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Prontosil

Prontosil structure

CAS No:
103-12-8
Formula:
C12H13N5O2S
Chemical Name:
Prontosil
Synonyms:
Benzenesulfonamide,4-[2-(2,4-diaminophenyl)diazenyl]-;Benzenesulfonamide,p-[(2,4-diaminophenyl)azo]-;Prontosil;Benzenesulfonamide,4-[(2,4-diaminophenyl)azo]-;4-[2-(2,4-Diaminophenyl)diazenyl]benzenesulfonamide;Red streptocide;Streptocide;Sulfamidochrysoidine;Prontosil red;Prontosil rubrum;Chrysoidine,4′-(aminosulfonyl)-;Prontosil flavum;Sulfamidochrysoidin;Parazol;Pronzin rubrum;Relbazon;p-[(2,4-Diaminophenyl)azo]benzenesulfonamide;Sulfonamidochrysoidine;498-10-2;93633-54-6;1071659-55-6
Categories:
Organic Chemistry > Amides

Description

ChEBI: A diphenyldiazene compound having two amino substituents at the 2- and 4-positions and an aminosulphonyl substituent at the 4'-position. It was the first antibacterial drug, (introduced 1935) and the first of the sulfonamide antibiotics.

Prontosil is a diphenyldiazene compound having two amino substituents at the 2- and 4-positions and an aminosulphonyl substituent at the 4'-position. It was the first antibacterial drug, (introduced 1935) and the first of the sulfonamide antibiotics. It has a role as an antimicrobial agent and an antibacterial drug. It is a member of azobenzenes and a sulfonamide. It derives from a sulfanilamide.|Sulfamidochrysoidine is derived from an azo dye, sulfamidochrysoidine was the first commercially available antibacterial antibiotic. It has broad effects against gram-positive cocci but not against enterobacteria. In the body sulfonamidochrysoidine is metabolized to sulfanilamide, the active form of the drug.

Prontosil Basic Attributes

Molecular Weight：

291.32892

Exact Mass：

291.33

EC Number：

203-081-2

UNII：

Q64Q9N6Q6O

DSSTox ID：

DTXSID60145608

NCI Thesaurus Code：

C98270

HScode：

2935009090

Characteristics

PSA：

145

XLogP3：

4.85730

Density：

1.4999 (rough estimate)

Melting Point：

249.5 °C

Boiling Point：

601.2±65.0 °C(Predicted)

Flash Point：

317.4ºC

Refractive Index：

1.5630 (estimate)

Drug Information

MeSH Entry Terms：

2',4'-diaminoazobenzene-4-sulfonamide

Computed Properties

Molecular Weight:291.33
XLogP3:0.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:291.07899585
Monoisotopic Mass:291.07899585
Topological Polar Surface Area:145
Heavy Atom Count:20
Complexity:439
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes