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Sulfamethazine

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Identification
Molecular formula
C6H8N2O2S
CAS number
57-68-1
IUPAC name
4-aminobenzenesulfonamide
State
State

At room temperature, sulfamethazine exists as a solid. It is commonly used in its solid form in the pharmaceutical industry to treat bacterial infections.

Melting point (Celsius)
166.00
Melting point (Kelvin)
439.00
Boiling point (Celsius)
310.00
Boiling point (Kelvin)
583.00
General information
Molecular weight
172.20g/mol
Molar mass
172.2040g/mol
Density
1.0800g/cm3
Appearence

Sulfamethazine is usually found as a white or off-white crystalline powder. It is odorless and has a slightly bitter taste. The compound is often used in its powder form for pharmaceutical purposes.

Comment on solubility

Solubility of 4-Aminobenzenesulfonamide (C6H8N2O2S)

4-Aminobenzenesulfonamide, commonly known as sulfanilamide, exhibits distinct solubility characteristics that are essential for its applications in various fields:

  • Water Solubility: 4-Aminobenzenesulfonamide is moderately soluble in water, making it suitable for formulation in aqueous solutions. However, its solubility can be influenced by factors such as pH and temperature.
  • Solvents: The compound exhibits varying solubility in organic solvents. It tends to be soluble in alcohol and slightly soluble in ether, which affects its use in organic synthesis.
  • Salt Formation: The solubility of 4-aminobenzenesulfonamide can be enhanced by converting it into its salt forms. This can improve its bioavailability in pharmaceutical applications.
  • pH Dependency: Changes in the pH of solutions can significantly affect the solubility, as the ionization of the amino and sulfonamide groups can vary.

In summary, the solubility of 4-aminobenzenesulfonamide is a critical factor influencing its pharmacological properties and therapeutic effectiveness. As noted, “the solubility is influenced by multiple factors,” which is crucial for anyone utilizing this compound in research or industry applications.

Interesting facts

Interesting Facts about 4-Aminobenzenesulfonamide

4-Aminobenzenesulfonamide, commonly recognized as sulfanilamide, is a compound that has significant historical and contemporary relevance in the field of medicinal chemistry. Here are some intriguing insights about this compound:

  • Antibacterial Properties: 4-Aminobenzenesulfonamide was one of the first sulfa drugs developed, heralding a new era in antibacterial therapy. It has played a crucial role in treating bacterial infections, particularly before the advent of penicillin.
  • Mechanism of Action: This compound works by inhibiting bacterial growth. It resembles the structure of para-aminobenzoic acid (PABA), a vital component in bacterial folic acid synthesis. By mimicking PABA, it effectively disrupts the production of folate.
  • Therapeutic Uses: Beyond its antibacterial properties, 4-aminobenzenesulfonamide has applications in treating conditions such as urinary tract infections, and it is also used in some formulations to reduce certain types of inflammation.
  • Structural Significance: The sulfonamide group is essential in determining the compound's biological activity, as the sulfonyl group enhances water solubility and bioavailability, making it more effective as a therapeutic agent.
  • Historical Milestone: The discovery of sulfanilamide in the 1930s is considered a major milestone in pharmaceutical development, leading to the synthetic production of many sulfa drugs and opening pathways for antibacterial research.

As stated by famous microbiologist Paul Ehrlich, "To find a drug is to find a new weapon to fight diseases." The development of 4-aminobenzenesulfonamide exemplifies this principle and reflects how chemistry continually shapes healthcare and medicine.

In summary, 4-aminobenzenesulfonamide is not just a compound of interest in academia but also a pivotal player in the history of modern medicine, illustrating the potent intersection between chemistry and healthcare.

Synonyms
sulfanilamide
4-Aminobenzenesulfonamide
63-74-1
Sulphanilamide
Sulfamine
p-Aminobenzenesulfonamide
Sulphonamide
Sulfonylamide
Prontylin
p-Aminobenzenesulfamide
Prontosil Album
4-Aminobenzene-1-Sulfonamide
Bacteramid
Streptasol
Streptocid
p-Sulfamoylaniline
Sulfonamide P
Prontosil I
Estreptocida
Exoseptoplix
Streptoclase
Sulfamidyl
Sulfanalone
Sulfanidyl
Sulfocidine
p-Sulfamidoaniline
Sulfana
Sulfanil
Benzenesulfonamide, 4-amino-
4-Sulfamoylaniline
Sulfanilimidic acid
p-Anilinesulfonamide
p-Aminophenylsulfonamide
Streptrocide
Ambeside
Antistrept
Astreptine
Astrocid
Bactesid
Collomide
Colsulanyde
Copticide
Deseptyl
Ergaseptine
Erysipan
Gombardol
Lysococcine
Neococcyl
Orgaseptine
Prontalbin
Proseptal
Proseptine
Proseptol
Pysococcine
Septanilam
Septinal
Septolix
Septoplex
Septoplix
Strepamide
Strepsan
Streptagol
Streptamid
Streptamin
Streptocide
Streptocom
Strepton
Streptopan
Streptosil
Streptozol
Streptozone
Sulfocidin
Therapol
Albexan
Albosal
Dipron
Gerison
Infepan
Sanamid
Stramid
Tolder
Lusil
Prontosil White
Septamide Album
Pronzin Album
Stopton Album
Streptocid album
Rubiazol A
White streptocide
4-Aminophenylsulfonamide
Streptocide White
PABS
p-Aminobenzenesulfonylamide
Aniline-p-sulfonic amide
Fourneau 1162
Streptocidum
Sulfanilamida
Sulfanilamidum
Sulfanilamide Vaginal Cream
Benzenesulfonamide, p-amino-
4-azanylbenzenesulfonamide
Solfanilamide
Sulphanilamidum
Caswell No. 809A
MFCD00007939
HSDB 223
4-(Aminosulfonyl)aniline
para-aminobenzenesulfonamide
1162 F
CCRIS 764
A-349
p-Aminobenzensulfonamide
F 1162
CHEBI:45373
4-Amino-benzenesulfonamide
4-aminobenzene sulfonic acid amide
NSC 7618
NSC-7618
Sulfanilamide Melting Point Standard
EINECS 200-563-4
Sulfanilamidum [INN-Latin]
Sulfanilamida [INN-Spanish]
EPA Pesticide Chemical Code 077902
BRN 0511852
(4-(Aminosulfonyl)phenyl)amine
AVC
DTXSID4023622
UNII-21240MF57M
AI3-00952
NSC7618
CHEMBL21
F-1162
21240MF57M
DTXCID903622
F1162
4-14-00-02658 (Beilstein Handbook Reference)
Sulfanilamide (INN)
CAS-63-74-1
NCGC00016285-02
NCGC00016285-05
4-Aminobenzenesulphonamide (Sulphanilamide)
Sulfanilamide, >=99%
SULFANILAMIDE [INN]
Sulfanilamidum (INN-Latin)
Sulfanilamida (INN-Spanish)
Streptocide (VAN)
SULFANILAMIDE (MART.)
SULFANILAMIDE [MART.]
4 aminobenzenesulfonamide
SULFANILAMIDE (USP-RS)
SULFANILAMIDE [USP-RS]
Solfanilamide [DCIT]
SULFANILAMIDE (EP MONOGRAPH)
SULFANILAMIDE [EP MONOGRAPH]
SMR000059035
SULFADIAZINE IMPURITY D (EP IMPURITY)
SULFADIAZINE IMPURITY D [EP IMPURITY]
SULFADIMIDINE IMPURITY D (EP IMPURITY)
SULFADIMIDINE IMPURITY D [EP IMPURITY]
SULFADIMETHOXINE IMPURITY E (EP IMPURITY)
SULFADIMETHOXINE IMPURITY E [EP IMPURITY]
SULFAMETHOXAZOLE IMPURITY E (EP IMPURITY)
SULFAMETHOXAZOLE IMPURITY E [EP IMPURITY]
SR-01000763435
Sulfanimide
Sulfanilamide [INN:DCF:NF]
sulphanilic amide
4-sulphanilamide
Sulfanimide,(S)
Streptocid (TN)
delta-Sulfanilamide
Prestwick_36
4-sulfamoyl-aniline
4-sulphamoyl aniline
STREPAMID
PRONTOSIL ALBOM
Spectrum_000489
4-aminobenzensulfonamide
aniline, 4-sulphamoyl-
Sulfanilamide (Standard)
WLN: ZSWR DZ
4-aminobenzenesulphonamide
p-aminobenzene sulfonamide
Prestwick0_000729
Prestwick1_000729
Prestwick2_000729
Prestwick3_000729
Spectrum2_000846
Spectrum3_001406
Spectrum4_000398
Spectrum5_001081
4-aminobenzene sulfonamide
4-aminobenzene-sulfonamide
p-aminosulfonyl phenylamine
SCHEMBL740
SULFANILAMIDE [MI]
4-amino-benzenesulphonamide
Epitope ID:122232
p-amino benzene sulfonamide
STREPTOCIDE (WHITE)
AVC (TN)
SULFANILAMIDE [HSDB]
Oprea1_273157
BSPBio_000658
BSPBio_003052
KBioGR_000955
KBioSS_000969
SULFANILAMIDE [VANDF]
MLS001074682
MLS002152940
BIDD:GT0170
DivK1c_000528
SPECTRUM1500646
SULPHANILAMIDUM [HPUS]
SPBio_000831
SPBio_002597
SULFANILAMIDE [WHO-DD]
aromatic sulfonamide compound 5
BPBio1_000724
halogenosulfanilamide deriv. 5a
SCHEMBL11880061
BDBM10857
GTPL12631
HMS501K10
HY-B0242R
KBio1_000528
KBio2_000969
KBio2_003537
KBio2_006105
KBio3_002272
Sulfanilamide, p.a., 99.0%
D06BA05
J01EB06
NINDS_000528
HMS1570A20
HMS1921O07
HMS2092E20
HMS2097A20
HMS2233B19
HMS3370J16
HMS3655K19
HMS3714A20
HMS3744M13
Pharmakon1600-01500646
Ro13354
SULFANILAMIDE [ORANGE BOOK]
HY-B0242
Tox21_110351
Tox21_201331
Tox21_303336
4-AMINO-1-BENZENESULFONAMIDE
AC9456
aromatic/heteroaromatic sulfonamide 2
BBL005257
c1264
CCG-40302
NSC757404
s1685
STK298902
AKOS000119305
Tox21_110351_1
DB00259
FS07881
NSC-757404
IDI1_000528
NCGC00016285-01
NCGC00016285-03
NCGC00016285-04
NCGC00016285-06
NCGC00016285-08
NCGC00091144-01
NCGC00091144-02
NCGC00091144-03
NCGC00257174-01
NCGC00258883-01
AS-13239
BP-12552
DA-58177
Sulfanilamide (4-Aminobenzenesulfonamide)
SY009959
SBI-0051575.P002
RO 1-3354
AB00052138
NS00000007
S0381
S0833
SW196353-3
EN300-16979
Sulfanilamide 1000 microg/mL in Acetonitrile
Sulfanilamide, JIS special grade, >=99.7%
Sulfanilamide, Vetec(TM) reagent grade, 97%
C07458
D08543
AB00052138-10
AB00052138_11
AB00052138_12
A834498
AC-907/25014139
Q423423
Sulfanilamide, VETRANAL(TM), analytical standard
SR-01000763435-2
SR-01000763435-3
SR-01000763435-4
BRD-K02594908-001-15-6
BRD-K02594908-001-16-4
SULFACETAMIDE SODIUM IMPURITY A [EP IMPURITY]
Sulfanilamide (166 degrees C) Melting Point Standard
Z56851240
F2190-0451
BENZENESULFONIC ACID,4-AMINO,AMIDE SULFANILAMIDE
Sulfanilamide, European Pharmacopoeia (EP) Reference Standard
Sulfanilamide, United States Pharmacopeia (USP) Reference Standard
Reagecon Melting Point Sulphanilamide +164 to +166 degrees C Standard
SULFADIMETHOXINE SODIUM FOR VETERINARY USE IMPURITY E [EP IMPURITY]
InChI=1/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10
Sulfanilamide Melting Point Standard, United States Pharmacopeia (USP) Reference Standard
1337-39-9
200-563-4
Sulfanilamide melting point standard, Pharmaceutical Secondary Standard; Certified Reference Material