amifostine ๐Ÿถ Veterinary Use | 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 ยตM/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
S (Water solubility) 18.70 mg/mL Bocci G, Oprea TI, Benet LZ

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 46.77 41.04 41 721 470437 63017823

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 132.10 36.08 55 1688 38567 34916621
Laryngeal pain 126.50 36.08 29 1714 2735 34952453
Pyrexia 90.91 36.08 96 1647 332917 34622271
Chills 67.99 36.08 45 1698 80998 34874190
Hypotension 65.71 36.08 67 1676 221582 34733606
Soft tissue disorder 63.15 36.08 13 1730 737 34954451
Rash 54.74 36.08 61 1682 222691 34732497
Dehydration 53.08 36.08 47 1696 129922 34825266
Nausea 47.06 36.08 70 1673 339838 34615350
Dermatitis 44.48 36.08 17 1726 9451 34945737
Injection site reaction 42.52 36.08 18 1725 13015 34942173
Vomiting 41.57 36.08 56 1687 247565 34707623
Radiation skin injury 40.47 36.08 9 1734 736 34954452
Rash maculo-papular 37.12 36.08 21 1722 28430 34926758

FDA Adverse Event Reporting System (Geriatric)

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
Laryngeal pain 154.95 33.94 36 2328 6078 79735946
Mucosal inflammation 117.46 33.94 53 2311 75527 79666497
Pyrexia 112.93 33.94 118 2246 678591 79063433
Hypotension 80.90 33.94 81 2283 440236 79301788
Chills 77.67 33.94 52 2312 160182 79581842
Dehydration 63.48 33.94 55 2309 248132 79493892
Radiation skin injury 61.48 33.94 13 2351 1421 79740603
Soft tissue disorder 59.69 33.94 15 2349 3500 79738524
Nausea 59.37 33.94 103 2261 957093 78784931
Rash 58.11 33.94 78 2286 578280 79163744
Injection site erythema 57.16 33.94 33 2331 78164 79663860
Dermatitis 53.29 33.94 21 2343 21300 79720724
Rash papular 52.73 33.94 21 2343 21895 79720129
Vomiting 51.06 33.94 79 2285 665749 79076275
Injection site reaction 50.66 33.94 27 2337 54758 79687266
Injection site rash 39.04 33.94 16 2348 17938 79724086
Pharyngitis 35.64 33.94 16 2348 22359 79719665

FDA Adverse Event Reporting System (Pediatric)

None

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 drugs
MeSH PA D020011 Protective Agents
MeSH PA D011837 Radiation-Protective Agents

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
M487QF2F4V UNII
133029 MMSL
4164 MMSL
d03868 MMSL
108823002 SNOMEDCT_US
386923005 SNOMEDCT_US
4020970 VANDF
112901-68-5 SECONDARY_CAS_RN
005536 NDDF

Pharmaceutical products:

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