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S144

Sigma-Aldrich

SQ 29,548

solid

Synonym(s):

[1S-[1α,2α(Z),3α,4α]]-7-[3-[[2 [(Phenylamino) carbonyl]hydrazino]methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptanoic acid

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About This Item

Empirical Formula (Hill Notation):
C21H29N3O4
CAS Number:
98672-91-4
Molecular Weight:
387.47
MDL number:
MFCD00153871
UNSPSC Code:
12352103

form

solid

optical activity

[α]22/D +19.8°, c = 1.4 in methanol(lit.)

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 4.7 mg/mL
H2O: insoluble
ethanol: soluble

storage temp.

−20°C

InChI

1S/C21H29N3O4/c25-20(26)11-7-2-1-6-10-16-17(19-13-12-18(16)28-19)14-22-24-21(27)23-15-8-4-3-5-9-15/h1,3-6,8-9,16-19,22H,2,7,10-14H2,(H,25,26)(H2,23,24,27)/b6-1-/t16-,17+,18+,19-/m1/s1

InChI key

RJNDVCNWVBWHLY-YVUOLYODSA-N

Biochem/physiol Actions

Potent and specific thromboxane A2 receptor antagonist.

Caution

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Naka et al.
The Journal of pharmacology and experimental therapeutics, 262(2), 632-637 (1992-08-11)
A high-affinity thromboxane (TX)A2/prostaglandin (PG) H2 receptor antagonist, I-SAP [7-[(1R,2S,3S,5R)-6,6-dimethyl-3-(4- iodobenzenesulfonylamino)bicyclo[3.1.1]hept-2-yl]-5(Z)-heptenoic acid] and its radiolabeled analog [125I]SAP (Mais et al., 1991) are characterized in the present study. I-SAP antagonized I-BOP ([1S-(1 alpha, 2 beta(5Z),3 alpha(1E,3R*),4 alpha)]-7-[3-(3-hydroxy-4- (4'-iodophenoxy)-1-butenyl)-7-oxabicyclo-[2.2.1]heptan-2y l]-5'heptenoic acid) and
H Monshizadegan et al.
Life sciences, 51(6), 431-437 (1992-01-01)
Binding of [3H]-SQ 29,548 was characterized to soluble thromboxane A2/prostaglandin H2 (TP) receptors from human platelet membranes as a means of examining ligand-receptor interactions outside the lipophilic environment of the cell membrane. Kinetic determination revealed a rate of ligand-receptor association
J A Hunt et al.
Biochemical pharmacology, 43(8), 1747-1752 (1992-04-15)
The thromboxane A2 (TXA2) mimetic, 9,11-dideoxy-11,9-epoxymethano-prostaglandin F 2 alpha (U46619), mobilized calcium in the bovine aortic endothelial cell line AG4762 and stimulated release of prostacyclin from these cells. The U46619-stimulated release of prostacyclin could be inhibited by TXA2 antagonists with

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