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Leukeran

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Chemistry

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Also known as: 305-03-3, Ambochlorin, Leukeran, Chloroambucil, Chloraminophen, Chlorbutin

Molecular Formula

C₁₄H₁₉Cl₂NO₂

Molecular Weight

304.2 g/mol

InChI Key

JCKYGMPEJWAADB-UHFFFAOYSA-N

FDA UNII

18D0SL7309

A nitrogen mustard alkylating agent used as antineoplastic for chronic lymphocytic leukemia, Hodgkin's disease, and others. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed)

Chlorambucil is an Alkylating Drug. The mechanism of action of chlorambucil is as an Alkylating Activity.

1 2D Structure

Chlorambucil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[4-[bis(2-chloroethyl)amino]phenyl]butanoic acid

2.1.2 InChI

InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)

2.1.3 InChI Key

JCKYGMPEJWAADB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1CCCC(=O)O)N(CCCl)CCCl

2.2 Other Identifiers

2.2.1 UNII

18D0SL7309

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(bis(2-chloroethyl)amino)benzenebutanoic Acid

2. Amboclorin

3. Cb 1348

4. Cb-1348

5. Cb1348

6. Chloraminophene

7. Chlorbutin

8. Leukeran

9. Lympholysin

10. N,n-di-(2-chloroethyl)-p-aminophenylbutyric Acid

11. Nsc 3088

12. Nsc-3088

13. Nsc3088

2.3.2 Depositor-Supplied Synonyms

1. 305-03-3

2. Ambochlorin

3. Leukeran

4. Chloroambucil

5. Chloraminophen

6. Chlorbutin

7. Chloraminophene

8. Chlorobutine

9. Amboclorin

10. Ecloril

11. Chlorbutine

12. Chlorobutin

13. Lympholysin

14. Chlocambucil

15. Linfolizin

16. Linfolysin

17. Elcoril

18. Phenylbutyric Acid Nitrogen Mustard

19. Leukersan

20. Leukoran

21. 4-{4-[bis(2-chloroethyl)amino]phenyl}butanoic Acid

22. Chlorambucilum

23. Nsc-3088

24. Cb L348

25. Cb 1348

26. Phenylbuttersaeure-lost

27. Benzenebutanoic Acid, 4-[bis(2-chloroethyl)amino]-

28. Nsc 3088

29. Rcra Waste Number U035

30. Cb-1348

31. Nci-c03485

32. 4-[p-[bis(2-chloroethyl)amino]phenyl]butyric Acid

33. 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoic Acid

34. 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoic Acid

35. N,n-di-2-chloroethyl-gamma-p-aminophenylbutyric Acid

36. 4-(bis(2-chloroethyl)amino)benzenebutanoic Acid

37. P-(n,n-di-2-chloroethyl)aminophenyl Butyric Acid

38. 4-(p-bis(beta-chloroethyl)aminophenyl)butyric Acid

39. Benzenebutanoic Acid, 4-(bis(2-chloroethyl)amino)-

40. Chebi:28830

41. Nsc3088

42. 4-[bis(2-chloroethyl)amino]benzenebutyric Acid

43. 4-[bis(2-chloroethyl)amino]benzenebutanoic Acid

44. Chembl515

45. 4-(p-(bis(2-chloroethyl)amino)phenyl)butyric Acid

46. Gamma-[p-di(2-chloroethyl)aminophenyl]butyric Acid

47. Mls000028443

48. Chloorambucol

49. Chlorbutinum

50. Elcorin

51. 4-(bis(2-chloroethyl)amino)phenylbutyric Acid

52. Nci-3088

53. Gamma-(p-di(2-chloroethyl)aminophenyl)butyric Acid

54. Butyric Acid, 4-(p-bis(2-chloroethyl)aminophenyl)-

55. 18d0sl7309

56. Kyselina 4-(n,n-bis-(2-chlorethyl)-p-aminofenyl)maselna

57. Ncgc00015199-08

58. Clorambucile

59. Clorambucilo

60. Cas-305-03-3

61. Smr000058372

62. Clorambucile [dcit]

63. Dsstox_cid_263

64. Leukeran Tablets

65. 4-[bis(2-chloroethyl)amino]phenylbutyric Acid

66. Dsstox_rid_75472

67. Dsstox_gsid_20263

68. 4-(4-[bis(2-chloroethyl)amino]phenyl)butyric Acid

69. .gamma.-[p-di(2-chloroethyl)aminophenyl]butyric Acid

70. Butyric Acid, 4-[p-[bis(2-chloroethyl)amino]phenyl]-

71. Chlorambucilum [inn-latin]

72. Clorambucilo [inn-spanish]

73. P-n,n-di-(.beta.-chloroethyl)aminophenyl Butyric Acid

74. N,n-di-2-chloroethyl-.gamma.-p-aminophenylbutyric Acid

75. Ccris 126

76. Phenylbuttersaeure-lost [german]

77. Hsdb 3026

78. Sr-01000000062

79. Leukeran (tn)

80. 4-[4-[bis(2-chloroethyl)amino]phenyl]butyric Acid

81. Einecs 206-162-0

82. .gamma.-(p-bis(2-chloroethyl)aminophenyl)butyric Acid

83. .gamma.-[p-bis(2-chloroethyl)aminophenyl]butyric Acid

84. 4-(p-bis(.beta.-chloroethyl)aminophenyl)butyric Acid

85. 4-[p-bis(.beta.-chloroethyl)aminophenyl]butyric Acid

86. Rcra Waste No. U035

87. Butyric Acid, 4-(p-[bis(2-chloroethyl)amino]phenyl)-

88. Brn 0999011

89. Chlorambucilddv

90. Chlorambucil [usp:inn:ban]

91. Ai3-26083

92. Unii-18d0sl7309

93. P-(n,n-di-2-chlorethylaminophenyl)butyric Acid

94. Para-(di(2-chloroethyl)aminophenyl)butyric Acid

95. Chlorambucil,(s)

96. Gamma-(p-bis(2-chloroethyl)aminophenyl)butyricacid

97. Butanoic Acid, 4-(bis(2-chloroethyl)amino) Benzene

98. Gamma-(p-bis(2-chloroethyl)aminophenyl)butyric Acid

99. Phenyl)butanoic Acid

100. Mfcd00021783

101. P-n,n-di-(beta-chloroethyl)aminophenyl Butyric Acid

102. Butyric Acid, 4-(p-(bis(2-chloroethyl)amino)phenyl)

103. Para-n,n-di(beta-chloroethyl)aminophenyl Butyric Acid

104. N,n-di-2-chloroethyl-gamma-para-aminophenyl Butyric Acid

105. Opera_id_51

106. Spectrum_000118

107. Kyselina 4-(n,n-bis-(2-chlorethyl)-p-aminofenyl)maselna [czech]

108. Prestwick0_001079

109. Prestwick1_001079

110. Prestwick2_001079

111. Prestwick3_001079

112. Spectrum2_000065

113. Spectrum3_000336

114. Spectrum4_000273

115. Spectrum5_000677

116. Chlorambucil [mi]

117. Lopac-c-0253

118. Chlorambucil [inn]

119. Chlorambucil [jan]

120. Epitope Id:139977

121. Chlorambucil [hsdb]

122. Chlorambucil [iarc]

123. Schembl4308

124. Chlorambucil [vandf]

125. Chlorambucil With Impurity G

126. Lopac0_000227

127. Wln: Qv3r Dn2g2g

128. Bspbio_001098

129. Bspbio_001971

130. Chlorambucil [mart.]

131. Kbiogr_000766

132. Kbioss_000558

133. 4-14-00-01715 (beilstein Handbook Reference)

134. Mls001076130

135. Chlorambucil [usp-rs]

136. Chlorambucil [who-dd]

137. Chlorambucil [who-ip]

138. Divk1c_000688

139. Spectrum1500171

140. Chlorambucil (jan/usp/inn)

141. Spbio_000249

142. Spbio_002999

143. Bpbio1_001208

144. Gtpl7143

145. Zinc1115

146. Dtxsid7020263

147. Hms502c10

148. Kbio1_000688

149. Kbio2_000558

150. Kbio2_003126

151. Kbio2_005694

152. Kbio3_001191

153. Ninds_000688

154. Chlorambucil [orange Book]

155. Chlorambucil For System Suitability

156. Hms1571g20

157. Hms1920m15

158. Hms2090m19

159. Hms2091a22

160. Hms2098g20

161. Hms2235a04

162. Hms3259i10

163. Hms3372o04

164. Hms3652p08

165. Pharmakon1600-01500171

166. 4-(4-(bis(2-chloroethyl)amino)

167. Chlorambucil [ep Monograph]

168. Amy33445

169. Bcp28394

170. Chlorambucil [usp Monograph]

171. Tox21_110096

172. Tox21_201390

173. Tox21_302996

174. Bdbm50003677

175. Ccg-39872

176. Nsc756674

177. S4288

178. Chlorambucilum [who-ip Latin]

179. Akos024319346

180. Tox21_110096_1

181. Chlorambucil, Purum, >=98.0% (t)

182. Cs-3118

183. Db00291

184. Gs-6200

185. Lp00227

186. Nc00555

187. Nsc-756674

188. Sdccgsbi-0050215.p005

189. Idi1_000688

190. Ncgc00015199-01

191. Ncgc00015199-02

192. Ncgc00015199-03

193. Ncgc00015199-04

194. Ncgc00015199-05

195. Ncgc00015199-06

196. Ncgc00015199-07

197. Ncgc00015199-09

198. Ncgc00015199-10

199. Ncgc00015199-11

200. Ncgc00015199-12

201. Ncgc00015199-13

202. Ncgc00015199-14

203. Ncgc00015199-15

204. Ncgc00015199-16

205. Ncgc00015199-17

206. Ncgc00015199-19

207. Ncgc00015199-20

208. Ncgc00023250-00

209. Ncgc00023250-03

210. Ncgc00023250-04

211. Ncgc00023250-05

212. Ncgc00023250-06

213. Ncgc00023250-07

214. Ncgc00023250-08

215. Ncgc00023250-09

216. Ncgc00023250-10

217. Ncgc00256464-01

218. Ncgc00258941-01

219. Bp-24028

220. Hy-13593

221. Nci60_002639

222. Sbi-0050215.p004

223. Db-047794

224. Wr-139013

225. Ab00051938

226. Eu-0100227

227. Ft-0617365

228. Sw197258-4

229. A14252

230. A18607

231. C 0253

232. C06900

233. D00266

234. H10484

235. Ab00051938-14

236. Ab00051938-15

237. Ab00051938_16

238. 305c033

239. Q415939

240. 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoicacid

241. 4[p-bis(.beta.-chloroethyl)aminophenyl]butyric Acid

242. Butanoic Acid, 4-(bis(2-chloroethyl)amino)benzene-

243. Sr-01000000062-2

244. Sr-01000000062-4

245. Sr-01000000062-7

246. W-106940

247. .gamma.-(p-bis(2-chloroethyl)aminophenyl)butyricacid

248. Brd-k29458283-001-04-2

249. Brd-k29458283-001-05-9

250. Brd-k29458283-001-17-4

251. 4-(4-[bis(2-chloroethyl)amino]phenyl)butanoic Acid #

252. Z1558572529

253. 4-[4-(n,n-bis(2-chloroethyl)-amino]phenyl)butanoic Acid

254. Chlorambucil, European Pharmacopoeia (ep) Reference Standard

255. Chlorambucil, United States Pharmacopeia (usp) Reference Standard

256. Chlorambucil For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₉Cl₂NO₂
Molecular Weight	304.2 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	9
Exact Mass	303.0792842 g/mol
Monoisotopic Mass	303.0792842 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	250
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Leukeran
PubMed Health	Chlorambucil (By mouth)
Drug Classes	Antineoplastic Agent
Drug Label	LEUKERAN (chlorambucil) was first synthesized by Everett et al. It is a bifunctional alkylating agent of the nitrogen mustard type that has been found active against selected human neoplastic diseases. Chlorambucil is known chemically as 4-[b...
Active Ingredient	Chlorambucil
Dosage Form	Tablet
Route	Oral
Strength	2mg
Market Status	Prescription
Company	Aspen Global

2 of 2
Drug Name	Leukeran
PubMed Health	Chlorambucil (By mouth)
Drug Classes	Antineoplastic Agent
Drug Label	LEUKERAN (chlorambucil) was first synthesized by Everett et al. It is a bifunctional alkylating agent of the nitrogen mustard type that has been found active against selected human neoplastic diseases. Chlorambucil is known chemically as 4-[b...
Active Ingredient	Chlorambucil
Dosage Form	Tablet
Route	Oral
Strength	2mg
Market Status	Prescription
Company	Aspen Global

4.2 Therapeutic Uses

Antineoplastic Agents, Alkylating; Carcinogens

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)

Chlorambucil is indicated in the treatment of chronic lymphatic (lymphocytic) leukemia, malignant lymphomas including lymphosarcoma, giant follicular lymphoma, and Hodgkin's disease. It is not curative in any of these disorders but may produce clinically useful palliation. /Include in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for LEUKERAN (chlorambucil) tablet, film coated (November 2012). Available from, as of March 1, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=6b2023e7-50dc-49c3-949d-1bc10ba256f0

Chlorambucil is considered by many clinicians to be the drug of choice for the treatment of (Waldenstrom's) macroglobulinemia. /Not included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 981

Chlorambucil has also been used effectively with prednisone in the treatment of children with minimal-change nephrotic syndrome (lipoid nephrosis, idiopathic nephrotic syndrome of childhood) who have frequent relapses, require corticosteroid therapy to maintain remissions, or whose disease is resistant to steroid therapy. In most of these children, chlorambucil and prednisone therapy has induced long-term remissions and decreased the frequency of relapses. Although this type of nephrotic syndrome only occasionally occurs in adults, it is treated similarly. /Not included in US product label/

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 981

For more Therapeutic Uses (Complete) data for CHLORAMBUCIL (9 total), please visit the HSDB record page.

4.3 Drug Warning

/BOXED WARNING/ Chlorambucil can severely suppress bone marrow function. Chlorambucil is a carcinogen in humans. Chlorambucil is probably mutagenic and teratogenic in humans. Chlorambucil produces human infertility.

US Natl Inst Health; DailyMed. Current Medication Information for LEUKERAN (chlorambucil) tablet, film coated (December 2011). Available from, as of March 1, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=6b2023e7-50dc-49c3-949d-1bc10ba256f0

Chlorambucil is contraindicated in patients with known hypersensitivity to the drug or in patients whose disease was resistant to prior therapy with the drug. The manufacturer states that there may be cross-sensitivity between chlorambucil and other alkylating agents manifested as rash. Chlorambucil should be discontinued promptly in patients who develop skin reactions.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 982

Adverse hematologic effects are the major and dose-limiting effects of chlorambucil. In usual doses, myelosuppression generally occurs gradually, is moderate in severity, and is usually reversible following discontinuance of the drug. Leukopenia, resulting from neutropenia and slowly progressive lymphopenia, occurs in many patients receiving chlorambucil. Thrombocytopenia and anemia may also occur.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 981

Chlorambucil appears to be relatively free of adverse GI effects unless single doses of 20 mg or more are administered. Adverse GI effects include nausea, vomiting, gastric discomfort or abdominal pain, anorexia, and diarrhea. Adverse GI effects are usually mild, last less than 24 hours, and disappear despite continued treatment; however, nausea and weakness have persisted up to 7 days in some patients following a single, high dose of the drug. If necessary, nausea and vomiting may usually be controlled with antiemetics. Oral ulceration has also been reported.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 981

For more Drug Warnings (Complete) data for CHLORAMBUCIL (25 total), please visit the HSDB record page.

4.4 Drug Indication

For treatment of chronic lymphatic (lymphocytic) leukemia, childhood minimal-change nephrotic syndrome, and malignant lymphomas including lymphosarcoma, giant follicular lymphoma, Hodgkin's disease, non-Hodgkin's lymphomas, and Waldenstrms Macroglobulinemia.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Chlorambucil is an antineoplastic in the class of alkylating agents that is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.

5.2 MeSH Pharmacological Classification

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.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CHLORAMBUCIL

5.3.2 FDA UNII

18D0SL7309

5.3.3 Pharmacological Classes

Alkylating Drug [EPC]; Alkylating Activity [MoA]

5.4 ATC Code

L01AA02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01A - Alkylating agents

L01AA - Nitrogen mustard analogues

L01AA02 - Chlorambucil

5.5 Absorption, Distribution and Excretion

Route of Elimination

Chlorambucil is extensively metabolized in the liver primarily to phenylacetic acid mustard. The pharmacokinetic data suggests that oral chlorambucil undergoes rapid gastrointestinal absorption and plasma clearance and that it is almost completely metabolized, having extremely low urinary excretion.

Chlorambucil is rapidly and completely absorbed from the GI tract. Following single oral doses of 0.6-1.2 mg/kg, peak plasma concentrations of chlorambucil are reached within 1 hour.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 983

In a limited number of patients given a single oral dose of chlorambucil 0.2 mg/kg, an average peak plasma chlorambucil concentration of 492 ng/mL (adjusted to a dose of 12 mg) was reached at about 0.83 hours, and a mean peak plasma concentration of phenylacetic acid mustard (the major metabolite of chlorambucil) of 306 ng/mL (adjusted to a chlorambucil dose of 12 mg) occurred at approximately 1.9 hours. The area under the plasma concentration-time curve (AUC) of phenylacetic acid mustard was about 1.36 times greater than the AUC of chlorambucil.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 983

In a study of 12 patients given single oral doses of 0.2 mg/kg of chlorambucil, the mean dose (12 mg) adjusted (+/-SD) plasma chlorambucil Cmax was 492 +/- 160 ng/mL, the AUC was 883 +/- 329 ng.hr/mL, t1/2 was 1.3 +/- 0.5 hours, and the tmax was 0.83 +/- 0.53 hours. For the major metabolite, phenylacetic acid mustard, the mean dose (12 mg) adjusted (+/- SD) plasma Cmax was 306 +/- 73 ng/mL, the AUC was 1204 +/- 285 ng.h/mL, the t1/2 was 1.8 +/- 0.4 hours, and the tmax was 1.9 +/- 0.7 hours.

Chlorambucil and its metabolites are extensively bound to plasma and tissue proteins. In vitro, chlorambucil is 99% bound to plasma proteins, specifically albumin.

For more Absorption, Distribution and Excretion (Complete) data for CHLORAMBUCIL (12 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Chlorambucil undergoes rapid metabolism to phenylacetic acid mustard, the major metabolite, and the combined chlorambucil and phenylacetic acid mustard urinary excretion is extremely low - less than 1% in 24 hours.

Chlorambucil and its major metabolite spontaneously degrade in vivo forming monohydroxy and dihydroxy derivatives.

Chlorambucil is extensively metabolized in rodents by monochloroethylation and by beta oxidation, forming the phenylacetic acid derivative, which also has anticancer activity.

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. V26 123 (1981)

Ten metabolites of chlorambucil were isolated, most of which were phenylacetic acid & benzoic acid derivatives.

PMID:868079 MITOMA C ET AL; XENOBIOTICA 7 (4): 205-20 (1977)

5.7 Biological Half-Life

1.5 hours

In a study of 12 patients given single oral doses of 0.2 mg/kg of chlorambucil, ... t1/2 was 1.3 +/- 0.5 hours, and the tmax was 0.83 +/- 0.53 hours. For the major metabolite, phenylacetic acid mustard, ... the t1/2 was 1.8 +/- 0.4 hours, and the tmax was 1.9 +/- 0.7 hours.

5.8 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.

As an alkylating agent, chlorambucil interferes with DNA replication and transcription of RNA, and ultimately results in the disruption of nucleic acid function. In vitro studies have shown that the major metabolite of chlorambucil (phenylacetic acid mustard), which is also a bifunctional alkylating compound, has antineoplastic activity against some neoplastic human cell lines that is approximately equal to that of chlorambucil. Therefore, the major metabolite of chlorambucil may contribute to the in vivo antitumor activity of the drug. Chlorambucil also possesses some immunosuppressive activity, principally due to its suppression of lymphocytes. The drug is the slowest acting and generally least toxic of the presently available nitrogen mustard derivatives.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 983

A marked transient increase was observed in ribonucleotide reductase activity within 2 hr of exposing BALB/c 3T3 mouse cells to DNA damaging concentrations of chlorambucil. Elevations in activity were accompanied by transient increases in the mRNA levels of both genes (R1 and R2) that code for ribonucleotide reductase. Only the protein for the limiting component for enzyme activity R2 was significantly elevated in chlorambucil treated cultures. The chlorambucil effects upon activity and regulation of ribonucleotide reductase occurred without any detectable changes in the rate of DNA synthesis, as would be expected if the elevation in enzyme activity is required for DNA repair. The chlorambucil-induced elevations in R1 and R2 message levels were blocked by treatment of cells with actinomycin D or the tumor promoter 12-O-tetradecanoylphorbol-13-acetate indicating the importance of the reductase transcriptional process in responding to the action of chlorambucil and providing evidence for the involvement of a protein kinase C pathway in the regulation of mammalian ribonucleotide reductase. In addition to the chlorambucil-induced elevations in enzyme activity, message, and protein levels, the drug was also shown to be an inhibitor of ribonucleotide reductase activity in cell-free preparations. Both R1 and R2 proteins were targets for chlorambucil, in keeping with the known alkylating abilities of the drug.

PMID:1551913 Hurta RA, Wright JA; J Biol Chem 267 (10): 7066-71 (1992)

/ALTERNATIVE and IN VITRO TESTS/ Reaction of one of the two chloroethyl groups of chlorambucil with the N7 position of guanine or adenine of double-stranded DNA leads to the formation of mono-adducts. These are repaired rapidly in an error-free fashion by methylguanine methyltransferase (sometimes called alkylguanine alkyltransferase). However, some cells lack this repair activity, usually because of silencing of the corresponding gene, and the unrepaired DNA mono-adduct then forms a complex with mismatch-repair enzymes. The subsequent inhibition of DNA replication can eventually induce DNA breakage. The second chloroethyl group of the DNA mono-adduct with chlorambucil can interact with proteins but more importantly, because of its juxtaposition to other bases in the major groove of DNA, it can react with a DNA base to form an interstrand DNA cross-link. This DNA crosslink complex is quite stable, and its repair requires nucleotide excision repair factors (such as xeroderma pigmentosum complementation group F-excison repair cross-complementing rodent repair deficiency, complementation group, 1-XPF-ERCC1) that act slowly by homologous recombination. The DNA cross-link attracts several binding proteins, probably the BRCA1 and BRCA2 proteins, Fanconi anemia gene product, and Nijmegen breakage syndrome gene product to form a complex. As shown in cultured HeLa cells, addition of chlorambucil prolongs S-phase and induces a corresponding mitotic delay. The magnitude of these effects correlates with the level of DNA cross-links. Treatment of cells in the G2-phase of the cell cycle does not induce mitotic delay but does inhibit DNA synthesis in the subsequent cell cycle, and causes a delay in the next mitosis, suggesting that at least some lesions induced by chlorambucil are long-lasting.

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