부설판

부설판 · busulphan · 1,4-BUTANEDIOL DIMETHANESULFONATE · myleran · busulfex · Butane-1,4-diyl dimethanesulfonate · gt41 · x149

https://huagongshe.com/ko/chemical/2478

식별자 및 물리적 특성

CAS No.	55-98-1
분자식	C6H14O6S2
평균 분자량	246.3 g/mol
단동위원소 질량	246.02318017 g/mol
SMILES	CS(=O)(=O)OCCCCOS(C)(=O)=O
InChIKey	COVZYZSDYWQREU-UHFFFAOYSA-N
PubChem CID	2478
ChEMBL	CHEMBL820
ChEBI	CHEBI:28901
EC No.	200-250-2
DTXSID	DTXSID3020910
현지명	부설판

화학 및 물리적 성질

XLogP	-0.5
극성 표면적	104
수소 결합 공여자 수	0
수소 결합 수용자 수	6
회전 가능 결합 수	7
무거운 원자 수	14
형식 전하	0
복잡도	293
의약품	Pharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties	Diamagnetic susceptibility
LogP(분배 계수)	log Kow = -0.52-0.3
Color/Form	White needlesCrystals
용해도	Decomposes (NTP, 1992)Solubility in acetone at 25 °C: 2.4 g/100mLin alcohol: 0.1g/100 mL. Practically insoluble in water but will dissolve slowly as hydrolysis takes place.5.16e+00 g/L물에는 아주 약간 용해되고, 아세톤과 아세토니트릴에는 잘 용해되며, 에탄올에는 아주 약간 용해됩니다(96%).
Human Drugs	Breast FeedingLactationAntineoplastic AgentsAlkylating AgentsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine
Endocrine Disruptors	Potential endocrine disrupting compound
녹는점	237 to 244 °F (NTP, 1992)106-107114-118 °C287 °C114-117 °C(lit.)
Physical Description	Myleran appears as white crystals or powder. (NTP, 1992)Solid
Stability/Shelf Life	... Solutions of busulfan diluted in 0.9% sodium chloride injection also have been shown to be stable when refrigerated at 2-8 °C for up to 12 hours, during which time the infusion must be completed.
Collision Cross Section	149.55 Å² [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
끓는 점	359.3°C (rough estimate)
밀도	1.305 (estimate)
굴절률	1.5630 (estimate)
인화점	9℃
저장 조건	Inert atmosphere,Room Temperature
물리적 상태	결정성 분말
색상	옅은 갈색
용해도	물에서 분해되다
Merck	14,1505
BRN	1791786
안정성	수분에 민감한
주요 응용	법의학 및 독성학수의사
InChI	1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
InChIKey	COVZYZSDYWQREU-UHFFFAOYSA-N
SMILES	CS(=O)(=O)OCCCCOS(C)(=O)=O
EPA	Busulfan (55-98-1)

화학적 성질

White Crystalline Solid

안전 및 규제

GHS 분류	DangerH300 (17.6%): Fatal if swallowed [Danger Acute toxicity, oral]P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral]
규제 정보	Hazard Traits - CarcinogenicityDevelopmental Toxicity
기타 안전 정보	IMAP assessments - 1,4-Butanediol, dimethanesulfonate: 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 compound may include nausea, vomiting, diarrhea, impotence, sterility, amenorrhea, fetal malformation, depression of erythropoiesis leading to aplastic anemia, diffuse pulmonary fibrosis, precipitation of uric acid in kidney tubules and hemorrhages.
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl busulfan, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
반응성 그룹	Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special Reports	National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 1,4-Butanediol Dimethanesulfonate (Myleran) (55-98-1) is listed as known to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s026buta.pdf]
Reactivity Profile	MYLERAN is an alkylating agent which hydrolyzes in water. (NTP, 1992). Strong reducers may yield hydrogen sulfide.

용도

개요

Chemically, busulfan is classified as an alkyl sulfonate. One or both of the methylsulfonate ester moieties can be displaced by the nucleophilic N7 of guanine, leading to monoalkylated and cross-linked DNA. The extent of alkyl sulfonate–mediated DNA interstrand cross-linking has been shown to vary with the length of the alkyl chain between sulfonate esters, with the tetramethylene-containing busulfan showing less interstrand cross-linking capability than hexamethylene, methylene, or octamethylene analogues. Intrastrand cross-linking also occurs, preferentially at 5′-GA-3′ but also at 5′-GG-3′ sequences. Alkylation of Cys sulfhydryl groups is yet another mechanism of cytotoxicity.

용도

Busulfan USP (Myleran) is used to treat Chronic granulocytic leukemia; other myeloproliferative disorders.

일반 설명

As an alternative to utilizing aziridines as electrophilic species,it was found that simply utilizing a carbon chain terminated atboth ends by leaving groups gave compounds capable of actingas cross-linking agents.Busulfan utilizestwo sulfonate functionalities as leaving groups separated by afour-carbon chain that reacts with DNA to primarily form intrastrandcross-link at 5'-GA-3' sequences.The sulfonatesare also subject to displacement by the sulfhydryl functionsfound in cysteine and glutathione, and metabolic products areformed as a result of nucleophilic attack by these groups togenerate sulfonium species along with methane sulfonicacid.This is followed by conversion to tetrahydrothiophene,and further oxidation products are subsequently produced togive the sulfoxide and sulfone. The cyclic sulfone known assulfolane may be further oxidized to give 3-hydroxysulfolane.