-7-5-6-8-11-22(26)27/h8,11-13,16-19,21,23,25H,3-7,9-10,14-15H2,1-2H3,(H,26,27)/b11-8+,13-12+/t16-,17+,18+,19+,21+/m0/s1

InChI key

OJZYRQPMEIEQFC-UAWLTFRCSA-N

Biochem/physiol Actions

Limaprost exhibits cytoprotective, vasodilatory, and antiplatelet activity. Limaprost has the potential to treat lumbar spinal canal stenosis (LSCS) and several ischaemic symptoms of thromboangiitis obliterans (TAO).

Other Notes

Potent analog of PGE1 with prolonged half-life.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Potent inhibition of superoxide anion generation by PGE1 and the PGE1 analogue OP-1206 in human PMN's--unrelated to its antiplatelet PGI2-like activity.
K Schrör et al.
VASA. Supplementum, 17, 11-16 (1987-01-01)
M Yamamoto et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 45(1), 63-70 (1997-01-01)
Prostaglandin E1 (PGE1) is commonly used in therapy for obstructive diseases, including ischemic retinopathy, in which pathogenetic reactive oxygen intermediates are responsible. However, the mechanism(s) of PGE1 in reducing tissue damage is still unclear. Adult T-cell leukemia-derived factor/human thioredoxin (ADF)
S Konno et al.
Journal of spinal disorders, 9(2), 103-106 (1996-04-01)
The effect of OP-1206, a prostaglandin E1 derivative, on cauda equina function was analyzed in a model for acute cauda equina compression in the dog. An inflatable balloon was placed under the lamina of the seventh lumbar vertebra in the
T Saji et al.
Japanese heart journal, 32(5), 735-740 (1991-09-01)
A small-for-gestational-age infant with cyanosis due to double outlet right ventricle with severe pulmonary stenosis and patent ductus arteriosus was treated with oral prostaglandin E1 derivative (OP-1206). The constricting ductus arteriosus dilated and the ductus-dependent pulmonary blood flow increased. The
[A new oral prostaglandin E1 derivative (OP 1206) compared with intravenous PGE1: assessment of the effect on macro- and microcirculation].
P Scheffler et al.
VASA. Supplementum, 32, 386-391 (1991-01-01)

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