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Sulfadimethoxine

Sulfadimethoxine structure

CAS No:
122-11-2
Formula:
C12H14N4O4S
Chemical Name:
Sulfadimethoxine
Synonyms:
Benzenesulfonamide,4-amino-N-(2,6-dimethoxy-4-pyrimidinyl)-;Sulfanilamide,N1-(2,6-dimethoxy-4-pyrimidinyl)-;4-Amino-N-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide;Abcid;Albon;4-(p-Aminobenzenesulfonamido)-2,6-dimethoxypyrimidine;N1-(2,6-Dimethoxy-4-pyrimidinyl)sulfanilamide;2,4-Dimethoxy-6-sulfanilamido-1,3-diazine;2,4-Dimethoxy-6-sulfanilamidopyrimidine;2,4-Dimethoxy-6-sulfanilamido-1,3-pyrimidine;Madribon;Madriqid;Madroxin;Omnibon;SDMO;Sulfadimethoxine;Sulfadimethoxydiazine;4-Sulfa-2,6-dimethoxypyrimidine;6-Sulfanilamido-2,4-dimethoxy-1,3-diazine;6-Sulfanilamido-2,4-dimethoxypyrimidine;4-Sulfanilamido-2,6-dimethoxypyrimidine;Sulfastop;2,6-Dimethoxy-4-sulfanilamidopyrimidine;Deposul;Sulxin;2,4-Dimethoxy-6-sulfonylamido-1,3-diazine;Sulfadimethoxin;Dimethoxysulfadiazine;Sudine;Madroxine;Symbio;Sulphadimethoxine;Sulfadimetoxin;Madrigid;Persulfen;Fuxal;Metoxidon;Scandisil;Dinosol;Sulfoplan;Dorisul;Arnosulfan;Redifal;Diasulfa;Mecozine;Lasibon;Sulforal;Sulfadimetoxine;Agribon;Sulfabon;Maxulvet;Bactrovet;Sumbio;Neostreptal;Ultrasulfon;Suldixine;NSC 683544;Sulfamed G;N-(2,6-Dimethoxypyrimidin-4-yl)-4-aminobenzenesulfonamide;8017-94-5;8023-12-9
Categories:
Organic Chemistry > Amides

Description

White SolidChEBI: A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.

Solid

Sulfadimethoxine is a sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position. It has a role as an antiinfective agent, an antimicrobial agent, a xenobiotic, an environmental contaminant and a drug allergen. It is a member of pyrimidines, a sulfonamide, a substituted aniline, an aromatic ether and a sulfonamide antibiotic. It derives from a sulfanilamide.|Sulfadimethoxine is a sulfonamide antibiotic. Sulfadimethoxine is used to treat many infections including treatment of respiratory, urinary tract, enteric, and soft tissue infections. It is most frequently used in veterinary medicine, although it is approved in some countries for use in humans. Sulfadimethoxine inhibits bacterial synthesis of folic acid (pteroylglutamic acid) from para-aminobenzoic acid. Sulfadimethoxine is approved in Russia for use in humans, including children, and has been successfully used there for more than 35 years. It is widely available in Russia as an over-the-counter drug manufactured by a number of Russian pharmaceutical companies.|Sulfadimethoxine is a long-acting sulfonamide antibiotic used in veterinary medicine. Sulfadimethoxine inhibits bacterial synthesis of folic acid by competing with para-aminobenzoic acid (PABA) for the binding site on dihydropteroate synthase.|A sulfanilamide that is used as an anti-infective agent.

Sulfadimethoxine Basic Attributes

Molecular Weight：

310.33

Exact Mass：

310.33

EC Number：

204-523-7

UNII：

30CPC5LDEX

NSC Number：

757860|683544

DSSTox ID：

DTXSID1023607

NCI Thesaurus Code：

C76975

ATC Code：

J01ED02|J - Antiinfectives for systemic use

HScode：

29350090

Characteristics

PSA：

125

XLogP3：

1.63

Appearance：

Solid

Density：

1.654 g/cm³

Melting Point：

203.5 °C

Boiling Point：

265.5°C (rough estimate)

Flash Point：

285.5±32.9 °C

Refractive Index：

1.6270 (estimate)

Water Solubility：

NH 4 OH 1 M: 50 mg/mL, clear, faintly yellow

Storage Conditions：

2-8°C

Toxicity：

LD50 orally in mice: >10 g/kg (Seki)

Collision Cross Section：

167.7 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|166 Å² [M+H]+ [CCS Type: TW]|170.5 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|178.4 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|171.3 Å² [M-H]-

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

3249

wgk germany：

hazard class code：

36/37/38-43

safety instructions：

26-36/37-24/25-23

RTECS Number：

WO9030000

Marks：

Precautionary statement(s)：

P280-P305 + P351 + P338

Hazard Statements：

H315-H317-H319-H335

GHS Classification：

|Warning|H315 (47.17%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 111 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

For use in the treatment of infections.

Drug Transformations：

Sulfadimethoxine has known transformation products that include N4-Acetylsulfadimethoxine.

Pharmacology：

Sulfadimethoxine has been shown to be effective against streptococci, klebsiella, proteus, shigella, staphylococci, escherichia, and salmonella.

MeSH：

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

MeSH Entry Terms：

Deposul

Sulfadimethoxine Use and Manufacturing

Methods of Manufacturing

(2), in 2000L reactor was added 600kg of methanol, condensation product 348.5kg, 20percent caustic soda 440kg, Stir the temperature to 85 ° C and reflux for 6h. After tracking the reaction is completed, cooled to below 10 , A 20percent hydrochloric acid solution was added dropwise until PH = 6.7.After cooling to 0 ° C for centrifugation, the crude sulfathiazine-2, 6-dimethoxypyrimidine (SDM) was obtained.In the crude product by adding methanol 800kg, activated carbon 15kg, heated to reflux 0.5h, while hot pressure filtration, The filtrate was cooled to 0 ° C, centrifuged and dried to give 294.6 kg of product (SDM) in 96percent yield, Purity is 99percent.

Uses

Antibacterial.

Manufacturing Info：

Benzenesulfonamide, 4-amino-N-(2,6-dimethoxy-4-pyrimidinyl)-, sodium salt (1:1): INACTIVE

Use Classification：

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan|Pharmaceuticals -> Antiinfectives for systemic use -> Antibacterials for systemic use -> Sulfonamides and trimethoprims -> Long-acting sulfonamides -> Antibiotics

Computed Properties

Molecular Weight:310.33
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:310.07357611
Monoisotopic Mass:310.07357611
Topological Polar Surface Area:125
Heavy Atom Count:21
Complexity:420
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Sulfadimethoxine in Methanol

CAS No.: 122-11-2

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