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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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[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
[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)
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
H Yasuda et al.
Metabolism: clinical and experimental, 41(7), 778-782 (1992-07-01)
In view of the possible implication of multifactorial mechanisms in the pathogenesis of diabetic neuropathy, the aldose reductase inhibitor (ARI), Statil, which ameliorates abnormal sorbitol or myo-inositol metabolism in diabetic nerves, and the prostaglandin E1 (PGE1) analogue, OP1206.alpha CD (OP)
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