Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H27NO9.ClH |
Molecular Weight | 533.955 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(C=CC=C5)C4=O)C(O)=C23)C(C)=O
InChI
InChIKey=JVHPTYWUBOQMBP-RVFAQHLVSA-N
InChI=1S/C26H27NO9.ClH/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31;/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3;1H/t10-,15-,16-,17-,21+,26-;/m0./s1
Molecular Formula | C26H27NO9 |
Molecular Weight | 497.4939 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Idarubicin is an antineoplastic in the anthracycline class.Idarubicin hydrochloride is a DNA-intercalating analog of daunorubicin which has an inhibitory effect on nucleic acid synthesis and interacts with the enzyme topoisomerase II. The absence of a methoxy group at position 4 of the anthracycline structure gives the compound a high lipophilicity which results in an increased rate of cellular uptake compared with other anthracyclines.Idarubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. Idarubicin in combination with other approved antileukemic drugs is indicated for the treatment of acute myeloid leukemia (AML) in adults.
Originator
Sources: http://adisinsight.springer.com/drugs/800001995
Curator's Comment: # Pfizer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | IDAMYCIN Approved UseIDAMYCIN PFS Injection in combination with other approved antileukemic drugs is indicated for the treatment of acute myeloid leukemia (AML) in adults. This includes French-American-British (FAB) classifications M1 through M7. Launch Date1990 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12621462 |
40 mg/m² single, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IDARUBICIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
423.2 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12621462 |
40 mg/m² single, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IDARUBICIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
38.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12621462 |
40 mg/m² single, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IDARUBICIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
IDARUBICIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Other AEs: Neutropenia, Thrombocytopenia... Other AEs: Neutropenia (all grades, 3 patients) Sources: Thrombocytopenia (all grades, 3 patients) Mucositis (all grades, 3 patients) Anorexia (all grades, 3 patients) Diarrhea (all grades, 3 patients) Vomiting (all grades, 2 patients) Left ventricular systolic dysfunction (all grades, 2 patients) Cardiac arrhythmia (all grades, 1 patient) Rash (all grades, 2 patients) Infection (all grades, 3 patients) |
15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Other AEs: Nausea, Vomiting... Other AEs: Nausea (50%) Sources: Vomiting (50%) Mucositis (20%) Diarrhea (20%) Alopecia (15%) Anorexia (11%) Sepsis (2%) Hepatitis (2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cardiac arrhythmia | all grades, 1 patient | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Left ventricular systolic dysfunction | all grades, 2 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Rash | all grades, 2 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Vomiting | all grades, 2 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Anorexia | all grades, 3 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Diarrhea | all grades, 3 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Infection | all grades, 3 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Mucositis | all grades, 3 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Neutropenia | all grades, 3 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Thrombocytopenia | all grades, 3 patients | 18 mg/m2 1 times / day multiple, intravenous MTD Dose: 18 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 mg/m2, 1 times / day Co-administed with:: cytarabine(100 mg/m^2/day) Sources: |
unhealthy, 23-60 n = 3 Health Status: unhealthy Condition: acute myeloid leukemia Age Group: 23-60 Sex: M+F Population Size: 3 Sources: |
Anorexia | 11% | 15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Alopecia | 15% | 15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Hepatitis | 2% | 15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Sepsis | 2% | 15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Diarrhea | 20% | 15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Mucositis | 20% | 15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Nausea | 50% | 15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Vomiting | 50% | 15 mg/m2 1 times / day multiple, oral Dose: 15 mg/m2, 1 times / day Route: oral Route: multiple Dose: 15 mg/m2, 1 times / day Co-administed with:: metoclopramide(10 mg; 2/day) Sources: |
unhealthy, 66 years (range: 40-85 years) n = 46 Health Status: unhealthy Condition: non-Hodgkin's lymphoma Age Group: 66 years (range: 40-85 years) Population Size: 46 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
High-dose idarubicin and busulphan as conditioning for autologous stem cell transplantation in acute myeloid leukemia: a feasibility study. | 2001 |
|
Autologous hematopoietic stem cell transplantation in chronic myeloid leukemia with different clinical stages. | 2001 |
|
Empirical therapy of febrile neutropenic patients with mucositis: challenge of risk-based therapy. | 2001 |
|
Double reinforcement with fludarabine/high-dose cytarabine enhances the impact of autologous stem cell transplantation in acute myeloid leukemia patients. | 2001 Apr |
|
Arsenic trioxide- and idarubicin-induced remissions in relapsed acute promyelocytic leukaemia: clinicopathological and molecular features of a pilot study. | 2001 Apr |
|
Acute basophilic leukemia. | 2001 Aug |
|
Amifostine does not inhibit the toxic effects of anthracycline derivates or mitoxantrone on MDR tumor cell lines. | 2001 Aug |
|
Generation of reactive oxygen species is not involved in idarubicin-induced apoptosis in human leukaemic cells. | 2001 Dec |
|
Therapy-related myelodysplastic syndrome/acute myeloid leukemia M2 and translocation (8;21). | 2001 Dec |
|
Contribution of specific transport systems to anthracycline transport in tumor and normal cells. | 2001 Dec |
|
Treatment of relapse after allogeneic bone marrow transplantation with reduced intensity conditioning (FLAG +/- Ida) and second allogeneic stem cell transplant. | 2001 Dec |
|
Histopathologic features of retinoblastoma and its relation with in vitro drug resistance measured by means of the MTT assay. | 2001 Dec 1 |
|
Comparison of idarubicin + ara-C-, fludarabine + ara-C-, and topotecan + ara-C-based regimens in treatment of newly diagnosed acute myeloid leukemia, refractory anemia with excess blasts in transformation, or refractory anemia with excess blasts. | 2001 Dec 15 |
|
Transfusion of peripheral blood stem cells from donor homozygous for a shared HLA-haplotype: avoiding fatal transfusion-associated graft-versus-host disease while preserving anti-leukemic effect. | 2001 Feb 15 |
|
Cyclosporin increases cellular idarubicin and idarubicinol concentrations in relapsed or refractory AML mainly due to reduced systemic clearance. | 2001 Jan |
|
Oligonucleotide enhanced cytotoxicity of Idarubicin for lymphoma cells. | 2001 Jul |
|
Cytosine arabinoside, idarubicin and divided dose etoposide for the treatment of acute myeloid leukemia in elderly patients. | 2001 Jul |
|
Treatment of newly-diagnosed acute promyelocytic leukemia with liposomal all-trans retinoic acid. | 2001 Jul |
|
Treatment of acute promyelocytic leukaemia using a combination of all-trans retinoic acid and chemotherapy. | 2001 Jul |
|
High-dose cytosine arabinoside and idarubicin treatment of chronic myeloid leukemia in myeloid blast crisis. | 2001 Jun |
|
Severe hepatic injury associated with lipid formulations of amphotericin B. | 2001 Mar 1 |
|
Improved treatment results in high-risk pediatric acute myeloid leukemia patients after intensification with high-dose cytarabine and mitoxantrone: results of Study Acute Myeloid Leukemia-Berlin-Frankfurt-Münster 93. | 2001 May 15 |
|
Development of hepatic veno-occlusive disease after Mylotarg infusion for relapsed acute myeloid leukemia. | 2001 Nov |
|
And the sun keeps shining. | 2001 Nov |
|
Inappropriate reporting and interpretation of subgroups in the AML-BFM 93 study. | 2001 Nov |
|
Recent advances in the prevention of anthracycline cardiotoxicity in childhood. | 2001 Nov |
|
Anthracyclines: recent developments in their separation and quantitation. | 2001 Nov 25 |
|
An adjustment for a post-randomization variable in the comparison of two treatments for survival. | 2001 Nov 30 |
|
A pharmacokinetic study of idarubicin in Japanese patients with malignant lymphoma: relationship with leukocytopenia and neutropenia. | 2001 Oct |
|
LFA-1 and ICAM-1 antibody-idarubicin conjugates separately prolong murine cardiac allograft survival. | 2001 Oct |
|
High dose of idarubicin-based regimen for diffuse large cell AIDS-related non-Hodgkin's lymphoma patients: a pilot study. | 2001 Oct |
|
High-dose chemotherapy in high-risk myelodysplastic syndrome: covariate-adjusted comparison of five regimens. | 2001 Oct 15 |
|
Intensive chemotherapy followed by allogeneic or autologous stem cell transplantation for patients with myelodysplastic syndromes (MDSs) and acute myeloid leukemia following MDS. | 2001 Oct 15 |
|
Pharmacokinetics and toxicity of idarubicin in the rat. | 2001 Oct-Dec |
|
Long-term follow-up of the clinical efficacy of chemotherapy for acute myeloid leukemia at a single institute. | 2001 Sep |
|
Drug-drug interactions arising from the use of liposomal vincristine in combination with other anticancer drugs. | 2001 Sep |
|
Granulomatous tubulointerstitial nephritis induced by all-trans retinoic acid. | 2001 Sep |
|
A case of zygomycosis and invasive candidiasis involving the epiglottis and tongue in an immunocompromised patient. | 2002 |
|
Differential antigenotoxic and cytoprotective effect of amifostine in idarubicin-treated mice. | 2002 |
|
Automated differential counts in acute promyelocytic leukemia patients may be misleading. | 2002 Apr |
|
Comparison of idarubicin and daunorubicin regarding intracellular uptake, induction of apoptosis, and resistance. | 2002 Apr 25 |
|
Diversity of the apoptotic response to chemotherapy in childhood leukemia. | 2002 Feb |
|
AIDA treatment for high-risk acute promyelocytic leukemia in a pregnant woman at 21 weeks of gestation. | 2002 Feb |
|
Retinoic acid syndrome: a case of massive lung consolidation. | 2002 Feb |
|
Evaluation of the clinical relevance of the expression and function of P-glycoprotein, multidrug resistance protein and lung resistance protein in patients with primary acute myelogenous leukemia. | 2002 Feb |
|
[Acute myelogenous leukemia associated with severe esophageal stricture after chemotherapy]. | 2002 Jan |
|
Standard versus alternative myeloablative conditioning regimens in allogeneic hematopoietic stem cell transplantation for high-risk acute leukemia. | 2002 Jan |
|
Effects of cytarabine and various anthracyclins on platelet activation: characterization of in vitro effects and their possible clinical relevance in acute myelogenous leukemia. | 2002 Jan 1 |
|
Cell-based assays for identification of novel double-strand break-inducing agents. | 2002 Jan 16 |
|
Multiple interference of anthracyclines with mitochondrial creatine kinases: preferential damage of the cardiac isoenzyme and its implications for drug cardiotoxicity. | 2002 Mar |
Sample Use Guides
For induction therapy in adult patients with AML the following dose schedule is recommended:
Idarubicin 12 mg/m2 daily for 3 days by slow (10 to 15 min) intravenous injection in combination with cytarabine. The cytarabine may be given as 100 mg/m2 daily by continuous infusion for 7 days or as cytarabine 25 mg/m2 intravenous bolus followed by cytarabine 200 mg/m2 daily for 5 days continuous infusion. In patients with unequivocal evidence of leukemia after the first induction course, a second course may be administered. Administration of the second course should be delayed in patients who experience severe mucositis, until recovery from this toxicity has occurred, and a dose reduction of 25% is recommended. In patients with hepatic and/or renal impairment, a dose reduction of IDAMYCIN PFS should be considered. Idarubicin should not be administered if the bilirubin level exceeds 5 mg%
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12684680
Treatment of HL-60 cells with 1 uM Idarubicin for 2 h could not induce internucleosomal DNA fragmentation, however, a ladder of DNA fragment, characteristic of apoptosis, was observed after incubation for 4 h. After 10-h,
extensive DNA degradation was observed. When HL-60 cells were incubated with different doses of Idarubicin for 8 h, the degree of DNA fragmentation increased at the higher concentration.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:15:40 GMT 2023
by
admin
on
Fri Dec 15 15:15:40 GMT 2023
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Record UNII |
5VV3MDU5IE
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
55890
Created by
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NCI_THESAURUS |
C1594
Created by
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FDA ORPHAN DRUG |
29388
Created by
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636362
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SUB02635MIG
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256439
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m6197
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82124
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DBSALT000341
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100000090504
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X-47
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DTXSID0047797
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260-990-7
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57852-57-0
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C1587
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5VV3MDU5IE
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1335701
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5VV3MDU5IE
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CHEMBL1117
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