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Sulfamerazine

Names

[ CAS No. ]:
127-79-7

[ Name ]:
Sulfamerazine

[Synonym ]:
2-sulfanilamido-4-methylpyrimidine
Mesulfa
4-Amino-N-(4-methyl-2-pyrimidinyl)benzenesulfonamide (N1-(4-Methylpyrimidin-2-yl)sulfanilamide
Mebacid
4-Amino-N-(4-methyl-2-pyrimidinyl)benzenesulfonamide
SMI
A-310
METSULFA
Romezin
sulfamerazine
Benzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)-
Sulfamerazin
RP 2632
4-amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
sulphamerazine
2643-RP
EINECS 204-866-2
DEBENAL
MFCD00023212

Biological Activity

[Description]:

Sulfamerazine(RP-2632) is a sulfonamide antibacterial.Target: AntibacterialSulfamerazine, the monomethyl derivative of sulfadiazine, is 2-sulfanilamido-4-methylpyrimidine. Sulfamerazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamerazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA [1].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial
Research Areas >> Infection

[References]

[1]. HALL, W.H. and W.W. SPINK, Sulfamerazine: clinical evaluation in 116 cases. Journal of the American Medical Association, 1943. 123(3): p. 125-131.


[Related Small Molecules]

Puromycin 2HCl | Geneticin | Tunicamycin | Hygromycin B | Salinomycin | Avibactam sodium | Neomycin sulfate | Vaborbactam | Methicillin SodiuM | Rifampicin | Metronidazole | Carbenicillin disodium | Ceftazidime | Eravacycline dihydrochloride | cefotaxime sodium

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
519.1±52.0 °C at 760 mmHg

[ Melting Point ]:
234-238°C

[ Molecular Formula ]:
C11H12N4O2S

[ Molecular Weight ]:
264.304

[ Flash Point ]:
267.8±30.7 °C

[ Exact Mass ]:
264.068085

[ PSA ]:
106.35000

[ LogP ]:
0.34

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.660

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WP0750000
CHEMICAL NAME :
Sulfanilamide, N(sup 1)-(4-methyl-2-pyrimidinyl)-
CAS REGISTRY NUMBER :
127-79-7
BEILSTEIN REFERENCE NO. :
0249133
LAST UPDATED :
199701
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C11-H12-N4-O2-S
MOLECULAR WEIGHT :
264.33
WISWESSER LINE NOTATION :
T6N CNJ BMSWR DZ& D1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1890 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 27,141,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 211,367,1950
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 94,338,1953
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 5,213,1955
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1190 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 27,141,1971 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
45020 mg/kg/17D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - changes in bladder weight Related to Chronic Data - death
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 81,17,1944 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
17934 mg/kg
SEX/DURATION :
male 6 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
REFERENCE :
JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 81,259,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 gm/kg
SEX/DURATION :
female 6-10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other neonatal measures or effects
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 101,362,1951 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80539 No. of Facilities: 963 (estimated) No. of Industries: 4 No. of Occupations: 8 No. of Employees: 4216 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80539 No. of Facilities: 48 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 707 (estimated) No. of Female Employees: 507 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
WP0750000

[ HS Code ]:
2935009090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2935009090

[ Summary ]:
2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

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