(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-amino-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-carboxylic acid

• ChemBase编号: 563
• 分子式: C47H73NO17
• 平均质量: 924.07902
• 单一同位素质量: 923.48784988
• SMILES: [C@H]12[C@@H]([C@H](C[C@](O1)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]([C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C2)O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)C)O)N)O)C)O)C)C)O)O)O)O)O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1CC[C@@H](O)[C@H](O)C[C@H](O)C[C@]2(O)C[C@H](O)[C@H]([C@@H](O2)C[C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H]([C@H]([C@H]([C@@H](OC(=O)C[C@@H](C1)O)C)C)O)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)C(=O)O
• InChI: InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
• InChIKey: APKFDSVGJQXUKY-INPOYWNPSA-N

名称和登记号

名称

• IUPAC标准名: (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-amino-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-carboxylic acid
• IUPAC传统名: amphotericin B
• 商标名: ABLC; Abelcet; AmB; AmBisome; Ampho-Moronal; Amphocin; Amphotec; Amphotericin; Amphozone; Fungilin; Fungisone; Fungizone; Fungizone Intravenous; HSDB 3008 IAB; Halizon; IAB; LNS-AmB; Mysteclin-F; Tegopen; SinuNase
• 别名: AMPH-B; Amphortericin B; Amphotericine B; Liposomal Amphotericin B; amphotericin B; Amphotericin B; Amphomoronal; Amphozone; Fungilin; Fungisone; Fungizone

登记号

• CAS号: 1397-89-3
• EC号: 215-742-2
• PubChem SID: 46505473; 160964026
• PubChem CID: 14956; 5280965
• CHEBI ID: 2682
• ATC码: A01AB04; A07AA07; G01AA03; J02AA01
• CHEMBL: 267345
• Chemspider ID: 10237579
• DrugBank ID: DB00681
• KEGG ID: D00203
• 维基百科标题: Amphotericin_B

理论计算性质

JChem

• Acid pKa: 3.5797393
• 质子受体: 17
• 质子供体: 12
• LogD (pH = 5.5): -2.3028812
• LogD (pH = 7.4): -2.3064086
• Log P: -2.3001616
• 摩尔折射率: 244.6705 cm^3
• 极化性: 94.662575 Å^3
• 极化表面积: 319.61 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -0.66
• LOG S: -4.05
• 溶解度: 8.19e-02 g/l

分子性质

理化性质

• 溶解度: 750 mg/L
• 熔点: >170°C
• 疏水性(logP): 0.8

安全信息

• 保存条件: 2-8°C
• RTECS编号: BU2625000

药理学性质

• 给药途径: slow i.v.-infusion only
• 生物利用度: 100% (IV)
• 排泄: 40% found in urine after single cumulated over several days ; biliar excretion also important
• 半衰期: initial phase : 24 hours, ; second phase : approx. 15 days
• 代谢: renal
• 法定药品分级: Rx-only, hospitalization recommended.
• 妊娠期药物分类: B (US)

详细说明

MP Biomedicals - 02195043

An Antifungal agent produced by Streptomyces species.

DrugBank - DB00681

• Drug Groups: approved; investigational
• Description: 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.
• Indication: Used to treat potentially life threatening fungal infections.
• Pharmacology: 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.
• Toxicity: Oral, rat: LD₅₀ = >5 gm/kg. Amphotericin B overdoses can result in cardio-respiratory arrest.
• Affected Organisms: Various Fungus Species
• Biotransformation: Exclusively renal
• Absorption: Bioavailability is 100% for intravenous infusion.
• Half Life: An elimination half-life of approximately 15 days follows an initial plasma half-life of about 24 hours.
• Protein Binding: Highly bound (>90%) to plasma proteins.
• Clearance: * 39 +/- 22 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day at Day 1]; * 17 +/- 6 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day 3-20 days later]; * 51 +/- 44 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 2.5 mg/kg/day at Day 1]; * 22 +/- 15 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 2.5 mg/kg/day 3-20 days later]; * 21 +/- 14 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 5 mg/kg/day at Day 1]; * 11 +/- 6 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 5 mg/kg/day 3-20 days later]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• R.C. Pandey, K.L. Rinehart, J. Antibiot., 29: 1035, (1976)
• Mechlinski, et al., Tetrahedron Letters, 3873, (1970).