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Sulfalene

HCID 9047
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
152-47-6
Standard SMILES
COc1nccnc1NS(=O)(=O)c1ccc(N)cc1
InChIKey
KXRZBTAEDBELFD-UHFFFAOYSA-N
Molecular formula
C11H12N4O3S
Average molar mass
280.31 g/mol
Monoisotopic mass
280.06301143

Overview

Sulfamethopyrazine is a sulfonamide, a member of pyrazines and a sulfonamide antibiotic.

Names & identifiers

Preferred name
Sulfalene
IUPAC
4-amino-N-(3-methoxypyrazin-2-yl)benzenesulfonamide
English name
Sulfalen
Molecular formula
C11H12N4O3S
Molecular weight
280.3

Names & synonyms

SULFALENE152-47-6SulfamethoxypyrazineSulfametopyrazine4-amino-N-(3-methoxypyrazin-2-yl)benzenesulfonamideSulfamethopyrazineKelfizinaKelfizineKelfizine WNSC-110433Benzenesulfonamide, 4-amino-N-(3-methoxypyrazinyl)-2-(p-Aminobenzenesulfanamide)-3-methoxypyrazine
Show more names
smp2Vetkellongumas18908dalysepsulfalenf.i.5978kelfizin
AS 18908FI 5978N(sup 1)-(3-Methoxypyrazinyl)sulfanilamideDTXSID2046179WR 4629AS-18908T6BL4ZC15G4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide

Database identifiers

CAS
152-47-6
PubChem CID
9047
DTXSID
DTXSID2046179
ChEMBL
CHEMBL1525826
ChEBI
CHEBI:32162
UNII
T6BL4ZC15G
EC Number
205-804-7
Nikkaji
J3.271I

Properties

Computed structural properties

XLogP
0.7
Topological polar surface area
116 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
7
Rotatable bonds
4
Heavy atoms
19
Formal charge
0
Complexity
376

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceutical

LogP · 2 items

0.7

0.19

Solubility · 2 items

4.06e-01 g/L

>42 [ug/mL] (The mean of the results at pH 7.4)

Human DrugsPharmaceuticals
Melting Point169.5 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
176 ° · 176°
Boiling point
488.6 · 488.6±55.0 °C(Predicted)
Density
1.3936 · 1.3936 (rough estimate)
refractive index
1.62 · 1.6200 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
DMSO (Slightly), Methanol (Slightly, heated)
form
Solid
pka
6.2 · pKa 6.20(H2O t = 25.0±0.5 I = 0.2) (Uncertain)
color
White to Yellow
λmax
250 nm · 250nm(NaOH aq.)(lit.)
Merck
14 · 14,8910
CAS DataBase Reference
152 · 152-47-6(CAS DataBase Reference)
FDA UNII
6 BL4ZC15G · T6BL4ZC15G
ATC code
1 ED02 · J01ED02
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
315 · H315-H319-H361-H362
Precautionary statements
201 · P201-P202-P260-P263-P264-P270-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P308+P313-P405-P501
RTECS
175000 · WP0175000
HS Code
2935.9 · 2935.90.9500
HazardClass
IRRITANT
Toxicity
50 in · LD50 in mice (g/kg): 2.164 orally; 1.41 i.v. (US 3098069)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P263, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Other Safety InformationIMAP assessments - Benzenesulfonamide, 4-amino-N-(3-methoxypyrazinyl)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (66.7%)

Safety data

rtecs
WP0175000
hs_code
2935.90.9500
Toxicity
LD50 in mice (g/kg): 2.164 orally; 1.41 i.v. (US 3098069)
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
hazard_class
IRRITANT
Hazard statements
H315-H319-H361-H362
Precautionary statements
P201-P202-P260-P263-P264-P270-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P308+P313-P405-P501

Chemistry & industry

Pharmacology

ATC Code · 2 items

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Pharmacodynamics · 1 item

Sulfametopyrazine 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 · 1 item

Sulfametopyrazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. Para-aminobenzoic acid (PABA), a substrate of the enzyme is prevented from binding. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

MeSH Pharmacological Classification · 3 items

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)

Uses & manufacturing

Use ClassificationPharmaceuticals

Applications

UsesA possible antimalarial drug.

Upstream & downstream products

Upstream raw materials

Hydrazinium hydroxide solutionSodium hydroxideSodium diacetateAcetamide, N-[4-[[(3-methoxy-2-pyrazinyl)amino]sulfonyl]phenyl]-2-Amino-3-methoxypyrazineN-Acetylsulfanilyl chloride

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18062128043 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
湖北恒硕化工有限公司027-82830253 13995541600 · [email protected]
江西瑞威尔生物科技有限公司400-880-2824 18107960669 · [email protected]
江苏普乐司生物科技有限公司0513-66017706 18551496367 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
ChemeGen 中国18818260767 · [email protected]
Hebei Qige Biological Technology Co. Ltd+86 +8618733132031
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
湖北威德利化学科技有限公司027-83989310 18627915365 · [email protected]
湖北宜好生物科技有限公司18995688786 · [email protected]
西安美川生物科技有限公司029-89275612 +8618991951683 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
湖北万业众诚化学试剂有限责任公司18671296875 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd+8613580539051 · [email protected]
上海炎泽化工有限公司15345144255 19901447308 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
舟山广兴化学有限公司15698059122 15698059122 · [email protected]
湖北齐飞医药化工有限公司027-59322506 18071128681 · [email protected]
常州合晶化工有限公司85528066 13775048983 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
南京罗迈美生物科技有限公司[email protected]

Additional notes

DefinitionChEBI: Sulfamethopyrazine is a member of pyrazines, a sulfonamide and a sulfonamide antibiotic.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes