(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-azaniumyl-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
기본 정보
- CAS
1397-89-3- 표준 SMILES
C[C@@H]1[C@H](O)[C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H]([NH3+])[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@H]1C)C[C@H](O)[C@H]2C(=O)[O-]- InChIKey
APKFDSVGJQXUKY-INPOYWNPSA-N- 분자식
- C47H73NO17
- 평균 분자량
- 924.1 g/mol
- 단동위원소 질량
- 923.48784986
개요
Amphotericin B shows a high order of in vitro activity against many species of fungi. Histoplasma capsulatum, Coccidioides immitis, Candida species, Blastomyces dermatitidis, Rhodotorula, Cryptococcus neoformans, Sporothrix schenckii, Mucor mucedo, and Aspergillus fumigatus are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL in vitro. While Candida albicans is generally quite susceptible to amphotericin B, non-albicans species may be less susceptible. Pseudallescheria boydii and Fusarium sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses.
이름 및 식별자
- 우선 이름
- (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-azaniumyl-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
- IUPAC
- (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-azaniumyl-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
- 영어명
- Amphotericin B
- 분자식
- C47H73NO17
- 분자량
- 924.08
이름 및 동의어
AMPHOTERICINAMBISOMEFUNGIZONEABELCETfungilinApotheconAMphotericin B (Abelcet)33-[(3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-Amino-3,6-dideoxy-.beta.-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acidns718
데이터베이스 식별자
- CAS
1397-89-3- PubChem CID
- 91819969
물성
구조 계산 물성
- XLogP
- 0.6
- 극성 표면적
- 324 Ų
- 수소 결합 공여자 수
- 11
- 수소 결합 수용자 수
- 17
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 65
- 형식 전하
- 0
- 복잡도
- 1,660
실험 및 물리화학적 성질
LipidsPolyketides [PK] -> Polyenes [PK06]
LogP0.8
Solubility8.19e-02 g/L
Melting Point170.0 °C
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 170 °C · >170°C
- 끓는 점
- 804.34 °C · 804.34°C (rough estimate)
- 밀도
- 1.34 · 1.34
- 굴절률
- 1.528 · 1.5280 (estimate)
- 저장 조건
- 2 · 2-8°C
- 용해도
- 20 mg/mL · 멸균수: 원액으로 20mg/mL. 스톡 솔루션은 −20°C에 보관되어야 합니다. 37°C에서 3일 동안 안정합니다.
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 5.7 · pKa ~5.7(DMF/H2O) (Uncertain)
- 색상
- 노란색
- 수용성
- 21 °C에서 · 21°C에서 <0.1g/100mL
- Merck
- 13 · 13,590
- BRN
- 78342 · 78342
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
안전 데이터
- wgk
- 3
- rtecs
- BU2625000
- ridadr
- UN 1759 8/PG 3
- 독성
- LD50 in mice (mg/kg): 88 i.p., 4 i.v. (Keim)
- HS 번호
- 29419090
- risk_code
- 36/37/38-22-40-23/24/25
- hazard_code
- C,Xi,Xn,T
- safety_code
- 26-36/37/39-45-36-60-37
- 포장분류
- III
- 위험 등급
- 6.1(b)
- F 고인화성물질
- 8-10-21
- Hazard Classifications
- STOT RE 1
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 유해 물질 데이터
- 1397-89-3(Hazardous Substances Data)
화학 및 산업
약리 정보
Protein BindingHighly bound (>90%) to plasma proteins.
Pharmacodynamics
Amphotericin B shows a high order of <i>in vitro</i> activity against many species of fungi. <i>Histoplasma capsulatum</i>, <i>Coccidioides immitis</i>, <i>Candida species</i>, <i>Blastomyces dermatitidis</i>, <i>Rhodotorula</i>, <i>Cryptococcus neoformans</i>, <i>Sporothrix schenckii</i>, <i>Mucor mucedo</i>, and <i>Aspergillus fumigatus</i> are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL <i>in vitro</i>. While <i>Candida albicans</i> is generally quite susceptible to amphotericin B, non-<i>albicans</i> species may be less susceptible. <i>Pseudallescheria boydii</i> and <i>Fusarium</i> sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses.
Mechanism of Action
Amphotericin B is fungistatic or fungicidal depending on the concentration obtained in body fluids and the susceptibility of the fungus. The drug acts by binding to sterols (ergosterol) in the cell membrane of susceptible fungi. This creates a transmembrane channel, and the resultant change in membrane permeability allowing leakage of intracellular components. Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of amphotericin B and the azoles. Amphotericin B, a polyene, binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death.
Biological Half-LifeAn elimination half-life of approximately 15 days follows an initial plasma half-life of about 24 hours.
Metabolism/MetabolitesExclusively renal
Absorption, Distribution and Excretion
Bioavailability is 100% for intravenous infusion.
39 +/- 22 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day at Day 1]
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