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Tranilast

HCID 5282230
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Grundinformationen

CAS
53902-12-8
Standard-SMILES
COc1ccc(/C=C/C(=O)Nc2ccccc2C(=O)O)cc1OC
InChIKey
NZHGWWWHIYHZNX-CSKARUKUSA-N
Summenformel
C18H17NO5
Durchschnittliche Molmasse
327,3 g/mol

Überblick

Tranilast is an amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group. It has a role as an antineoplastic agent, a calcium channel blocker, an anti-asthmatic drug, an anti-allergic agent, a hepatoprotective agent, an aryl hydrocarbon receptor agonist and a nephroprotective agent. It is a secondary carboxamide, a member of cinnamamides, an amidobenzoic acid and a dimethoxybenzene. It is functionally related to an anthranilic acid.

Namen und Bezeichner

Bevorzugter Name
Tranilast
IUPAC
2-[[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino]benzoic acid
Englischer Name
Tranilast
Summenformel
C18H17NO5
Molmasse
327.33

Namen und Synonyme

tranilast53902-12-8RizabenTranilastumMK-341HVF50SMY6EN-(3,4-Dimethoxycinnamoyl)anthranilic acidNSC-758970CHEBI:775722-((3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic AcidBENZOIC ACID, 2-((3-(3,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL)AMINO)-
Weitere Namen anzeigen
n-5’MK 341TraniLQunistTranproranilasQunisterSB-252218
2-{[(2e)-3-(3,4-Dimethoxyphenyl)prop-2-Enoyl]amino}benzoic Acid2-(((2E)-3-(3,4-Dimethoxyphenyl)prop-2-enoyl)amino)benzoic acidBenzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-RefChem:898664MK341N (3', 4'-dimethoxycinnamoyl) anthranilic acid (N-5')1 N-(3'-4'-dimethoxycinnamoyl) anthranilic acid (N-5'), N(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5')trans-Tranilast

Datenbank-Bezeichner

CAS
53902-12-8

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,2
Polarare Oberfläche (TPSA)
84,9 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
6
Schwere Atome
24
Formalladung
0
Komplexität
464

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physikochemische Eigenschaften

Schmelzpunkt
166.2 · 166.2-168.2 °C (lit.)
Siedepunkt
465.23 °C · 465.23°C (rough estimate)
Dichte
1.3185 · 1.3185 (rough estimate)
Brechungsindex
1.51 · 1.5100 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
18 mg/mL · DMSO: 18 mg/mL
Aggregatzustand
powder
pka
3.47 · 3.47±0.36(Predicted)
Farbe
white to beige
Merck
14 · 14,9570
Stabilität
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
InChI
1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8+

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Tranilast

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Sicherheitsdaten

wgk
3
hs_code
2924.29.6250
RTECS-Nr.
DG8731000
risk_code
22
Toxizität
LD50 in male, female mice, male, female rats (mg/kg): 780, 680, 1600, 1100 orally; 410, 385, 405, 395 i.p.; 2630, 2820, 3630, 3060 s.c. (Nakazawa, p 385)
hazard_code
Xn
safety_code
26-36
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 Oral

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 5 Einträge

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

A class of drugs that act by selective inhibition of calcium influx through cellular membranes.

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)

Anwendungen · 1 Eintrag

VerwendenTranilast is a compound that exhibits anti-inflammatory and immunomodulatory effects by inhibiting lipid mediator and cytokine release from inflammatory cells and interfering with PDGF- and TGF-β1-induced proliferation and migration of vascular medial smooth muscle cells. Tranilast suppresses production of prostaglandin D2 (IC50 = 0.1 mM), prostaglandin E2 (IC50 = ~1-20 μM), thromboxane B2 (IC50 = ~10-50 μM), TGF-β1 (IC50 = ~100-200 μM), and interleukin-8 (IC50 = ~100 μM) in in vitro models as well as attenuates of the proinflammatory activity of human monocytes. While originally marketed as an antiallergenic drug, the efficacy of tranilast in preventing restenosis after percutaneous coronary intervention has been tested in a large-scale clinical trial. Additionally, tranilast inhibits VEGF-induced angiogenetic activities (i.e., proliferation, migration and tube formation of vascular endothelial cells) with IC50 values of 22, 18 and 193 μM, which may prove therapeutic for various retinal diseases.[Cayman Chemical]

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
5282230
ChEMBL
CHEMBL415324
ChEBI
CHEBI:77572
UNII
HVF50SMY6E
EC Number
621-256-5
Nikkaji
J1.065K、J68.174A
InChIKey
NZHGWWWHIYHZNX-CSKARUKUSA-N
SMILES
COc1ccc(\C=C\C(=O)Nc2ccccc2C(O)=O)cc1OC
CAS Datenbank
53902 · 53902-12-8(CAS DataBase Reference)

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Anthranilic acidNatriumhydroxidBenzolsulfonsäurechlorid4-Dimethoxycinnamic AcidMethylanthranilat3,4-Dimethoxycinnamic acid

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Ergänzende Hinweise

DefinitionChEBI: An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.