Details of the Drug

General Information of Drug (ID: DM5FL14)

Drug Name
Amifostine
Synonyms Ethiofos; Ethyol; Gammaphos; WR-1064; WR-2721; WR-2721C; YM-08310
Indication
Disease Entry ICD 11 Status REF
Mucositis CA00 Approved [1]
Affected Organisms
Humans and other mammals
ATC Code
V03AF05: Amifostine
V03AF: Detoxifying agents for antineoplastic treatment
V03A: ALL OTHER THERAPEUTIC PRODUCTS
V03: ALL OTHER THERAPEUTIC PRODUCTS
V: VARIOUS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 214.23
Logarithm of the Partition Coefficient (xlogp) -4.5
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Bioavailability
99% of drug becomes completely available to its intended biological destination(s) [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 30.65 mL/min/kg [4]
Elimination
0.69% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 8 minutes [4]
Metabolism
The drug is metabolized via the alkaline phosphatase in tissues primarily to the active free thiol metabolite and, subsequently, to a less active disulfide metabolite []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 105 micromolar/kg/day [5]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.09 L/kg [4]
Chemical Identifiers
Formula
C5H15N2O3PS
IUPAC Name
2-(3-aminopropylamino)ethylsulfanylphosphonic acid
Canonical SMILES
C(CN)CNCCSP(=O)(O)O
InChI
InChI=1S/C5H15N2O3PS/c6-2-1-3-7-4-5-12-11(8,9)10/h7H,1-6H2,(H2,8,9,10)
InChIKey
JKOQGQFVAUAYPM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2141
ChEBI ID
CHEMBL1006
CAS Number
20537-88-6
UNII
ILA426L95O
DrugBank ID
DB01143
TTD ID
D06CIE
INTEDE ID
DR0085
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Toxic reactive metabolite (TRM) TT0C9DV NOUNIPROTAC Modulator [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Alkaline phosphatase (ALPL)
Main DME 		DEVEFKM PPBT_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [7]
Etoposide-induced protein 2.4 homolog (EI24) OTD4NOYS EI24_HUMAN Gene/Protein Processing [7]
Quinone oxidoreductase PIG3 (TP53I3) OTSCM68G QORX_HUMAN Gene/Protein Processing [7]
Transcription factor p65 (RELA) OTUJP9CN TF65_HUMAN Protein Interaction/Cellular Processes [8]
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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Amifostine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Etelcalcetide DMHP9BL Major Increased risk of hypocalcemia by the combination of Amifostine and Etelcalcetide. Hyper-parathyroidism [5A51] [9]

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 BDDCS applied to over 900 drugs
3 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Pharmacokinetic profile of amifostine. Semin Oncol. 1996 Aug;23(4 Suppl 8):18-22.
7 Amifostine impairs p53-mediated apoptosis of human myeloid leukemia cells. Mol Cancer Ther. 2003 Sep;2(9):893-900.
8 Amifostine inhibits hematopoietic progenitor cell apoptosis by activating NF-kappaB/Rel transcription factors. Blood. 1999 Dec 15;94(12):4060-6.
9 Cerner Multum, Inc. "UK Summary of Product Characteristics.".