アザチオプリン

アザチオプリン · 6-(1-メチル-4-ニトロ-5-イミダゾリルチオ)-9H-プリン · イムレル · アザニン · 6-(1-メチル-4-ニトロ-1H-イミダゾール-5-イルチオ)-1H-プリン · 6-[(1-メチル-4-ニトロ-1H-イミダゾール-5-イル)チオ]-1H-プリン · イムラン · 6-(1-メチル-4-ニトロイミダゾール-5-イル)チオプリン

https://huagongshe.com/ja/chemical/2265

識別子と物理属性

CAS No.	446-86-6
分子式	C9H7N7O2S
平均分子量	277.27 g/mol
単同位体質量	277.03819346 g/mol
SMILES	Cn1cnc([N+](=O)[O-])c1Sc1ncnc2nc[nH]c12
InChIKey	LMEKQMALGUDUQG-UHFFFAOYSA-N
PubChem CID	2265
ChEMBL	CHEMBL1542
ChEBI	CHEBI:2948
EC No.	207-175-4
DTXSID	DTXSID4020119
現地名	アザチオプリン

化学・物理的性質

XLogP	0.1
極性表面積	143
水素結合供与体数	1
水素結合受容体数	7
回転可能結合数	2
重原子数	19
形式電荷	0
複雑度	354
物質分類	Other Uses -> Pharmaceuticals
医薬品	PharmaceuticalsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland
LogP（分配係数）	log Kow = 0.100.70.89
Color/Form	Pale yellow crystals from 50% aq acetone
溶解度	less than 1 mg/mL at 73 °F (NTP, 1992)InsolubleVery slightly soluble in ethanol and chloroformsparingly soluble in dilute mineral acidssoluble in dilute alkali solutionsInsoluble in water1.07e+00 g/L>41.6 [ug/mL] (The mean of the results at pH 7.4)ジクロロメタンおよびジメチルスルホキシドに可溶。<0.1 g/100 mL で 23 ºC
Human Drugs	Breast FeedingLactationMilk, HumanImmunosuppressive AgentsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicinePharmaceuticalsDisease-modifying anti-rheumatic drugs (DMARDs)
Decomposition	When heated to decomposition it emits toxic fumes of /nitric oxides & sulfur oxides/.
融点	469 to 471 °F (decomposes) (NTP, 1992)dec 243-244 °C243.5 °C243-244°C
Physical Description	Azathioprine appears as pale yellow crystals or yellowish powder. Decomposes at 243-244 °C. Used for the treatment of rheumatoid arthritis. A known carcinogen.Solid
Stability/Shelf Life	Azathioprine... is stated to be stable in neutral or acid solns but is hydrolyzed to mercaptopurine in alkaline solns, expecially on warming. Max stability occurs at pH 5.5-6.5. Hydrolysis to mercaptopurine also occurs in the presence of sulfhydryl compounds such as cysteine. /Azathioprine sodium/
Dissociation Constants	7.87 (at 25 °C)pKa = 8.2
Collision Cross Section	172.4 Å² [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID4020119]155.1 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
沸点	521.0±60.0 °C(Predicted)
密度	1.5379 (rough estimate)
屈折率	1.7400 (estimate)
貯蔵条件	2-8°C
pKa（酸解離定数）	8.2(at 25℃)
外観・状態	Solid
色	Me2CO (aq) からの淡黄色の結晶
由来生物	synthetic (organic)
Merck	14,902
BCS Class	4
安定性	安定。強酸化剤、強塩基とは相容れない。
InChI	1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChIKey	LMEKQMALGUDUQG-UHFFFAOYSA-N
SMILES	Cn1cnc(c1Sc2ncnc3[nH]cnc23)[N+]([O-])=O
CAS データベース	446-86-6(CAS DataBase Reference)
EPAの化学物質情報	Azathioprine (446-86-6)

化学的特性

Azathioprine is a complex heterocyclic compound which forms pale yellow crystals.

安全性と法規制

GHS 分類	DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, 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 107 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302: Harmful if swallowed [Warning Acute toxicity, oral]
規制情報	Hazard Traits - CarcinogenicityDevelopmental ToxicityAzathioprine: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報	IMAP assessments - 1H-Purine, 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-: Environment tier I assessment
火災危険	Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
健康有害性	SYMPTOMS: Symptoms of exposure to this compound may include bone marrow depression, increased risk of infection, toxic hepatitis and biliary stastis.
有害性の概要	Allergic contact dermatitis reported in pharmaceutical workers (a packaging worker and a mechanic)[Kanerva, p. 1753]
FDA 要件	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl azathioprine and azathioprine sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
反応性グループ	Amines, Phosphines, and Pyridines
Special Reports	/A review of literature/ to assess the short-term effects of azathioprine for the treatment of rheumatoid arthritis.[Suarez-Almazor ME et alCochrane Database Sysy Rev 4: CD001461 (2001)]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. Azathioprine (446-86-6) 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/s018azat.pdf]

用途

解説

アザチオプリン，6-[(1-methyl-4-nitroimidazol-5-yl)thio]purine．C9H7N7O2S(277.27)．6-スルファニルプリンと5-クロロ-1-メチル-4-ニトロイミダゾールとを縮合させると得られる淡黄色の結晶．分解点約240 ℃．λmax 276 nm(ε 1.82×104)．アルカリ水溶液に可溶，ピリジン，DMFに微溶．プリン代謝を阻害し，抗体産生を抑制する免疫抑制剤で，腎移植手術に使用される

用途

生体内で 6- メルカプトプリンに変換され、DNA 合成抑制作用を示します。

用途

生体内で 6- メルカプトプリンに変換され、DNA 合成阻害作用を示します。

用途

免疫抑制剤。臓器移植、関節リウマチの治療に使用。

説明

This immunosuppressive and antineoplastic drug is derived from 6-mercaptopurine. It caused occupational dermatitis in a pharmaceutical worker, reconditioner of old tablet packaging machines and in a production mechanic, working in packaging for a pharmaceutical company.

使用

An immunosuppressive antimetabolite. Also active as disease modifying antirheumatic drug (DMARD). Azathioprine is a purine analog with immunosuppressive effects.

一般的な説明

Pale yellow crystals or yellowish powder. Decomposes at 243-244°C. Used for the treatment of rheumatoid arthritis. A known carcinogen.