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Mechlorethamine
Also known as: 55-86-7, Chlormethine hydrochloride, Mechlorethamine hcl, Nitrogen mustard hydrochloride, Chlorethamine, 2-chloro-n-(2-chloroethyl)-n-methylethanamine hydrochloride
Molecular Formula
C5H12Cl3N
Molecular Weight
192.5  g/mol
InChI Key
QZIQJVCYUQZDIR-UHFFFAOYSA-N
FDA UNII
L0MR697HHI

A biologic alkylating agent that exerts its cytotoxic effects by forming DNA ADDUCTS and DNA interstrand crosslinks, thereby inhibiting rapidly proliferating cells. The hydrochloride is an antineoplastic agent used to treat HODGKIN DISEASE and LYMPHOMA.
1 2D Structure

Mechlorethamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-chloro-N-(2-chloroethyl)-N-methylethanamine;hydrochloride
2.1.2 InChI
InChI=1S/C5H11Cl2N.ClH/c1-8(4-2-6)5-3-7;/h2-5H2,1H3;1H
2.1.3 InChI Key
QZIQJVCYUQZDIR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(CCCl)CCCl.Cl
2.2 Other Identifiers
2.2.1 UNII
L0MR697HHI
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bis(2-chloroethyl)methylamine

2. Caryolysine

3. Chlorethazine

4. Chlormethine

5. Cloramin

6. Embichin

7. Hydrochloride N-oxide, Mechlorethamine

8. Hydrochloride, Mechlorethamine

9. Mechlorethamine

10. Mechlorethamine Hydrochloride N Oxide

11. Mechlorethamine Hydrochloride N-oxide

12. Mechlorethamine N Oxide

13. Mechlorethamine N-oxide

14. Mechlorethamine Oxide

15. Methylchlorethamine

16. Mitomen

17. Mustargen

18. Mustine

19. N-oxide, Mechlorethamine Hydrochloride

20. N-oxide, Nitrogen Mustard

21. Nitrogen Mustard

22. Nitrogen Mustard N Oxide

23. Nitrogen Mustard N-oxide

24. Nitrogranulogen

25. Nitromin

26. Nsc 10107

27. Nsc 762

28. Nsc-10107

29. Nsc-762

30. Nsc10107

31. Nsc762

2.3.2 Depositor-Supplied Synonyms

1. 55-86-7

2. Chlormethine Hydrochloride

3. Mechlorethamine Hcl

4. Nitrogen Mustard Hydrochloride

5. Chlorethamine

6. 2-chloro-n-(2-chloroethyl)-n-methylethanamine Hydrochloride

7. Hn2 Hydrochloride

8. Chlormethinum

9. Stickstofflost

10. Chloramin

11. Mustine Hydrochloride

12. Bis(2-chloroethyl)methylamine Hydrochloride

13. Azotoyperite

14. Dichloren

15. Embikhine

16. Mitoxine

17. Dimitan

18. Erasol

19. Nitol

20. Dema

21. Nitol Takeda

22. Erasol-ido

23. Chlormethine Hcl

24. Caryolysine

25. Mustin Hydrochloride

26. Embichin

27. Nitrogranulogen Hydrochloride

28. N-mustard

29. Mechlorethamine Chloridrate

30. N-methylbis(2-chloroethyl)amine Hydrochloride

31. Stickstofflost-ebewe

32. 2,2'-dichloro-n-methyldiethylamine Hydrochloride

33. Dichloromethyldiethylamine Hydrochloride

34. 1,5-dichloro-3-methyl-3-azapentane Hydrochloride

35. Di(2-chloroethyl)methylamine Hydrochloride

36. Methyldi(2-chloroethyl)amine Hydrochloride

37. Nci-c56382

38. Mba Hydrochloride

39. Methylbis(2-chloroethyl)amine Hydrochloride

40. Ethanamine, 2-chloro-n-(2-chloroethyl)-n-methyl-, Hydrochloride

41. Chlormethine (hydrochloride)

42. Sk 101

43. N-methyl-2,2'-dichlorodiethylamine Hydrochloride

44. Nsc-762

45. Methyldi(beta-chloroethyl)amine Hydrochloride

46. N-methyl-di-2-chloroethylamine Hydrochloride

47. N-lost

48. Methyl-bis(beta-chloroethyl)amine Hydrochloride

49. N-methyl-bis-beta-chlorethylamine Hydrochloride

50. C 6866

51. N,n-bis(2-chloroethyl)methylamine Hydrochloride

52. Nitrogen Mustard (hn-2), Hydrochloride

53. L0mr697hhi

54. Beta,beta'-dichlorodiethyl-n-methylamine Hydrochloride

55. Nsc762

56. 2-chloro-n-(2-chloroethyl)-n-methylethanamine Hydrochlroide

57. Chebi:55368

58. N,n-bis(2-chloraethyl)methylamin-hydrochlorid

59. Bis(2-chloroethyl)-n-methylamine Hydrochloride

60. Mechlorethamine Hydrochloride [usp]

61. Carolysine

62. Mebichloramine

63. Nitrogranulogen

64. Embechine

65. Valchlor

66. Ncgc00091835-01

67. 2-chloro-n-(2-chloroethyl)-n-methylethanamine;hydrochloride

68. Embiquine

69. Zagreb

70. Pliva

71. Bis-(2-chloroethyl)methylamine Hydrochloride

72. Dsstox_cid_5757

73. Dsstox_rid_77910

74. Dsstox_gsid_25757

75. Kloramin (van)

76. N-mustard [german]

77. Mechlorethamine Hydrochloride (usp)

78. Cas-55-86-7

79. Ccris 448

80. Dichloren Hydrochloride

81. Hsdb 7176

82. Einecs 200-246-0

83. Unii-l0mr697hhi

84. Ai3-16195

85. Mustine Hydrochlor

86. Nitol 'takeda'

87. Mustargen (tn)

88. Prestwick_37

89. Valchlor (tn)

90. Erasol Hydrochloride

91. Mfcd00012517

92. Nitrogen Mustard Hcl

93. Embichin Hydrochloride

94. Chloramin Hydrochloride

95. Mustargen Hydrochloride

96. N,n-bis(2-chloraethyl)methylamin-hydrochlorid [german]

97. Caryolysine Hydrochloride

98. Nsc-762 Hydrochloride

99. Chlormethini Hydrochloridum

100. Chloromethine Hydrochloride

101. Mechorethamine Hydrochloride

102. Schembl3855

103. Mls003899210

104. Diethylamine, 2,2'-dichloro-n-methyl, Hydrochloride

105. Chembl1201001

106. Dtxsid8025757

107. Wln: G2n1&2g &gh

108. Mechlorethamine Hydrochloride, 98%

109. Hy-b1253

110. Tox21_111170

111. Tox21_200638

112. S4252

113. Akos015915356

114. Tox21_111170_1

115. Ccg-264667

116. Cs-5080

117. Bis(2-chloroethyl)methylammonium Chloride

118. Ncgc00091835-10

119. Ncgc00258192-01

120. Bp-20221

121. Chlormethine Hydrochloride [mart.]

122. Mechlorethamine Hydrochloride [mi]

123. Smr000059226

124. Chlormethine Hydrochloride [who-dd]

125. Chlormethine Hydrochloride [who-ip]

126. Db-007290

127. Mechlorethamine Hydrochloride [hsdb]

128. Bis(2-chloroethyl)-methylamine Hydrochloride

129. Bis(2-chloroethyl)methyl Amine Hydrochloride

130. Mechlorethamine Hydrochloride [vandf]

131. N,n-bis(chloroethyl)methylamine Hydrochloride

132. Sw220100-1

133. Bis (2-chloroethyl)-methylamine Hydrochloride

134. Bis (2-chloroethyl)methyl Amine Hydrochloride

135. Bis-(2-chloroethyl)-methylamine Hydrochloride

136. Mechlorethamine Hydrochloride [usp-rs]

137. N-methylbis (2-chloroethyl)amine Hydrochloride

138. Bis-(2-chloroethyl)-methyl-amine Hydrochloride

139. D04872

140. F11444

141. Methyldi(.beta.-chloroethyl)amine Hydrochloride

142. N-methyl-bis-(2-chloroethyl)amine Hydrochloride

143. N-methylbis(2-chloroethyl)-amine Hydrochloride

144. 2,2'-dichloro-n-methyldiethylamino Hydrochloride

145. Bis(2-chloroethyl)methylamine-[d4] Hydrochloride

146. Bis-(2-chloro-ethyl)-methyl-amine Hydrochloride

147. Diethylamine,2'-dichloro-n-methyl, Hydrochloride

148. Methylbis(.beta.-chloroethyl)amine Hydrochloride

149. Chlormethini Hydrochloridum [who-ip Latin]

150. Diethylamine,2'-dichloro-n-methyl-, Hydrochloride

151. Mechlorethamine Hydrochloride [orange Book]

152. Methyl Bis(.beta.-chloroethyl)amine, Hydrochloride

153. N-methylbis(.beta.-chlorethyl)amine Hydrochloride

154. 1,5-dichloro-3-methyl-3-azapentane, Hydrochloride

155. Mechlorethamine Hydrochloride [usp Monograph]

156. N,n-bis(2-chloroethyl)-n-methylamine Hydrochloride

157. W-105542

158. Q27124263

159. .beta.,.beta.'-dichlorodiethyl-n-methylamine Hydrochloride

160. 2-chloro-n-(chloroethyl)-n-methylethanamine Hydrochloride

161. 2-chloro-n-(2 -chloroethyl)-n-methylethanamine Hydrochloride

162. 2-chloro-n-(2-chloroethyl) -n-methylethanamine Hydrochloride

163. 2-chloro-n-(2-chloroethyl)-n-methylethanamine Hydrochloride (1:1)

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 192.5 g/mol
Molecular Formula C5H12Cl3N
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count4
Exact Mass191.003532 g/mol
Monoisotopic Mass191.003532 g/mol
Topological Polar Surface Area3.2 Ų
Heavy Atom Count9
Formal Charge0
Complexity43.7
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Alkylating Agents; Antineoplastic Agents, Alkylating;

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Antineoplastic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1032


VET: Antineoplastic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1032


MEDICATION (VET): ... MECHLORETHAMINE HYDROCHLORIDE IS REPORTED TO BE USED FOR TREATMENT OF LYMPHOSARCOMA & OF MAST CELL SARCOMA IN DOGS & OF FOWL LEUKOSIS ... /MECHLORETHAMINE HYDROCHLORIDE/

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V9 198 (1975)


For more Therapeutic Uses (Complete) data for MECHLORETHAMINE HYDROCHLORIDE (11 total), please visit the HSDB record page.


4.2 Drug Warning

Adverse CNS effects which have occurred following IV administration of mechlorethamine include weakness, headache, drowsiness, vertigo, lightheadedness, convulsions, progressive muscle paralysis, paresthesia, cerebral degeneration, coma, and death. Serious neurotoxicity appears to be a problem only when high doses or intra-arterial and regional perfusion administration techniques are used. Immediate and delayed neurotoxicity, sometimes severe, has been reported in patients receiving higher than recommended doses of the drug in preparation for bone marrow transplantation; neurotoxicity appeared to increase with age and dose administered and occurred more frequently in patients who also received procarbazine or cyclophosphamide.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1069


Adverse dermatologic effects of systemic mechlorethamine therapy occasionally include a maculopapular skin eruption which is apparently idiosyncratic. The maculopapular skin eruption does not necessarily recur with subsequent doses and is not a contraindication to future use of the drug. Erythema multiforme also has been reported. Hypersensitivity reactions, including anaphylaxis, have been reported in patients receiving IV mechlorethamine. ... Herpes zoster, which occurs commonly in patients with lymphoma, may be precipitated by treatment with mechlorethamine.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1069


Major and dose-limiting adverse effects of mechlorethamine are nausea and vomiting, which occur in up to 90% of patients who receive the drug and are presumably due to CNS stimulation.Vomiting, which may be severe enough to precipitate vascular accidents in patients with hemorrhagic tendencies, occurs within 0.5-8 hours (usually 1-3 hours) after administration of mechlorethamine. Emesis generally subsides within 8 hours, but nausea may persist 24 hours or longer. ... Other GI effects of mechlorethamine include anorexia, diarrhea, severe hematemesis and dehydration secondary to vomiting, and rarely, peptic ulcers.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1069


Mechlorethamine must be used with extreme caution in patients with leukopenia, thrombocytopenia, or anemia caused by infiltration of bone marrow with malignant cells. In these patients, a good response to mechlorethamine therapy with disappearance of tumor from the bone marrow may be associated with improved bone marrow function; however, in the absence of good response or in patients who have received previous treatment with antineoplastic agents, hematopoiesis may be further compromised, resulting in more severe leukopenia, thrombocytopenia, anemia, and possibly death. Patients with chronic lymphocytic leukemia appear to be especially sensitive to the hematopoietic effects of mechlorethamine and should receive the drug with extreme caution, if at all.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1069


For more Drug Warnings (Complete) data for MECHLORETHAMINE HYDROCHLORIDE (17 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Alkylating Agents

Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases. (See all compounds classified as Alkylating Agents.)


Irritants

Drugs that act locally on cutaneous or mucosal surfaces to produce inflammation; those that cause redness due to hyperemia are rubefacients; those that raise blisters are vesicants and those that penetrate sebaceous glands and cause abscesses are pustulants; tear gases and mustard gases are also irritants. (See all compounds classified as Irritants.)


Antineoplastic Agents, Alkylating

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)


Chemical Warfare Agents

Chemicals that are used to cause the disturbance, disease, or death of humans during WARFARE. (See all compounds classified as Chemical Warfare Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Alkylating Drug [EPC]; Alkylating Activity [MoA]
5.3 Absorption, Distribution and Excretion

Following IV injection, the drug undergoes rapid chemical transformation and unchanged mechlorethamine is undetectable in the blood within a few minutes. Less than 0.01% of an IV dose is excreted unchanged in the urine.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1070


Mice given 35 mg/kg body wt mechlorethamine hydrochloride iv and examined by autoradiography had significant levels of compound in brain, spinal cord, lung and submaxillary glands.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V9 201 (1975)


Mechlorethamine is incompletely absorbed following intracavitary administration, probably because of rapid deactivation by body fluids.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1804


5.4 Metabolism/Metabolites

Following its in vivo admin, mechlorethamine or its hydrochloride is probably converted into ethyleneimmonium ion which reacts with guanine residues in /either the same or/ adjacent strands of DNA as well as with SH groups.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V9 201 (1975)


5.5 Mechanism of Action

Mechlorethamine, as an alkylating agent, interferes with DNA replication and transcription of RNA and ultimately results in the disruption of nucleic acid function. Mechlorethamine also possesses weak immunosuppressive activity.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1070


Mechlorethamine, as an alkylating agent, interferes with DNA replication and transcription of RNA, and ultimately results in the disruption of nucleic acid function.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 95. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 694


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  • GEL;TOPICAL - EQ 0.016% BASE
  • INJECTABLE;INJECTION - 10MG/VIAL
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