프로베네시드

프로베네시드 · 4-(N,N-Dipropylsulfamoyl)benzoic acid · PROBENICID · Binghuangshu · 4-(Dipropylsulfamoyl)benzoic acid · 4-((dipropylamino)sulfonyl)-benzoicaci · 4-[(dipropylamino)sulphonyl]benzoic acid · Benemid

https://huagongshe.com/ko/chemical/4911

식별자 및 물리적 특성

CAS No.	57-66-9
분자식	C13H19NO4S
평균 분자량	285.36 g/mol
단동위원소 질량	285.10347909 g/mol
SMILES	CCCN(CCC)S(=O)(=O)c1ccc(C(=O)O)cc1
InChIKey	DBABZHXKTCFAPX-UHFFFAOYSA-N
PubChem CID	4911
ChEMBL	CHEMBL897
ChEBI	CHEBI:8426
EC No.	200-344-3
DTXSID	DTXSID9021188
현지명	프로베네시드

화학 및 물리적 성질

XLogP	3.2
극성 표면적	83.1
수소 결합 공여자 수	1
수소 결합 수용자 수	5
회전 가능 결합 수	7
무거운 원자 수	19
형식 전하	0
복잡도	374
의약품	PharmaceuticalsPharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties	Crystal structure
LogP(분배 계수)	2.33.21
냄새	PRACTICALLY ODORLESS
맛	SLIGHTLY BITTERPLEASANT AFTERTASTE
Color/Form	CRYSTALS FROM DIL ALCOHOLWHITE OR NEARLY WHITE, FINE, CRYSTALLINE POWDER
용해도	less than 1 mg/mL at 68 °F (NTP, 1992)FREELY SOL IN WATER /SODIUM SALT/SOL IN DIL ALKALI, ALCOHOL, CHLOROFORM & ACETONEPRACTICALLY INSOL IN WATER & DIL ACIDS4.25e-01 g/L>42.8 [ug/mL] (The mean of the results at pH 7.4)DMSO(약간 용해됨), 메탄올(약간 용해됨)
Human Drugs	Breast FeedingLactationAntigout AgentsGout SuppressantsSulfonamidesUricosuric AgentsFDA approved drugs -> Active ingredientPharmaceuticals
Decomposition	When heated to decomposition it emits very toxic fumes of oxides of sulfur and oxides of nitrogen.
녹는점	381 to 385 °F (NTP, 1992)194-196 °C195 °C194-196°C
Physical Description	Probenecid appears as odorless white or almost white crystalline powder. Slightly bitter tastepleasant aftertaste. (NTP, 1992)Solid
Stability/Shelf Life	Probenecid tablets should be stored in well closed containers at a temperature less than 40 °C, preferably between 15-30 °C. Commercially available preparations containing probenecid and colchicine should be protected from light. Following the date of manufacture, commercially available probenecid tablets have an expiration date of 3-5 yr depending on the packaging.
끓는 점	438.0±47.0 °C(Predicted)
밀도	1.2483 (rough estimate)
굴절률	1.6800 (estimate)
저장 조건	Store at RT
물리적 상태	Solid
pKa(산도 계수)	5.8(at 25℃)
색상	흰색에서 황백색까지
용해도	20°C에서 <0.1g/100mL
Merck	14,7754
안정성	안정적이지만 빛에 민감할 수 있습니다. 강한 산화제와 호환되지 않습니다.
InChI	1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)
InChIKey	DBABZHXKTCFAPX-UHFFFAOYSA-N
SMILES	CCCN(CCC)S(=O)(=O)c1ccc(cc1)C(O)=O
NIST	P-(dipropylsulfamoyl) benzoic acid(57-66-9)
EPA	Probenecid (57-66-9)

화학적 성질

White to Off-White Solid

안전 및 규제

Special Reports
GHS 분류	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 81 reports by companies from 5 notifications to the ECHA C&L Inventory.
기타 안전 정보	IMAP assessments - Benzoic acid, 4-[(dipropylamino)sulfonyl]-: Environment tier I assessment
운송 라벨(DOT)	Poison
화재 위험	Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
건강 유해성	SYMPTOMS: Symptoms of exposure to this chemical include nausea, vomiting, headache, sore gums, flushing, dizziness, urinary frequency and anemia. On rare occasions an anaphylactic reaction or a hypersensitivity reaction with fever, dermatitis and pruritis has occurred, and there have been reports of hepatic necrosis, the nephrotic syndrome and aplastic anemia. Exposure may precipitate an acute attack of gout, and renal colic or renal calculi with or without hematuria may occur. It may also cause gastrointestinal upset. Other symptoms include urticaria, nephrosis, coma and status epilepticus. In massive overdosage, stimulation of the central nervous system with convulsions and death from respiratory failure may occur. Exposure may also cause increased plasma concentrations of methotrexate, costovertebral pain, precipitation of acute gouty arthritis, anorexia, leukopenia, alopecia and hemolytic anemia (which could be related to genetic deficiency of glucose-6-phosphate dehydrogenase in red blood cells). It may also cause skin rashes. It may occasionally cause drug fever. Jaundice, asthma and eosinophilia have preceded a massive hepatic necrosis.
FDA 요건	Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl probenecid, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.
반응성 그룹	Acids, Carboxylic

용도

개요

Probenecid is insoluble in water and acidic solutions but is soluble in alkaline solutions buffered to pH 7.4. Probenecid initially was synthesized as a result of studies in the 1940s on sulfonamides that indicated the sulfonamides decreased the renal clearance of penicillin, extending the half-life of penicillin as supplies diminished. Probenecid thus was initially used—and is still indicated—for that purpose. Probenecid promotes the excretion of uric acid by inhibiting the urate anion exchange transporter (URAT 1), decreasing the reabsorption of uric acid in the proximal tubules. The overall effect is to decrease plasma uric acid concentrations, thereby decreasing the rate and extent of urate crystal deposition in joints and synovial fluids. Within the series of N-dialkylsulfamyl benzoates from which probenecid is derived, renal clearance of these compounds is decreased as the length of the N-alkyl substituents is increased. Uricosuric activity increases with increasing size of the alkyl group in the series methyl, ethyl, and propyl.

용도

It is a uricosuric drug, that is, it increases uric acid excretion in the urine. It is primarily used in treating gout and hyperuricemia. Probenecid was developed as an alternative to caronamide to competitively inhibit renal excretion of some drugs, thereby increasing their plasma concentration and prolonging their effects.

일반 설명

Probenecid (Benemid) is the most widely used uricosuricagent in the United States. It is selectively excreted into therenal tubules by OATS. It is extensively metabolized via Ndealkylationor ω-oxidation, followed by phase II conjugationinto the active metabolite, p-sulfamyl hippurate, whichexhibits a high affinity, similar to p-aminohippurate, forbinding to OATS, thereby preventing uric acid reabsorptionfrom the renal proximal tubules.