138-39-6 Usage
Originator
Sulfamylon,Winthrop,US,1949
Uses
antibacterial
Manufacturing Process
For the preparation of mafenide 50 g of acetylbenzylamine are introduced
while stirring into 150 cc of chlorosulfonic acid, whereby the temperature is
kept below 40°C by external cooling. After several hours' storing at ordinary temperature the mixture is heated for 1 hour in the boiling water-bath and
after cooling, poured on to ice. Thereupon the 4-acetylaminoethylbenzenesulfonic acid chloride precipitates at first in an oily form, but solidifies
after short stirring to crystals. The product sucked off and washed with cold
water is introduced into a 10% aqueous ammonia solution. Thereby
dissolution takes place while heating and after a short time the 4-
acetylaminomethyl-benzenesulfonic acid amide precipitates in a crystalline
form. After heating to 70°C for 30 minutes the solution is cooled, filtered with
suction and washed out. The product is obtained when recrystallized from
water or dilute alcohol in colorless crystals melting at 177%. It is readily
soluble in warm water, extremely readily soluble in dilute sodium hydroxide
solution.
Brand name
Sulfamylon (Sterling Winthrop).
Therapeutic Function
Antibacterial
Pharmaceutical Applications
p-Aminomethylbenzene sulfonamide; Sulfamylon.
A topical agent formerly used extensively in burns, especially
for its action in suppressing Ps. aeruginosa. It is rapidly
absorbed through burned skin and is unusual in that it is not neutralized by p-aminobenzoic acid or by tissue exudates.
Disadvantages of its use are local pain and burning, a variety
of allergic reactions including erythema multiforme and
its capacity to inhibit carbonic anhydrase, necessitating careful
observation to detect the development of metabolic acidosis.
Its metabolite, p-carboxybenzene sulfonamide, also
inhibits carbonic anhydrase but has no antibacterial activity.
Mafenide propionate was formerly used in ophthalmic
preparations.
Synthesis
Maphenide, n-(aminomethyl)-benzenesulfamide (33.1.48), is structurally somewhat different from all drugs examined above in that the amino group in the p-position to the
sulfonamide group is distanced from the benzene ring by one methyl group. This drug is synthesized from N-benzylacetamide, subsequent reaction of which with chlorosulfonic acid and
then with ammonia gives 4-(acetamidomethyl)-benzene-sulfonamide (33.1.47). Hydrolyzing
this product with a base gives maphenid.Synonyms of this drug are marfanil, mezudin, ambamide, septicid, and others.
Check Digit Verification of cas no
The CAS Registry Mumber 138-39-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 8 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 138-39:
(5*1)+(4*3)+(3*8)+(2*3)+(1*9)=56
56 % 10 = 6
So 138-39-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H10N2O2S/c8-5-6-1-3-7(4-2-6)12(9,10)11/h1-4H,5,8H2,(H2,9,10,11)
138-39-6Relevant articles and documents
Novel synthesis of mafenide and other amino sulfonamides by electrochemical reduction of cyano sulfonamides
Lateef, Shaik,Mohan, Srinivasulu Reddy Krishna,Rameshraju, Rudraraju,Reddy, Srinivasulu,Reddy, Javarama
, p. 1254 - 1257 (2006)
Both aliphatic and aromatic amino sulfonamides such as mafenide (1a) were synthesized in good yields (80-86%) by direct electrochemical hydrogenation of the corresponding nitriles in an undivided cell containing a Ni cathode, a Pt anode, and Raney Ni as catalyst (Table 1). The reaction can be performed without external supply of pressurized gas by in situ generation of H2. Slightly elevated temperatures (45°) and low current densities (10 mA/cm2) are favorable conditions for this type of electrochemical nitrile hydrogenation. Our synthetic protocol does not require high-pressure equipment or chemical hazards, is environmentally very friendly, and more economical than traditional methods. The concentration of adsorbed H. radicals on the catalyst surface can be easily controlled by adjusting the electric potential, which may lead to improved product selectivity and, at the same time, reduces the risk of explosion and fire.
INHIBITORS OF SARM1
-
Paragraph 0274; 0310-0311, (2020/12/30)
The present disclosure provides compounds and methods useful for inhibiting SARM1 and/or treating and/or preventing axonal degeneration.
BIARYL UREA DERIVATIVE OR SALT THEREOF, AND MANUFACTURING AND APPLICATION OF SAME
-
Paragraph 0071, (2019/05/10)
The present invention discloses a biaryl urea RORγt inhibitor, and specifically relates to a biaryl urea derivative, as represented by formula I, with an RORγt inhibiting activity, and a preparation process thereof, and a pharmaceutical composition comprising the compound. Further disclosed is use of the compound for treating an RORγt-related disease.
CYTOTOXIC AND ANTI-MITOTIC COMPOUNDS, AND METHODS OF USING THE SAME
-
, (2014/09/29)
Compounds having cytotoxic and/or anti-mitotic activity are disclosed. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed. Also disclosed are compositions having the structure: (T)-(L)-(D), wherein (T) is a targeting moiety, (L) is an optional linker, and (D) is a compound having cytotoxic and/or anti-mitotic activity.
