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도옥소루비신

Adriamycin

HCID 6916127
노트반응

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기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
23214-92-8
표준 SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3OC1C[C@H](N)[C@H](O)[C@H](C)O1
분자식
C27H29NO11
평균 분자량
543.52 g/mol

이름 및 식별자

우선 이름
Adriamycin
현지명
도옥소루비신
영어명
Adriamycin
분자식
C27H29NO11
분자량
543.52

이름 및 동의어

도옥소루비신도옥소루비신(DOXORUBICIN)DOXORUBICINDoxilAdriamycin PFSPK 2RubexHydroxydaunoMycinDoxorubicin hydrohloride10-((3-amino-2,3,6-trideoxy-alpha-l-lyso-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione(1s,3s)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside(8S-cis)-10-(3-Amino-2,3,6-Trideoxy-alpha-L-Lyxo-Hexopyranosyl)Oxy-7,8,9,10-Tetrahydro-6,8,11-Trihydroxy-8-(Hydroxyacetyl)-1-Methoxy-5,12-Naphthacenedione

데이터베이스 식별자

CAS
23214-92-8
PubChem CID
6916127
ChEBI
CHEBI:91746

물성

물리화학적 성질

녹는점
205 °C · 205°C
끓는 점
617.77 °C · 617.77°C (rough estimate)
밀도
1.3783 · 1.3783 (rough estimate)
굴절률
1.64 · 1.6400 (estimate)
저장 조건
2 · Keep in dark place,Sealed in dry,2-8°C
용해도
27.2 mg/mL · ≥27.2 mg/mL in DMSO; insoluble in EtOH; ≥24.8 mg/mL in H2O with ultrasonic
물리적 상태
고체
산도 계수 (pKa)
8.2 · pKa 8.2 (Uncertain)
수용성
녹는
InChIKey
AOJJSUZBOXZQNB-XFGIOHMQNA-N
SMILES
OC1C2C(C3=CC=CC(OC)=C3C(=O)C=2C(O)=C2[C@H](C[C@](O)(C(=O)CO)CC=12)O[C@]1([H])O[C@@H](C)[C@@H](O)[C@@H](N)C1)=O |&1:18,20,29,32,34,36,r|
EPA
Doxorubicin (23214-92-8)

화학적 성질

Adriamycin is an orange to red cake-like or needle-like crystalline solid.

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 데이터

독성
An anthracycline cytotoxic antineoplastic that is produced by Streptomyces peucetius. The LD50 in mice is 9.4 mg/kg, i.v. It is a carcinogen that inhibits DNA and RNA synthesis by intercalating in double-stranded DNA with the amino sugar in the minor groove and the 90-OH group of the anthracycline ring hydrogen-bonded to the adjacent guanine. It also alters membrane fluidity and ion transport, and generates free radicals through a cytochrome P450-mediated reductive process. In humans, it causes alopecia, stomatitis, nausea, vomiting, diarrhea, cardiotoxicity (manifested by tachycardia), and potentially fatal congestive heart failure.
HS 번호
2941900000
유해 물질 데이터
23214-92-8(Hazardous Substances Data)

화학 및 산업

응용 분야 · 2건

역사Adriamycin was first discovered in 1967 by Arcamone, Cassinelli, Di Marco, and Gaetani at the FI Research Laboratory. It was found in cultures of a mutant Streptomyces peucetius (Streptomyces peucetius caesius) (Arcamone, 1969). The compound's chemical structure is very similar to daunomycin, the only difference being that a hydrogen atom on the acetyl group is replaced by a hydroxyl group. The new compound is named after the view of the Adriatic Sea from Castel del Monte, where the strain that produced it was isolated. Subsequently, researchers conducted extensive preclinical, pharmacological, toxicological, and formulation studies. However, it wasn't until 1969, when Monfardini published authoritative results in a journal confirming the drug's broad activity spectrum, that it gained widespread attention from the scientific community.

용도Doxorubicin (adriamycin) is the most extensively studied of a family of highly fluorescent anthracycline antibiotics produced by several Streptomyces species, first reported in 1967 and later approved for human therapeutic use as an antitumour agent for the treatment of a wide range of cancers. Doxorubicin also exhibits anti-HIV and antibacterial activity. The mode of action of doxorubicin is thought to be due to intercalation of DNA and inhibition of nucleic acid synthesis.

상·하류 제품 정보

상류 원료

디클로로메탄글루코즈

하류 제품

PirarubicinDoxorubicinol Citrate (Mixture of Diastereomers)

공급사100 곳

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