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SML3083

Sigma-Aldrich

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
MDL number:
MFCD10565968
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

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

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+

InChI key

YTFHCXIPDIHOIA-DHZHZOJOSA-N

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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
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
Gabriel J Pavey et al.
Bone, 90, 159-167 (2016-07-03)
Heterotopic ossification (HO) involves formation of endochondral bone at non-skeletal sites, is prevalent in severely wounded service members, and causes significant complications and delayed rehabilitation. As common prophylactic treatments such as anti-inflammatory drugs and irradiation cannot be used after multi-system
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