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S3065

Sigma-Aldrich

SC 19220

≥98% (HPLC), solid

Synonym(s):

2-Acetylhydrazide 10(11H)-carboxylic acid, 8-Chloro-dibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C16H14N3O3Cl
CAS Number:
19395-87-0
Molecular Weight:
331.75
MDL number:
MFCD02259329
UNSPSC Code:
12352200
PubChem Substance ID:
24278701
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white

mp

190-191 °C (lit.)

solubility

DMSO: soluble 10 mg/mL
H2O: insoluble

SMILES string

CC(=O)NNC(=O)N1Cc2ccccc2Oc3ccc(Cl)cc13

InChI

1S/C16H14ClN3O3/c1-10(21)18-19-16(22)20-9-11-4-2-3-5-14(11)23-15-7-6-12(17)8-13(15)20/h2-8H,9H2,1H3,(H,18,21)(H,19,22)

InChI key

KNURFLJTOUGOOQ-UHFFFAOYSA-N

Gene Information

human ... PTGER1(5731)
rat ... Ptger1(25637)

Application

SC 19220 was used to study the role of prostaglandin E2 in oxygen-glucose deprivation-induced neurotoxicity and preconditioning-induced neuroprotection in rat cortical cultures.

Biochem/physiol Actions

SC 19220 is a competitive antagonist of prostaglandin E receptors. It competes with PGE2 in regulating vesicourethral motility and increases the bladder capacity of rats. It inhibits the contraction of smooth muscles in response to prostaglandins E2 and F2α. SC 19220 also inhibits the formation of osteoclasts induced by vitamin D3, parathyroid hormone, IL-11 and IL-6.
EP1 Prostanoid receptor antagonist

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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H Inoue et al.
The Journal of endocrinology, 161(2), 231-236 (1999-05-13)
1,25 Dihydroxy vitamin D3 (1,25(OH)2D3), prostaglandin (PG) E2 and parathyroid hormone (PTH) induce osteoclast formation in cell cultures. Previously, we have shown that SC-19220, an antagonist of the EP1 subtype of PGE receptors, inhibited tartrate-resistant acid phosphatase (TRAP)-positive cell formation
Alexander V Timoshenko et al.
Experimental cell research, 289(2), 265-274 (2003-09-23)
Aberrant upregulation of COX-2 enzyme resulting in accumulation of PGE2 in a cancer cell environment is a marker for progression of many cancers, including breast cancer. Four subtypes of cell surface receptors (EP1, EP2, EP3, and EP4), which are coupled
J B Farmer et al.
British journal of pharmacology, 52(4), 559-565 (1974-12-01)
1 The effects of the prostaglandin synthetase inhibitor, indomethacin and the prostaglandin antagonist SC-19220 (1-acetyl-2-[8-chloro-10,11-dihydrodibenz (b,f) (1,4)oxazepine-10-carbonyl] hydrazine), were examined on the tone of the guinea-pig isolated tracheal preparation and on the responses of the preparation to prostaglandin F(2alpha), arachidonic
Micaela Zonta et al.
The Journal of physiology, 553(Pt 2), 407-414 (2003-09-23)
The synaptic release of glutamate evokes in astrocytes periodic increases in [Ca2+]i, due to the activation of metabotropic glutamate receptors (mGluRs). The frequency of these [Ca2+]i oscillations is controlled by the level of neuronal activity, indicating that they represent a
K Fushimi et al.
Osteoarthritis and cartilage, 12(11), 895-903 (2004-10-27)
Calpains are known as Ca(2+)-dependent intracellular neutral cysteine proteases. However, m-calpain is detected in synovial fluid of arthritic joints and is shown to possess the proteoglycanase activity in vitro. The mechanism of m-calpain release into the extracellular spaces during arthritis
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