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Oxatomide

Oxatomide structure

CAS No:
60607-34-3
Formula:
C27H30N4O
Chemical Name:
Oxatomide
Synonyms:
2H-Benzimidazol-2-one,1-[3-[4-(diphenylmethyl)-1-piperazinyl]propyl]-1,3-dihydro-;1-[3-[4-(Diphenylmethyl)-1-piperazinyl]propyl]-1,3-dihydro-2H-benzimidazol-2-one;Oxatomide;R 35443;KW 4354;Dasten;Celtect;Tinset;Cobiona;NSC 309710;1-[3-[4-(Diphenylmethyl)piperazin-1-ium-1-yl]propyl]-1H-benzimidazol-2-olate;1-[3-(4-Benzhydrylpiperazin-1-ium-1-yl)propyl]benzimidazol-2-olate
Categories:
Active Pharmaceutical Ingredients > Antiallergic Drugs

Description

White Powder

Oxatomide is a N-alkylpiperazine. It has a role as a geroprotector.|Oxatomide has been used in trials studying the treatment of Muscular Dystrophy, Duchenne.

Oxatomide Basic Attributes

Molecular Weight：

426.55

Exact Mass：

426.55

EC Number：

262-320-9

UNII：

J31IL9Z2EE

NSC Number：

309710

DSSTox ID：

DTXSID4045181

ATC Code：

R - Respiratory system

HScode：

2933990090

Characteristics

PSA：

38.8

XLogP3：

4.00270

Appearance：

white

Density：

1.175 g/cm3

Melting Point：

153.6 °C

Boiling Point：

621.1ºC at 760 mmHg

Flash Point：

329.4ºC

Refractive Index：

1.619

Water Solubility：

DMSO: soluble

Storage Conditions：

Refrigerator

Toxicity：

LD50 in guinea pigs, mice, rats (mg/kg): 320, >2560, >2560 orally; 23, 27, 30 i.v. (Richards)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

26-36

RTECS Number：

DE2276000

Marks：

Xn,Xi

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 45 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Drugs that are used to treat asthma. (See all compounds classified as Anti-Asthmatic Agents.)|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) (See all compounds classified as Anti-Allergic Agents.)|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. (See all compounds classified as Histamine H1 Antagonists.)

MeSH Entry Terms：

KW 4354

Oxatomide Use and Manufacturing

Methods of Manufacturing

The alcohol solution of o-phenylenediamine, ethyl acetoacetate and potassium hydroxide is dissolved in xylene and dehydrated under reflux. Concentrate and cool to 4°C. The solid was collected by filtration, washed with water, and dried to obtain compound (I) with a yield of 82%. Compound (I), 1-bromo-3-chloropropane, potassium hydroxide and PEG-400 were dissolved in toluene and refluxed. Decant the toluene solution, add 10 mol/L sulfuric acid, and hydrolyze at room temperature. Add water and stir. The precipitate was filtered off, and the filtrate was washed with water until neutral and dried. The compound (II) was evaporated to dryness with a yield of 74%. N-benzylpiperazine, compound (II), triethylamine and potassium iodide are dissolved in toluene and refluxed. Add toluene and water and stir. The water layer was separated, the toluene layer was washed with water, dried, filtered and evaporated to dryness. The residue was recrystallized with 95% ethanol to obtain oxamate as a white solid with a yield of 51.5% and a melting point of 153°C.

Uses

Inhibits the release and actions of leukotrienes

Computed Properties

Molecular Weight:426.6
XLogP3:4.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:426.24196159
Monoisotopic Mass:426.24196159
Topological Polar Surface Area:38.8
Heavy Atom Count:32
Complexity:575
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes