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Chemistry

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Also known as: 13010-47-4, 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea, Ccnu, Belustine, Ceenu, Cecenu
Molecular Formula
C9H16ClN3O2
Molecular Weight
233.69  g/mol
InChI Key
GQYIWUVLTXOXAJ-UHFFFAOYSA-N
FDA UNII
7BRF0Z81KG

Lomustine
An alkylating agent of value against both hematologic malignancies and solid tumors.
Lomustine is an Alkylating Drug. The mechanism of action of lomustine is as an Alkylating Activity.
1 2D Structure

Lomustine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea
2.1.2 InChI
InChI=1S/C9H16ClN3O2/c10-6-7-13(12-15)9(14)11-8-4-2-1-3-5-8/h8H,1-7H2,(H,11,14)
2.1.3 InChI Key
GQYIWUVLTXOXAJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CCC(CC1)NC(=O)N(CCCl)N=O
2.2 Other Identifiers
2.2.1 UNII
7BRF0Z81KG
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Belustine

2. Ccnu

3. Cecenu

4. Ceenu

5. Nsc 79037

6. Nsc-79037

7. Nsc79037

2.3.2 Depositor-Supplied Synonyms

1. 13010-47-4

2. 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea

3. Ccnu

4. Belustine

5. Ceenu

6. Cecenu

7. Cinu

8. Chloroethylcyclohexylnitrosourea

9. Urea, N-(2-chloroethyl)-n'-cyclohexyl-n-nitroso-

10. Lomustina

11. Lomustinum

12. Lomustinum [inn-latin]

13. Lomustina [inn-spanish]

14. N-(2-chloroethyl)-n'-cyclohexyl-n-nitrosourea

15. 1-(2-chloroethyl)-3-cyclohexylnitrosourea

16. Nsc 79037

17. Nsc-79037

18. Gleostine

19. Cyclohexyl Chloroethyl Nitrosourea

20. Sri 2200

21. Icig 1109

22. Nci-c04740

23. (chloro-2-ethyl)-1-cyclohexyl-3-nitrosourea

24. Rb 1509

25. (cloro-2-etil)-1-cicloesil-3-nitrosourea

26. Nsc79037

27. Lomustine (ceenu)

28. 1-nitrosourea, 1-(2-chloroethyl)-3-cyclohexyl-

29. Chebi:6520

30. Urea, 1-(2-chloroethyl)-3-cyclohexyl-1-nitroso-

31. Ccn-u

32. 7brf0z81kg

33. Ccnu; Nsc 79037

34. 1-(2-chloroethyl)-3-cyclohexyl-1-nitroso-urea

35. Ncgc00167466-01

36. Dsstox_cid_3222

37. 3-(2-chloroethyl)-1-cyclohexyl-3-nitrosourea

38. Dsstox_rid_76930

39. Dsstox_gsid_23222

40. Ccris 860

41. Cas-13010-47-4

42. Ccnu [chloroethyl Nitrosoureas]

43. Hsdb 6519

44. Sr-05000001497

45. Einecs 235-859-2

46. Unii-7brf0z81kg

47. Brn 2125058

48. (cloro-2-etil)-1-cicloesil-3-nitrosourea [italian]

49. Lomustine [usan:inn:ban]

50. Ai3-52779

51. Gleostine (tn)

52. Lomustine- Bio-x

53. Lomustine, >=98%

54. Lomustine (usp/inn)

55. Lomustine [inn]

56. Lomustine [mi]

57. Lomustine [hsdb]

58. Lomustine [usan]

59. Lomustine [vandf]

60. 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea [chloroethyl Nitrosoureas]

61. Chembl514

62. Lomustine [mart.]

63. Ncimech_000220

64. Lomustine [usp-rs]

65. Lomustine [who-dd]

66. Schembl3995

67. Wln: L6tj Amvnno&2g

68. Gtpl7214

69. Lomustine [orange Book]

70. Dtxsid2023222

71. Lomustine [ep Monograph]

72. Lomustine [usp Monograph]

73. Hms2090a17

74. Hms3655i16

75. Pharmakon1600-01502301

76. Bcp06551

77. Zinc3831006

78. Tox21_112470

79. Bdbm50247919

80. Mfcd00012392

81. Nsc759635

82. S1840

83. Akos005766022

84. Tox21_112470_1

85. Ac-8062

86. Ccg-213022

87. Cs-1461

88. Db01206

89. Ds-1269

90. Nsc-759635

91. Ncgc00167466-02

92. Ncgc00167466-03

93. Bl164634

94. Hy-13669

95. Nci60_041743

96. Db-017097

97. Am20070540

98. Ft-0627972

99. L0251

100. Sw220040-1

101. C07079

102. D00363

103. Ab00173884-02

104. Ab00173884-03

105. Ab00173884-04

106. Ab00173884_05

107. Ab00173884_06

108. 010l474

109. A806019

110. Q415378

111. Sr-05000001497-1

112. Sr-05000001497-3

113. Urea, 1-(2-chloroethyl)-3-cyclohexyl)-1-nitroso-

114. W-108355

115. Lomustine, European Pharmacopoeia (ep) Reference Standard

116. 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea [iarc]

117. Lomustine, United States Pharmacopeia (usp) Reference Standard

118. 1-(2-chloroethyl)-1-[(cyclohexylamino)carbonyl]-2-oxohydrazine #

119. 2-chloro-n-(cyclohexyl-c-hydroxycarbonimidoyl)-n-nitrosoethan-1-amine

120. 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea1-(2-chloroethyl)-3-cyclohexyl-1-nitroso-urea13010-47-4nci60_0417431-(2-chloroethyl)-3-cyclohexylnitrosourea1-nitrosourea, 1-(2-chloroethyl)-3-cyclohexyl-be

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 233.69 g/mol
Molecular Formula C9H16ClN3O2
XLogP32.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass233.0931045 g/mol
Monoisotopic Mass233.0931045 g/mol
Topological Polar Surface Area61.8 Ų
Heavy Atom Count15
Formal Charge0
Complexity219
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Antineoplastic Agents, Alkylating

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


CeeNU has been shown to be useful as a single agent in addition to other treatment modalities, or in established combination therapy with other approved chemotherapeutic agents in the following: Brain tumors-both primary and metastatic, in patients who have already received appropriate surgical and/or radiotherapeutic procedures. Hodgkin's Disease-secondary therapy in combination with other approved drugs in patients who relapse while being treated with primary therapy, or who fail to respond to primary therapy. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for CeeNU (lomustine) (June 2009). Available from, as of November 4, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=10860


Antineoplastic agent. The compound has had limited use since the early 1970s in the treatment of Hodgkin's disease and various solid tumors. These include primary and metastatic brain tumors, colorectal tumors, and certain pulmonary malignancies. It is usually used in conjunction with other antineoplastic drugs.

DHHS/National Toxicology Program; Eleventh Report on Carcinogens: Lomustine (1-(2-Chloroethyl)-3-Cyclohexyl-1-Nitrosourea) (13010-47-4) (January 2005). Available from, as of September 29, 2009: https://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s035ccnu.pdf


Although lomustine is labeled for use in combination with other agents as secondary therapy for the treatment of refractory or relapsed Hodgkin's disease, combination regimens containing other agents currently are preferred for this cancer. /Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1153


For more Therapeutic Uses (Complete) data for LOMUSTINE (8 total), please visit the HSDB record page.


4.2 Drug Warning

/BOXED WARNING/ WARNINGS: CeeNU (lomustine) should be administered under the supervision of a qualified physician experienced in the use of cancer chemotherapeutic agents. Bone marrow suppression, notably thrombocytopenia and leukopenia, which may contribute to bleeding and overwhelming infections in an already compromised patient, is the most common and severe of the toxic effects of CeeNU. Since the major toxicity is delayed bone marrow suppression, blood counts should be monitored weekly for at least 6 weeks after a dose. At the recommended dosage, courses of CeeNU should not be given more frequently than every 6 weeks. The bone marrow toxicity of CeeNU is cumulative and therefore dosage adjustment must be considered on the basis of nadir blood counts from prior dose

US Natl Inst Health; DailyMed. Current Medication Information for CeeNU (lomustine) (Updated: November 2012). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=17893de9-7d54-448c-9fca-d10642046d14


Because some lomustine metabolites are present in milk, women receiving the drug probably should not nurse their infants.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1154


Delayed onset of pulmonary fibrosis occurring up to 17 years after treatment has been reported in patients receiving related nitrosoureas combined with cranial radiation therapy for intracranial tumors during childhood and adolescence (age 1-16 years). Late onset of reduction in pulmonary function was observed in all long-term survivors. Nitrosourea-induced pulmonary fibrosis may be slowly progressive and can cause death.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1153


Nausea and vomiting occur in 45-100% of patients within 45 min to 6 hr after ingestion of an oral dose of lomustine. Although these symptoms are not severe and usually abate within 24 hr, they may persist up to 36 hr and are often followed by 2-3 days of anorexia. Stomatitis has occurred infrequently.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1153


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


4.3 Drug Indication

For the treatment of primary and metastatic brain tumors as a component of combination chemotherapy in addition to appropriate surgical and/or radiotherapeutic procedures. Also used in combination with other agents as secondary therapy for the treatment of refractory or relapsed Hodgkin's disease.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Lomustine is an alkylating agent of the nitrosourea type. Lomustine and its metabolites interferes with the function of DNA and RNA. It is cell cycle–phase nonspecific. Cancers form when some cells within the body multiply uncontrollably and abnormally. These cells then spread and destroy nearby tissues. Lomustine acts by slowing this process down. It kills cancer cells by damaging the DNA (the genetic material inside the cells) and stops them from dividing.


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
LOMUSTINE
5.3.2 FDA UNII
7BRF0Z81KG
5.3.3 Pharmacological Classes
Alkylating Drug [EPC]; Alkylating Activity [MoA]
5.4 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01A - Alkylating agents

L01AD - Nitrosoureas

L01AD02 - Lomustine


5.5 Absorption, Distribution and Excretion

Absorption

Well and rapidly absorbed from the gastrointestinal tract.


Route of Elimination

Following oral administration of radioactive CeeNU at doses ranging from 30 mg/m2 to 100 mg/m2, about half of the radioactivity given was excreted in the urine in the form of degradation products within 24 hours.


Lomustine is excreted primarily in the urine as metabolites. Following oral administration of (14)C-labeled lomustine, about 50% of the radioactivity is excreted within 12 hr and about 75% within 4 days.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1154


Lomustine is reported to be widely distributed. Lomustine and/or its metabolites cross the blood-brain barrier and are rapidly transported into cells due to their high lipid solubility. Although intact lomustine is not detectable in the CSF, active metabolites of the drug appear in substantial concentrations within 30 minutes after oral administration of lomustine. CSF concentrations of metabolites have been reported to be 15-50% or greater than concurrent plasma concentrations. Lomustine metabolites are present in milk, but in concentrations than those in maternal plasma.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1154


Lomustine is rapidly absorbed from the GI tract; the drug is also absorbed following topical application. Peak plasma concentrations of metabolites occur within 1-6 hours following administration of an oral dose of lomustine.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1154


Following its ip or iv injection or oral administration, (14)C-labelled CCNU was rapidly distributed to many tissues in mice, rats, rabbits and dogs.. About 80% of label was excreted in the urine of mice 24 hours after a single parenteral or oral dose of 50 mg/kg bw.

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 142 (1981)


5.6 Metabolism/Metabolites

Hepatic. Rapid and complete, with active metabolites.


CCNU undergoes spontaneous decomposition under physiological conditions to release both alkylating and carbamoylating entities. It disappears from plasma within 5 minutes following its oral administration, but the antitumor effect of its metabolites may persist for up to 15 minutes. ... In addition to chemical decomposition, CCNU may be converted by microsomal metabolism to 6 isomeric hydroxylated derivatives, some of which may differ in their biological properties from CCNU.

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 142 (1981)


Virtually all of a dose of lomustine is metabolized within 1 hour after oral administration. The half-life of lomustine metabolites is biphasic; although the initial plasma half-life is 6 hours, the second phase plasma half-life is 1-2 days, and 15-20% of the metabolites remain in the body 5 days after administration of lomustine. Prolongation of plasma concentrations is thought to reflect a combination of protein binding and enterohepatic circulation of metabolites.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1154


5.7 Biological Half-Life

Approximately 94 minutes, however the metabolites have a serum half-life of 16 to 48 hours.


The half-life of lomustine metabolites is biphasic; although the initial plasma half-life is 6 hours, the second phase plasma half-life is 1-2 days, and 15-20% of the metabolites remain in the body 5 days after administration of lomustine.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1154


5.8 Mechanism of Action

Lomustine is a highly lipophilic nitrosourea compound which undergoes hydrolysis in vivo to form reactive metabolites. These metabolites cause alkylation and cross-linking of DNA (at the O6 position of guanine-containing bases) and RNA, thus inducing cytotoxicity. Other biologic effects include inhibition of DNA synthesis and some cell cycle phase specificity. Nitrosureas generally lack cross-resistance with other alkylating agents. As lomustine is a nitrosurea, it may also inhibit several key processes such as carbamoylation and modification of cellular proteins.


Although lomustine is believed to act by alkylation, the mechanism of action has not been completely elucidated, and other effects as carbamoylation and modification of cellular proteins may be involved. The overall result is thought to be the inhibition of both DNA and RNA synthesis.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1154


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D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"USP","supplierCountry":"INDIA","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.00005","unit":"KGS","unitRateFc":"36520000","totalValueFC":"1886.4","currency":"USD","unitRateINR":"3144755000","date":"23-May-2024","totalValueINR":"157237.75","totalValueInUsd":"1886.4","indian_port":"Hyderabad Air","hs_no":"29242190","bill_no":"3620237","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK,MD, US 21704, UNITED STATES OF AMERICA United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1716402600,"product":"LOMUSTINE RELATED COMPOUND D(QTY:1 X 25 MG, VALUE: USD 903)(FOC)","address":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"USP","supplierCountry":"INDIA","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.000025","unit":"KGS","unitRateFc":"36120000","totalValueFC":"932.9","currency":"USD","unitRateINR":"3110310800","date":"23-May-2024","totalValueINR":"77757.77","totalValueInUsd":"932.9","indian_port":"Hyderabad Air","hs_no":"29299090","bill_no":"3620237","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK,MD, US 21704, UNITED STATES OF AMERICA United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"}]
29-May-2021
28-May-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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