Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H11Cl2N.ClH |
Molecular Weight | 192.514 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(CCCl)CCCl
InChI
InChIKey=QZIQJVCYUQZDIR-UHFFFAOYSA-N
InChI=1S/C5H11Cl2N.ClH/c1-8(4-2-6)5-3-7;/h2-5H2,1H3;1H
Mechlorethamine also known as mustine, brand name MUSTARGEN administered intravenously is the prototype anticancer chemotherapeutic drug, is indicated for the palliative treatment of Hodgkin's disease (Stages III and IV), lymphosarcoma, chronic myelocytic or chronic lymphocytic leukemia, polycythemia vera, mycosis fungoides, and bronchogenic carcinoma. In 2013 was approved orphan drug Valchlor (mechlorethamine) gel for the topical treatment of stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma (CTCL) in patients who have received prior skin-directed therapy. Mechlorethamine belongs to the group of nitrogen mustard alkylating agents. Alkylating agents work by three different mechanisms: attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations all of which achieve the same end result - disruption of DNA function and cell death.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19480393 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | MUSTARGEN Approved UseVALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy. VALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy (1). Launch Date1949 |
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Palliative | MUSTARGEN Approved UseVALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy. VALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy (1). Launch Date1949 |
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Palliative | MUSTARGEN Approved UseVALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy. VALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy (1). Launch Date1949 |
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Palliative | MUSTARGEN Approved UseVALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy. VALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy (1). Launch Date1949 |
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Palliative | MUSTARGEN Approved UseVALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy. VALCHLOR is an alkylating drug indicated for the topical treatment of Stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma in patients who have received prior skin-directed therapy (1). Launch Date1949 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.72 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11129502 |
0.2 mg/kg single, oral dose: 0.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MECHLORETHAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.17 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11129502 |
0.2 mg/kg single, oral dose: 0.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MECHLORETHAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.16 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11129502 |
0.2 mg/kg single, oral dose: 0.2 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
MECHLORETHAMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
0.4 mg/kg single, intravenous Recommended Dose: 0.4 mg/kg Route: intravenous Route: single Dose: 0.4 mg/kg Sources: Page: p.413 |
unhealthy, 14-80 n = 26 Health Status: unhealthy Condition: Reticulum cell sarcoma Age Group: 14-80 Sex: M+F Population Size: 26 Sources: Page: p.413 |
Disc. AE: Thrombocytopenia, Hemorrhage... AEs leading to discontinuation/dose reduction: Thrombocytopenia (severe, 3.8%) Sources: Page: p.413Hemorrhage (3.8%) |
0.4 mg/kg single, intravenous Recommended Dose: 0.4 mg/kg Route: intravenous Route: single Dose: 0.4 mg/kg Sources: Page: p.413 |
unhealthy, 32-81 n = 18 Health Status: unhealthy Condition: Lymphosarcoma Age Group: 32-81 Sex: M+F Population Size: 18 Sources: Page: p.413 |
Disc. AE: Pancytopenia... AEs leading to discontinuation/dose reduction: Pancytopenia (5.6%) Sources: Page: p.413 |
0.02 % 1 times / day multiple, topical Recommended Dose: 0.02 %, 1 times / day Route: topical Route: multiple Dose: 0.02 %, 1 times / day Sources: Page: p.517 |
unhealthy, 44 n = 20 Health Status: unhealthy Condition: Psoriasis Age Group: 44 Sex: M+F Population Size: 20 Sources: Page: p.517 |
Disc. AE: Contact dermatitis... AEs leading to discontinuation/dose reduction: Contact dermatitis (75%) Sources: Page: p.517 |
0.016 % 1 times / day multiple, topical Recommended Dose: 0.016 %, 1 times / day Route: topical Route: multiple Dose: 0.016 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Stage IA and IB mycosis fungoides‐type cutaneous T‐cell lymphoma Sources: Page: p.1 |
Disc. AE: Eye injury, Dermatitis... AEs leading to discontinuation/dose reduction: Eye injury Sources: Page: p.1Dermatitis Cancer of skin (excl melanoma) Disorder fetal |
0.4 mg/kg single, intravenous (total) Recommended Dose: 0.4 mg/kg Route: intravenous Route: single Dose: 0.4 mg/kg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Hodgkin's disease| lymphosarcoma|chronic myelocytic leukemia| chronic lymphocytic leukemia| polycythemia vera| mycosis fungoides|bronchogenic carcinoma Sources: Page: p.2 |
Disc. AE: Amyloidosis... AEs leading to discontinuation/dose reduction: Amyloidosis Sources: Page: p.2 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hemorrhage | 3.8% Disc. AE |
0.4 mg/kg single, intravenous Recommended Dose: 0.4 mg/kg Route: intravenous Route: single Dose: 0.4 mg/kg Sources: Page: p.413 |
unhealthy, 14-80 n = 26 Health Status: unhealthy Condition: Reticulum cell sarcoma Age Group: 14-80 Sex: M+F Population Size: 26 Sources: Page: p.413 |
Thrombocytopenia | severe, 3.8% Disc. AE |
0.4 mg/kg single, intravenous Recommended Dose: 0.4 mg/kg Route: intravenous Route: single Dose: 0.4 mg/kg Sources: Page: p.413 |
unhealthy, 14-80 n = 26 Health Status: unhealthy Condition: Reticulum cell sarcoma Age Group: 14-80 Sex: M+F Population Size: 26 Sources: Page: p.413 |
Pancytopenia | 5.6% Disc. AE |
0.4 mg/kg single, intravenous Recommended Dose: 0.4 mg/kg Route: intravenous Route: single Dose: 0.4 mg/kg Sources: Page: p.413 |
unhealthy, 32-81 n = 18 Health Status: unhealthy Condition: Lymphosarcoma Age Group: 32-81 Sex: M+F Population Size: 18 Sources: Page: p.413 |
Contact dermatitis | 75% Disc. AE |
0.02 % 1 times / day multiple, topical Recommended Dose: 0.02 %, 1 times / day Route: topical Route: multiple Dose: 0.02 %, 1 times / day Sources: Page: p.517 |
unhealthy, 44 n = 20 Health Status: unhealthy Condition: Psoriasis Age Group: 44 Sex: M+F Population Size: 20 Sources: Page: p.517 |
Cancer of skin (excl melanoma) | Disc. AE | 0.016 % 1 times / day multiple, topical Recommended Dose: 0.016 %, 1 times / day Route: topical Route: multiple Dose: 0.016 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Stage IA and IB mycosis fungoides‐type cutaneous T‐cell lymphoma Sources: Page: p.1 |
Dermatitis | Disc. AE | 0.016 % 1 times / day multiple, topical Recommended Dose: 0.016 %, 1 times / day Route: topical Route: multiple Dose: 0.016 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Stage IA and IB mycosis fungoides‐type cutaneous T‐cell lymphoma Sources: Page: p.1 |
Disorder fetal | Disc. AE | 0.016 % 1 times / day multiple, topical Recommended Dose: 0.016 %, 1 times / day Route: topical Route: multiple Dose: 0.016 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Stage IA and IB mycosis fungoides‐type cutaneous T‐cell lymphoma Sources: Page: p.1 |
Eye injury | Disc. AE | 0.016 % 1 times / day multiple, topical Recommended Dose: 0.016 %, 1 times / day Route: topical Route: multiple Dose: 0.016 %, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Stage IA and IB mycosis fungoides‐type cutaneous T‐cell lymphoma Sources: Page: p.1 |
Amyloidosis | Disc. AE | 0.4 mg/kg single, intravenous (total) Recommended Dose: 0.4 mg/kg Route: intravenous Route: single Dose: 0.4 mg/kg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Hodgkin's disease| lymphosarcoma|chronic myelocytic leukemia| chronic lymphocytic leukemia| polycythemia vera| mycosis fungoides|bronchogenic carcinoma Sources: Page: p.2 |
PubMed
Title | Date | PubMed |
---|---|---|
[Z-form of intraphage DNA]. | 2002 |
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ABVD versus stanford V versus MEC in unfavourable Hodgkin's lymphoma: results of a randomised trial. | 2002 |
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Treatment of cutaneous T cell lymphoma: current status and future directions. | 2002 |
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Pulmonary toxicity secondary to procarbazine. | 2002 Apr |
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Paucity of hematological neoplasia after treatment of Hodgkin disease: observation after long-term follow-up at Cancer Institute, Chennai, south India. | 2002 Apr-May |
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The ability to engage enterocyte apoptosis does not predict long-term crypt survival in p53 and Msh2 deficient mice. | 2002 Aug 29 |
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[Psoriasis of the scalp]. | 2002 Dec |
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Postpneumonectomy-like syndrome after chemoradiation therapy for lymphoma. | 2002 Dec |
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Serum levels of soluble CD30 improve International Prognostic Score in predicting the outcome of advanced Hodgkin's lymphoma. | 2002 Dec |
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Pathways of reductive fragmentation of heterocyclic nitroarylmethyl quaternary ammonium prodrugs of mechlorethamine. | 2002 Dec |
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An elevated serum beta-2-microglobulin level is an adverse prognostic factor for overall survival in patients with early-stage Hodgkin disease. | 2002 Dec 15 |
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The modulation of the DNA-damaging effect of polycyclic aromatic agents by xanthines. Part I. Reduction of cytostatic effects of quinacrine mustard by caffeine. | 2002 Feb 15 |
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Biological effects of DNA damage in the hyperthermophilic archaeon Sulfolobus acidocaldarius. | 2002 Feb 19 |
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Lung cancer following chemotherapy and radiotherapy for Hodgkin's disease. | 2002 Feb 6 |
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Local interstitial chemotherapy with sustained release bucladesine in de novo glioblastoma multiforme: a preliminary study. | 2002 Jan |
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Inhibition of nucleotide excision repair and sensitisation of cells to DNA cross-linking anticancer drugs by F 11782, a novel fluorinated epipodophylloid. | 2002 Jan 15 |
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Acrolein-induced cell death: a caspase-influenced decision between apoptosis and oncosis/necrosis. | 2002 Jan 22 |
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[Advanced oxidation protein products in pregnancy]. | 2002 Jul |
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Fifteen-year secondary leukaemia risk observed in 761 patients with Hodgkin's disease prospectively treated by MOPP or ABVD chemotherapy plus high-dose irradiation. | 2002 Jul |
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Dietary curcumin inhibits chemotherapy-induced apoptosis in models of human breast cancer. | 2002 Jul 1 |
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[Cured from Hodgkin's disease]. | 2002 Jul-Aug |
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Topical treatment with povidone iodine reduces nitrogen mustard-induced skin collagenolytic activity. | 2002 Mar |
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Covalent binding of nitrogen mustards to the cysteine-34 residue in human serum albumin. | 2002 Mar |
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Involvement of phosphatidylinositol-3-kinase in membrane ruffling induced by P-glycoprotein substrates in multidrug-resistant carcinoma cells. | 2002 Mar 1 |
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European Organization for Research and Treatment of Cancer and Groupe d'Etude des Lymphomes de l'Adulte very favorable and favorable, lymphocyte-predominant Hodgkin disease. | 2002 Mar 15 |
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Sulfur mustard-stimulated protease: a target for antivesicant drugs. | 2002 Mar-Apr |
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Evaluation of a 1-h exposure time to mechlorethamine in patients undergoing topical treatment. | 2002 Nov |
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Long-term results of conventional-dose salvage chemotherapy in patients with refractory and relapsed Hodgkin's disease (Croatian experience). | 2002 Oct |
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Stanford V regimen and concomitant HAART in 59 patients with Hodgkin disease and HIV infection. | 2002 Sep 15 |
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Radiotherapy alone for lymphocyte-predominant Hodgkin's disease. | 2002 Sep-Oct |
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MOPP chemotherapy for treatment of resistant lymphoma in dogs: a retrospective study of 117 cases (1989-2000). | 2002 Sep-Oct |
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From poison gas to wonder drug. | 2002 Summer |
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Bexarotene gel: a new skin-directed treatment option for cutaneous T-cell lymphomas. | 2003 Apr |
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Topical nitrogen mustard in the treatment of alopecia areata: a bilateral comparison study. | 2003 Aug |
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Secondary myelodysplastic syndrome and acute myelogenous leukemia are significant complications following autologous stem cell transplantation for lymphoma. | 2003 Aug |
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Topical nitrogen mustard in the management of mycosis fungoides: update of the Stanford experience. | 2003 Feb |
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Randomized comparison of ABVD and MOPP/ABV hybrid for the treatment of advanced Hodgkin's disease: report of an intergroup trial. | 2003 Feb 15 |
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Advanced Hodgkin's disease: ABVD is better, yet is not good enough! | 2003 Feb 15 |
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Topical nitrogen mustard ointment with occlusion for Langerhans' cell histiocytosis of the scalp. | 2003 Jan |
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Improved survival in HIV-related Hodgkin's lymphoma since the introduction of highly active antiretroviral therapy. | 2003 Jan 3 |
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Quantitative determination of the hydrolysis products of nitrogen mustards in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry. | 2003 Jan-Feb |
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Injury induced by chemical warfare agents: characterization and treatment of ocular tissues exposed to nitrogen mustard. | 2003 Jul |
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Radiation therapy in the treatment of Hodgkin's disease--do you see what I see? | 2003 Jul 2 |
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Myeloid clonogenic assays for comparison of the in vitro toxicity of alkylating agents. | 2003 Jun |
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High-dose therapy and autologous stem-cell transplantation versus conventional therapy for patients with advanced Hodgkin's lymphoma responding to front-line therapy. | 2003 Jun 15 |
|
Myelodysplastic syndrome and acute myeloid leukemia after autotransplantation for lymphoma: a multicenter case-control study. | 2003 Mar 1 |
|
Cutaneous granulomas as the first manifestation of Hodgkin's disease. | 2003 May-Jun |
|
Impaired healing of nitrogen mustard wounds in CXCR2 null mice. | 2003 May-Jun |
|
The treatment of adults with medulloblastoma: a prospective study. | 2003 Nov 1 |
|
Radiotherapy for advanced Hodgkin's disease. | 2003 Sep 18 |
Sample Use Guides
Intravenous Administration: the dosage of MUSTARGEN (MECHLORETHAMINE HCl ) varies with the clinical situation, the therapeutic response and the magnitude of hematologic depression. A total dose of 0.4 mg/kg of body weight for each course usually is given either as a single dose or in divided doses of 0.1 to 0.2 mg/kg per day.
Intracavitary Administration: The usual dose of nitrogen mustard for intracavitary injection is 0.4 mg/kg of body weight, though 0.2 mg/kg (or 10 to 20 mg) has been used by the intrapericardial route.5,11-13 The solution is prepared, as previously described for intravenous injection, by adding 10 mL of Sterile Water for Injection or 10 mL of Sodium Chloride Injection to the vial containing 10 mg of mechlorethamine hydrochloride. (Amounts of diluent of 50 to 100 mL of normal saline have also been used.4,5) The position of the patient should be changed every 5 to 10 minutes for an hour after injection to obtain more uniform distribution of the drug throughout the serous cavity. The remaining fluid may be removed from the pleural or peritoneal cavity by
paracentesis 24 to 36 hours later. The patient should be followed carefully by clinical and x-ray examination to detect reaccumulation of fluid.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22043910
Curator's Comment: It was examined the ability of mechlorethamine (MCT) to conceal the 6H4 epitope and block prion protein PrP conversion in the presence of a reducing reagent. Mechlorethamine treatment significantly decreased in vitro amplification of cellular prion protein (PrP(C)) in the highly efficient protein misfolding cyclic amplification system, thus was suggest that MCT might serve as a potential therapeutic agent for prion diseases.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C697
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200-246-0
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7176
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L0MR697HHI
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DBSALT000904
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1376505
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155036
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CHEMBL427
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100000090553
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762
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55-86-7
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DTXSID8025757
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55368
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L0MR697HHI
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m7116
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C627
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ACTIVE MOIETY
SUBSTANCE RECORD