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Merck
CN

SML3083

Palovarotene

≥98% (HPLC)

Synonym(s):

(E)-4-(2-(3-((1H-Pyrazol-1-yl)methyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid, 4-[(1E)-2-[5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-3-(1H-pyrazol-1-ylmethyl)-2-naphthalenyl]ethenyl]benzoic acid, 4-[(E)-2-(5,5,8,8-Tetramethyl-3-pyrzol-1-ylmethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoic acid, R 667, R-667, R667, RG 667, RG-667, RG667, RO 3300074, RO-3300074, RO3300074

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About This Item

Empirical Formula (Hill Notation):
C27H30N2O2
CAS Number:
410528-02-8
Molecular Weight:
414.54
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD10565968
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

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InChI

1S/C27H30N2O2/c1-26(2)12-13-27(3,4)24-17-22(18-29-15-5-14-28-29)21(16-23(24)26)11-8-19-6-9-20(10-7-19)25(30)31/h5-11,14-17H,12-13,18H2,1-4H3,(H,30,31)/b11-8+

SMILES string

CC1(C2=CC(CN3C=CC=N3)=C(/C=C/C4=CC=C(C=C4)C(O)=O)C=C2C(C)(CC1)C)C

InChI key

YTFHCXIPDIHOIA-DHZHZOJOSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Orally active, selective retinoic acid receptor gamma (RARγ) agonist that reduces heterotopic ossification (HO) in cultures and in animal models in vivo.
Palovarotene is an orally active, selective retinoic acid receptor gamma (RARγ) agonist that reduces heterotopic ossification (HO) in cultures (15-300 nM) and in murine and rat fibrodysplasia ossificans progressiva (FOP) models in vivo (1 mg/kg rat, 0.27-2.49 mg/kg mouse or 15-100 μg/mouse via daily p.o.).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000130224
0000130223
0000127846

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William P Shield et al.
Journal of orthopaedic research : official publication of the Orthopaedic Research Society, 38(5), 1045-1051 (2019-12-07)
Chondrosarcoma is the second most common primary bone sarcoma. Treatment of chondrosarcoma is limited to surgery due to radiation and chemotherapy resistance of this cancer. An ideal treatment for chondrosarcoma would be a well-tolerated, minimally invasive local or systemic treatment
Sayantani Sinha et al.
Bone, 90, 59-68 (2016-02-20)
Heterotopic ossification (HO) consists of ectopic cartilage and bone formation following severe trauma or invasive surgeries, and a genetic form of it characterizes patients with Fibrodysplasia Ossificans Progressiva (FOP). Recent mouse studies showed that HO was significantly inhibited by systemic
Carter M Lindborg et al.
Bone, 109, 153-157 (2017-10-01)
Genesis of a cartilaginous scaffold is an obligate precursor to bone formation in heterotopic endochondral ossification (HEO). We tested the hypothesis that cartilage-derived retinoic acid-sensitive protein (CD-RAP) can serve as a plasma biomarker for the pre-osseous cartilaginous stage of HEO.
Benjamin M Wheatley et al.
Journal of orthopaedic research : official publication of the Orthopaedic Research Society, 36(4), 1135-1144 (2017-09-30)
Heterotopic ossification (HO) develops in the extremities of wounded service members and is common in the setting of high-energy penetrating injuries and blast-related amputations. No safe and effective prophylaxis modality has been identified for this patient population. Palovarotene has been
Salin A Chakkalakal et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 31(9), 1666-1675 (2016-02-21)
Fibrodysplasia ossificans progressiva (FOP), a rare and as yet untreatable genetic disorder of progressive extraskeletal ossification, is the most disabling form of heterotopic ossification (HO) in humans and causes skeletal deformities, movement impairment, and premature death. Most FOP patients carry
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