Sulfadiazine

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Names

[ CAS No. ]:
68-35-9

[ Name ]:
Sulfadiazine

[Synonym ]:
Sulfadiazine
A-306
2-sulfanilylaminopyrimidine
2-sulfanilamidopyrimidine
PYRIMAL
FLAMAZINE
sulfapyrimidine
MFCD00006065
Silvadene
sulphadiazine
Adiazine
EINECS 200-685-8
4-amino-N-(pyrimidin-2-yl)benzenesulfonamide
DEBENAL
4-Amino-N-pyrimidin-2-yl-benzenesulfonamide
Ultradiazin
Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-
Adiazin
rp2616
N1-2-Pyrimidinylsulfanilamide
4-Amino-N-(2-pyrimidinyl)benzenesulfonamide
Diazin
DIAZYL
N1-2-Pyrimidylsulfanilamide
SD-Na
Trisem

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
512.6±52.0 °C at 760 mmHg

[ Melting Point ]:
253 °C (dec.)(lit.)

[ Molecular Formula ]:
C10H10N4O2S

[ Molecular Weight ]:
250.277

[ Flash Point ]:
263.8±30.7 °C

[ Exact Mass ]:
250.052444

[ PSA ]:
106.35000

[ LogP ]:
-0.12

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.679

[ Storage condition ]:
0-6°C

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WP1925000
CHEMICAL NAME :
Sulfanilamide, N(sup 1)-2-pyrimidinyl-
CAS REGISTRY NUMBER :
68-35-9
BEILSTEIN REFERENCE NO. :
0235192
LAST UPDATED :
199707
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C10-H10-N4-O2-S
MOLECULAR WEIGHT :
250.30
WISWESSER LINE NOTATION :
T6N CNJ BMSWR DZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
229 mg/kg/8D-I
TOXIC EFFECTS :
Gastrointestinal - other changes Kidney, Ureter, Bladder - urine volume decreased
REFERENCE :
IJMDAI Israel Journal of Medical Sciences. (POB 1435, Jerusalem 91013, Israel) V.1- 1965- Volume(issue)/page/year: 6,561,1970
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
138 mg/kg
TOXIC EFFECTS :
Behavioral - general anesthetic Kidney, Ureter, Bladder - urine volume decreased Kidney, Ureter, Bladder - hematuria
REFERENCE :
PGMJAO Postgraduate Medical Journal. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1925- Volume(issue)/page/year: 53,103,1977
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
446 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
KLWOAZ Klinische Wochenscrift. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.1- 1922- Volume(issue)/page/year: 27,449,1949
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
880 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 :
1500 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: 21,571,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
750 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
29ZVAB "Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969 Volume(issue)/page/year: -,109,1969
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,386,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
180 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#03347
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 79,354,1943 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
91200 mg/kg/22W-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes Endocrine - thyroid weight (goiter) 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: 79,354,1943
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5250 mg/kg/2W-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
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
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2640 mg/kg/30D-C
TOXIC EFFECTS :
Endocrine - other changes Blood - changes in spleen Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 14,2856,1980 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 gm/kg
SEX/DURATION :
female 9-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
SEIJBO Senten Ijo. Congenital Anomalies. (Nippon Senten Ijo Gakkai, c/o Kinki Daigaku Igakubu Kaibagaku Kyoshitsu, 380 Nishiyama, Sayama-cho, Mirami-Kawachi-gun, Osaka-fu, Japan) V.1-26, 1960-86. For publisher information, see CGANE7. Volume(issue)/page/year: 13,7,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 gm/kg
SEX/DURATION :
female 7-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - eye/ear
REFERENCE :
SEIJBO Senten Ijo. Congenital Anomalies. (Nippon Senten Ijo Gakkai, c/o Kinki Daigaku Igakubu Kaibagaku Kyoshitsu, 380 Nishiyama, Sayama-cho, Mirami-Kawachi-gun, Osaka-fu, Japan) V.1-26, 1960-86. For publisher information, see CGANE7. Volume(issue)/page/year: 13,7,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 gm/kg
SEX/DURATION :
female 7-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
SEIJBO Senten Ijo. Congenital Anomalies. (Nippon Senten Ijo Gakkai, c/o Kinki Daigaku Igakubu Kaibagaku Kyoshitsu, 380 Nishiyama, Sayama-cho, Mirami-Kawachi-gun, Osaka-fu, Japan) V.1-26, 1960-86. For publisher information, see CGANE7. Volume(issue)/page/year: 13,17,1973 *** REVIEWS *** TOXICOLOGY REVIEW JMSHAO Journal of the Mount Sinai Hospital (New York). (New York, NY) V.1-36, 1934-69. For publisher information, see MSJMAZ. Volume(issue)/page/year: 10,343,1943 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80538 No. of Facilities: 1033 (estimated) No. of Industries: 4 No. of Occupations: 9 No. of Employees: 5001 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80538 No. of Facilities: 95 (estimated) No. of Industries: 2 No. of Occupations: 20 No. of Employees: 2854 (estimated) No. of Female Employees: 849 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H317-H319-H334-H335

[ Precautionary Statements ]:
P261-P280-P284-P304 + P340-P305 + P351 + P338-P342 + P311

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

[ Hazard Codes ]:
Xn,Xi

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
3249

[ WGK Germany ]:
3

[ RTECS ]:
WP1925000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2935009090

Synthetic Route

Precursor & DownStream

Precursor

  • N-benzylidene-sulfanilic acid pyrimidin-2-ylamide
  • 4-nitro-N-pyrimidin-2-ylbenzenesulfonamide
  • 4'-(pyrimidin-2-ylsulphamoyl)acetanilide
  • 4-Acetamidobenzenesulfonyl chloride
  • nosyl chloride
  • chloropyrimidine
  • Sulfanilamide
  • 2-Aminopyrimidine
  • 3-(4-acetylamino-benzenesulfonyl)-2-benzenesulfonylimino-2,3-dihydro-thiazole

DownStream

  • 4'-(pyrimidin-2-ylsulphamoyl)acetanilide
  • Benzenesulfonamide,4-[2-(1-acetyl-2-oxopropyl)diazenyl]-N-2-pyrimidinyl-
  • Benzenesulfonamide,4-isothiocyanato-N-2-pyrimidinyl-
  • 4-[(6-oxo-1-cyclohexa-2,4-dienylidene)methylamino]-N-pyrimidin-2-yl-benzenesulfonamide
  • 3-[[4-(pyrimidin-2-ylsulfamoyl)phenyl]carbamoyl]propanoic acid

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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Related Compounds

  • Sulfadiazine D4
  • Sulfadiazine-13C6
  • SULFADIAZINE ZINC
  • Acetylsulfadiazine
  • Sulfadiazine sodium
  • Silver sulfadiazine