Anidulafungin
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Anidulafungin(F04749) |
| 2D Structure | |
| Description | Anidulafungin or Eraxis is an anti-fungal drug manufactured by Pfizer that gained approval by the Food and Drug Administration (FDA) in February 21, 2006; it was previously known as LY303366. There is preliminary evidence that it has a similar safety profile to caspofungin. |
| FRCD ID | F04749 |
| CAS Number | 166663-25-8 |
| PubChem CID | 166548 |
| Formula | C58H73N7O17 |
| IUPAC Name | None |
| InChI Key | JHVAMHSQVVQIOT-MFAJLEFUSA-N |
| InChI | InChI=1S/C58H73N7O17/c1-5-6-7-24-82-40-22-18-35(19-23-40)33-10-8-32(9-11-33)34-12-14-37(15-13-34)51(74)59-41-26-43(70)54(77)63-56(79)47-48(71)29(2)27-65(47)58(81)45(31(4)67)61-55(78)46(50(73)49(72)36-16-20-38(68)21-17-36)62-53(76)42-25-39(69)28-64(42)57(80)44(30(3)66)60-52(41)75/h8-23,29-31,39,41-50,54,66-73,77H,5-7,24-28H2,1-4H3,(H,59,74)(H,60,75)(H,61,78)(H,62,76)(H,63,79)/t29-,30+,31+,39+,41-,42-,43+,44-,45-,46-,47-,48-,49-,50-,54+/m0/s1 |
| Canonical SMILES | CCCCCOC1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=C(C=C3)C(=O)NC4CC(C(NC(=O)C5C(C(CN5C(=O)C(NC(=O)C(NC(=O)C6CC(CN6C(=O)C(NC4=O)C(C)O)O)C(C(C7=CC=C(C=C7)O)O)O)C(C)O)C)O)O)O |
| Isomeric SMILES | CCCCCOC1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=C(C=C3)C(=O)N[C@H]4C[C@H]([C@H](NC(=O)[C@@H]5[C@H]([C@H](CN5C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]6C[C@H](CN6C(=O)[C@@H](NC4=O)[C@@H](C)O)O)[C@@H]([C@H](C7=CC=C(C=C7)O)O)O)[C@@H](C)O)C)O)O)O |
| Wikipedia | Anidulafungin |
| Synonyms |
V-Echinocandin
Anidulafungin [USAN:INN]
Anidulafungin
Eraxis
166663-25-8
Ecalta
Anidulafungina
Anidulafungine
Anidulafunginum
UNII-9HLM53094I
|
| Classifies |
Predicted: Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Peptides |
| Direct Parent | Oligopeptides |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Alpha-oligopeptide - Cyclic alpha peptide - Para-terphenyl - Terphenyl - N-acyl-alpha amino acid or derivatives - Macrolactam - Biphenyl - Alpha-amino acid or derivatives - Benzamide - Benzoic acid or derivatives - Phenol ether - Phenoxy compound - Benzoyl - Alkyl aryl ether - Phenol - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Monocyclic benzene moiety - Tertiary carboxylic acid amide - Pyrrolidine - Carboxamide group - Secondary carboxylic acid amide - Secondary alcohol - Lactam - Alkanolamine - Azacycle - Organoheterocyclic compound - Polyol - Ether - Carbonyl group - Organic nitrogen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Aromatic alcohol - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 1140.254 |
| Hydrogen Bond Donor Count | 14 |
| Hydrogen Bond Acceptor Count | 17 |
| Rotatable Bond Count | 14 |
| Complexity | 2150 |
| Monoisotopic Mass | 1139.506 |
| Exact Mass | 1139.506 |
| XLogP | 2.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 82 |
| Defined Atom Stereocenter Count | 15 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9833 |
| Human Intestinal Absorption | HIA+ | 0.6513 |
| Caco-2 Permeability | Caco2- | 0.7967 |
| P-glycoprotein Substrate | Substrate | 0.9066 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6298 |
| Inhibitor | 0.6296 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9085 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5421 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7737 |
| CYP450 2D6 Substrate | Non-substrate | 0.8428 |
| CYP450 3A4 Substrate | Substrate | 0.6440 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9490 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8978 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8104 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8827 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8221 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8637 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9863 |
| Inhibitor | 0.6881 | |
| AMES Toxicity | Non AMES toxic | 0.7638 |
| Carcinogens | Non-carcinogens | 0.8077 |
| Fish Toxicity | High FHMT | 0.9953 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9945 |
| Honey Bee Toxicity | Low HBT | 0.7562 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.6908 |
| Carcinogenicity (Three-class) | Non-required | 0.6467 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2132 | LogS |
| Caco-2 Permeability | -0.1476 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7797 | LD50, mol/kg |
| Fish Toxicity | 1.3469 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5421 | pIGC50, ug/L |
Targets
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 Da
References
- Damle BD, Dowell JA, Walsky RL, Weber GL, Stogniew M, Inskeep PB: In vitro and in vivo studies to characterize the clearance mechanism and potential cytochrome P450 interactions of anidulafungin. Antimicrob Agents Chemother. 2009 Mar;53(3):1149-56. doi: 10.1128/AAC.01279-08. Epub 2008 Nov 24. [19029327 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Damle BD, Dowell JA, Walsky RL, Weber GL, Stogniew M, Inskeep PB: In vitro and in vivo studies to characterize the clearance mechanism and potential cytochrome P450 interactions of anidulafungin. Antimicrob Agents Chemother. 2009 Mar;53(3):1149-56. doi: 10.1128/AAC.01279-08. Epub 2008 Nov 24. [19029327 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Damle BD, Dowell JA, Walsky RL, Weber GL, Stogniew M, Inskeep PB: In vitro and in vivo studies to characterize the clearance mechanism and potential cytochrome P450 interactions of anidulafungin. Antimicrob Agents Chemother. 2009 Mar;53(3):1149-56. doi: 10.1128/AAC.01279-08. Epub 2008 Nov 24. [19029327 ]
- Uniprot ID:
- Q5DRK6
- Mechanism of Action:
- Anidulafungin is a semi-synthetic echinocandin with antifungal activity. Anidulafungin inhibits glucan synthase, an enzyme present in fungal, but not mammalian cells. This results in inhibition of the formation of 1,3-β-D-glucan, an essential component of the fungal cell wall.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
- Gene Name:
- CYP2D6
- Uniprot ID:
- P10635
- Molecular Weight:
- 55768.94 Da
References
- Damle BD, Dowell JA, Walsky RL, Weber GL, Stogniew M, Inskeep PB: In vitro and in vivo studies to characterize the clearance mechanism and potential cytochrome P450 interactions of anidulafungin. Antimicrob Agents Chemother. 2009 Mar;53(3):1149-56. doi: 10.1128/AAC.01279-08. Epub 2008 Nov 24. [19029327 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Damle BD, Dowell JA, Walsky RL, Weber GL, Stogniew M, Inskeep PB: In vitro and in vivo studies to characterize the clearance mechanism and potential cytochrome P450 interactions of anidulafungin. Antimicrob Agents Chemother. 2009 Mar;53(3):1149-56. doi: 10.1128/AAC.01279-08. Epub 2008 Nov 24. [19029327 ]