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

Key Documents

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Quality Level

200

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
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P264 - P301 + P310

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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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)
M Nishikawa et al.
Cellular signalling, 4(4), 453-463 (1992-07-01)
We examined the involvement of cAMP-dependent protein kinase (A kinase)2 in the inhibition by cilostamide, a specific inhibitor of the low Km cAMP-phosphodiesterase (PDE), on 9,11-epithio-11,12-methanothromboxane A2 (STA2)-induced platelet aggregation. For comparative purposes, the PGE1 analogue, 17S-20-dimethyl-trans-delta 2-PGE1 (OP-1206) was
Yi Liu et al.
Pain, 109(1-2), 64-72 (2004-04-15)
Extracellular signal-regulated protein kinase (ERK) is a mitogen-activated protein kinase (MAPK) that mediates several cellular responses to mitogenic and differentiation signals, and activation of ERK in dorsal horn neurons by noxious stimulation is known to contribute to pain hypersensitivity. In
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