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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

1949
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

1949
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

1949
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

1949
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

1949
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
A pilot study on the influence of a corticotropin (4-9) analogue on Vinca alkaloid-induced neuropathy.
1992 Oct
[Z-form of intraphage DNA].
2002
ABVD versus stanford V versus MEC in unfavourable Hodgkin's lymphoma: results of a randomised trial.
2002
Treatment of cutaneous T cell lymphoma: current status and future directions.
2002
Pulmonary toxicity secondary to procarbazine.
2002 Apr
Paucity of hematological neoplasia after treatment of Hodgkin disease: observation after long-term follow-up at Cancer Institute, Chennai, south India.
2002 Apr-May
The ability to engage enterocyte apoptosis does not predict long-term crypt survival in p53 and Msh2 deficient mice.
2002 Aug 29
[Psoriasis of the scalp].
2002 Dec
Pathways of reductive fragmentation of heterocyclic nitroarylmethyl quaternary ammonium prodrugs of mechlorethamine.
2002 Dec
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
Biological effects of DNA damage in the hyperthermophilic archaeon Sulfolobus acidocaldarius.
2002 Feb 19
Local interstitial chemotherapy with sustained release bucladesine in de novo glioblastoma multiforme: a preliminary study.
2002 Jan
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
Dietary curcumin inhibits chemotherapy-induced apoptosis in models of human breast cancer.
2002 Jul 1
[Cured from Hodgkin's disease].
2002 Jul-Aug
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
Sulfur mustard-stimulated protease: a target for antivesicant drugs.
2002 Mar-Apr
Stanford V regimen and concomitant HAART in 59 patients with Hodgkin disease and HIV infection.
2002 Sep 15
Radiotherapy alone for lymphocyte-predominant Hodgkin's disease.
2002 Sep-Oct
From poison gas to wonder drug.
2002 Summer
Bexarotene gel: a new skin-directed treatment option for cutaneous T-cell lymphomas.
2003 Apr
Bilateral renal artery stenosis after abdominal radiotherapy for Hodgkin's disease.
2003 Apr
Differential diagnosis of Fanconi anemia by nitrogen mustard and diepoxybutane.
2003 Apr
[Hodgkin's disease manifesting as paraneoplastic limbic encephalitis].
2003 Apr
The protective and therapeutic effects of zinc chloride and desferrioxamine on skin exposed to nitrogen mustard.
2003 Aug
Topical nitrogen mustard in the treatment of alopecia areata: a bilateral comparison study.
2003 Aug
Secondary myelodysplastic syndrome and acute myelogenous leukemia are significant complications following autologous stem cell transplantation for lymphoma.
2003 Aug
Topical nitrogen mustard ointment with occlusion for Langerhans' cell histiocytosis of the scalp.
2003 Jan
[Cutaneous T-cell lymphoma following renal transplantation].
2003 Jan
Improved survival in HIV-related Hodgkin's lymphoma since the introduction of highly active antiretroviral therapy.
2003 Jan 3
Quantitative determination of the hydrolysis products of nitrogen mustards in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.
2003 Jan-Feb
Revascularization for acute coronary occlusion in a young woman following radiation.
2003 Jul
Injury induced by chemical warfare agents: characterization and treatment of ocular tissues exposed to nitrogen mustard.
2003 Jul
Analysis of treatment results in advanced Hodgkin's disease: the case for adjuvant radiotherapy.
2003 Jul 1
Radiation therapy in the treatment of Hodgkin's disease--do you see what I see?
2003 Jul 2
Myeloid clonogenic assays for comparison of the in vitro toxicity of alkylating agents.
2003 Jun
Involved-field radiotherapy for advanced Hodgkin's lymphoma.
2003 Jun 12
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
Early and intermediate stage Hodgkin's lymphoma--report from the Swedish National Care Programme.
2003 Mar
Topical mechlorethamine restores autoimmune-arrested follicular activity in mice with an alopecia areata-like disease by targeting infiltrated lymphocytes.
2003 Mar
Synthesis and in vivo biodisposition of [14C]-quaternary ammonium-melphalan conjugate, a potential cartilage-targeted alkylating drug.
2003 Mar-Apr
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
Management of mycosis fungoides: Part 2. Treatment.
2003 Oct
[Hematologic tumors].
2003 Oct
Old wine in new bottles: reviving old therapies for alopecia areata using rodent models.
2003 Oct
[Second malignancies following Hodgkin's disease treatment in Tunisia. Retrospective study of 26 cases observed at the institute Salah-Azaïz].
2003 Oct
Radiotherapy for advanced Hodgkin's disease.
2003 Sep 18
Alleviation of mutagenic effects of polycyclic aromatic agents (quinacrine mustard, ICR-191 and ICR-170) by caffeine and pentoxifylline.
2003 Sep 29
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:11:00 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
NCI_THESAURUS C697
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
NDF-RT N0000175558
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WHO-VATC QL01AA05
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FDA ORPHAN DRUG 188404
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
EU-Orphan Drug EU/3/12/963
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
NDF-RT N0000000236
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
WHO-ATC L01AA05
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
Code System Code Type Description
RXCUI
6674
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
1647
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
WIKIPEDIA
MECHLORETHAMINE
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
NSC
757087
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL427
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PRIMARY
NCI_THESAURUS
C62056
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PRIMARY
INN
586
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PRIMARY
DAILYMED
50D9XSG0VR
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID2020975
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
CAS
51-75-2
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PRIMARY
NSC
10107
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PRIMARY
IUPHAR
7218
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PRIMARY
ECHA (EC/EINECS)
200-120-5
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
PUBCHEM
4033
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
CHEBI
28925
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PRIMARY
EVMPD
SUB06186MIG
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PRIMARY
NSC
128663
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PRIMARY
DRUG BANK
DB00888
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PRIMARY
FDA UNII
50D9XSG0VR
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
MERCK INDEX
m7116
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY Merck Index
SMS_ID
100000089953
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
MESH
D008466
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
HSDB
5083
Created by admin on Fri Dec 15 15:11:00 GMT 2023 , Edited by admin on Fri Dec 15 15:11:00 GMT 2023
PRIMARY
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