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6-티오구아닌

6-티오구아닌
6-티오구아닌 구조식 이미지
카스 번호:
154-42-7
한글명:
6-티오구아닌
동의어(한글):
6-티오구아닌;치오구아닌;싸이오구아닌
상품명:
6-Thioguanine
동의어(영문):
6-tg;bw5071;lanvis;nsc-752;tabloid;tioguanin;tioguanine;Guanine, t;thio-guanin;wellcomeu3b
CBNumber:
CB6361837
분자식:
C5H5N5S
포뮬러 무게:
167.19
MOL 파일:
154-42-7.mol

6-티오구아닌 속성

녹는점
≥300 °C(lit.)
밀도
1.483 (estimate)
굴절률
1.5605 (estimate)
저장 조건
2-8°C
용해도
Practically insoluble in water and in ethanol (96%). It dissolves in dilute solutions of alkali hydroxides.
끓는 점
555.4±42.0 °C(Predicted)
산도 계수 (pKa)
pKa 8.22 (Uncertain)
물리적 상태
lyophilized powder
색상
Yellow to green
수용성
soluble
Merck
14,9337
BRN
157765
CAS 데이터베이스
154-42-7(CAS DataBase Reference)
EPA
Thioguanine (154-42-7)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,Xi
위험 카페고리 넘버 25-23/24/25
안전지침서 28-36/37/39-45-28A
유엔번호(UN No.) UN 2811 6.1/PG 3
WGK 독일 3
RTECS 번호 UP0740000
F 고인화성물질 13
위험 참고 사항 Irritant
위험 등급 6.1
포장분류 III
HS 번호 29335990
유해 물질 데이터 154-42-7(Hazardous Substances Data)
독성 LD50 oral in mouse: 160mg/kg
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H301 삼키면 유독함 급성 독성 물질 - 경구 구분 3 위험 P264, P270, P301+P310, P321, P330,P405, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
예방조치문구:
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P321 (…) 처치를 하시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

6-티오구아닌 MSDS


6-Thioguanine

6-티오구아닌 C화학적 특성, 용도, 생산

화학적 성질

Crystalline, lyophilized, sterile, endot

Originator

Thioguanine,Burroughs-Wellcome,US,1966

용도

6-Thioguanine acts as an antineoplastic and purine antimetabolite. It is also useful as an inhibition of stimulated expression of TNF-related apoptosis-inducing ligand (TRAIL) protein. It is involved in the treatment of acute leukemias and Psoriasis. Further, it is used for the treatment of ulcerative colitis and autoimmune diseases.

용도

antineoplastic, purine antimetabolite

용도

The compound produced dose-dependent inhibition of stimulated expression of TRAIL protein

용도

Thioguanine USP (Tabloid)is used to treat acute leukemia; chronic granulocytic leukemia.

Indications

Thioguanine is an analogue of the natural purine guanine in which a hydroxyl group has been replaced by a sulfhydryl group in the 6-position. Two major mechanisms of cytotoxicity have been proposed for 6-thioguanine: (1) incorporation of the thio nucleotide analogue into DNA or RNA and (2) feedback inhibition of purine nucleotide synthesis.
The product of this reaction, 6-TGMP, can eventually be converted to deoxy-6-thioguanosine-triphosphate (dTGTP), which has been shown to be incorporated into DNA. Resistance of human leukemia cells to thioguanine has been correlated with decreased activity of HGPRTase and to increased inactivation of the thio nucleotides by alkaline phosphatase.
Thioguanine is slowly absorbed after oral administration; parent drug levels are barely detectable, and peak levels of metabolites occur only after 6 to 8 hours. Total urinary excretion of metabolites in the first 24 hours is 24 to 46% of the administered dose.
Thioguanine is used primarily as part of a combined induction of chemotherapy in acute myelogenous leukemia.
Myelosuppression, with leukopenia and thrombocytopenia appearing 7 to 10 days after treatment, and mild nausea are the most common adverse effects. Liver toxicity with jaundice has been reported in some patients but appears to be less common than with mercaptopurine.

Indications

6-Thioguanine is a purine analogue structurally related to 6-mercaptopurine and azathioprine. Thioguanine interferes with several enzymes required for de novo purine synthesis, and its metabolites are incorporated into DNA and RNA, further impeding nucleic acid synthesis. The mechanism of action of thioguanine in psoriasis is not clearly understood; it has been hypothesized to affect the proliferation and trafficking of lymphocytes as well as the proliferation of keratinocytes.

정의

ChEBI: A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine.

Manufacturing Process

A mixture of 2.7 grams of finely divided guanine, 10 grams of pulverized phosphorus pentasulfide, 10 ml of pyridine and 100 ml of tetralin was heated at 200°C with mechanical stirring for 5 hours. After cooling, the mixture was filtered and the insoluble residue treated with 150 ml of water and 50 ml of concentrated ammonium hydroxide. The ammoniacal solution was filtered, heated to boiling and acidified with acetic acid. Upon cooling, 2-amino-6- mercaptopurine precipitated as a dark yellow powder, according to US Patent 2,697,709.

상표명

Tioguanine is INN and BAN.

Therapeutic Function

Cancer chemotherapy

일반 설명

The drug is available in 40-mg tablets for oral use.Thioguanine is used to treat acute nonlymphocytic leukemia.The mechanism of action involves incorporation of thetriphosphate into DNA and RNA, resulting in inhibition ofprocessing and function. Intracellular phosphorylation is requiredfor activity and inhibition of purine biosynthesis.Resistance can include decreased expression of the activatingenzyme, decreased drug transport, and/or increased expressionof catabolic enzymes. The oral absorption ofthioguanine is poor, and the drug does not appear to cross theblood-brain barrier. Major metabolic pathways involvedeamination or methylation. Thioguanine is not a substratefor the enzyme xanthine oxidase in contrast to mercaptopurine.Toxicities include myelosuppression, immunosuppression,nausea, vomiting, mucositis, and diarrhea.

일반 설명

Odorless or almost odorless pale yellow crystalline powder.

공기와 물의 반응

6-Thioguanine may be sensitive to prolonged exposure to air. Insoluble in water.

반응 프로필

6-Thioguanine is incompatible with strong oxidizing agents. .

화재위험

Flash point data for 6-Thioguanine are not available; however, 6-Thioguanine is probably combustible.

Biochem/physiol Actions

Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.

Mechanism of action

Absorption of orally administered 6-thioguanine is slow and incomplete; only approximately 30% of the oral dose is achieved in the plasma, peak levels being reached after 8 hours. Thioguanine is extensively metabolized prior to excretion. The elimination half-life is on the order of 80 minutes.

Clinical Use

Although 6-thioguanine is chiefly used in chemotherapy for acute myelocytic leukemia and other marrow-based malignancies, lower doses are very effective for moderate to severe psoriasis, particularly in patients who cannot tolerate alternative systemic agents such as methotrexate and cyclosporine.

부작용

Dose-related myelosuppression is the major adverse effect produced by 6-thioguanine. Patients deficient in thiopurine methyltransferase (TPMT), a cytosolic enzyme required for metabolism of 6-thioguanine, are at heightened risk. Other adverse effects include gastrointestinal complaints and elevations of liver transaminases. There have been rare reports of more serious hepatotoxicity, including acute hepatitis, acute cholestasis, and hepatic venoocclusive disease.

Safety Profile

Poison by ingestion andintraperitoneal routes. Human mutation data reported. Anexperimental teratogen. Other reproductive effects. Ahuman skin irritant. When heated to decomposition itemits very toxic fumes of SOx and NOx.

Chemical Synthesis

Thioguanine, 2-aminopurin-6-thiol (30.1.2.12), is made from 2,8-dichloro- 6-hydroxypurine (30.1.2.7), in which the second chlorine atom at C2 is replaced with an amino group when reacted with ammonia, forming 2-amino-8-chloro-6-hydroxy-purine (30.1.2.7), which is then reduced by hydrogen iodide to 2-aminopurin-6-ol (30.1.2.11). Replacement of the hydroxyl group with a mercapto group at C6 is carried out by reacting it with phosphorous pentasulfide, which forms thioguanine (30.1.2.12).

Veterinary Drugs and Treatments

Thioguanine may be useful as adjunctive therapy for acute lymphocytic or granulocytic leukemia in dogs or cats.

Purification Methods

It crystallises from H2O as needles. It has UV at 258 and 347nm (H2O, pH 1) and 242, 270 and 322nm max (H2O, pH 11). [Elion & Hitchings J Am Chem Soc 77 1676 1955, Fox et al. J Am Chem Soc 80 1669 1958.] It is an antineoplastic agent [Kataoka et al. Cancer Res 44 519 1984]. [Beilstein 26 III/IV 3926.]

6-티오구아닌 준비 용품 및 원자재

원자재

준비 용품


6-티오구아닌 공급 업체

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