amifostine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
insecticides, anthelminthics, pesticides etc., phosphorous derivatives 156 20537-88-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • amifostine
  • aminopropylaminoethyl thiophosphate
  • ethiofos
  • gammaphos
  • WR-2721
  • amifostine trihydrate
A phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia.
  • Molecular weight: 214.22
  • Formula: C5H15N2O3PS
  • CLOGP: -1.85
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 4
  • TPSA: 95.58
  • ALOGS: -1.06
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.70 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.69 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 105 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.09 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 30.65 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.15 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 8, 1995 FDA CLINIGEN HLTHCARE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pyrexia 45.33 40.80 39 655 403154 52945218

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Mucosal inflammation 133.09 35.59 54 1669 33380 32478423
Laryngeal pain 123.77 35.59 29 1694 2830 32508973
Pyrexia 89.25 35.59 96 1627 319872 32191931
Chills 67.02 35.59 45 1678 78039 32433764
Hypotension 63.72 35.59 67 1656 216043 32295760
Soft tissue disorder 62.86 35.59 13 1710 709 32511094
Rash 54.81 35.59 61 1662 209272 32302531
Dehydration 50.94 35.59 47 1676 128911 32382892
Nausea 46.89 35.59 70 1653 320779 32191024
Dermatitis 44.86 35.59 17 1706 8687 32503116
Injection site reaction 43.54 35.59 18 1705 11551 32500252
Vomiting 41.10 35.59 56 1667 235501 32276302
Radiation skin injury 40.05 35.59 9 1714 726 32511077
Injection site erythema 36.30 35.59 17 1706 14651 32497152
Rash maculo-papular 36.23 35.59 21 1702 28001 32483802
Pruritus 36.13 35.59 39 1684 128663 32383140

Pharmacologic Action:

SourceCodeDescription
ATC V03AF05 VARIOUS
ALL OTHER THERAPEUTIC PRODUCTS
ALL OTHER THERAPEUTIC PRODUCTS
Detoxifying agents for antineoplastic treatment
CHEBI has role CHEBI:22586 antioxidants
CHEBI has role CHEBI:50266 Prodrugs
CHEBI has role CHEBI:66987 radiation protective agents
MeSH PA D020011 Protective Agents
MeSH PA D011837 Radiation-Protective Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Prevention of Xerostomia Secondary to Radiation Therapy indication
Prevention of Cancer Chemotherapy-Induced Renal Impairment indication
Myelodysplastic syndrome off-label use 109995007
Drug-induced mucositis off-label use 403666006
Chemotherapy-induced neutropenia off-label use 425229001
Prevention of Chemotherapy-Induced Neurotoxicity off-label use
Prevention of Radiation Therapy-Induced Mucositis off-label use
Hypocalcemia contraindication 5291005
Hypovolemia contraindication 28560003
Dehydration contraindication 34095006
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Cerebrovascular accident contraindication 230690007
Transient ischemic attack contraindication 266257000 DOID:224
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Vomiting contraindication 422400008
Nausea contraindication 422587007

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.67 acidic
pKa2 10.06 Basic
pKa3 8.46 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
D(3) dopamine receptor GPCR Ki 6.18 DRUG MATRIX
Alkaline phosphatase, tissue-nonspecific isozyme Enzyme WOMBAT-PK

External reference:

IDSource
4020970 VUID
N0000148443 NUI
D00226 KEGG_DRUG
1545987 RXNORM
C0015020 UMLSCUI
CHEBI:2636 CHEBI
CHEMBL1006 ChEMBL_ID
DB01143 DRUGBANK_ID
D004999 MESH_DESCRIPTOR_UI
2141 PUBCHEM_CID
112901-68-5 SECONDARY_CAS_RN
M487QF2F4V UNII
133029 MMSL
4164 MMSL
d03868 MMSL
005536 NDDF
108823002 SNOMEDCT_US
386923005 SNOMEDCT_US
4020970 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ethyol HUMAN PRESCRIPTION DRUG LABEL 1 76310-017 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS NDA 20 sections