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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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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

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

Related Categories

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

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Certificates of Analysis (COA)

Lot/Batch Number
SLCG9800
SLCF8085
SLCD8834
SLCD2671
SLBN9010V

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T Kanayama et al.
The Journal of pharmacology and experimental therapeutics, 255(3), 1210-1217 (1990-12-01)
A chemically stable prostacyclin analog, KP-10614 [(4z,16s)-4,5,18,18,19,19-hexadehydro-16,20-dimethyl-delta 6(9;alpha)-9(o)- methano-PGI1], has been compared with two other prostacyclin derivatives (Iloprost and TEI-7165) and one prostaglandin E1 derivative (OP-1206) with respect to ADP-induced in vitro aggregation of human platelets and ex vivo platelet
P Ney et al.
Biomedica biochimica acta, 47(10-11), S186-S189 (1988-01-01)
The present study investigates the inhibitory action of the PGE1-analogue OP-1206 on stimulated LTB4 release from human PMN. In comparison with PGE2, PGE1 and iloprost, OP-1206 was equipotent to PGE2 and PGE1 as inhibitor of PAF (3 microM) and FMLP
Tracy Swainston Harrison et al.
Drugs, 67(1), 109-118 (2007-01-11)
Limaprost, an alprostadil (prostaglandin E1) analogue, is a vasodilator that increases blood flow and inhibits platelet aggregation. The efficacy of oral limaprost was evaluated in adult Japanese patients in three randomised, double-blind, 6-week trials. One study included patients with thromboangiitis
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)
Katsuhiko Nakai et al.
Prostaglandins & other lipid mediators, 71(3-4), 253-263 (2003-10-02)
The systemic treatment effects of OP-1206 alpha-CD (17S-20-dimethyl-trans-delta 2-PGE1 alpha-cyclodextrin clathrate), a prostaglandin E1 (PGE1) analogue, on walking dysfunction, spinal cord blood flow (SCBF) and skin blood flow (SKBF) were assessed in the rat neuropathic intermittent claudication (IC) model in
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