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Irsogladine

Irsogladine structure

CAS No:
57381-26-7
Formula:
C9H7Cl2N5
Chemical Name:
Irsogladine
Synonyms:
1,3,5-Triazine-2,4-diamine,6-(2,5-dichlorophenyl)-;6-(2,5-Dichlorophenyl)-1,3,5-triazine-2,4-diamine;2,4-Diamino-6-(2,5-dichlorophenyl)-s-triazine;2,4-Diamino-6-(2,5-dichlorophenyl)-1,3,5-triazine;Irsogladine;Dicloguamine
Categories:
Active Pharmaceutical Ingredients > Digestive System Drugs

Description

Irsogladine is a PDE4 inhibitor and muscarinic acetylcholine receptor binder.Target: PDE4; mACHRIrsogladine treatment (300 and 500 mg/kg/day) resulted in a dose-dependent reduction of angiogenesis in wild-type mice by 21 and 45.3% (P < 0.02, P < 0.001), in tPA-deficient mice by 42.6 and 46% (P < 0.001, P < 0.001), and in uPA-deficient mice by 27.2 and 46% (P < 0.05, p < 0.001), respectively. Irsogladine inhibits bFGF-induced angiogenesis in wild-type, tPA-knockout, and uPA-knockout mice

6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine is a dichlorobenzene.|Irsogladine is under investigation in clinical trial NCT02581696 (The Drug-drug Interaction and Safety of Lafutidine and Irsogladine Maleate in Healthy Adult Volunteers).

Irsogladine Basic Attributes

Molecular Weight：

256.09

Exact Mass：

256.09

UNII：

QBX79NZC1D

NSC Number：

759836

DSSTox ID：

DTXSID8043999

HScode：

2942000000

Characteristics

PSA：

90.7

XLogP3：

Appearance：

white or colorless crystal or crystalline powder, odorless, slightly bitter

Density：

1.572

Melting Point：

268-269 °C

Boiling Point：

552.2°C at 760 mmHg

Flash Point：

287.8±32.9 °C

Refractive Index：

1.706

Safety Information

Packing level：

III

Hazard category：

Transport codes：

UN 2618 3/PG 3

wgk germany：

hazard class code：

R20:Harmful by inhalation. R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .

safety instructions：

S24-S61

RTECS Number：

WL5075900

Marks：

Xn,N

Drug Information

MeSH：

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military. (See all compounds classified as Radiation-Protective Agents.)|Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

MeSH Entry Terms：

2,4-diamino-6-(2,5-dichlorophenyl)-s-triazine maleate

Irsogladine Use and Manufacturing

Methods of Manufacturing

Irsogladine Maleate (0.3g, 0.80 mmol) was dissolved in ethyl acetate (50mL) and stirred with saturated NaHCO2, 5-dichlorobenzonitrile 44.7g (0.26mol), hexamethylphosphoramide (HMPA) 90ml, was heated to 65 ~ 70 , dicyandiamide was added 22.7g (0.27mol) and sodium tungstate 8.6g (0.026 mol), maintaining the reaction was stirred for 65 ~ 70 2h, the reaction end point TLC (developing solvent: butanol - acetic acid - water = 5: 2: 0.5), completion of the reaction, cooled to room temperature, 90ml of deionized water was added, with stirring 20min, filtered, the solid washed with deionized water, and dried in vacuo 70 ~ 75 4h, to give a white solid intermediate (irsogladine) (66g, 0.258mol), HPLC content 98.6percent, yield 99.2percent, Mp: 265 ~ 269 , was used directly in the next step.

Uses

Thiadiazole derivatives; pharmaceutical intermediates

Computed Properties

Molecular Weight:256.09
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:255.0078506
Monoisotopic Mass:255.0078506
Topological Polar Surface Area:90.7
Heavy Atom Count:16
Complexity:232
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Potassium hydroxide

Dicyandiamide

Sulfamic acid

Ethanol