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Chemistry

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Also known as: 148-82-3, Alkeran, Melfalan, L-pam, Phenylalanine mustard, L-sarcolysine
Molecular Formula
C13H18Cl2N2O2
Molecular Weight
305.20  g/mol
InChI Key
SGDBTWWWUNNDEQ-LBPRGKRZSA-N
FDA UNII
Q41OR9510P

Melphalan
An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.
Melphalan is an Alkylating Drug. The mechanism of action of melphalan is as an Alkylating Activity.
1 2D Structure

Melphalan

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid
2.1.2 InChI
InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
2.1.3 InChI Key
SGDBTWWWUNNDEQ-LBPRGKRZSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1CC(C(=O)O)N)N(CCCl)CCCl
2.1.5 Isomeric SMILES
C1=CC(=CC=C1C[C@@H](C(=O)O)N)N(CCCl)CCCl
2.2 Other Identifiers
2.2.1 UNII
Q41OR9510P
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-(bis(2-chloroethyl)amino)phenylalanine

2. Alkeran

3. L-pam

4. Medphalan

5. Merphalan

6. Mustard, Phenylalanine

7. Phenylalanine Mustard

8. Sarcolysine

9. Sarkolysin

2.3.2 Depositor-Supplied Synonyms

1. 148-82-3

2. Alkeran

3. Melfalan

4. L-pam

5. Phenylalanine Mustard

6. L-sarcolysine

7. L-phenylalanine Mustard

8. L-sarcolysin

9. P-l-sarcolysin

10. 4-[bis(2-chloroethyl)amino]-l-phenylalanine

11. Melphalanum

12. Melfalano

13. Phenylalanine Nitrogen Mustard

14. Levofalan

15. P-di-(2-chloroethyl)amino-l-phenylalanine

16. Sarcolysinum

17. Cb 3025

18. Nci-c04853

19. Levopholan

20. Levofolan

21. P-bis(beta-chloroethyl)aminophenylalanine

22. L-3-(p-(bis(2-chloroethyl)amino)phenyl)alanine

23. 3-(p-(bis(2-chloroethyl)amino)phenyl)-l-alanine

24. L-sarkolysin

25. P-n-bis(2-chloroethyl)amino-l-phenylalanine

26. 4-(bis(2-chloroethyl)amino)-l-phenylalanine

27. (2s)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic Acid

28. 3-p-(di(2-chloroethyl)amino)-phenyl-l-alanine

29. Alanine Nitrogen Mustard

30. Cb-3025

31. Sk 15673

32. Sk-15673

33. Sarcolycin, L-

34. Nsc-8806

35. Evomela

36. L-phenylalanine, 4-(bis(2-chloroethyl)amino)-

37. Chebi:28876

38. P-n,n-bis(2-chloroethyl)amino-l-phenylalanine

39. Chembl852

40. Alkeran (tn)

41. Rcra Waste Number U150

42. Q41or9510p

43. Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, L-

44. Alanine, 3-[p-[bis(2-chloroethyl)amino]phenyl]-, L-

45. Nsc-241286

46. 8057-25-8

47. Ncgc00090757-02

48. (2s)-2-azaniumyl-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoate

49. Dsstox_cid_804

50. L-phenylalanine, 4-[bis(2-chloroethyl)amino]-

51. Dsstox_rid_75797

52. Dsstox_gsid_20804

53. Melfalano [inn-spanish]

54. Melphalanum [inn-latin]

55. Phenylalanine, 4-[bis(2-chloroethyl)amino]-

56. (s)-2-amino-3-(4-(bis(2-chloroethyl)amino)phenyl)propanoic Acid

57. (2s)-2-amino-3-(4-[bis(2-chloroethyl)amino]phenyl)propanoic Acid

58. (s)-2-amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic Acid

59. Nsc8806

60. Cas-148-82-3

61. Smr000058720

62. Ccris 374

63. Hsdb 3234

64. Einecs 205-726-3

65. Rcra Waste No. U150

66. Nsc 241286

67. Brn 2816456

68. L-3-(para-(bis(2-chloroethyl)amino)phenyl)alanine

69. Phelinun

70. Unii-q41or9510p

71. (2s)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic Acid

72. Nsc241286

73. Melphalan, Powder

74. Prestwick_1006

75. Melphalan [usan:usp:inn:ban:jan]

76. Spectrum_000397

77. Melphalan [inn]

78. Melphalan [jan]

79. Melphalan [mi]

80. 3025 C.b.

81. Melphalan [hsdb]

82. Melphalan [iarc]

83. Melphalan [usan]

84. Spectrum2_000074

85. Spectrum3_000684

86. Spectrum4_000882

87. Spectrum5_001601

88. Melphalan [vandf]

89. Dl-melphalan Hydrochloride

90. 3-(p-(bis(2-chloroethyl)amino)phenyl)alanine

91. Epitope Id:141802

92. Melphalan [mart.]

93. 4-[bis-(2-chloroethyl)amino]-l-phenylalanine

94. Melphalan [who-dd]

95. Schembl5872

96. Bspbio_002407

97. Kbiogr_001284

98. Kbioss_000877

99. 4-14-00-01689 (beilstein Handbook Reference)

100. Mls001333666

101. Mls002153368

102. Bidd:gt0044

103. Divk1c_000653

104. Spectrum1500382

105. Spbio_000287

106. Melphalan (jp17/usp/inn)

107. Gtpl7620

108. Zinc1673

109. Melphalan [orange Book]

110. Dtxsid6020804

111. Melphalan [ep Monograph]

112. Niosh/ay3360000

113. Hms502a15

114. Kbio1_000653

115. Kbio2_000877

116. Kbio2_003445

117. Kbio2_006013

118. Kbio3_001627

119. L-phenylalanine Mustard (l-pam)

120. Melphalan [usp Monograph]

121. Ninds_000653

122. Hms2090b09

123. Hms2091b16

124. Hms2235d21

125. Pharmakon1600-01500382

126. Tox21_111010

127. Tox21_202522

128. Bdbm50025837

129. Ccg-39704

130. Dl-442

131. Mfcd00057717

132. Nsc757098

133. S8266

134. Akos015895374

135. Tox21_111010_1

136. Cs-3120

137. Db01042

138. Nsc-757098

139. Idi1_000653

140. Smp2_000174

141. Ncgc00090757-01

142. Ncgc00090757-03

143. Ncgc00090757-04

144. Ncgc00090757-05

145. Ncgc00090757-06

146. Ncgc00260071-01

147. As-13314

148. Hy-17575

149. Sbi-0052787.p003

150. Ay33600000

151. 4-[bis(2-chloroethyl)-amino]-l-phenylalanine

152. 4-[bis(2-chloroethyl)-amino]-l-phenyl-alanine

153. 4-[bis(2-chloroethyl)amino]-(l)-phenylalanine

154. C07122

155. D00369

156. Ab00053282-07

157. Ab00053282-08

158. Ab00053282_09

159. 148m823

160. A808810

161. Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-

162. Sr-05000001667

163. Q2298283

164. Sr-05000001667-1

165. W-108096

166. Brd-k87827419-001-02-8

167. 2-amino-3-[4-bis(2-chloroethyl)amino]phenylpropanoic Acid

168. (2s)-2-azanyl-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic Acid

169. 2-amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic Acid

170. 2-amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic Acid(l-pam)

171. 2-amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic Acid (melphalan)

172. 2-amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic Acid(melphalan)

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 305.20 g/mol
Molecular Formula C13H18Cl2N2O2
XLogP3-0.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count8
Exact Mass304.0745332 g/mol
Monoisotopic Mass304.0745332 g/mol
Topological Polar Surface Area66.6 Ų
Heavy Atom Count19
Formal Charge0
Complexity265
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameAlkeran
PubMed HealthMelphalan (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelALKERAN (melphalan), also known as L-phenylalanine mustard, phenylalanine mustard, L-PAM, or L-sarcolysin, is a phenylalanine derivative of nitrogen mustard. Melphalan is a bifunctional alkylating agent which is active against selective human neoplas...
Active IngredientMelphalan hydrochloride; Melphalan
Dosage FormInjectable; Tablet
RouteInjection; Oral
Strength2mg; eq 50mg base/vial
Market StatusPrescription
CompanyGlaxosmithkline

2 of 2  
Drug NameAlkeran
PubMed HealthMelphalan (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelALKERAN (melphalan), also known as L-phenylalanine mustard, phenylalanine mustard, L-PAM, or L-sarcolysin, is a phenylalanine derivative of nitrogen mustard. Melphalan is a bifunctional alkylating agent which is active against selective human neoplas...
Active IngredientMelphalan hydrochloride; Melphalan
Dosage FormInjectable; Tablet
RouteInjection; Oral
Strength2mg; eq 50mg base/vial
Market StatusPrescription
CompanyGlaxosmithkline

4.2 Therapeutic Uses

Antineoplastic Agents, Alkylating; Myeloablative Agonists

National Library of Medicine's Medical Subject Headings. Melphalan. Online file (MeSH, 2016). Available from, as of December 5, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Melphalan is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of February 1, 2017: https://clinicaltrials.gov/ct2/results?term=MELPHALAN&Search=Search


Melphalan is used as a drug to treat cancer and other medical conditions, including ovarian cancer, malignant melanoma, multiple myeloma, breast cancer, advanced prostate cancer, testicular cancer, chronic myelogenous leukemia, osteogenic sarcoma, polycythemia vera, amyloidosis, and scleromyxedema (a rare skin disease). It is also used as an insect chemosterilant.

NTP; Report on Carcinogens, Fourteenth Edition (November, 2016); Available from, as of December 5, 2016: https://ntp.niehs.nih.gov/go/roc


Melphalan is used alone and as a component of various chemotherapeutic regimens in the treatment of myltiple myeloma.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1172


For more Therapeutic Uses (Complete) data for Melphalan (17 total), please visit the HSDB record page.


4.3 Drug Warning

Although its safety during pregnancy has not been evaluated, melphalan is potentially teratogenic and should not be used during this period unless absolutely necessary.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2015


Melphalan should be used cautiously in patients with severe renal insufficiency.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2015


With prolonged use, sterility occurs with all alkylators; females appear more sensitive than males. /Alkalating agents, oral/

Knoben, J.E. and P.O. Anderson (eds.) Handbook of Clinical Drug Data. 6th ed. Bethesda, MD: Drug Intelligence Publications, Inc. 1988., p. 400


Arterial or venous thrombosis, or pulmonary embolism, sometimes fatal, has been reported in patients receiving melphalan by regional isolated perfusion.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1172


For more Drug Warnings (Complete) data for Melphalan (11 total), please visit the HSDB record page.


4.4 Drug Indication

For the palliative treatment of multiple myeloma and for the palliation of non-resectable epithelial carcinoma of the ovary. Has also been used alone or as part of various chemotherapeutic regimens as an adjunct to surgery in the treatment of breast cancer, alone or in combination regimens for palliative treatment of locally recurrent or unresectable in-transit metastatic melanoma of the extremities, as well as for the treatment of amyloidosis with prednisone.


FDA Label


High-dose of Phelinun used alone or in combination with other cytotoxic medicinal products and/or total body irradiation is indicated in the treatment of:

- multiple myeloma,

- malignant lymphoma (Hodgkin, non-Hodgkin lymphoma),

- acute lymphoblastic and myeloblastic leukemia,

- childhood neuroblastoma,

- ovarian cancer ,

- mammary adenocarcinoma.

Phelinun in combination with other cytotoxic medicinal products is indicated as reduced intensity conditioning (RIC) treatment prior to allogeneic haematopoietic stem cell transplantation (allo-HSCT) in malignant haematological diseases in adults.

Phelinun in combination with other cytotoxic medicinal products is indicated as conditioning regimen prior to allogeneic haematopoietic stem cell transplantation in haematological diseases in the paediatric population as:

- Myeloablative conditioning (MAC) treatment in case of malignant haematological diseases

- RIC treatment in case of non-malignant haematological diseases.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Melphalan is an antineoplastic in the class of alkylating agents and 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.)


Myeloablative Agonists

Agents that destroy bone marrow activity. They are used to prepare patients for BONE MARROW TRANSPLANTATION or STEM CELL TRANSPLANTATION. (See all compounds classified as Myeloablative Agonists.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
MELPHALAN
5.3.2 FDA UNII
Q41OR9510P
5.3.3 Pharmacological Classes
Alkylating Drug [EPC]; Alkylating Activity [MoA]
5.4 ATC Code

L01AA03


L01AA03

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

L01AA03 - Melphalan


5.5 Absorption, Distribution and Excretion

Absorption

Incomplete, variable, 25-89% post oral dose


Route of Elimination

The 24-hour urinary excretion of parent drug in these patients was 10% 4.5%, suggesting that renal clearance is not a major route of elimination of parent drug.


Volume of Distribution

0.5 L/kg


Absorption melphalan from the GI tract is incomplete and extremely variable.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1172


After admin of (3)H-labeled melphalan to Walker carcinoma-bearing rats, radioactivity was found in liver, spleen, kidney, intestine and Walker carcinoma and to lesser extent in bone marrow, muscle, skin, testis and brain, but not in DNA fraction of any of these tissues. Approx 25% of admin radioactivity was excreted in urine during 1st 48 hr.

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 174 (1975)


We have studied the disposition and elimination of melphalan after intravenous administration in 9 patients with cancer. High-pressure liquid chromatography and (14)C-melphalan were used to assay drug concentration in plasma and urine. Composite plasma t1/2alpha was 7.7 +/- 3.3 and t1/2beta was 108 +/- 20.8 min for 8 of the patients. The mean 24-hr urinary excretion of melphalan was 13.0 +/- 5.4% of the administered dose. In 2 patients, 80% to 100% of the measured (14)C counts in plasma and urine samples at each study interval, up to 24 hr after drug administration, could be accounted for by the sum of parent compound, monohydroxy and dihydroxy products, and methanol nonextractable radioactivity (i.e., protein-bound activity). These data and evidence of rapid disappearance from plasma at 37 degrees /C/ in vitro suggest that spontaneous degradation, and not enzymatic metabolism, is the major determinant of the t1/2 of melphalan in vivo.

PMID:445964 Alberts DS et al; Clin Pharmacol Ther 26 (1): 73-80 (1979)


After iv admin of (14)C-labeled melphalan in female, weanling Yorkshire white pigs, tissue samples indicated bone and fat may be acting as depots for the drug. After 8 days, avg of 70% eliminated in urine. An avg of 4.02% of applied dose was absorbed after 14 days. Significant levels of radioactivity were also detected in skin surrounding site of application.

Skierkowski P et al; Report; Iss Oorder No PB-290436, 1978, 41


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


5.6 Metabolism/Metabolites

Melphalan is not actively metabolised, it spontaneously degrades to mono and dihydroxy products.


... Most of administered dose is chemically altered and metabolites persist in the body.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2015


We have studied the disposition and elimination of melphalan after intravenous administration in 9 patients with cancer. High-pressure liquid chromatography and (14)C-melphalan were used to assay drug concentration in plasma and urine. Composite plasma t1/2alpha was 7.7 +/- 3.3 and t1/2beta was 108 +/- 20.8 min for 8 of the patients. The mean 24-hr urinary excretion of melphalan was 13.0 +/- 5.4% of the administered dose. In 2 patients, 80% to 100% of the measured (14)C counts in plasma and urine samples at each study interval, up to 24 hr after drug administration, could be accounted for by the sum of parent compound, monohydroxy and dihydroxy products, and methanol nonextractable radioactivity (i.e., protein-bound activity). These data and evidence of rapid disappearance from plasma at 37 degrees /C/ in vitro suggest that spontaneous degradation, and not enzymatic metabolism, is the major determinant of the t1/2 of melphalan in vivo.

PMID:445964 Alberts DS et al; Clin Pharmacol Ther 26 (1): 73-80 (1979)


Melphalan is apparently eliminated from plasma by spontaneous hydrolysis, froming the monohydroxy and dihydroxy derivatives of the drug; no other metabolites have been identified in humans.

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1172


5.7 Biological Half-Life

1.5 (±0.83) hours


We have studied the disposition and elimination of melphalan after intravenous administration in 9 patients with cancer. High-pressure liquid chromatography and (14)C-melphalan were used to assay drug concentration in plasma and urine. Composite plasma t1/2alpha was 7.7 +/- 3.3 and t1/2beta was 108 +/- 20.8 min for 8 of the patients. The mean 24-hr urinary excretion of melphalan was 13.0 +/- 5.4% of the administered dose. In 2 patients, 80% to 100% of the measured 14C counts in plasma and urine samples at each study interval, up to 24 hr after drug administration, could be accounted for by the sum of parent compound, monohydroxy and dihydroxy products, and methanol nonextractable radioactivity (i.e., protein-bound activity). These data and evidence of rapid disappearance from plasma at 37 degrees /C/ in vitro suggest that spontaneous degradation, and not enzymatic metabolism, is the major determinant of the t1/2 of melphalan in vivo.

PMID:445964 Alberts DS et al; Clin Pharmacol Ther 26 (1): 73-80 (1979)


Intravenous admin (14)C-labeled melphalan in female, weanling Yorkshire white pigs indicated very slow elimination phase (half-life= 214 hr).

Skierkowski P et al; Report; Iss Oorder No PB-290436, 1978, 41


After iv admin in humans, the drug was distributed in total body water and disappeared with half-lives of approx 67 min and 160 hr. Up to 65% of label was recovered in urine over period of 7 days.

PMID:648565 Tattersall MH et al; Eur J Cancer 14 (5): 507-13 (1978)


The disappearance of L-PAM (intact drug) from the serum was biphasic after iv administration, with half-lives of 14 and 66 minutes for the alpha and beta phases, respectively.

PMID:597816 Furner RL et al; Cancer Treat Rep 61 (9): 1637-46 (1977)


For more Biological Half-Life (Complete) data for Melphalan (6 total), please visit the HSDB record page.


5.8 Mechanism of Action

Melphalan attaches alkyl groups to the N-7 position of guanine and N-3 position of adenine, leading to the formation of monoadducts, and DNA fragmenting when repair enzymes attempt to correct the error. It can also cause DNA cross-linking from the N-7 position of one guanine to the N-7 position of another, preventing DNA strands from separating for synthesis or transcription. Finally, melphalan can induce a number of different mutations.


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

American Society of Health-System Pharmacists 2016; Drug Information 2016. Bethesda, MD. 2016, p. 1172


Melphalan is a direct-acting alkylating agent that is carcinogenic via genotoxic mechanism.

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. V 100A P113


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23-Jan-2021
29-Apr-2024
KGS
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