Amifostine
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Also known as AmifostinaAmifostine anhydrousAmifostine disulfideAmifostine trihydrateEthiofosEthiofos anhydrousEthyolGammaphosNSC-296961NSC-758236WR-2721WR-2721 TRIHYDRATEYM-08310SID11110755SID50105748SID90341753SID147094SID144203628SID170465179
Summary
Amifostine (CHEMBL1006) is an approved small-molecule prodrug (ATC V03AF05); indicated across 39 conditions including head and neck cancer and ovarian cancer.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: V03AF05
- Indications: 39 conditions
- Clinical trials: 75
- Chemistry: 214.23 Da · C5H15N2O3PS
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1006 |
| Name | Amifostine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 2141 |
| ChEBI | CHEBI:2636 |
| ATC | V03AF05 |
| Molecular formula | C5H15N2O3PS |
| Molecular weight | 214.23 |
| InChIKey | JKOQGQFVAUAYPM-UHFFFAOYSA-N |
SMILES: C(CN)CNCCSP(=O)(O)O
IUPAC name: 2-(3-aminopropylamino)ethylsulfanylphosphonic acid
ChEBI definition: An organic thiophosphate that is the S-phospho derivative of 2-[(3-aminopropyl)amino]ethanethiol. A prodrug for the free thiol, WR-1065, which is used as a cytoprotectant in cancer chemotherapy and radiotherapy.
Pharmacological roles (ChEBI): prodrug, radiation protective agent, antioxidant.
Also known as: Amifostina, Amifostine, Amifostine anhydrous, Amifostine disulfide, Amifostine trihydrate, Ethiofos, Ethiofos anhydrous, Ethyol, Gammaphos, NSC-296961, NSC-758236, WR-2721
Patent coverage: 8,491 distinct patent families (34,963 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: RecQ-like DNA helicase BLM, D(3) dopamine receptor, Muscarinic acetylcholine receptor M1.
Bioactivity
ChEMBL activities: 3 potent at pChembl ≥ 5 of 5 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P08482 | 7.95 | Potency | 11.2 | nM | CHEMBL_ACT_4811419 |
| DRD3 | 6.18 | Ki | 655 | nM | CHEMBL_ACT_7632116 |
| DRD3 | 5.71 | IC50 | 1929 | nM | CHEMBL_ACT_7632115 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
39 indications (4 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| head and neck cancer | 4 | MONDO:0005627 | EFO:0006859 |
| ovarian cancer | 4 | MONDO:0008170 | MONDO:0008170 |
| trigeminal neuralgia | 3 | MONDO:0008599 | EFO:1001219 |
| plasma cell myeloma | 3 | MONDO:0009693 | EFO:0001378 |
| peripheral neuropathy | 3 | MONDO:0005244 | EFO:0003100 |
| hepatoblastoma | 3 | MONDO:0018666 | EFO:1000292 |
| lung neoplasm | 3 | MONDO:0021117 | MONDO:0008903 |
| undifferentiated carcinoma | 3 | MONDO:0005617 | EFO:0006772 |
| myelodysplastic syndrome | 2 | MONDO:0018881 | EFO:0000198 |
| prostate adenocarcinoma | 2 | MONDO:0005082 | EFO:0000673 |
| rectal cancer | 2 | MONDO:0006519 | EFO:1000657 |
| Hodgkins lymphoma | 2 | MONDO:0004952 | EFO:0000183 |
| leukemia | 2 | MONDO:0005059 | EFO:0000565 |
| lymphoma | 2 | MONDO:0005062 | EFO:0000574 |
| non-Hodgkin lymphoma | 2 | MONDO:0018908 | EFO:0005952 |
| sarcoma | 2 | MONDO:0005089 | EFO:0000691 |
| central nervous system neoplasm | 2 | MONDO:0006130 | EFO:1000158 |
| peritoneal neoplasm | 2 | MONDO:0006901 | MONDO:0002087 |
| fallopian tube neoplasm | 2 | MONDO:0021092 | MONDO:0002158 |
| breast neoplasm | 2 | MONDO:0021100 | MONDO:0007254 |
| endometrium neoplasm | 2 | MONDO:0021251 | MONDO:0011962 |
| colorectal neoplasm | 2 | MONDO:0005335 | MONDO:0005575 |
| acute myeloid leukemia | 1 | MONDO:0018874 | EFO:0000222 |
| neoplasm | 1 | MONDO:0005070 | EFO:0000616 |
| malignant pleural mesothelioma | 1 | MONDO:0005112 | EFO:0000770 |
| neuroblastoma | 1 | MONDO:0005072 | EFO:0000621 |
| myeloproliferative neoplasm | 1 | MONDO:0020076 | EFO:0002428 |
| kidney cancer | 1 | MONDO:0002367 | MONDO:0002367 |
| retinoblastoma | 1 | MONDO:0008380 | MONDO:0008380 |
| chordoma | 1 | MONDO:0008978 | MONDO:0008978 |
| Fanconi anemia | 1 | MONDO:0019391 | MONDO:0019391 |
| plasma cell neoplasm | 1 | MONDO:0004959 | EFO:0000200 |
7 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 75.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 39 |
| PHASE1 | 14 |
| PHASE1/PHASE2 | 11 |
| PHASE3 | 8 |
| PHASE4 | 2 |
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00003252 | PHASE4 | COMPLETED | Amifostine in Treating Patients With Cancer Who Have Neurological Changes Caused by Chemotherapy |
| NCT01288625 | PHASE4 | WITHDRAWN | Prospective Study of Head and Neck Cancer Radiation Treatment With or Without Amifostine |
| NCT00003313 | PHASE3 | COMPLETED | Amifostine in Treating Patients With Stage II or Stage III Non-small Cell Lung Cancer |
| NCT00003994 | PHASE3 | COMPLETED | Combination Chemotherapy With or Without Amifostine in Treating Young Patients With Liver Cancer |
| NCT00004166 | PHASE3 | COMPLETED | Amifostine in Treating Patients With Ovarian Epithelial Cancer Who Are Receiving Chemotherapy |
| NCT00058071 | PHASE3 | COMPLETED | Amifostine in Treating Peripheral Neuropathy in Patients Who Have Received Chemotherapy for Cancer |
| NCT00158691 | PHASE3 | COMPLETED | Intravenous Versus Subcutaneous Amifostine in Prevention of Xerostomia After RT for Head and Neck Carcinomas |
| NCT00217438 | PHASE3 | COMPLETED | Melphalan and Amifostine Followed By One or Two Autologous or Syngeneic Stem Cell Transplants and Maintenance Therapy in Treating Patients With Stage II-III Multiple Myeloma |
| NCT00274937 | PHASE3 | COMPLETED | Radiation Therapy, Amifostine, and Chemotherapy in Treating Young Patients With Newly Diagnosed Nasopharyngeal Cancer |
| NCT01364259 | PHASE3 | TERMINATED | A Study of Amifostine for Prevention of Facial Numbness in Radiosurgery Treatment of Trigeminal Neuralgia |
| NCT00002643 | PHASE2 | COMPLETED | Combination Chemotherapy in Treating Patients With Newly Diagnosed Metastatic Ewing’s Sarcoma or Primitive Neuroectodermal Tumor |
| NCT00003048 | PHASE2 | COMPLETED | Amifostine in Treating Patients With Myelodysplastic Syndrome |
| NCT00003068 | PHASE2 | COMPLETED | High-Dose Chemotherapy and Autologous Blood Cell Transplantation in Treating Patients With Primary, Locally Advanced, or Stage IV Breast Cancer |
| NCT00003072 | PHASE2 | COMPLETED | Combination Chemotherapy in Treating Patients With Metastatic Ovarian Cancer or Non-small Cell Lung Cancer |
| NCT00003089 | PHASE2 | COMPLETED | Chemotherapy, Amifostine, and Radiation Therapy in Treating Patients With Non-small Cell Lung Cancer |
| NCT00003123 | PHASE2 | UNKNOWN | Amifostine in Treating Patients With Advanced Myelodysplastic Syndrome |
| NCT00003127 | PHASE2 | COMPLETED | S9720 Combination Chemotherapy in Treating Patients With Metastatic, Recurrent, or Refractory Endometrial Cancer |
| NCT00003136 | PHASE1/PHASE2 | COMPLETED | Combination Chemotherapy and Peripheral Stem Cell Transplantation in Treating Patients With Epithelial Ovarian Cancer or Primary Peritoneal Cancer |
| NCT00003143 | PHASE2 | COMPLETED | Combination Chemotherapy With or Without Amifostine in Treating Patients With Recurrent or Refractory Non-Hodgkin’s Lymphoma or Hodgkin’s Disease Undergoing Stem Cell Transplantation |
| NCT00003193 | PHASE1/PHASE2 | COMPLETED | Paclitaxel and Radiation Therapy Plus Chemoprotection With Amifostine in Treating Patients With Stage III or Stage IV Head and Neck Cancer |
| NCT00003211 | PHASE2 | COMPLETED | Chemotherapy, Radiation Therapy, and Peripheral Stem Cell Transplantation in Treating Children With Newly Diagnosed Medulloblastoma or Supratentorial Primitive Neuroectodermal Tumor |
| NCT00003225 | PHASE1/PHASE2 | COMPLETED | Amifostine Plus Irinotecan in Treating Patients With Metastatic Colorectal Cancer |
| NCT00003251 | PHASE1/PHASE2 | UNKNOWN | Amifostine Plus Chemotherapy and Radiation Therapy in Treating Patients With Advanced, Unresectable Head and Neck Cancer |
| NCT00003269 | PHASE2 | COMPLETED | Amifostine Followed by High Dose Chemotherapy in Treating Patients With Hematologic Cancer or Solid Tumors |
| NCT00003307 | PHASE2 | COMPLETED | Radiation Therapy Plus Amifostine in Treating Patients With Primary Prostate Cancer |
| NCT00003405 | PHASE2 | WITHDRAWN | Combination Chemotherapy Plus Biological Therapy in Treating Patients With Acute Myelogenous Leukemia |
| NCT00003407 | PHASE2 | WITHDRAWN | Amifostine & High-Dose Combination Chemotherapy in Treating Patients With Acute ML or CML |
| NCT00003415 | PHASE1/PHASE2 | COMPLETED | Amifostine Plus Topotecan in Treating Patients With Myelodysplastic Syndrome |
| NCT00003425 | PHASE1/PHASE2 | COMPLETED | Phase I/II Study of Escalating-Dose Melphalan w/Autologous SCS & Amifostine Cytoprotect |
| NCT00003580 | PHASE2 | COMPLETED | Amifostine to Treat Side Effects of Treatment in Patients Receiving Radiation Therapy and Cisplatin for Advanced Head and Neck Cancer |
| NCT00003582 | PHASE1/PHASE2 | COMPLETED | Radiation Therapy, Combination Chemotherapy, and Amifostine in Treating Patients With Head and Neck Cancer |
| NCT00003583 | PHASE2 | UNKNOWN | Amifostine to Prevent Side Effects in Patients Who Are Receiving Chemotherapy and Radiation Therapy for Limited-Stage Small Cell Lung Cancer |
| NCT00003624 | PHASE2 | TERMINATED | Amifostine in Treating Women With Ovarian, Peritoneal, Cervical, Fallopian Tube, Uterine, or Endometrial Cancer |
| NCT00003657 | PHASE2 | COMPLETED | High-dose ICE With Amifostine |
| NCT00003681 | PHASE2 | UNKNOWN | Amifostine With or Without Epoetin Alfa in Treating Patients With Myelodysplastic Syndrome |
| NCT00003777 | PHASE2 | TERMINATED | Surgery, Radiation Therapy, and Combination Chemotherapy in Treating Patients With Recurrent Head and Neck Cancer |
| NCT00003811 | PHASE2 | COMPLETED | Combination Chemotherapy Plus Amifostine in Treating Children With Malignant Germ Cell Tumors |
| NCT00003827 | PHASE2 | UNKNOWN | Combination Chemotherapy in Treating Patients With Myelodysplastic Syndrome |
| NCT00004176 | PHASE2 | COMPLETED | Amifostine, Chemotherapy, and Radiation Therapy in Treating Patients With Limited-Stage Small Cell Lung Cancer |
| NCT00004264 | PHASE1/PHASE2 | UNKNOWN | Docetaxel, Cisplatin, and Amifostine in Treating Patients With Advanced Non-small Cell Lung Cancer |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).