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Merck
CN

L6538

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:
74397-12-9
Molecular Weight:
380.52
NACRES:
NA.77
PubChem Substance ID:
329817640
UNSPSC Code:
51111800
MDL number:
MFCD00868275

Key Documents

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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

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 key

OJZYRQPMEIEQFC-UAWLTFRCSA-N

assay

≥99%

form

crystalline

solubility

DMF: soluble, DMSO: soluble, ethanol: soluble

shipped in

wet ice

storage temp.

−20°C

Quality Level

200

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
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLCG9800
SLCF8085
SLCD8834
SLCD2671
SLBN9010V

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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
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
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)
[Intracellular actions of antiplatelet drugs which affect cyclic AMP metabolism in platelets--their effects on Ca2+ mobilization and protein phosphorylation in human platelets].
M Nishikawa et al.
Rinsho byori. The Japanese journal of clinical pathology, Suppl 86, 54-61 (1990-07-01)
Kohji Hirata et al.
Cancer chemotherapy and pharmacology, 51(3), 216-220 (2003-03-26)
5-Fluorouracil (5-FU) causes intestinal mucosal damage and malabsorption. We have recently reported that coadministration of 17 S,20-dimethyl- trans- lower right triangle (2)-prostaglandin E(1) (OP-1206), a stable synthetic analogue of prostaglandin E(1), with 5-FU to rats protects the small intestine from
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