Mercaptopurine Anhydrous
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Also known as MercaptopurineSID26748122SID49675007SID50086850SID538245SID124891196SID144204709SID170464985SID174006957SID1442097891H-purine-6(7H)-thioneC0164506
Summary
Mercaptopurine Anhydrous (CHEMBL1425) is an approved small-molecule antineoplastic agent.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Clinical trials: 183
- Chemistry: 152.18 Da · C5H4N4S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1425 |
| Name | Mercaptopurine Anhydrous |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 667490 |
| ChEBI | CHEBI:2208 |
| Molecular formula | C5H4N4S |
| Molecular weight | 152.18 |
| InChIKey | GLVAUDGFNGKCSF-UHFFFAOYSA-N |
SMILES: C1=NC2=C(N1)C(=S)N=CN2
IUPAC name: 3,7-dihydropurine-6-thione
ChEBI definition: A thiol that is the tautomer of mercaptopurine.
Pharmacological roles (ChEBI): antineoplastic agent.
Other ChEBI roles (chemical / environmental): antimetabolite.
Also known as: Mercaptopurine anhydrous, Mercaptopurine, mercaptopurine, SID26748122, SID49675007, SID50086850, SID538245, SID124891196, SID144204709, MERCAPTOPURINE, SID170464985, SID174006957
Parent form; salt/anhydrous children: CHEMBL1200751
Patent coverage: 118,654 distinct patent families (475,838 SureChEMBL compound mentions), from 7 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: 13 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Purine nucleoside phosphorylase, Lysine-specific demethylase 4E, Survival motor neuron protein, Fructose-bisphosphate aldolase, 4’-phosphopantetheinyl transferase ffp, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Beta-lactamase, Prostaglandin G/H synthase 1, Tyrosinase.
Bioactivity
ChEMBL activities: 8 potent at pChembl ≥ 5 of 18 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| HBB | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4537500 |
| SMN1 | 5.35 | Potency | 4467 | nM | CHEMBL_ACT_3888322 |
| A8B2U2 | 5.25 | Potency | 5610 | nM | CHEMBL_ACT_4606495 |
| HBB | 5.2 | Potency | 6310 | nM | CHEMBL_ACT_3765580 |
| ALDH1A1 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_4162071 |
| A8B2U2 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_4606142 |
| TP53 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_4878025 |
| TP53 | 5 | Potency | 10000 | nM | CHEMBL_ACT_4834799 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
0 indications (0 at ChEMBL trial phase 4).
Clinical trials
Total trials: 183.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 64 |
| PHASE2 | 62 |
| PHASE4 | 17 |
| Not specified | 16 |
| PHASE1/PHASE2 | 9 |
| PHASE1 | 8 |
| PHASE2/PHASE3 | 7 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00198978 | PHASE4 | COMPLETED | German Multicenter Trial for Treatment of Elderly Patients With Newly Diagnosed Acute Lymphoblastic Leukemia |
| NCT00198991 | PHASE4 | COMPLETED | German Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (07/2003) |
| NCT00199004 | PHASE4 | COMPLETED | Trial for Treatment of Adult Patients With Standard Risk Acute Lymphoblastic Leukemia With Chemotherapy and Rituximab |
| NCT00199017 | PHASE4 | COMPLETED | German Multicenter Trial for the Treatment of Newly Diagnosed T-lymphoblastic Lymphoma in Adults |
| NCT00199056 | PHASE4 | COMPLETED | German Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (06/99) |
| NCT00199069 | PHASE4 | COMPLETED | German Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (05/93) |
| NCT00199095 | PHASE4 | COMPLETED | Treatment of Elderly Patients (>65 Years) With Acute Lymphoblastic Leukemia |
| NCT00494897 | PHASE4 | COMPLETED | PETHEMA LAL-RI/96: Treatment for Patients With Standard Risk Acute Lymphoblastic Leukemia |
| NCT00526175 | PHASE4 | COMPLETED | LAL-BR/2001: Study Treatment to Low Risk ALL |
| NCT00526305 | PHASE4 | COMPLETED | LAL-Ph-2000: Treatment of Acute Lymphoblastic Leukemia Chromosome Philadelphia Positive |
| NCT00846703 | PHASE4 | UNKNOWN | The GD-2008 ALL Protocol for Childhood Acute Lymphoblastic Leukemia |
| NCT00853008 | PHASE4 | COMPLETED | Treatment of High Risk Adult Acute Lymphoblastic Leukemia |
| NCT01358253 | PHASE4 | COMPLETED | Rituximab Plus Chemotherapy for CD20+ Adult Acute Lymphoblastic Leukemia |
| NCT02036489 | PHASE4 | COMPLETED | Pethema LAL-RI/2008: Treatment for Patients With Standard Risk Acute Lymphoblastic Leukemia |
| NCT02177071 | PHASE4 | COMPLETED | A proSpective Randomized Controlled Trial comParing infliximAb-antimetabolites Combination Therapy to Anti-metabolites monotheRapy and Infliximab monothErapy in Crohn’s Disease Patients in Sustained Steroid-free Remission on Combination Therapy |
| NCT02894645 | PHASE4 | UNKNOWN | Malaysia-Singapore Acute Lymphoblastic Leukemia 2010 Study |
| NCT03920813 | PHASE4 | UNKNOWN | Determinants of Mercaptopurine Toxicity in Paediatric Acute Lymphoblastic Leukemia Maintenance Therapy |
| NCT02003222 | PHASE3 | ACTIVE_NOT_RECRUITING | Combination Chemotherapy With or Without Blinatumomab in Treating Patients With Newly Diagnosed BCR-ABL-Negative B Lineage Acute Lymphoblastic Leukemia |
| NCT02101853 | PHASE3 | ACTIVE_NOT_RECRUITING | Blinatumomab in Treating Younger Patients With Relapsed B-cell Acute Lymphoblastic Leukemia |
| NCT02112916 | PHASE3 | ACTIVE_NOT_RECRUITING | Combination Chemotherapy With or Without Bortezomib in Treating Younger Patients With Newly Diagnosed T-Cell Acute Lymphoblastic Leukemia or Stage II-IV T-Cell Lymphoblastic Lymphoma |
| NCT02205762 | PHASE2/PHASE3 | ACTIVE_NOT_RECRUITING | LCH-IV, International Collaborative Treatment Protocol for Children and Adolescents With Langerhans Cell Histiocytosis |
| NCT02845882 | PHASE3 | ACTIVE_NOT_RECRUITING | LBL-2016 for Children or Adolescents in China |
| NCT03007147 | PHASE3 | ACTIVE_NOT_RECRUITING | Imatinib Mesylate and Combination Chemotherapy in Treating Patients With Newly Diagnosed Philadelphia Chromosome Positive Acute Lymphoblastic Leukemia |
| NCT03020030 | PHASE3 | ACTIVE_NOT_RECRUITING | Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Children and Adolescents |
| NCT03117751 | PHASE2/PHASE3 | ACTIVE_NOT_RECRUITING | Total Therapy XVII for Newly Diagnosed Patients With Acute Lymphoblastic Leukemia and Lymphoma |
| NCT03150693 | PHASE3 | RECRUITING | Inotuzumab Ozogamicin and Frontline Chemotherapy in Treating Young Adults With Newly Diagnosed B Acute Lymphoblastic Leukemia |
| NCT03643276 | PHASE3 | RECRUITING | Treatment Protocol for Children and Adolescents With Acute Lymphoblastic Leukemia - AIEOP-BFM ALL 2017 |
| NCT03914625 | PHASE3 | ACTIVE_NOT_RECRUITING | A Study to Investigate Blinatumomab in Combination With Chemotherapy in Patients With Newly Diagnosed B-Lymphoblastic Leukemia |
| NCT03959085 | PHASE3 | RECRUITING | Inotuzumab Ozogamicin and Post-Induction Chemotherapy in Treating Patients With High-Risk B-ALL, Mixed Phenotype Acute Leukemia, and B-LLy |
| NCT04043494 | PHASE3 | RECRUITING | International Cooperative Treatment Protocol for Children and Adolescents With Lymphoblastic Lymphoma |
| NCT04773366 | PHASE3 | RECRUITING | A Prospective Study for the Treatment of Children With Newly Diagnosed LCH Using a Cytarabine Contained Protocol |
| NCT05681260 | PHASE3 | RECRUITING | Capizzi Escalating Methotrexate Versus High Dose Methotrexate in Children With Newly Diagnosed T-cell Lymphoblastic Lymphoma (T-LBL) |
| NCT07072585 | PHASE2/PHASE3 | NOT_YET_RECRUITING | Testing the Addition of Daratumumab to Chemotherapy for Treating Patients With Newly-Diagnosed T-Cell Lymphoblastic Leukemia (T-ALL) and T-Cell Lymphoblastic Lymphoma (T-LL) |
| NCT00002514 | PHASE3 | COMPLETED | Stem Cell Transplantation Compared With Standard Chemotherapy in Treating Patients With Acute Lymphoblastic Leukemia in First Remission |
| NCT00002618 | PHASE3 | COMPLETED | Combination Chemotherapy in Treating Pediatric Patients With Advanced-Stage Large Cell Lymphoma |
| NCT00002700 | PHASE3 | COMPLETED | Chemotherapy With or Without Bone Marrow Transplantation in Treating Patients With Acute Lymphoblastic Leukemia |
| NCT00002701 | PHASE3 | UNKNOWN | Combination Chemotherapy With or Without Bone Marrow Transplantation in Treating Patients With Acute Promyelocytic Leukemia |
| NCT00002744 | PHASE3 | COMPLETED | Combination Chemotherapy in Treating Children With Newly Diagnosed Acute Lymphoblastic Leukemia |
| NCT00002766 | PHASE3 | COMPLETED | Comparison of Two Combination Chemotherapy Regimens in Treating Adults With Previously Untreated Leukemia or Lymphoma |
| NCT00002812 | PHASE3 | COMPLETED | Combination Chemotherapy in Treating Children With Acute Lymphocytic Leukemia |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
PharmGKB dosing guidelines (4) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):
| Guideline | Source | Gene(s) | Dosing | Recommendation |
|---|---|---|---|---|
| Annotation of CPIC Guideline for mercaptopurine and NUDT15, TPMT | CPIC | NUDT15;TPMT | yes | yes |
| Annotation of DPWG Guideline for mercaptopurine and TPMT | DPWG | TPMT | yes | yes |
| Annotation of DPWG Guideline for mercaptopurine and NUDT15 | DPWG | NUDT15 | yes | yes |
| Annotation of RNPGx Guideline for mercaptopurine and TPMT | RNPGx | TPMT | yes |
PharmGKB also curates 35 clinical and 400 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).
Related Atlas pages
No linked Atlas pages yet — the cross-entity mesh grows as the corpus expands.