Amifostine (CED0004747)

Record Information

Version

1.0

Creation Date

2016-05-22 03:37:01 UTC

Update Date

2026-08-22 21:11:30 UTC

SynCED ID

CED0004747

Secondary Accession Numbers

CHEM016559

Identification

Common Name

Amifostine

Class

Small Molecule

Description

Amifostine is an organic compound with the formula C5H15N2O3PS and an average molecular weight of 214.22 g/mol. Amifostine belongs to the organothiophosphorus compounds, a class of organophosphorus compounds within the organic compounds. It is recorded as being released from healthcare, pharmaceuticals & veterinary products, specifically unclassified therapeutic products, and is administered via intravenous exposure. Regarding its biological activity, amifostine acts as an inducer of the protein target Alkaline phosphatase, germ cell type (ALPG).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Amifostina	ChEBI
Amifostinum	ChEBI
Ethyol	ChEBI
Amifostine ethiofos	HMDB
Aminopropylaminoethyl thiophosphate	HMDB
Apaetp	HMDB
Ethiofos	HMDB
Gammaphos	HMDB
SAPEP	HMDB
WR-1065	HMDB
Alza brand OF amifostine	HMDB
Amifostine disodium salt	HMDB
Amifostine trihydrate	HMDB
Anhydrous, amifostine	HMDB
Anhydrous, ethiofos	HMDB
Monohydrochloride, amifostine	HMDB
S-(N-(3-Aminopropyl)-2-aminoethyl)thiophosphoric acid	HMDB
Schering plough brand OF amifostine	HMDB
Amifostine alza brand	HMDB
Amifostine monohydrochloride	HMDB
Disodium salt, amifostine	HMDB
Trihydrate, amifostine	HMDB
US bioscience brand OF amifostine	HMDB
Amifostine lilly brand	HMDB
Aminopropylaminoethylthiophosphoric acid	HMDB
Essex brand OF amifostine	HMDB
Ethiofos anhydrous	HMDB
Lilly brand OF amifostine	HMDB
Schering-plough brand OF amifostine	HMDB
Amifostine anhydrous	HMDB
Amifostine essex brand	HMDB
Amifostine monohydrate	HMDB
Amifostine schering-plough brand	HMDB
Aminopropyl aminoethylthiophosphate	HMDB
Aminopropylaminoethylthiophosphate	HMDB
Monohydrate, amifostine	HMDB
Acid, aminopropylaminoethylthiophosphoric	HMDB
Ethanethiol, 2-((3-aminopropyl)amino)-, dihydrogen phosphate (ester), trihydrate	HMDB

Chemical Formula

C₅H₁₅N₂O₃PS

Average Molecular Mass

214.223 g/mol

Monoisotopic Mass

214.054 g/mol

CAS Registry Number

20537-88-6

IUPAC Name

({2-[(3-aminopropyl)amino]ethyl}sulfanyl)phosphonic acid

Traditional Name

amifostine

SMILES

NCCCNCCSP(O)(O)=O

InChI Identifier

InChI=1S/C5H15N2O3PS/c6-2-1-3-7-4-5-12-11(8,9)10/h7H,1-6H2,(H2,8,9,10)

InChI Key

JKOQGQFVAUAYPM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organothiophosphorus compounds. These are organic derivatives of thiophosphonic acid, thiophosphoric acid, dithiophosphoric acid, or phosphorotrithioic acid, or derivatives thereof. Thiophosphonic acid, dithiophosphoric acid, thiophosphoric acid, and phosphorotrithioic acid are thiophosphorus compounds with the formula OP(O)(=S), OP(S)(=S)O, OP(O)(=S)O, and OP(=S)(S)S, respectively.

Kingdom

Organic compounds

Super Class

Organophosphorus compounds

Class

Organothiophosphorus compounds

Sub Class

Not Available

Direct Parent

Organothiophosphorus compounds

Alternative Parents

Substituents

Sulfenyl compound
Secondary amine
Organothiophosphorus compound
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:2636 )
diamine (CHEBI:2636 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	18.7 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-3.7	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.06	ChemAxon
pKa (Strongest Basic)	11.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	95.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	51.28 m³·mol⁻¹	ChemAxon
Polarizability	21.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001i-9300000000-8f3e83d23b65b9a18769	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-5350b8c906608c1eb7e4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-bcddc871edb434e577ae	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-2900000000-58ff84f991edcac36e7d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05nb-9200000000-ef847b9b156a08e7fa17	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4l-9000000000-c58215f6bca055f13ab7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014s-2930000000-d9f7a8f51a3e0639844f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kal-9500000000-deee317641b354488f7c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-9200000000-b4b822595957219239b7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-7690000000-f26c0991b61c8d4975ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-003s-7900000000-4a37816d6ed768e56c53	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05dm-9800000000-940b1a6dd1f6e79e9c0f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0390000000-2033745753817e8b82af	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9100000000-220c1777754513503a2d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08fr-9000000000-8b437daef02c3cdba4c4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0090000000-c0bd8a7c35f5f698e7fb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9300000000-19aa33fa42f40d1742f5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9000000000-a5e502a2627af2048a1f	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
237.0 Log mg/kg [130:420]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000409	Unclassified therapeutic products?Unclassified therapeutic products encompass a range of substances used in medical and veterinary contexts that have not undergone formal classification processes.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000732	Spectacle Cases?Spectacle cases can serve as a source of synthetic chemical contamination due to the materials used in their production, such as polycarbonate, PVC, and various plastics, which may leach harmful substances over time.	Healthcare, pharmaceuticals & veterinary products	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Amifostine Drug Metabolism

Amifostine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Acetylpolyamine amidohydrolase	Q48935	Mycoplana ramosa	Predicted (SEA)	Prediction Confidence Score 0.359 Applicability Domain 0.359 Statistical Significance 3.00e-05 Supporting Reference Compounds 1 E-value 0.233548
Click to view 3D structure	Carbonic anhydrase 4	P22748	Humans	Predicted (SEA)	Prediction Confidence Score 0.337 Applicability Domain 0.462 Statistical Significance 0.0074 Supporting Reference Compounds 193 E-value 57.842
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.462 Statistical Significance 0.0117 Supporting Reference Compounds 242 E-value 91.3171
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.462 Statistical Significance 0.0066 Supporting Reference Compounds 151 E-value 51.3026
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.462 Statistical Significance 0.0088 Supporting Reference Compounds 172 E-value 68.5073
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.462 Statistical Significance 0.0074 Supporting Reference Compounds 157 E-value 57.5306
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.462 Statistical Significance 0.0089 Supporting Reference Compounds 165 E-value 69.1301
Click to view 3D structure	Isopentenyl-diphosphate Delta-isomerase 1	O35760	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.282 Applicability Domain 0.282 Low confidence Statistical Significance 8.00e-05 Supporting Reference Compounds 1 E-value 0.622794
Click to view 3D structure	Farnesyl pyrophosphate synthase	P05369	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.282 Applicability Domain 0.282 Low confidence Statistical Significance 8.00e-05 Supporting Reference Compounds 1 E-value 0.622794
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	Prediction Confidence Score 0.278 Applicability Domain 0.444 Statistical Significance 0.0613 Supporting Reference Compounds 372 E-value 477.138
Click to view 3D structure	Deoxyhypusine synthase	Q6AY53	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.277 Applicability Domain 0.324 Statistical Significance 1.00e-04 Supporting Reference Compounds 3 E-value 0.778492
Click to view 3D structure	Farnesyl synthetase, putative	Q964Q8	Trypanosoma cruzi	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.308 Statistical Significance 3.90e-04 Supporting Reference Compounds 2 E-value 3.03612
Click to view 3D structure	Farnesyl diphosphate synthase	Q197X6	Toxoplasma gondii	Predicted (SEA)	Prediction Confidence Score 0.252 Applicability Domain 0.308 Statistical Significance 3.20e-04 Supporting Reference Compounds 4 E-value 2.49118
Click to view 3D structure	Deoxyhypusine synthase	Q9GSW0	Plasmodium falciparum	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.25 Low confidence Statistical Significance 0.001 Supporting Reference Compounds 1 E-value 8.01847
Click to view 3D structure	Sodium- and chloride-dependent GABA transporter 2	P31646	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.25 Low confidence Statistical Significance 5.20e-04 Supporting Reference Compounds 1 E-value 4.04816
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.444 Statistical Significance 0.1949 Supporting Reference Compounds 472 E-value 1517.28
Click to view 3D structure	Putative agmatine deiminase	Q8DW17	Streptococcus mutans serotype c (strain ATCC 700610 / UA159)	Predicted (SEA)	Prediction Confidence Score 0.243 Applicability Domain 0.243 Low confidence Statistical Significance 2.00e-04 Supporting Reference Compounds 1 E-value 1.55698
Click to view 3D structure	Glutamate receptor 1	P19490	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.304 Statistical Significance 0.0151 Supporting Reference Compounds 37 E-value 117.708
Click to view 3D structure	Putative amino acid permease/transporter	D5FGE8	Trypanosoma cruzi	Predicted (SEA)	Prediction Confidence Score 0.239 Applicability Domain 0.239 Low confidence Statistical Significance 0.0013 Supporting Reference Compounds 1 E-value 9.809
Click to view 3D structure	Carbonic anhydrase 15	Q99N23	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.233 Applicability Domain 0.444 Statistical Significance 0.0461 Supporting Reference Compounds 78 E-value 358.651
Click to view 3D structure	Polyamine oxidase 1	O64411	Zea mays	Predicted (SEA)	Prediction Confidence Score 0.229 Applicability Domain 0.257 Low confidence Statistical Significance 5.80e-04 Supporting Reference Compounds 2 E-value 4.51525
Click to view 3D structure	Farnesyl diphosphate synthase	Q8WS26	Trypanosoma cruzi	Predicted (SEA)	Prediction Confidence Score 0.225 Applicability Domain 0.308 Statistical Significance 4.60e-04 Supporting Reference Compounds 5 E-value 3.58106
Click to view 3D structure	Ornithine transcarbamylase, mitochondrial	P00480	Humans	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.222 Low confidence Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 13.5458
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	Prediction Confidence Score 0.221 Applicability Domain 0.444 Statistical Significance 0.3168 Supporting Reference Compounds 407 E-value 2466.34
Click to view 3D structure	Isopentenyl-diphosphate Delta-isomerase	Q46822	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.22 Applicability Domain 0.22 Low confidence Statistical Significance 3.80e-04 Supporting Reference Compounds 1 E-value 2.95827