ICI 192605
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531966

CAS#: 117621-64-4

Description: ICI 192605 is a potent thromboxane A2 receptor (TP receptor) antagonist.


Chemical Structure

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ICI 192605
CAS# 117621-64-4

Theoretical Analysis

MedKoo Cat#: 531966
Name: ICI 192605
CAS#: 117621-64-4
Chemical Formula: C22H23ClO5
Exact Mass: 402.12
Molecular Weight: 402.871
Elemental Analysis: C, 65.59; H, 5.75; Cl, 8.80; O, 19.86

Price and Availability

Size Price Availability Quantity
5mg USD 300 2 Weeks
10mg USD 550 2 Weeks
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Synonym: ICI 192605 ; ICI192605; ICI-192605 .

IUPAC/Chemical Name: (E)-6-[(2S,4S,5R)-2-(2-chlorophenyl)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid

InChi Key: WHUIENZXNGAHQI-BNGKFCBFSA-N

InChi Code: InChI=1S/C22H23ClO5/c23-18-11-6-4-9-16(18)22-27-14-15(8-2-1-3-13-20(25)26)21(28-22)17-10-5-7-12-19(17)24/h1-2,4-7,9-12,15,21-22,24H,3,8,13-14H2,(H,25,26)/b2-1+/t15-,21+,22+/m1/s1

SMILES Code: O=C(O)CC/C=C/C[C@H]1[C@@H](C2=CC=CC=C2O)O[C@@H](C3=CC=CC=C3Cl)OC1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: ICI 192605 is a potent TXA2R (thromboxane A2 receptor) antagonist as cell signaling prostaglandin. ICI 192605 blocks contraction of isolated guinea pig trachea induced by U-46619.
In vitro activity: ICI 192605 is a highly selective TP receptor blocker with pA2 of approximately 8. In the present study, 8-iso PGE2-evoked contractions were markedly and significantly reduced by 10−8 m ICI 192605, and abolished when the concentration of this blocker was increased 10-fold (Figures 3 and 4), indicating that they are likely directed through TP receptors. Reference: Br J Pharmacol. 2003 Oct;140(4):759-63. https://pubmed.ncbi.nlm.nih.gov/14504139/
In vivo activity: Compound 3 (ICI 192605) was competitive and selective with pA2 values of 8.0 +/- 0.1 (rabbit) and 8.4 +/- 0.05 (rat) on smooth muscle preparations and 8.16 +/- 0.01 on human platelets. In vivo activity of 3 was demonstrated in a Konzett Rossler guinea pig model at 0.01 mg/kg p.o. Reference: Prostaglandins. 1988 Aug;36(2):173-8. https://pubmed.ncbi.nlm.nih.gov/2973084/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 74.47
DMSO 30.0 74.47
DMSO:PBS (pH 7.2) (1:3) 0.3 0.62
Ethanol 25.0 62.05

Preparing Stock Solutions

The following data is based on the product molecular weight 402.87 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Tazzeo T, Miller J, Janssen LJ. Vasoconstrictor responses, and underlying mechanisms, to isoprostanes in human and porcine bronchial arterial smooth muscle. Br J Pharmacol. 2003 Oct;140(4):759-63. doi: 10.1038/sj.bjp.0705482. Epub 2003 Sep 22. PMID: 14504139; PMCID: PMC1574071. 2. Daray FM, Minvielle AI, Puppo S, Rothlin RP. Pharmacological characterization of prostanoid receptors mediating vasoconstriction in human umbilical vein. Br J Pharmacol. 2003 Aug;139(8):1409-16. doi: 10.1038/sj.bjp.0705375. PMID: 12922927; PMCID: PMC1573974. 3. Gao YJ, Lee RM. Hydrogen peroxide induces a greater contraction in mesenteric arteries of spontaneously hypertensive rats through thromboxane A(2) production. Br J Pharmacol. 2001 Dec;134(8):1639-46. doi: 10.1038/sj.bjp.0704420. PMID: 11739239; PMCID: PMC1572900. 4. Brewster AG, Brown GR, Foubister AJ, Jessup R, Smithers MJ. The synthesis of a novel thromboxane receptor antagonist 4(Z)-6-(2-o-chlorophenyl-4-o-hydroxyphenyl-1,3-dioxan-cis-5-yl) hexenoic acid ICI 192605. Prostaglandins. 1988 Aug;36(2):173-8. doi: 10.1016/0090-6980(88)90304-8. PMID: 2973084.
In vitro protocol: 1. Tazzeo T, Miller J, Janssen LJ. Vasoconstrictor responses, and underlying mechanisms, to isoprostanes in human and porcine bronchial arterial smooth muscle. Br J Pharmacol. 2003 Oct;140(4):759-63. doi: 10.1038/sj.bjp.0705482. Epub 2003 Sep 22. PMID: 14504139; PMCID: PMC1574071. 2. Daray FM, Minvielle AI, Puppo S, Rothlin RP. Pharmacological characterization of prostanoid receptors mediating vasoconstriction in human umbilical vein. Br J Pharmacol. 2003 Aug;139(8):1409-16. doi: 10.1038/sj.bjp.0705375. PMID: 12922927; PMCID: PMC1573974.
In vivo protocol: 1. Gao YJ, Lee RM. Hydrogen peroxide induces a greater contraction in mesenteric arteries of spontaneously hypertensive rats through thromboxane A(2) production. Br J Pharmacol. 2001 Dec;134(8):1639-46. doi: 10.1038/sj.bjp.0704420. PMID: 11739239; PMCID: PMC1572900. 2. Brewster AG, Brown GR, Foubister AJ, Jessup R, Smithers MJ. The synthesis of a novel thromboxane receptor antagonist 4(Z)-6-(2-o-chlorophenyl-4-o-hydroxyphenyl-1,3-dioxan-cis-5-yl) hexenoic acid ICI 192605. Prostaglandins. 1988 Aug;36(2):173-8. doi: 10.1016/0090-6980(88)90304-8. PMID: 2973084.

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1: Brown GR, Foubister AJ, Hudson JA. Improved synthetic routes to the novel thromboxane receptor antagonist ICI 192605: activity of synthetic 1,3-dioxane intermediates. J Pharm Pharmacol. 1990 Jan;42(1):53-5. PubMed PMID: 1969951.

2: Brewster AG, Brown GR, Foubister AJ, Jessup R, Smithers MJ. The synthesis of a novel thromboxane receptor antagonist 4(Z)-6-(2-o-chlorophenyl-4-o-hydroxyphenyl-1,3-dioxan-cis-5-yl) hexenoic acid ICI 192605. Prostaglandins. 1988 Aug;36(2):173-8. PubMed PMID: 2973084.