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Diaveridine

Diaveridine structure

CAS No:
5355-16-8
Formula:
C13H16N4O2
Chemical Name:
Diaveridine
Synonyms:
2,4-Pyrimidinediamine,5-[(3,4-dimethoxyphenyl)methyl]-;Pyrimidine,2,4-diamino-5-veratryl-;5-[(3,4-Dimethoxyphenyl)methyl]-2,4-pyrimidinediamine;2,4-Diamino-5-(3,4-dimethoxybenzyl)pyrimidine;2,4-Diamino-5-veratrylpyrimidine;Diaveridine;Diaveridin;EGIS 5645;NSC 408735;BW 49-210
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

Diaveridine (EGIS-5645) is a dihydrofolate reductase (DHFR) inhibitor with a Ki of 11.5 nM for the wild type DHFR and also an antibacterial agent.

Diaveridine is an aminopyrimidine in which the pyrimidine ring carries amino substituents at C-2 and C-4 and a 3,4-dimethoxybenzyl group at C-5. A folic acid antagonist, it is used as a synergist with sulfonamides against the parasitic Eimeria species. It has a role as an antiparasitic agent and a drug allergen.

Diaveridine Basic Attributes

Molecular Weight：

260.29

Exact Mass：

260.29

EC Number：

226-333-3

UNII：

7KVX81XA87

NSC Number：

759634|408735

DSSTox ID：

DTXSID2046200

HScode：

2933599090

Characteristics

PSA：

96.3

XLogP3：

Appearance：

White solid

Density：

1.3±0.1 g/cm3

Melting Point：

233 °C

Boiling Point：

506.1°C

Flash Point：

259.9±32.9 °C

Refractive Index：

1.626

Storage Conditions：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

RTECS Number：

UV8142000

Marks：

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

2,4-diamino-5-(3,4-dimethoxybenzyl)pyrimidine

Diaveridine Use and Manufacturing

Methods of Manufacturing

Using vanillin as raw material, first methylate with dimethyl sulfate to obtain 3, 4-dimethoxybenzaldehyde (veratraldehyde), and then condense with methoxypropionitrile to form 3', 4'-dimethoxy -2-cyano-3-methoxypropene, after addition, and finally cyclized with guanidine nitrate. Vanillin was dissolved in sodium hydroxide solution and dimethyl sulfate was added dropwise at 60-80°C, and the reaction was refluxed for 3h under alkaline conditions (HP7-9). After the reaction solution is slightly cooled, it is extracted with toluene, and the solvent is recovered from the extract to obtain veratraldehyde. In methanol and sodium methoxide solution, veratraldehyde and methoxypropionitrile were refluxed for 5h at 65-70°C. After cooling with water, it is crystallized, filtered and dried to obtain 3', 4'-dimethoxy-2-cyano-3-methoxypropene. The above condensate was stirred and reacted with guanidine nitrate in methanol and sodium methoxide at 75°C for 2h, and then continued to react at 95°C for 5h. After cooling, crystals were precipitated and filtered to obtain crude dimethoprim. The crude product is recrystallized with acetic acid, decolorized by activated carbon (95℃, 1h), ammonia water is alkalized, separated, and dried to obtain the finished product.

Uses

It has antibacterial effect and has obvious synergistic effect on sulfonamides and antibiotics

Use Classification：

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:260.29
XLogP3:1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:260.12732577
Monoisotopic Mass:260.12732577
Topological Polar Surface Area:96.3
Heavy Atom Count:19
Complexity:279
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Benzaldehyde

Chlorine dioxide

Vanillin

Drug Function and Efficacy

When used in combination with sulfonamides, it can double block the bacterial folic acid anabolism, have a synergistic effect, enhance the antibacterial activity of sulfonamides, and convert the antibacterial effect into a bactericidal effect, thereby reducing the production of drug-resistant strains.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Compound sulfamethoxazole tablets
Ingredients	The main ingredients and chemical names of this product are: sulfaguanidine N-(aminoiminomethyl)-4-aminobenzenesulfonamide; dimethoprim 5-(3,4-dimethoxybenzyl)-2,4-pyrimidinediamine, etc.
Indication	Not yet clear
Specifications	Sulfamidine 0.25g, trimethoprim 25mg
Manufacturer	Jilin Jinheng Pharmaceutical Co., Ltd.

Compound sulfamethoxazole tablets
Ingredients	The main ingredients and chemical names of this product are: sulfaguanidine N-(aminoiminomethyl)-4-aminobenzenesulfonamide; dimethoprim 5-(3,4-dimethoxybenzyl)-2,4-pyrimidinediamine, etc.
Indication	Not yet clear
Specifications	Sulfamidine 0.1g, trimethoprim 50mg
Manufacturer	Tonghua AiXin Pharmaceutical Co., Ltd.

Compound sulfamethoxazole tablets
Ingredients	The main ingredients and chemical names of this product are: sulfaguanidine N-(aminoiminomethyl)-4-aminobenzenesulfonamide; dimethoprim 5-(3,4-dimethoxybenzyl)-2,4-pyrimidinediamine, etc.
Indication	Not yet clear
Specifications	Sulfamidine 0.25g, trimethoprim 25mg
Manufacturer	Kaifeng Kangnuo Pharmaceutical Co., Ltd.

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