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SML1651

Sigma-Aldrich

Iloprost

≥98% (HPLC)

Synonym(s):

(E)-(3aS, 4R, 5R, 6aS)-Hexahydro-5-hydroxy-4-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-Δ2(1H),Δ-pentalenevaleric acid, Cilaprost, ZK 36374; (5E)-5-[(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-ynyl]-2(1H)-pentalenylidene]pentanoic acid

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About This Item

Empirical Formula (Hill Notation):
C22H32O4
CAS Number:
78919-13-8
Molecular Weight:
360.49
MDL number:
MFCD00867145
UNSPSC Code:
51111800
PubChem Substance ID:
329825991
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

assay

≥98% (HPLC)

form

film

storage condition

desiccated

color

colorless

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

[H][C@@]12[C@@](C/C(C2)=C/CCCC(O)=O)([H])[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C1

InChI

1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18?,19-,20+,21+/m0/s1

InChI key

HIFJCPQKFCZDDL-SGSAMSKHSA-N

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material

316L stainless steel cannula (ASTM), TPE tubing (medical grade), silicone septum (medical grade platinum-cured), PETG bottle, polyester body

material

316L stainless steel cannula (ASTM), PETG bottle, TPE tubing (medical grade), polyester body, silicone septum (medical grade platinum-cured)

material

316L stainless steel cannula (ASTM), PETG bottle, TPE tubing (medical grade), polyester body, silicone septum (medical grade platinum-cured)

material

316L stainless steel cannula (ASTM), PETG bottle, TPE tubing (medical grade), polyester body, silicone septum (medical grade platinum-cured)

fitting

inlet septum unit (with 1 mm or 2 mm needle), Luer outlet fitting (3-piece)

fitting

inlet septum unit (with 1 mm or 2 mm needle), Luer outlet fitting (3-piece)

fitting

inlet septum unit (with 1 mm or 2 mm needle), Luer outlet fitting (3-piece)

fitting

inlet septum unit (with 1 mm or 2 mm needle), Luer outlet fitting (3-piece)

parameter

-80-50 °C max. temp., 0.5 bar max. sampling pressure (7.25 psi)

parameter

-80-50 °C max. temp., 0.5 bar max. sampling pressure (7.25 psi)

parameter

-80-50 °C max. temp., 0.5 bar max. sampling pressure (7.25 psi)

parameter

-80-50 °C max. temp., 0.5 bar max. sampling pressure (7.25 psi)

sterility

sterile

sterility

sterile

sterility

sterile

sterility

sterile

needle size

2.0 mm

needle size

2.0 mm

needle size

2.0 mm

needle size

2.0 mm

packaging

pkg of 125 mL

packaging

pkg of 250 mL

packaging

pkg of 60 mL

packaging

pkg of 125 mL

Biochem/physiol Actions

Iloprost is a potent prostacyclin PGI2 analog that binds with equal affinity to human prostacyclin (Prostanoid IP) and prostaglandin EP1 receptors.
Iloprost is a potent prostacyclin PGI2 analog that binds with equal affinity to human prostacyclin (Prostanoid IP) and prostaglandin EP1 receptors. Iloprost acts as a vasodilator and antihypertensive, and inhibits the ADP, thrombin, and collagen-induced aggregation of human platelets. Iloprost dilates systemic and pulmonary arterial vascular beds and has been used clinically for pulmonary arterial hypertension (PAH), scleroderma, and Raynaud′s syndrome.
Iloprost is used to treat children with PH (pulmonary hypertension) after the surgery to clear CHD (congenital heart disease).[1] In transplant patients, this prostacyclin analogue is used to inhibit renal dysfunction.[2] Iloprost performs various functions like vasodilatation and cytoprotection. It has higher stability than prostacyclin.[3]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    076M4745V

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    Meyler's Side Effects of Endocrine and Metabolic Drugs (2009)
    A review of the use of iloprost, a synthetic prostacyclin, in the prevention of radiocontrast nephropathy in patients undergoing coronary angiography and intervention.
    Kassis HM, et al.
    Clinical Cardiology, 38(8), 492-498 (2015)
    Iloprost for children with pulmonary hypertension after surgery to correct congenital heart disease.
    Xu Z, et al.
    Pediatric Pulmonology, 50(6), 588-595 (2015)
    Joseph Castillo et al.
    Cancer research, 79(15), 3916-3927 (2019-06-12)
    Regulatory T cells (Treg) are immunosuppressive and negatively impact response to cancer immunotherapies. CREB-binding protein (CBP) and p300 are closely related acetyltransferases and transcriptional coactivators. Here, we evaluate the mechanisms by which CBP/p300 regulate Treg differentiation and the consequences of

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