톨메틴

톨메틴 · C07149 · olmetin · McN 2559 · Tolmetin · Methyiin · Tolmetine · TOLMETINUM

식별자 및 물리적 특성

CAS No.	26171-23-3
분자식	C15H15NO3
평균 분자량	257.28 g/mol
단동위원소 질량	257.10519334 g/mol
SMILES	Cc1ccc(C(=O)c2ccc(CC(=O)O)n2C)cc1
InChIKey	UPSPUYADGBWSHF-UHFFFAOYSA-N
PubChem CID	5509
ChEMBL	CHEMBL1020
ChEBI	CHEBI:71941
EC No.	247-497-2
DTXSID	DTXSID2043951
현지명	톨메틴

화학 및 물리적 성질

XLogP	2.8
극성 표면적	59.3
수소 결합 공여자 수	1
수소 결합 수용자 수	3
회전 가능 결합 수	4
무거운 원자 수	19
형식 전하	0
복잡도	347
의약품	DEA NFLIS-Drug Category -> AnalgesicsPharmaceuticals -> Listed in ZINC15
LogP(분배 계수)	2.6
Color/Form	CRYSTALS FROM ACETONITRILE
용해도	1.31e-01 g/L클로로포름(약간 용해됨), 메탄올(약간 용해됨)
Human Drugs	Breast FeedingLactationMilk, HumanAnalgesic AgentsAnti-inflammatory Agents, NonsteroidalPharmaceuticals
녹는점	155-157 °C (DECOMPOSES)156 °C
Physical Description	Solid
Dissociation Constants	3.5
Collision Cross Section	163.1 Å² [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]156.7 Å² [M+H]+ [CCS Type: TW]
Other Experimental Properties	PYRROLE-ACETIC ACID DERIVATIVE /TOLMETIN SODIUM/
끓는 점	400.53°C (rough estimate)
밀도	1.1391 (rough estimate)
굴절률	1.5200 (estimate)
저장 조건	2-8°C
pKa(산도 계수)	pKa 3.5(H2O t undefined I undefined) (Uncertain)
물리적 상태	고체
색상	황백색에서 연한 노란색
용해도	222mg/L
InChI	InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
InChIKey	UPSPUYADGBWSHF-UHFFFAOYSA-N
SMILES	N1(C)C(C(=O)C2=CC=C(C)C=C2)=CC=C1CC(O)=O
NIST	Tolmetin(26171-23-3)
EPA	1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)- (26171-23-3)

안전 및 규제

Hepatotoxicity
GHS 분류	DangerH301 (33.3%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, 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.
기타 안전 정보	IMAP assessments - 1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)-: Environment tier I assessment
Special Reports	REVIEW ARTICLE INCLUDES TOLMETIN.[SIMON LS, MILLS JANONSTEROIDAL ANTIINFLAMMATORY DRUGS (SECOND OF TWO PARTS)N ENGL J MED 302 (22) 1237 (1980)]TOLMETIN'S PHARMACOLOGICAL PROPERTIES & THERAPEUTIC EFFICACY IN RHEUMATIC DISEASES ARE REVIEWED.[BROGDEN RN ET ALTOLMETIN: A REVIEW OF ITS PHARMACOLOGICAL PROPERTIES & THERAPEUTIC EFFICACY IN RHEUMATIC DISEASESDRUGS 15(6) 429 (1978)]THE HISTORY OF RESEARCH & DEVELOPMENT OF NONSTEROIDAL ANTI-INFLAMMATORY AGENTS, INCL TOLMETIN.[GRINGAUZ ANONSTEROIDAL ANTI-INFLAMMATORY AGENTS--ANYTHING NEW UNDER THE SUN?HOSP FORMUL 14(MAR) 290 (1979)]
Hazard Classes and Categories	Acute Tox. 3 (33.3%)
상호 작용	PT RECEIVING CORTICOSTEROID OR GOLD THERAPY OBTAINED GREATER RELIEF OF SYMPTOMS WHEN TOLMETIN WAS ADDED TO THE REGIMEN, & THERE WAS EVIDENCE THAT TOLMETIN HAD A STEROID-SPARING EFFECT. /TOLMETIN SODIUM/CONCOMITANT ADMIN OF TOLMETIN & ACETAMINOPHEN PRODUCED A GREATER IMPROVEMENT IN SYMPTOMS THAN WITH TOLMETIN ALONE, BUT FURTHER STUDIES ARE NEEDED TO SUBSTANTIATE THIS EFFECT. /TOLMETIN SODIUM/CONCOMITANT ASPIRIN REDUCES PLASMA LEVELS OF TOLMETIN BY ABOUT 20%, BUT THE INTERACTION PROBABLY IS NOT CLINICALLY IMPORTANT. /TOLMETIN SODIUM/IN DOGS, PROSTAGLANDIN SYNTHETASE INHIBITORS INDOMETHACIN & TOLMETIN BLOCKED FUROSEMIDE-INDUCED INCR IN RENIN SECRETION WHETHER FUROSEMIDE WAS GIVEN IV OR INTO RENAL ARTERY.DESPITE ITS EXTENSIVE BINDING TO ALBUMIN...NO CHANGE IN PROTHROMBIN TIME WHEN WARFARIN & TOLMETIN WERE GIVEN TOGETHER.

용도

개요

An antiinflammatory, analgesic, and antipyretic that is as efficacious as moderate doses of aspirin and better tolerated. Tolmetin produces a number of adverse effects including epigastric pain, dyspepsia, nausea, and vomiting. Tolmetin is approximately 99% plasma protein bound, yet does not interfere with concurrent treatment with oral hypoglycemics. Tolmetin has been found to be effective in the treatment of osteoarthritis and rheumatoid arthritis.

용도

Tolmetine is an NSAID.

일반 설명

Tolmetin sodium (Tolectin), is an arylacetic acid derivativewith a pyrrole as the aryl group. This drug is well absorbed and has a relatively short plasma half-life (1 hour). It is recommendedfor use in the management of acute and chronicRA. Its efficacy is similar to aspirin and indomethacin, butwith less frequency of the adverse effects and tinnitus associatedwith aspirin. It does not potentiate coumarin-likedrugs nor alter the blood levels of sulfonylureas or insulin.However, tolmetin, and especially its closely related drug,zomepirac (i.e., with a p-chlorobenzoyl group and an additionalmethyl group on the pyrrole ring), can produce a rarebut fatal anaphylactic reaction because of irreversible bindingof their unstable acyl glucuronides. Zomepirac waswithdrawn from market because it is eliminated only via theester-type, acyl glucuronide. It is possible that tolmetin isless toxic in this regard because it undergoes additional hepaticbenzylic hydroxylation via its p-methyl group and isexcreted as its stable ether glucuronide.