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술파디아진

Sulfadiazine

HCID 5215
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
68-35-9
표준 SMILES
Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1
InChIKey
SEEPANYCNGTZFQ-UHFFFAOYSA-N
분자식
C10H10N4O2S
평균 분자량
250.28 g/mol
단동위원소 질량
250.05244656

개요

Sulfadiazine is a sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position. It has a role as an antimicrobial agent, an antiinfective agent, a xenobiotic, a coccidiostat, an antiprotozoal drug, an EC 2.5.1.15 (dihydropteroate synthase) inhibitor, an EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor, an environmental contaminant and a drug allergen. It is a sulfonamide, a member of pyrimidines, a substituted aniline and a sulfonamide antibiotic. It is functionally related to a sulfanilamide. It is a conjugate acid of a sulfadiazinate.

이름 및 식별자

우선 이름
Sulfadiazine
IUPAC
4-amino-N-pyrimidin-2-ylbenzenesulfonamide
현지명
술파디아진
영어명
Sulfadiazine
분자식
C10H10N4O2S
분자량
250.28

이름 및 동의어

sulfadiazine68-35-9SulphadiazineSulfapyrimidineSulfadiazinAdiazineCoco-Diazine2-SulfanilamidopyrimidineSulfolexBenzenesulfonamide, 4-amino-N-2-pyrimidinyl-2-Sulfanilylaminopyrimidine4-amino-N-pyrimidin-2-ylbenzenesulfonamide
이름 더 보기
설파다이아진술파디아진설파디아진Sulfadiazine,(S)SulfadiazeneDiazinSulfoseTerfonylDiazoloneNeotrizinesuldadiazine
N(1)-2-pyrimidylsulfanilamideN(sup 1)-2-Pyrimidinylsulfanilamide4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamideN(1)-2-pyrimidinylsulfanilamide4-AMINO-N-2-PYRIMIDINYLBENZENESULFONAMIDEDTXSID7044130CHEBI:9328NSC35600

데이터베이스 식별자

CAS
68-35-9
PubChem CID
5215
DTXSID
DTXSID7044130

물성

구조 계산 물성보충 중

XLogP
-0.1
극성 표면적
106 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
6
회전 가능 결합 수
3
무거운 원자 수
17
형식 전하
0
복잡도
327

실험 및 물리화학적 성질

Drugs · 4건

Pharmaceuticals -> Antibiotics (Sulfonamide)

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

SpringerMaterials PropertiesFusion temperature
LogP · 2건

-0.2

-0.04

Solubility6.01e-01 g/L
Human Drugs · 3건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Anti-infective medicines

Animal Drugs · 3건

Active Ingredients (Sulfadiazine) -> FDA Greenbook

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Physical DescriptionSolid
Dissociation Constants6.36
Collision Cross Section · 5건

153.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 1.2% (2 of 171) of reports.

Danger

H302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P233, P260, P261, P263, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 171 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 2건

Status: Active Update: 23-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17511

Sulphadiazine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (98.2%)

독성 정보

Hepatotoxicity · 1건

Sulfadiazine, like other sulfonamides, causes a characteristic idiosyncratic liver injury which has features of drug-allergy or hypersensitivity. The typical onset is sudden development of fever and rash followed by jaundice within a few days or weeks of starting the medication. The pattern of injury is typically mixed, although fatal cases are often hepatocellular and prolonged cholestatic cases have also been described. Eosinophilia or atypical lymphocytosis are also common and the clinical pattern can be considered a part of DRESS syndrome (drug rash with eosinophilia and systemic symptoms). Cases of Stevens Johnson syndrome due to sulfadiazine have also been described. Sulfonamides such as sulfadiazine have been linked to many cases of acute liver failure and as a class, the sulfonamides still rank in the top 5 to 10 causes of drug induced, idiosyncratic fulminant hepatic failure. However, most cases of sulfonamide induced liver injury resolve rapidly, usually within 2 to 4 weeks unless cholestasis is severe. Onset of injury is more rapid with rechallenge and can appear within a day or reexposure. Patients with hepatic injury due to sulfadiazine may have a history of previous exposure to the drug without injury. Sulfonamides such as sulfadiazine can also cause mild and transient ALT elevations that do not progress to jaundice or more severe liver injury either alone or as a part of a generalized hypersensitivity reaction. Sulfonamides have also been linked to hepatic granulomas.

화학 및 산업

약리 정보

ATC Code · 4건

J01EC02

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

J01EC02

Pharmacodynamics · 1건

Sulfadiazine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum 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 · 1건

Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Metabolism/MetabolitesSulfadiazine has known human metabolites that include Sulfadiazine hydroxylamine.
FDA Pharmacological Classification · 6건

0N7609K889

SULFADIAZINE

Established Pharmacologic Class [EPC] - Sulfonamide Antibacterial

Chemical Structure [CS] - Sulfonamides

Sulfadiazine is a Sulfonamide Antibacterial.

SULFADIAZINE

MeSH Pharmacological Classification · 3건

Substances that are destructive to protozoans.

Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals.

관련 반응

36건
반응 기록 만들기
HRID 3696 반응식
HRID 3696반응물로uspto-grants-1998_03
HRID 94566 반응식
HRID 94566반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 156477 반응식
HRID 156477반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 213337 반응식
HRID 213337반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 365062 반응식
HRID 365062생성물로uspto-grants-1986_08
HRID 489948 반응식
HRID 489948반응물로uspto-grants-2005_12
HRID 583483 반응식
HRID 583483반응물로uspto-grants-1999_07
HRID 697622 반응식
HRID 697622반응물로Training data from https://doi.org/10.1039/C8SC04228D (3/10)
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
ChEMBL
CHEMBL439
ChEBI
CHEBI:9328
UNII
0N7609K889
EC Number
200-685-8
Nikkaji
J1.418D

150.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

148.7 Ų [M+H]+ [CCS Type: TW]

157.85 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

151.96 Ų [M+H]+

물리화학적 성질

녹는점
253 °C · 253 °C (dec.) (lit.)
끓는 점
512.6 · 512.6±52.0 °C(Predicted)
밀도
1.378 · 1.3780 (rough estimate)
굴절률
1.644 · 1.6440 (estimate)
저장 조건
2 · 2-8°C
용해도
디메틸설폭사이드에 용해됩니다.
산도 계수 (pKa)
2.21 · pKa 2.21(H2O t = 25 I = 0.5 (NaCl)) (Uncertain)
물리적 상태
가루
색상
하얀색
수용성
67.13 mg/L · 67.13mg/L(25℃)
Merck
14 · 14,8903
BRN
6733588 · 6733588
BCS Class
4 · 4/3
주요 응용
임상 시험
InChI
1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
InChIKey
SEEPANYCNGTZFQ-UHFFFAOYSA-N
SMILES
Nc1ccc(cc1)S(=O)(=O)Nc2ncccn2
NIST
Sulfadiazine(68-35-9)
EPA
4 · Benzenesulfonamide, 4-amino-N-2-pyrimidinyl- (68-35-9)

화학적 성질

White to slightly yellow crystalline pow

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Sulfadiazine

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
WP1925000
ridadr
3249
독성
LD50 oral in mouse: 1500mg/kg
HS 번호
29335990
risk_code
22-36/37/38-42/43-43-42
hazard_code
Xn,Xi
safety_code
26-36
포장분류
III
위험 등급
6.1(b)
기존화학 물질
KE-01586
F 고인화성물질
10
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2Repr. 2
스토리지 클래스
11 - Combustible Solids

Substances that inhibit the growth or reproduction of BACTERIA.

Absorption, Distribution and ExcretionSulfadiazine is excreted largely in the urine.
Cellular LocationsMembrane

용도 및 제조

UsesUse (kg) in Switzerland (2009): >250
Use Classification · 3건

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pharmaceuticals -> Antiinfectives for systemic use -> Antibacterials for systemic use -> Sulfonamides and trimethoprims -> Intermediate-acting sulfonamides -> Antibiotics

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

General Manufacturing InformationBenzenesulfonamide, 4-amino-N-2-pyrimidinyl-: ACTIVE
응용 분야 · 2건

용도It is used in the form of silver salts (sulfadiazine silver) as an external antibacterial agent, primarily for treating burns. It is believed that the presence of the silver ion in the molecule facilitates increased antimicrobial and wound-healing action.

일반 설명Sulfadiazine’s plasma half-life is 17 hours. It is a white,odorless crystalline powder soluble in water to the extentof 1:8,100 at 37°C and 1:13,000 at 25°C, in human serumto the extent of 1:620 at 37°C, and sparingly soluble in alcoholand acetone. It is readily soluble in dilute mineralacids and bases. Its pKa is 6.3.

상·하류 제품 정보

상류 원료

Thiamine chloride에틸비닐에테르에틸알코올N,N-다이메틸폼아마이드프로파질 알코올다이에틸아민탄화칼슘메틸산 나트륨삼염화 인설파구아니딘4-나이트로벤젠설포닐 염화물2-Aminopyrimidine

하류 제품

2-CHLORO-N-{4-[(PYRIMIDIN-2-YLAMINO)술포닐]페닐}아세트아미드2-chloro-5-nitro-N-[4-(pyrimidin-2-ylsulfamoyl)phenyl]benzamide

추가 설명

정의ChEBI: A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.