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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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$170.00

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1 MG
$170.00

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

$170.00

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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).[1]

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SLCG9800
SLCF8085
SLCD8834
SLCD2671
SLBN9010V

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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
[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)
H Yasuda et al.
Prostaglandins, 47(5), 367-378 (1994-05-01)
We investigated the dose-dependent effects of prostaglandin E1 (PGE1) analogue, OP1206.alpha CD (OP), on motor nerve conduction velocity (MNCV), nerve blood flow (NBF) and Na(+)-K(+)-ATPase (ATPase) activity in streptozocin-induced diabetic rats. At 10 micrograms/kg/day, OP ameliorated MNCV and NBF, but
Katsuhiko Nakai et al.
Prostaglandins, leukotrienes, and essential fatty acids, 69(4), 269-273 (2003-08-09)
An orally active prostaglandin E1 analogue, OP-1206 alpha-CD improves walking dysfunction in the rat spinal stenosis model. Loxoprofen-Na, a non-steroidal anti-inflammatory drug, is used to relieve chronic pain in patients with lumbar spinal canal stenosis. To determine whether the OP-1206
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
View All Related Papers

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