15(R)-Iloprost

Cayman Chemical Item Number 10043

(CAS 85026-51-3)

15(R)-Iloprost (CAS 85026-51-3)

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Description

Iloprost is a second generation structural analog of prostacyclin (PGI2) with about ten-fold greater potency than the first generation stable analogs, typified by carbaprostacyclin.1 Iloprost binds with equal affinity to the recombinant human IP and EP receptors with a Ki of 11 nM.2 15(R)-Iloprost is the “unnatural” or inverted C-15 epimer of iloprost. This transformation frequently attenuates the biological agonist activity of prostaglandin analogs by several orders of magnitude. There are no literature reports of the biological activity of 15(R)-iloprost.

1 Schrör, K., Darius, H., Matzky, R., et al. The antiplatelet and cardiovascular actions of a new carbacyclin derivative (ZK36374) - equipotent to PGI2 in vitro. Naunyn Schmiedebergs Arch Pharmacol 316 252-255 (1981).

2 Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta 1483 285-293 (2000).

Formal Name 6,​9α-​methylene-​11α,​15R-​dihydroxy-​16-​methyl-​prosta-​5E,​13E-​dien-​18-​yn-​1-​oic acid
CAS Number 85026-51-3
Molecular Formula C22H32O4
Formula Weight 360.5
Formulation A solution in methyl acetate
Purity ≥97%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@H]​1[C@H]​(/C=C/[C@H]​(O)​C(C)​CC#CC)​[C@@H]​(C/C(C2)​=C/CCCC(O)​=O)​[C@@H]​2C1
InCHI Code
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​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
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HIFJCPQKFCZDDL-GAGQTBDJSA-N

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15(R)-Iloprost is available in the following screening library:

Size Price Quantity Subtotal
500 µg $88.00 $0.00
1 mg $167.00 $0.00
5 mg $704.00 $0.00
10 mg $1,232.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-24. Prices are subject to change without notice.

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Related Products

15-keto Iloprost
5-cis-15(R)-Iloprost
5-cis Carbaprostacyclin
5-cis Iloprost
Carbaprostacyclin
Cicaprost
Iloprost
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