Basic information
- Standard SMILES
CC(=O)NS(=O)(=O)c1ccc(N)cc1- InChIKey
SKIVFJLNDNKQPD-UHFFFAOYSA-N- Molecular formula
- C8H10N2O3S
- Average molar mass
- 214.24 g/mol
- Monoisotopic mass
- 214.04121318
Overview
Sulfacetamide is a white powder. (NTP, 1992)
Names & identifiers
- Preferred name
- Sulfacetamide
- IUPAC
- N-(4-aminophenyl)sulfonylacetamide
- English name
- Sulfacetamide
- Molecular formula
- C8H10N2O3S
- Molecular weight
- 214.24
Names & synonyms
Show more names
Database identifiers
- CAS
144-80-9- PubChem CID
- 5320
- DTXSID
DTXSID8026060- ChEMBL
CHEMBL455- ChEBI
CHEBI:63845- UNII
- 4965G3J0F5
- EC Number
- 205-640-6
- Nikkaji
- J8.635E
Properties
Computed structural properties
- XLogP
- -1
- Topological polar surface area
- 97.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 299
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP
-0.6
-0.1
Solubility
less than 0.1 mg/mL at 61 °F (NTP, 1992)
4.21e+00 g/L
>32.1 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
360 to 363 °F (NTP, 1992)
183 °C
Physical Description
Sulfacetamide is a white powder. (NTP, 1992)
Solid
Collision Cross Section
154.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID8026060]
141.79 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
146.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
152.76 Ų [M+Na]+
Physicochemical properties
- Melting point
- 182 · 182-184 °C
- Density
- 1.3844 · 1.3844 (rough estimate)
- refractive index
- 1.569 · 1.5690 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- 50 mg/mL · ethanol: soluble50mg/mL
- pka
- 1.76 · pKa 1.76±0.04(H2O t = 25 I = 0.15 (KCl) Ar atmosphere)(Approximate);5.22±0.01(H2O t = 25 I = 0.15 (KCl) Ar atmosphere)(Approximate)
- form
- powder
- color
- white to off-white
- Water Solubility
- 0.01 g/100 · <0.01 g/100 mL at 16 ºC
- Merck
- 14 · 14,8899
- BRN
- 981718 · 981718
- Stability
- Stable. Incompatible with strong oxidizing agents, strong bases, strong reducing agents, strong acids.
- Major Application
- clinical testing
- InChI
- 1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)
- InChIKey
- SKIVFJLNDNKQPD-UHFFFAOYSA-N
- SMILES
- CC(=O)NS(=O)(=O)c1ccc(N)cc1
- CAS DataBase Reference
- 144 · 144-80-9(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4965 G3J0F5 · 4965G3J0F5
- ATC code
- 10 AF06,S01AB04 · D10AF06,S01AB04
- NIST Chemistry Reference
- N-(p-Aminobenzenesulfonyl)acetamide(144-80-9)
- EPA Substance Registry System
- Sulfacetamide (144-80-9)
- UNSPSC Code
- 51283901 · 51283901
- NACRES
- 85 · NA.85
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317-H335
- Precautionary statements
- 261 · P261-P271-P272-P280-P302+P352-P304+P340+P312
- target organs
- Respiratory system
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 20 · 20/21/22-36/37/38
- Safety Statements
- 22 · 22-24/25-36-26
- WGK Germany
- 2 · 2
- RTECS
- 8450000 · AC8450000
- TSCA
- TSCA listed
- HS Code
- 29350090 · 29350090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 STOT · Skin Sens. 1STOT SE 3
- Toxicity
- 50 orally · LD50 orally in dogs: 8000 mg/kg (Fisher)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 10% (4 of 40) of reports.
Warning
H317 (77.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P203, P261, P271, P272, P280, P302+P352, P304+P340, P318, P319, P321, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Reactivity Profile
SULFACETAMIDE is an amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generate mixed oxides of nitrogen (NOx)
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- AC8450000
- hs_code
- 29350090
- Toxicity
- LD50 orally in dogs: 8000 mg/kg (Fisher)
- risk_code
- 20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 22-24/25-36-26
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H317-H335
- REACH Registrations
- Active
- Hazard Classifications
- Skin Sens. 1STOT SE 3
- Precautionary statements
- P261-P271-P272-P280-P302+P352-P304+P340+P312
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
S - Sensory organs
QS - Sensory organs
QJ - Antiinfectives for systemic use
QD - Dermatologicals
Pharmacodynamics
Sulfacetamide is a sulfonamide antibiotic with bacteriostatic actions and broad-spectrum activity against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of <i>p</i>-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
Mechanism of Action
Sulfacetamide is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), an essential component for bacterial growth (according to the Woods-Fildes theory). The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
FDA Pharmacological Classification
4965G3J0F5
SULFACETAMIDE
Established Pharmacologic Class [EPC] - Sulfonamide Antibacterial
Chemical Structure [CS] - Sulfonamides
Sulfacetamide is a Sulfonamide Antibacterial.
MeSH Pharmacological Classification
Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that inhibit the growth or reproduction of BACTERIA.
Uses & manufacturing
Applications
UsesSulfacetamide is an antibiotic used for the treatment of skin infections and urinary tract infections. Sulfacetamide is also used to treat acne and seborrheic dermatitis. Sulfacetamide was investigated for potential anti-inflammatory properties
General DescriptionSulfacetamide’s plasmahalf-life is 7 hours. This compound is a white crystallinepowder, soluble in water (1:62.5 at 37°C) and in alcohol. It is very soluble in hot water, and its water solution is acidic.It has a pKa of 5.4.
General DescriptionWhite powder.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: A sulfonamide that is sulfanilamide acylated on the sulfonamide nitrogen.
Related reactions
Linked notes
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