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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
Structure of MECHLORETHAMINE HYDROCHLORIDE

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

HIDE SMILES / InChI
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
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
Postpneumonectomy-like syndrome after chemoradiation therapy for lymphoma.
2002 Dec
Serum levels of soluble CD30 improve International Prognostic Score in predicting the outcome of advanced Hodgkin's lymphoma.
2002 Dec
Pathways of reductive fragmentation of heterocyclic nitroarylmethyl quaternary ammonium prodrugs of mechlorethamine.
2002 Dec
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
[Advanced oxidation protein products in pregnancy].
2002 Jul
[Cured from Hodgkin's disease].
2002 Jul-Aug
Evaluation of a 1-h exposure time to mechlorethamine in patients undergoing topical treatment.
2002 Nov
Long-term results of conventional-dose salvage chemotherapy in patients with refractory and relapsed Hodgkin's disease (Croatian experience).
2002 Oct
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
MOPP chemotherapy for treatment of resistant lymphoma in dogs: a retrospective study of 117 cases (1989-2000).
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 in the management of mycosis fungoides: update of the Stanford experience.
2003 Feb
Randomized comparison of ABVD and MOPP/ABV hybrid for the treatment of advanced Hodgkin's disease: report of an intergroup trial.
2003 Feb 15
Advanced Hodgkin's disease: ABVD is better, yet is not good enough!
2003 Feb 15
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
Myelodysplastic syndrome and acute myeloid leukemia after autotransplantation for lymphoma: a multicenter case-control study.
2003 Mar 1
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
Name Type Language
MECHLORETHAMINE HYDROCHLORIDE
HSDB   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
VALCHLOR
Brand Name English
MECHLORETHAMINE HYDROCHLORIDE [VANDF]
Common Name English
MECHLORETHAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
MECHLORETHAMINE HCL
Common Name English
CHLORMETHINE HYDROCHLORIDE [MART.]
Common Name English
CHLORMETHINE HYDROCHLORIDE [WHO-IP]
Common Name English
2,2'-DICHLORO-N-METHYLDIETHYLAMINE HYDROCHLORIDE
Common Name English
MECHLORETHAMINE HYDROCHLORIDE [MI]
Common Name English
MUSTARGEN
Brand Name English
MECHLORETHAMINE HYDROCHLORIDE [USP-RS]
Common Name English
NSC-762
Code English
MECHLORETHAMINE HYDROCHLORIDE [HSDB]
Common Name English
CHLORMETHINE HCL
Common Name English
MECHLORETHAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
CHLORMETHINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
CHLORMETHINE HYDROCHLORIDE
MART.   WHO-DD   WHO-IP  
Common Name English
ETHANAMINE, 2-CHLORO-N-(2-CHLOROETHYL)-N-METHYL-, HYDROCHLORIDE
Systematic Name English
Chlormethine hydrochloride [WHO-DD]
Common Name English
2-CHLORO-N-(2-CHLOROETHYL)-N-METHYLETHANAMINE HYDROCHLORIDE
Systematic Name English
MUSTINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C697
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
200-246-0
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
HSDB
7176
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
DAILYMED
L0MR697HHI
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
DRUG BANK
DBSALT000904
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
RS_ITEM_NUM
1376505
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
RXCUI
155036
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL427
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
SMS_ID
100000090553
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
NSC
762
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
EVMPD
SUB01220MIG
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
CAS
55-86-7
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID8025757
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
PUBCHEM
5935
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
CHEBI
55368
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
FDA UNII
L0MR697HHI
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY
MERCK INDEX
m7116
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C627
Created by admin on Fri Dec 15 15:14:27 GMT 2023 , Edited by admin on Fri Dec 15 15:14:27 GMT 2023
PRIMARY