amifostine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT2,AKT3,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,CHUK,CSF1R,DDR1,DYRK1B,EGFR,EIF2AK3,EPHA2,EPHB4,ERBB2,FGFR1,FLT1,FLT3,GRK2,GSK3B,IGF1R,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAPK10,MAPK7,MAPK9,MAPKAPK2,MARK4,MTOR,NTRK1,NTRK2,PDK1,PDK2,PDK4,PIK3CB,PIK3CD,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,SRC,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ULK2,ZAP70 70
kinase-selectivity-class ACVRL1,ALK,AURKB,AXL,BRAF,CAMK2D,CDK1,CDK4,CDK6,CDK7,CDK9,CHEK1,CHUK,DDR1,DYRK1B,EPHB4,ERBB2,FLT3,GRK2,IRAK1,IRAK3,IRAK4,MAP2K6,MAP3K21,MAP3K7,MAP4K1,MAPK7,PAK4,PIK3CB,PIK3CD,PRKCD,SIK2,SIK3,STK33,SYK,TEK,ULK2,ZAP70 38
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 44.50 42.45 40 740 660445 89967222

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 146.75 36.28 61 1777 49313 42570184
Laryngeal pain 132.21 36.28 29 1809 2593 42616904
Pyrexia 90.74 36.28 97 1741 393945 42225552
Chills 67.80 36.28 45 1793 94021 42525476
Hypotension 65.36 36.28 67 1771 257564 42361933
Soft tissue disorder 63.35 36.28 13 1825 841 42618656
Dehydration 55.44 36.28 47 1791 141720 42477777
Rash 51.08 36.28 61 1777 276893 42342604
Nausea 50.88 36.28 73 1765 396726 42222771
Dermatitis 50.27 36.28 19 1819 11856 42607641
Vomiting 44.11 36.28 58 1780 289665 42329832
Injection site reaction 41.78 36.28 18 1820 15703 42603794
Radiation skin injury 41.30 36.28 9 1829 776 42618721

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 166.02 33.52 36 2426 5939 110580898
Mucosal inflammation 119.76 33.52 53 2409 96088 110490749
Pyrexia 113.45 33.52 118 2344 898147 109688690
Hypotension 88.64 33.52 81 2381 523768 110063069
Chills 83.02 33.52 52 2410 190528 110396309
Dehydration 71.56 33.52 55 2407 279456 110307381
Nausea 68.56 33.52 108 2354 1235582 109351255
Soft tissue disorder 63.92 33.52 15 2447 3509 110583328
Radiation skin injury 63.51 33.52 13 2449 1619 110585218
Dermatitis 60.84 33.52 23 2439 27814 110559023
Injection site erythema 60.25 33.52 33 2429 94143 110492694
Vomiting 55.08 33.52 83 2379 910592 109676245
Rash 54.20 33.52 78 2384 820886 109765951
Rash papular 53.83 33.52 21 2441 27618 110559219
Injection site reaction 45.62 33.52 27 2435 89043 110497794
Injection site rash 39.35 33.52 16 2446 23403 110563434
Pharyngitis 38.28 33.52 16 2446 25082 110561755

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 antioxidant
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:66987 radiation protective agent
CHEBI has role CHEBI:75835 anti-anaemic agent
MeSH PA D011837 Radiation-Protective Agents
MeSH PA D020011 Protective Agents

Related Drugs by ATC class:

V03AF Detoxifying agents for antineoplastic treatment 10 drugs
argininedexrazoxaneglucarpidaseleucovorinlevofolinic acidlysinemesnapaliferminrasburicasetrilaciclib

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




🐶 Veterinary Drug Use

None

🐶 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
112901-68-5 SECONDARY_CAS_RN
4020970 VANDF
005536 NDDF
108823002 SNOMEDCT_US
386923005 SNOMEDCT_US
M487QF2F4V INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ethyol HUMAN PRESCRIPTION DRUG LABEL 1 83107-030 INJECTION 500 mg INTRAVENOUS NDA 26 sections