Identification

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Name
Mechlorethamine
Accession Number
DB00888  (APRD00249)
Type
Small Molecule
Groups
Approved, Investigational
Description

A vesicant and necrotizing irritant destructive to mucous membranes, mechlorethamine is an alkylating drug. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkin's disease and lymphomas. It causes severe gastrointestinal and bone marrow damage. [PubChem]

The FDA granted marketing approval for the orphan drug Valchlor (mechlorethamine) gel on August 23, 2013 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. Each tube of Valchlor contains 0.016% of mechlorethamine which is equivalent to 0.02% mechlorethamine HCL.

Structure
Thumb
Synonyms
  • 2,2'-dichloro-N-methyldiethylamine
  • bis(2-chloroethyl)methylamine
  • bis(β-chloroethyl)methylamine
  • Chlormethine
  • Chlormethinum
  • Clormetina
  • Mechlorethamine
  • methylbis(2-chloroethyl)amine
  • methylbis(β-chloroethyl)amine
  • Mustine
  • N-methyl-bis(2-chloroethyl)amine
  • N-methyl-bis(β-chloroethyl)amine
  • Nitrogen mustard
  • β,β'-dichlorodiethyl-N-methylamine
External IDs
NSC-128663
Product Ingredients
IngredientUNIICASInChI Key
Mechlorethamine hydrochlorideL0MR697HHI55-86-7QZIQJVCYUQZDIR-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MustargenPowder, for solution10 mg/10mLIntracavitary; IntravenousRECORDATI RARE DISEASES, INC.1949-03-152019-03-31Us
MustargenPowder, for solution10 mgIntravenousLundbeck Pharmaceuticals Llc1951-12-312011-11-11Canada
MustargenPowder, for solution10 mg/10mLIntracavitary; IntravenousLundbeck Inc.1949-03-152013-04-15Us
ValchlorGel0.012 g/60gTopicalHelsinn Therapeutics (U.S.), Inc.2018-11-08Not applicableUs
ValchlorGel0.012 g/60gTopicalCeptaris Therapeutics, Inc.2013-10-212013-10-22Us
ValchlorGel0.012 g/60gTopicalActelion Pharmaceuticals US, Inc.2013-10-212020-05-31Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
50D9XSG0VR
CAS number
51-75-2
Weight
Average: 156.054
Monoisotopic: 155.026854771
Chemical Formula
C5H11Cl2N
InChI Key
HAWPXGHAZFHHAD-UHFFFAOYSA-N
InChI
InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3
IUPAC Name
bis(2-chloroethyl)(methyl)amine
SMILES
CN(CCCl)CCCl

Pharmacology

Indication

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. Also for the palliative treatment of metastatic carcinoma resulting in effusion.

Associated Conditions
Pharmacodynamics

Mechlorethamine also known as mustine, nitrogen mustard, and HN2, is the prototype anticancer chemotherapeutic drug. Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an analogue of mustard gas and was derived from toxic gas warfare research. Mechlorethamine is a nitrogen mustard alkylating agent. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.

Mechanism of action

Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 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. Mechlorethamine is cell cycle phase-nonspecific.

TargetActionsOrganism
ADNA
intercalation
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Partially absorbed following intracavitary administration, most likely due to rapid deactivation by body fluids. When it is topically administered, systemic exposure was undetectable.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Undergoes rapid chemical transformation and combines with water or reactive compounds of cells, so that the drug is no longer present in active form a few minutes after administration.

Route of elimination
Not Available
Half life

15 minutes

Clearance
Not Available
Toxicity

Symptoms of overexposure include severe leukopenia, anemia, thrombocytopenia, and a hemorrhagic diathesis with subsequent delayed bleeding may develop. Death may follow. The most common adverse reactions (≥5%) of the topical formulation are dermatitis, pruritus, bacterial skin infection, skin ulceration or blistering, and hyperpigmentation. The oral LD50 for a rat is 10 mg/kg.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when (R)-warfarin is combined with Mechlorethamine.
(S)-WarfarinThe risk or severity of bleeding can be increased when (S)-Warfarin is combined with Mechlorethamine.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Mechlorethamine is combined with 2-Methoxyethanol.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when 4-hydroxycoumarin is combined with Mechlorethamine.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when Mechlorethamine is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.
AbataceptThe risk or severity of adverse effects can be increased when Mechlorethamine is combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Mechlorethamine.
AbetimusThe risk or severity of adverse effects can be increased when Mechlorethamine is combined with Abetimus.
AcebutololMechlorethamine may increase the bradycardic activities of Acebutolol.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Mechlorethamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

References

Synthesis Reference

Paul Siedlecki, "Preparation of nitrogen mustard derivatives." U.S. Patent US20030162990, issued August 28, 2003.

US20030162990
General References
Not Available
External Links
Human Metabolome Database
HMDB0015025
KEGG Drug
D07671
KEGG Compound
C07115
PubChem Compound
4033
PubChem Substance
46505784
ChemSpider
3893
BindingDB
200297
ChEBI
28925
ChEMBL
CHEMBL427
Therapeutic Targets Database
DAP000790
PharmGKB
PA450336
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mechlorethamine
ATC Codes
L01AA05 — Chlormethine
FDA label
Download (306 KB)
MSDS
Download (37.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingSupportive CareSkin Irritation1
0RecruitingTreatmentAgnogenic Myeloid Metaplasia / Hematopoietic Cell Transplantation Recipient / Primary Myelofibrosis / Secondary Myelofibrosis1
1Active Not RecruitingTreatmentAdult Burkitt Lymphoma / Adult Diffuse Large B-Cell Lymphoma / Burkitt's Lymphoma / CD20-Positive Neoplastic Cells Present / Indolent Adult Non-Hodgkin Lymphoma / Indolent Non-Hodgkin's Lymphomas / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Mantle Cell Lymphoma (MCL) / Recurrent B-Cell Non-Hodgkin Lymphoma / Refractory Mature B-Cell Non-Hodgkin Lymphoma1
1RecruitingTreatmentAccelerated Phase Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Acute Biphenotypic Leukemia (ABL) / Acute Lymphoblastic Leukaemia Recurrent / Acute Lymphoblastic Leukemia in Remission / Acute myeloid leukaemia (in remission) / Acute, recurrent Myeloid Leukemia / Chronic Lymphocytic Leukaemia (CLL) / Chronic Lymphocytic Leukemia (CLL) - Refractory / Chronic Phase Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Chronic, recurrent Lymphocytic Leukemia / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma / High Grade B-Cell Lymphoma With MYC and BCL2 or BCL6 Rearrangements / ISS Stage II Plasma Cell Myeloma / ISS Stage III Plasma Cell Myeloma / Leukemias / Myelodysplastic Syndrome / Recurrent Hodgkin Lymphoma / Recurrent Non-Hodgkin Lymphoma / Recurrent Small Lymphocytic Lymphoma / Refractory Acute Lymphoblastic Leukemia / Refractory Hodgkin Lymphoma / Refractory Non-Hodgkin's lymphoma / Refractory Small Lymphocytic Lymphoma / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Therapy-Related Acute Myeloid Leukemia / Therapy-Related Myelodysplastic Syndrome1
1RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Lymphoblastic Leukemia in Remission / Acute myeloid leukaemia (in remission) / Hematopoietic Cell Transplantation Recipient / Leukemia Acute Myeloid Leukemia (AML) / Minimal Residual Disease / Myelodysplastic Syndrome / Secondary Acute Myeloid Leukemia (Secondary AML, sAML)1
1RecruitingTreatmentAcute myeloid leukaemia (in remission) / Acute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Adult Acute Lymphoblastic Leukemia in Complete Remission / Aplastic Anaemia (AA) / Blasts Under 10 Percent of Bone Marrow Nucleated Cells / Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Chronic Myelomonocytic Leukemia / Chronic, recurrent Lymphocytic Leukemia / Hematopoietic Cell Transplantation Recipient / Leukemias / Minimal Residual Disease / Myeloproliferative Neoplasms / Plasma Cell Myeloma / Recurrent Hodgkin Lymphoma / Recurrent Non-Hodgkin Lymphoma / Recurrent Plasma Cell Myeloma / Recurrent Small Lymphocytic Lymphoma / Therapy-Related Myelodysplastic Syndrome1
1RecruitingTreatmentAllogeneic Hematopoietic Stem Cell Transplant Recipient / Blasts 15 Percent or Less of Bone Marrow Nucleated Cells / Blasts 5 Percent or Less of Bone Marrow Nucleated Cells / Secondary Myelofibrosis1
1RecruitingTreatmentHLA-A*0201 Positive Cells Present / HLA-DP4 Positive Cells Present / Platinum-Resistant Ovarian Carcinoma / Recurrent Fallopian Tube Carcinoma / Recurrent Ovarian Carcinoma / Recurrent Primary Peritoneal Carcinoma / Refractory Fallopian Tube Carcinoma / Refractory Ovarian Carcinoma / Refractory Primary Peritoneal Carcinoma1
1RecruitingTreatmentMalignant Lymphomas / Malignant Neoplasms Stated as Primary Lymphoid Haematopoietic / Recurrent Diffuse Large B-Cell Lymphoma / Recurrent T-Cell Non-Hodgkin Lymphoma / Refractory Diffuse Large B Cell Lymphoma / Refractory Hodgkin Lymphoma / Refractory T-Cell Non-Hodgkin Lymphoma1
1RecruitingTreatmentPrimary Myelofibrosis / Secondary Myelofibrosis1
1WithdrawnSupportive CareAcute myeloid leukaemia (in remission) / Primary Myelofibrosis / Primary Myelofibrosis, Prefibrotic Stage / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Secondary Myelofibrosis1
1WithdrawnTreatmentHLA-A*0201 Positive Cells Present / NY-ESO-1 Positive Tumor Cells Present / Recurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
1, 2Active Not RecruitingTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / B-cell Adult Acute Lymphoblastic Leukemia / B-Cell Chronic Lymphocytic Leukemia / Chronic Lymphocytic Leukemia (CLL) - Refractory / Cutaneous B-Cell Non-Hodgkin Lymphoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Hepatosplenic T-Cell Lymphoma / Intraocular Lymphoma / Nodal marginal zone B-cell lymphomas / Noncutaneous Extranodal Lymphoma / Peripheral T-Cell Lymphoma (PTCL) / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent B-Cell Non-Hodgkin Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Hodgkin Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Recurrent T-Cell Non-Hodgkin Lymphoma / Refractory B-Cell Non-Hodgkin Lymphoma / Refractory Hairy Cell Leukemia / Refractory Hodgkin Lymphoma / Refractory Mantle Cell Lymphoma / Refractory T-Cell Non-Hodgkin Lymphoma / Small Intestine Lymphoma / Splenic Marginal Zone Lymphoma / T-cell Adult Acute Lymphoblastic Leukemia / T-Cell Large Granular Lymphocyte Leukemia / Testicular Lymphoma / Waldenström's Macroglobulinemia (WM)1
1, 2Active Not RecruitingTreatmentChronic Lymphocytic Leukemia (CLL) - Refractory / Chronic, recurrent Lymphocytic Leukemia / Leukemia, Prolymphocytic / Recurrent Adult Hodgkin's Lymphoma / Recurrent Childhood Hodgkin Lymphoma / Recurrent Childhood Non-Hodgkin Lymphoma / Recurrent Non-Hodgkin Lymphoma / Recurrent Small Lymphocytic Lymphoma / Refractory Childhood Hodgkin Lymphoma / Refractory Hodgkin Lymphoma / Refractory Non-Hodgkin's lymphoma / Refractory Small Lymphocytic Lymphoma / T-cell chronic lymphocytic leukaemia / T-Cell Prolymphocytic Leukemia1
1, 2Active Not RecruitingTreatmentDS Stage I Plasma Cell Myeloma / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
1, 2CompletedTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Anaplastic Large Cell Lymphoma, ALK-Negative / Angioimmunoblastic T-Cell Lymphoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Nodal marginal zone B-cell lymphomas / Peripheral T-Cell Lymphoma (PTCL) / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Anaplastic Large Cell Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mature T- and NK-Cell Non-Hodgkin Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Non-Hodgkin Lymphoma / Recurrent Small Lymphocytic Lymphoma / Recurrent Transformed Non-Hodgkin Lymphoma / Splenic Marginal Zone Lymphoma / Stage III Adult Burkitt Lymphoma / Stage III Adult Diffuse Large Cell Lymphoma / Stage III Adult Diffuse Mixed Cell Lymphoma / Stage III Adult Diffuse Small Cleaved Cell Lymphoma / Stage III Adult Immunoblastic Large Cell Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage III Grade 1 Follicular Lymphoma / Stage III Grade 2 Follicular Lymphoma / Stage III Grade 3 Follicular Lymphoma / Stage III Mantle Cell Lymphoma / Stage III Marginal Zone Lymphoma / Stage III Mycosis Fungoides/Sezary Syndrome / Stage III Small Lymphocytic Lymphoma / Stage IV Adult Burkitt Lymphoma / Stage IV Adult Diffuse Large Cell Lymphoma / Stage IV Adult Diffuse Mixed Cell Lymphoma / Stage IV Adult Diffuse Small Cleaved Cell Lymphoma / Stage IV Adult Immunoblastic Large Cell Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IV Grade 1 Follicular Lymphoma / Stage IV Grade 2 Follicular Lymphoma / Stage IV Grade 3 Follicular Lymphoma / Stage IV Mantle Cell Lymphoma / Stage IV Marginal Zone Lymphoma / Stage IV Mycosis Fungoides/Sezary Syndrome / Stage IV Small Lymphocytic Lymphoma / Waldenström's Macroglobulinemia (WM)1
1, 2Not Yet RecruitingTreatmentAllogeneic Hematopoietic Stem Cell Transplant Recipient / Donor / Hematopoietic and Lymphoid Cell Neoplasm1
1, 2Not Yet RecruitingTreatmentCD19 Positive / Mantle Cell Lymphoma (MCL) / Recurrent Diffuse Large B-Cell Lymphoma / Recurrent Follicular Lymphoma / Refractory B-Cell Non-Hodgkin Lymphoma / Refractory Diffuse Large B Cell Lymphoma / Refractory Follicular Lymphoma1
1, 2RecruitingTreatmentAccelerated Phase Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Acute myeloid leukaemia (in remission) / Acute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Acute Myeloid Leukemia With Gene Mutations / Acute, recurrent Myeloid Leukemia / Blast Phase Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Chronic Myelogenous Leukemia, BCR-ABL1 Positive in Remission / De Novo Myelodysplastic Syndrome / Leukemias / Myelodysplastic Syndrome / Myeloproliferative Disorders / Previously Treated Myelodysplastic Syndromes / Recurrent Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Therapy-Related Acute Myeloid Leukemia1
1, 2RecruitingTreatmentAdult Anaplastic Oligodendroglioma / Adult Mixed Glioma / Adult Oligodendroglioma / Oligoastrocytoma / Recurrent Adult Brain Neoplasm1
1, 2RecruitingTreatmentHematopoietic Cell Transplantation Recipient / Recurrent Diffuse Large B-Cell Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Non-Hodgkin Lymphoma / Refractory Diffuse Large B Cell Lymphoma / Refractory Follicular Lymphoma / Refractory Marginal Zone Lymphoma / Refractory Non-Hodgkin's lymphoma / Refractory Transformed Indolent Non-Hodgkin Lymphoma1
1, 2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Mature T-Cell and NK-Cell Non-Hodgkin Lymphoma / Plasmablastic Lymphoma / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Non-Hodgkin Lymphoma / Recurrent Burkitt Lymphoma / Recurrent Follicular Lymphoma / Stage III Follicular Lymphoma / Stage III Mantle Cell Lymphoma / Stage IV Follicular Lymphoma / Stage IV Mantle Cell Lymphoma1
1, 2SuspendedTreatmentAdult Central Nervous System Germ Cell Tumor / Adult Embryonal Tumor With Multilayered Rosettes, C19MC-Altered / Adult Ependymoblastoma / Adult Medulloblastoma / Adult Pineoblastoma / Adult Supratentorial Embryonal Tumor, Not Otherwise Specified / Adult Supratentorial Primitive Neuroectodermal Tumor / Atypical Teratoid/Rhabdoid Tumor / Central Nervous System Embryonal Tumor / Childhood Atypical Teratoid/Rhabdoid Tumor / Childhood Central Nervous System Germ Cell Tumor / Childhood Embryonal Tumor With Multilayered Rosettes, C19MC-Altered / Childhood Ependymoblastoma / Germ Cell Tumors / Medulloepithelioma / Ototoxicity / Recurrent Adult Brain Neoplasm / Recurrent Childhood Central Nervous System Embryonal Neoplasm / Recurrent Childhood Malignant Germ Cell Tumor / Recurrent Childhood Medulloblastoma / Recurrent Childhood Pineoblastoma / Recurrent Childhood Supratentorial Embryonal Tumor, Not Otherwise Specified / Recurrent Childhood Supratentorial Primitive Neuroectodermal Tumor1
1, 2WithdrawnTreatmentPlasma Cell Leukemia in Remission / Plasma Cell Myeloma1
2Active Not RecruitingTreatmentAccelerated Phase Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Acute Biphenotypic Leukemia (ABL) / Acute Lymphoblastic Leukaemias (ALL) / Acute Lymphoblastic Leukemia in Remission / Acute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Chemotherapy-Related Leukemia / Chronic Lymphocytic Leukaemia (CLL) / Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Chronic Myelomonocytic Leukemia / Hematopoietic/Lymphoid Cancer / Langerhans Cell Histiocytosis (LCH) / Leukemia Acute Myeloid Leukemia (AML) / Leukemia, Acute / Lymphoma, Hodgkins / Minimal Residual Disease / Myelodysplastic Syndrome / Myelodysplastic Syndrome With Excess Blasts / Non-Hodgkin's Lymphoma (NHL) / Recurrent Hodgkin Lymphoma / Refractory Acute Lymphoblastic Leukemia / Refractory Myelodysplastic Syndrome / Small Lymphocytic Lymphoma (SLL) / Therapy-Related Myelodysplastic Syndrome1
2Active Not RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Adult B Acute Lymphoblastic Leukemia With t(9;22)(q34.1;q11.2); BCR-ABL1 / Adult B Acute Lymphoblastic Leukemia With t(9;22)(q34;q11.2); BCR-ABL1 / Untreated Adult Acute Lymphoblastic Leukemia1
2Active Not RecruitingTreatmentAdult Diffuse Large B-Cell Lymphoma / B-cell Non-Hodgkin's Lymphomas / Follicular Lymphoma (FL) / Mantle Cell Lymphoma (MCL) / Non-Hodgkin's Lymphoma (NHL) / T-Cell Non-Hodgkin Lymphoma1
2Active Not RecruitingTreatmentLymphoma, Hodgkins1
2Active Not RecruitingTreatmentMalignant Lymphomas1
2Active Not RecruitingTreatmentRefractory Plasma Cell Myeloma1
2CompletedTreatmentB-Cell Prolymphocytic Leukemia / Chronic Lymphocytic Leukemia (CLL) - Refractory / Chronic, recurrent Lymphocytic Leukemia / Hypodiploidy / Leukemia, Plasma Cell / Loss of Chromosome 17p / Progression of Multiple Myeloma or Plasma Cell Leukemia / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Non-Hodgkin Lymphoma / Recurrent Childhood Hodgkin Lymphoma / Recurrent Childhood Non-Hodgkin Lymphoma / Recurrent Plasma Cell Myeloma / Recurrent Small Lymphocytic Lymphoma / Refractory Childhood Hodgkin Lymphoma / Refractory Non-Hodgkin's lymphoma / Refractory Plasma Cell Myeloma / Refractory Small Lymphocytic Lymphoma / T(14;16) / T(4;14) / T-Cell Prolymphocytic Leukemia / Waldenström's Macroglobulinemia (WM)1
2CompletedTreatmentBrain and Central Nervous System Tumors1
2CompletedTreatmentCD20 Positive / Hematopoietic and Lymphoid Cell Neoplasm / Lymphocytic Neoplasm / Malignant Lymphomas1
2CompletedTreatmentJuvenile Myelomonocytic Leukemia1
2CompletedTreatmentLichen Planopilaris1
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentMycosis Fungoides (MF)2
2Not Yet RecruitingTreatmentCutaneous T-Cell Lymphoma (CTCL) / Mycosis Fungoides (MF)1
2RecruitingSupportive CareCutaneous T-Cell Lymphoma (CTCL) / Cutaneous T-cell Lymphoma Stage I / Folliculotropic Mycosis Fungoides / Granulomatous Slack Skin / Mycosis Fungoides (MF) / Mycosis Fungoides Variant / Syringotropic Mycosis Fungoides / Transformed Mycosis Fungoides1
2RecruitingTreatmentAccelerated Phase Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Acute Biphenotypic Leukemia (ABL) / Acute Lymphoblastic Leukaemias (ALL) / Acute Lymphoblastic Leukemia in Remission / Acute Myeloid Leukemia With Myelodysplasia-Related Changes / Acute Myeloid Leukemia With Variant MLL Translocations / Acute, recurrent Myeloid Leukemia / B Acute Lymphoblastic Leukemia With t(9;22)(q34.1;q11.2); BCR-ABL1 / Chemotherapy-Related Leukemia / Chronic Myelomonocytic Leukemia / Chronic Phase Chronic Myelogenous Leukemia, BCR-ABL1 Positive / High Grade B-Cell Lymphoma With MYC and BCL2 or BCL6 Rearrangements / ISS Stage II Plasma Cell Myeloma / ISS Stage III Plasma Cell Myeloma / Leukemias / Malignant Lymphomas / Myelodysplastic Syndrome / Myelodysplastic Syndrome With Excess Blasts / Myelodysplastic Syndrome With Gene Mutation / Myelodysplastic/Myeloproliferative Neoplasms / Myeloproliferative Disorders / Plasma Cell Myeloma / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Recurrent Hodgkin Lymphoma / Recurrent Non-Hodgkin Lymphoma / Refractory Acute Lymphoblastic Leukemia / Refractory Adult Acute Lymphoblastic Leukemia / Refractory Childhood Acute Lymphoblastic Leukemia / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Therapy-Related Myelodysplastic Syndrome1
2RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Allogeneic Hematopoietic Stem Cell Transplantation Recipient / B Acute Lymphoblastic Leukemia / CD22 Positive / Lymphocytic Neoplasm / Malignant Lymphomas1
2RecruitingTreatmentAutoimmune Diseases / Autoimmune Disorders / Autologous Transplant Autoimmune / CIDP Transplant / HCT for Neurologic Autoimmune Disorders / MS Stem Cell Transplant / Multiple Sclerosis Stem Cell Transplant / Multiple Sclerosis Transplant / Myasthenia Gravis Transplant / Neurologic Autoimmune Disease / Stiff Person Syndrome1
2RecruitingTreatmentB-cell Non-Hodgkin's Lymphomas / Mantle Cell Lymphoma (MCL) / Recurrent Diffuse Large B-Cell Lymphoma / Recurrent Follicular Lymphoma / Recurrent Indolent Adult Non-Hodgkin Lymphoma / Refractory Diffuse Large B Cell Lymphoma / Refractory Follicular Lymphoma / Refractory Indolent Adult Non-Hodgkin Lymphoma1
2RecruitingTreatmentAcute, recurrent Myeloid Leukemia / Blasts 10 Percent or More of Bone Marrow Nucleated Cells / Chronic Myelomonocytic Leukemia-2 / High Grade Malignant Neoplasm / Myelodysplastic Syndrome / Myelodysplastic Syndrome With Excess Blasts-2 / Myeloid Neoplasm / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Myeloid Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Refractory Acute Myeloid Leukemia1
2RecruitingTreatmentGanglioneuroblastoma / High-Risk Neuroblastoma / NMYC Gene Amplification1
2RecruitingTreatmentLeukemia, Plasma Cell / Multiple Myeloma (MM) / Plasmacytoma / Recurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
2RecruitingTreatmentLeukemia, Plasma Cell / Plasma Cell Myeloma1
2RecruitingTreatmentPlasma Cell Myeloma / Secondary amyloidosis1
2RecruitingTreatmentPrimary Myelofibrosis / Secondary Myelofibrosis1
2Unknown StatusTreatmentMalignant Lymphomas2
2WithdrawnTreatmentDS Stage I Plasma Cell Myeloma / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma / Refractory Multiple Myeloma / Refractory Plasma Cell Myeloma / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
2WithdrawnTreatmentMycosis Fungoides (MF)1
3Active Not RecruitingTreatmentDS Stage I Plasma Cell Myeloma / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma / Refractory Plasma Cell Myeloma / Smoldering Plasma Cell Myeloma1
3Active Not RecruitingTreatmentMalignant Lymphomas2
3Active Not RecruitingTreatmentPlasma Cell Myeloma / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
3CompletedTreatmentLocalized Resectable Neuroblastoma / Localized Unresectable Neuroblastoma / Recurrent Neuroblastoma / Regional Neuroblastoma / Stage 4 Neuroblastoma / Stage 4S Neuroblastoma1
3CompletedTreatmentMalignant Lymphomas1
3RecruitingTreatmentActivated B-Cell-Like Diffuse Large B-Cell Lymphoma / Autologous Hematopoietic Stem Cell Transplant Recipient / B-Cell Lymphoma, Unclassifiable, With Features Intermediate Between Diffuse Large B-Cell Lymphoma and Burkitt Lymphoma / Diffuse Large B-Cell Lymphoma Activated B-Cell Type / Diffuse Large B-Cell Lymphoma, Not Otherwise Specified / High Grade B-Cell Lymphoma, Not Otherwise Specified / Recurrent Burkitt Lymphoma / Recurrent Diffuse Large B-Cell Lymphoma / Recurrent Diffuse Large B-Cell Lymphoma Activated B-Cell Type / Refractory Burkitt Lymphoma / Refractory Diffuse Large B Cell Lymphoma / Refractory Diffuse Large B-Cell Lymphoma Activated B-Cell Type1
3RecruitingTreatmentChildhood Ganglioneuroblastoma / Childhood Neuroblastoma / Ganglioneuroblastoma / INRG Stage L2 / INRG Stage M / INRG Stage MS / Neuroblastomas / NMYC Gene Amplification / Recurrent Neuroblastoma1
3Unknown StatusTreatmentMalignant Lymphomas1
Not AvailableActive Not RecruitingTreatmentUnilateral Retinoblastoma1
Not AvailableCompletedNot AvailableMycosis Fungoides (MF)1

Pharmacoeconomics

Manufacturers
  • Lundbeck inc
Packagers
  • Lundbeck Inc.
  • Merck & Co.
Dosage forms
FormRouteStrength
Powder, for solutionIntracavitary; Intravenous10 mg/10mL
Powder, for solutionIntravenous10 mg
GelTopical0.012 g/60g
Prices
Unit descriptionCostUnit
Mustargen 10 mg vial178.71USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7872050No2011-01-182029-07-08Us
US8501819No2013-08-062026-03-07Us
US8450375No2013-05-282026-03-07Us
US8501818No2013-08-062026-03-07Us
US7838564No2010-11-232026-03-07Us
US9382191No2016-07-052026-03-07Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)108 - 110°CMSDS
boiling point (°C)87°C at 1.80E+01 mm HgPhysProp
water solubilityVery solubleFDA label
logP0.91SELASSIE,CD ET AL. (1990)
pKa6.43 (at 25°C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility33.4 mg/mLALOGPS
logP1.31ALOGPS
logP1.52ChemAxon
logS-0.67ALOGPS
pKa (Strongest Basic)6.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.67 m3·mol-1ChemAxon
Polarizability15.84 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.987
Blood Brain Barrier+0.9735
Caco-2 permeable+0.754
P-glycoprotein substrateNon-substrate0.5964
P-glycoprotein inhibitor INon-inhibitor0.9388
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterInhibitor0.6023
CYP450 2C9 substrateNon-substrate0.7811
CYP450 2D6 substrateNon-substrate0.6069
CYP450 3A4 substrateNon-substrate0.5986
CYP450 1A2 substrateNon-inhibitor0.6607
CYP450 2C9 inhibitorNon-inhibitor0.9504
CYP450 2D6 inhibitorNon-inhibitor0.9153
CYP450 2C19 inhibitorNon-inhibitor0.8068
CYP450 3A4 inhibitorNon-inhibitor0.9804
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9421
Ames testAMES toxic0.9108
CarcinogenicityCarcinogens 0.6585
BiodegradationNot ready biodegradable0.9258
Rat acute toxicity4.1619 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5662
hERG inhibition (predictor II)Non-inhibitor0.792
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.14 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-7900000000-66a0ef3007bd03bd9367
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as nitrogen mustard compounds. These are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Nitrogen mustard compounds
Direct Parent
Nitrogen mustard compounds
Alternative Parents
Trialkylamines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives / Alkyl chlorides
Substituents
Nitrogen mustard / Tertiary aliphatic amine / Tertiary amine / Organopnictogen compound / Hydrocarbon derivative / Organochloride / Organohalogen compound / Amine / Alkyl halide / Alkyl chloride
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organochlorine compound, nitrogen mustard (CHEBI:28925)

Targets

Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Intercalation
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. De Alencar TA, Leitao AC, Lage C: Nitrogen mustard- and half-mustard-induced damage in Escherichia coli requires different DNA repair pathways. Mutat Res. 2005 Apr 4;582(1-2):105-15. [PubMed:15781216]
  4. Loeber RL, Michaelson-Richie ED, Codreanu SG, Liebler DC, Campbell CR, Tretyakova NY: Proteomic analysis of DNA-protein cross-linking by antitumor nitrogen mustards. Chem Res Toxicol. 2009 Jun;22(6):1151-62. doi: 10.1021/tx900078y. [PubMed:19480393]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da

Drug created on June 13, 2005 07:24 / Updated on November 02, 2019 04:19