Rupatadine

Modify Date: 2024-01-05 12:50:14

Rupatadine structure	Common Name	Rupatadine
	CAS Number	158876-82-5	Molecular Weight	415.958
	Density	1.2±0.1 g/cm3	Boiling Point	586.4±50.0 °C at 760 mmHg
	Molecular Formula	C₂₆H₂₆ClN₃	Melting Point	58-61ºC
	MSDS	N/A	Flash Point	308.4±30.1 °C

Use of Rupatadine

Rupatadine (UR-12592) is a potent dual PAF/H1 antagonist with Ki of 0.55/0.1 uM(rabbit platelet membranes/guinea pig cerebellum membranes).IC50 value:Target: PAF/H1 antagonistin vitro: Rupatadine competitively inhibited histamine-induced guinea pig ileum contraction (pA2 = 9.29 +/- 0.06) without affecting contraction induced by ACh, serotonin or leukotriene D4 (LTD4). It also competitively inhibited PAF-induced platelet aggregation in washed rabbit platelets (WRP) (pA2 = 6.68 +/- 0.08) and in human platelet-rich plasma (HPRP) (IC50 = 0.68 microM), while not affecting ADP- or arachidonic acid-induced platelet aggregation [1]. The IC50 for rupatadine in A23187, concanavalin A and anti-IgE induced histamine release was 0.7+/-0.4 microM, 3.2+/-0.7 microM and 1.5+/-0.4 microM, respectively whereas for loratadine the IC50 was 2.1+/-0.9 microM, 4.0+/-1.3 M and 1.7+/-0.5 microM. SR-27417A exhibited no inhibitory effect [2].in vivo: Rupatadine blocked histamine- and PAF-induced effects in vivo, such as hypotension in rats (ID50 = 1.4 and 0.44 mg/kg i.v., respectively) and bronchoconstriction in guinea pigs (ID50 = 113 and 9.6 micrograms/kg i.v.). Moreover, it potently inhibited PAF-induced mortality in mice (ID50 = 0.31 and 3.0 mg/kg i.v. and p.o., respectively) and endotoxin-induced mortality in mice and rats (ID50 = 1.6 and 0.66 mg/kg i.v.) [1]. rupatadine treatment improved the declined lung function and significantly decreased animal death. Moreover, rupatadine was able not only to attenuate silica-induced silicosis but also to produce a superior therapeutic efficacy compared to pirfenidone, histamine H1 antagonist loratadine, or PAF antagonist CV-3988 [3].

Name	8-chloro-11-[1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene]-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine
Synonym	More Synonyms

Description	Rupatadine (UR-12592) is a potent dual PAF/H1 antagonist with Ki of 0.55/0.1 uM(rabbit platelet membranes/guinea pig cerebellum membranes).IC50 value:Target: PAF/H1 antagonistin vitro: Rupatadine competitively inhibited histamine-induced guinea pig ileum contraction (pA2 = 9.29 +/- 0.06) without affecting contraction induced by ACh, serotonin or leukotriene D4 (LTD4). It also competitively inhibited PAF-induced platelet aggregation in washed rabbit platelets (WRP) (pA2 = 6.68 +/- 0.08) and in human platelet-rich plasma (HPRP) (IC50 = 0.68 microM), while not affecting ADP- or arachidonic acid-induced platelet aggregation [1]. The IC50 for rupatadine in A23187, concanavalin A and anti-IgE induced histamine release was 0.7+/-0.4 microM, 3.2+/-0.7 microM and 1.5+/-0.4 microM, respectively whereas for loratadine the IC50 was 2.1+/-0.9 microM, 4.0+/-1.3 M and 1.7+/-0.5 microM. SR-27417A exhibited no inhibitory effect [2].in vivo: Rupatadine blocked histamine- and PAF-induced effects in vivo, such as hypotension in rats (ID50 = 1.4 and 0.44 mg/kg i.v., respectively) and bronchoconstriction in guinea pigs (ID50 = 113 and 9.6 micrograms/kg i.v.). Moreover, it potently inhibited PAF-induced mortality in mice (ID50 = 0.31 and 3.0 mg/kg i.v. and p.o., respectively) and endotoxin-induced mortality in mice and rats (ID50 = 1.6 and 0.66 mg/kg i.v.) [1]. rupatadine treatment improved the declined lung function and significantly decreased animal death. Moreover, rupatadine was able not only to attenuate silica-induced silicosis but also to produce a superior therapeutic efficacy compared to pirfenidone, histamine H1 antagonist loratadine, or PAF antagonist CV-3988 [3].
Related Catalog	Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor Research Areas >> Inflammation/Immunology
References	[1]. Merlos M, et al. Rupatadine, a new potent, orally active dual antagonist of histamine and platelet-activating factor (PAF). J Pharmacol Exp Ther. 1997 Jan;280(1):114-21. [2]. Queralt M, et al. In vitro inhibitory effect of rupatadine on histamine and TNF-alpha release from dispersed canine skin mast cells and the human mast cell line HMC-1. Inflamm Res. 2000 Jul;49(7):355-60. [3]. Lv XX, et al. Rupatadine protects against pulmonary fibrosis by attenuating PAF-mediated senescence in rodents. PLoS One. 2013 Jul 15;8(7):e68631.

Description

Related Catalog

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Research Areas >> Inflammation/Immunology

References

[1]. Merlos M, et al. Rupatadine, a new potent, orally active dual antagonist of histamine and platelet-activating factor (PAF). J Pharmacol Exp Ther. 1997 Jan;280(1):114-21.

[2]. Queralt M, et al. In vitro inhibitory effect of rupatadine on histamine and TNF-alpha release from dispersed canine skin mast cells and the human mast cell line HMC-1. Inflamm Res. 2000 Jul;49(7):355-60.

[3]. Lv XX, et al. Rupatadine protects against pulmonary fibrosis by attenuating PAF-mediated senescence in rodents. PLoS One. 2013 Jul 15;8(7):e68631.

Density	1.2±0.1 g/cm3
Boiling Point	586.4±50.0 °C at 760 mmHg
Melting Point	58-61ºC
Molecular Formula	C₂₆H₂₆ClN₃
Molecular Weight	415.958
Flash Point	308.4±30.1 °C
Exact Mass	415.181519
PSA	29.02000
LogP	6.11
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.646
Storage condition	2-8℃

HS Code	2933990090

3-(Bromomethyl)...

CAS#:120276-47-3

Desloratadine

CAS#:100643-71-8

Rupatadine

CAS#:158876-82-5

Literature: Journal of Medicinal Chemistry, , vol. 37, # 17 p. 2697 - 2703

3,5-Dimethylpyridine

CAS#:591-22-0

Desloratadine

CAS#:100643-71-8

Rupatadine

CAS#:158876-82-5

Literature: WO2006/103688 A1, ; Page/Page column 5-6 ;

3,5-Dimethylpyridine

CAS#:591-22-0

Rupatadine

CAS#:158876-82-5

Literature: Journal of Medicinal Chemistry, , vol. 37, # 17 p. 2697 - 2703

5-Methylnicotin...

CAS#:3222-49-9

Rupatadine

CAS#:158876-82-5

Literature: Journal of Medicinal Chemistry, , vol. 37, # 17 p. 2697 - 2703

Precursor 4
CAS#:120276-47-3 3-(Bromomethyl)... CAS#:100643-71-8 Desloratadine CAS#:591-22-0 3,5-Dimethylpyridine CAS#:3222-49-9 5-Methylnicotin...
DownStream 0

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Rupatadine [INN]

5H-Benzo[5,6]cyclohepta[1,2-b]pyridine, 8-chloro-6,11-dihydro-11-[1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinylidene]-

8-Chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridinyl)methyl)-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

8-Chloro-11-{1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene}-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

8-chloro-6,11-dihydro-11-[1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinylidene]-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

UR-12592

8-Chloro-11-{1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinylidene}-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

8-chloro-11-[1-[(5-methyl-3-pyridyl)methyl]piperidin-4-ylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

MFCD00926499

8-chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridyl)methyl)-4-piperidylidene)-5h-benzo(5,6)cyclohepta(1,2-b)pyridine

5H-Benzo(5,6)cyclohepta(1,2-b)pyridine, 8-chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridinyl)methyl)-4-piperidinylidene)-

Rupatadinefumarate

8-chloro-11-[1-[(5-methyl-3-pyridyl)methyl]-4-piperidyliden]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Rupatadine

UNII-2AE8M83G3E

8-Chloro-11-(1-((5-methylpyridin-3-yl)methyl)piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Rupatadine Fumarate

Henan Tianfu Chemical Co., Ltd.
China
Product Name: Rupatadine fumarate
Price: $Inquiry/1kg $Inquiry/25kg $Inquiry/1000kg $Inquiry/10ton
Purity: 99.0%
Stocking Period: Inquiry
Contact: Anson

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Rupatadine

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