Product Name

Chlormethine Hydrochloride

CAS Number

55-86-7

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Product Name:
Chlormethine Hydrochloride
CAS Number:
55-86-7
Indication:
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. Also for the palliative treatment of metastatic carcinoma resulting in effusion.
Mode 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. Mechlorethamine is cell cycle phase-nonspecific.

Pharmacodynamics:

Mechlorethamine also known as mustine, nitrogen mustard, and HN2, is the prototype anticancer chemotherapeutic drug. Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an analogue of mustard gas and was derived from toxic gas warfare research. It belongs to the group of nitrogen mustard alkylating agents. Alkylating agents work by three different mechanisms all of which achieve the same end result – disruption of DNA function and cell death.

Metabolism:

Undergoes rapid chemical transformation and combines with water or reactive compounds of cells, so that the drug is no longer present in active form a few minutes after administration.

Toxicity:

Symptoms of overexposure include severe leukopenia, anemia, thrombocytopenia, and a hemorrhagic diathesis with subsequent delayed bleeding may develop. Death may follow. The most common adverse reactions (≥5%) of the topical formulation are dermatitis, pruritus, bacterial skin infection, skin ulceration or blistering, and hyperpigmentation. The oral LD50 for a rat is 10 mg/kg.

IUPAC:
Chlormethine hydrochloride Diethylamine, 2, 2'-dichloro-N-methyl, hydrochloride Ethanamine, 2-chloro-N-(2-chloroethyl)-N-methyl-, hydrochloride Nitrogen mustard hydrochloride Stickstofflost-ebewe
ATC:
L01AA05
PubChem:
4033
DrugBank:
DB00888 (APRD00249)
Formula:
C5-H11-Cl2-N.Cl-H
Molecular Mass:
192.5158
Synonyms:
1,5-Dichloro-3-methyl-3-azapentane hydrochloride, 2,2'-Dichloro-N-methyldiethylamine hydrochloride, 2-Chloro-N-(2-chloroethyl)-N-methylethanamine hydrochlroide, AI3-16195, Azotoyperite, beta,beta'-Dichlorodiethyl-N-methylamine hydrochloride, Bis(2-chloroethyl)methylamine hydrochloride, C 6866, Caryolysine, CCRIS 448, Chloramin, Chlorethamine, Chlormethine hydrochloride, Chlormethinum, Dema, Di(2-chloroethyl)methylamine hydrochloride, Dichloren, Dichloromethyldiethylamine hydrochloride, Dimitan, EINECS 200-246-0, Embichin, Embikhine, Embiquine, Erasol, Erasol-Ido, HN2 hydrochloride, HSDB 7176, Kloramin (VAN), Mechlorethamine chloridrate, Mechlorethamine HCl, Mechlorethamine hydrochloride, Methyl-bis(beta-chloroethyl)amine hydrochloride, Methylbis(2-chloroethyl)amine hydrochloride, Methyldi(2-chloroethyl)amine hydrochloride, Methyldi(beta-chloroethyl)amine hydrochloride, Mitoxine, Mustargen, Mustin hydrochloride, Mustine hydrochloride, N,N-Bis(2-chloraethyl)methylamin-hydrochlorid, N,N-Bis(2-chloraethyl)methylamin-hydrochlorid [German], N,N-Bis(2-chloroethyl)methylamine hydrochloride, N-Methyl-2,2'-dichlorodiethylamine hydrochloride, N-Methyl-bis-beta-chlorethylamine hydrochloride, N-Methyl-di-2-chloroethylamine hydrochloride, N-Methylbis(2-chloroethyl)amine hydrochloride, N-Mustard, N-Mustard [German], NCI-C56382, Nitol, Nitol takeda, Nitrogen mustard (HN-2), hydrochloride, Nitrogen mustard hydrochloride, Nitrogranulogen hydrochloride, NSC 762, Pliva, SK 101, Stickstofflost, UNII-L0MR697HHI, Zagreb
SMILES:
CN(CCCl)CCCl.Cl
AHFS Code:
10:00.00, 84:92
InChi:
1S/C5H11Cl2N.ClH/c1-8(4-2-6)5-3-7;/h2-5H2,1H3;1H
General Reference:
General Reference:

  1. FDA label

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