U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C5H11Cl2N
Molecular Weight 156.054
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECHLORETHAMINE

SMILES

CN(CCCl)CCCl

InChI

InChIKey=HAWPXGHAZFHHAD-UHFFFAOYSA-N
InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3

HIDE SMILES / InChI

Molecular Formula C5H11Cl2N
Molecular Weight 156.054
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
MUSTARGEN

Approved Use

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. 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 Date

-6.5638079E11
Palliative
MUSTARGEN

Approved Use

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. 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 Date

-6.5638079E11
Palliative
MUSTARGEN

Approved Use

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. 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 Date

-6.5638079E11
Palliative
MUSTARGEN

Approved Use

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. 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 Date

-6.5638079E11
Palliative
MUSTARGEN

Approved Use

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. 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 Date

-6.5638079E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.72 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
3.17 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
0.16 h
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

Doses

DosePopulationAdverse 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%)
Hemorrhage (3.8%)
Sources: Page: p.413
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
Dermatitis
Cancer of skin (excl melanoma)
Disorder fetal
Sources: Page: p.1
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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Chlorophyllin protects cells from the cytostatic and cytotoxic effects of quinacrine mustard but not of nitrogen mustard.
2001 Apr
Chromatin structure at the 3'-boundary of the human beta-globin locus control region hypersensitive site-2.
2001 Dec
Persistent paraneoplastic neurologic syndrome after successful therapy of Hodgkin's disease.
2001 Jan
[Gene protective effect of the short-chain derivative of Vitamin E under the action of alkylating compounds].
2001 Jan-Feb
Genetic damage by bifunctional agents in repair-active pre-meiotic stages of Drosophila males.
2001 Jul 1
[Successful chemotherapy of cancer. Remission of Hodgkin's disease. IV].
2001 May-Jun
Adult lymphoblastic lymphoma in Taiwan: an analysis of treatment results of 26 patients.
2001 Nov
[Z-form of intraphage DNA].
2002
ABVD versus stanford V versus MEC in unfavourable Hodgkin's lymphoma: results of a randomised trial.
2002
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
Lung cancer following chemotherapy and radiotherapy for Hodgkin's disease.
2002 Feb 6
Differential diagnosis of Fanconi anemia by nitrogen mustard and diepoxybutane.
2003 Apr
Topical nitrogen mustard in the management of mycosis fungoides: update of the Stanford experience.
2003 Feb
[Cutaneous T-cell lymphoma following renal transplantation].
2003 Jan
Synthesis and in vivo biodisposition of [14C]-quaternary ammonium-melphalan conjugate, a potential cartilage-targeted alkylating drug.
2003 Mar-Apr
Management of mycosis fungoides: Part 2. Treatment.
2003 Oct
Patents

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
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.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:11:00 UTC 2023
Edited
by admin
on Fri Dec 15 15:11:00 UTC 2023
Record UNII
50D9XSG0VR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MECHLORETHAMINE
HSDB   MI   VANDF  
Common Name English
2,2'-DICHLORO-N-METHYLDIETHYLAMINE
Common Name English
MECHLORETHAMINE [MI]
Common Name English
chlormethine [INN]
Common Name English
MECHLORETHAMINE [HSDB]
Common Name English
METHYL-.BETA.,.BETA.-DICHLORODIETHYLAMINE
Common Name English
DIETHYLAMINE, 2,2'-DICHLORO-N-METHYL-
Systematic Name English
NITROGEN MUSTARD (HN 2)
Common Name English
NSC-128663
Code English
CHLORETHAZINE
Common Name English
CHLORMETHINE
INN   WHO-DD  
INN  
Official Name English
ETHANAMINE, 2-CHLORO-N-(2-CHLOROETHYL)-N-METHYL-
Systematic Name English
NSC-757087
Code English
NITROGEN MUSTARD
Common Name English
MECHLORETHAMINE [VANDF]
Common Name English
NITROGEN MUSTARD [IARC]
Common Name English
Chlormethine [WHO-DD]
Common Name English
NSC-10107
Code English
Classification Tree Code System Code
LIVERTOX NBK548509
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
NCI_THESAURUS C697
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
NDF-RT N0000175558
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
WHO-VATC QL01AA05
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
FDA ORPHAN DRUG 188404
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
EU-Orphan Drug EU/3/12/963
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
NDF-RT N0000000236
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
WHO-ATC L01AA05
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
Code System Code Type Description
RXCUI
6674
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
1647
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
WIKIPEDIA
MECHLORETHAMINE
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
NSC
757087
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
ChEMBL
CHEMBL427
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
NCI_THESAURUS
C62056
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
INN
586
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
DAILYMED
50D9XSG0VR
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID2020975
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
CAS
51-75-2
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
NSC
10107
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
IUPHAR
7218
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-120-5
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
PUBCHEM
4033
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
CHEBI
28925
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
EVMPD
SUB06186MIG
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
NSC
128663
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
DRUG BANK
DB00888
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
FDA UNII
50D9XSG0VR
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
MERCK INDEX
m7116
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY Merck Index
SMS_ID
100000089953
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
MESH
D008466
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
HSDB
5083
Created by admin on Fri Dec 15 15:11:00 UTC 2023 , Edited by admin on Fri Dec 15 15:11:00 UTC 2023
PRIMARY
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