Mechlorethamine

Mechlorethamine: Mechlorethamine

Systematic (IUPAC) name

2-chloro-N-(2-chloroethyl)-N-methyl-ethanamine

Clinical data

AHFS/Drugs.com Consumer Drug Information

MedlinePlus a682223

Pregnancy cat. D (US)

Legal status ℞ Prescription only

Routes IV, intracavitary, intrapericardially, topical

Pharmacokinetic data

Bioavailability ?

Metabolism Rapid hydrolysis and demethylation, possibly in plasma

Half-life < 1 minute

Excretion Urine (50% as metabolites, <0.01% as unchanged drug)

Identifiers

CAS number 51-75-2^Y

ATC code L01AA05

PubChem CID 4033

DrugBank APRD00249

ChemSpider 3893^Y

UNII 50D9XSG0VR^Y

ChEBI CHEBI:28925^N

ChEMBL CHEMBL427^N

Chemical data

Formula C₅H₁₁Cl₂N

Mol. mass 156.055 g mol⁻¹

SMILES eMolecules & PubChem

InChI

InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3^N
Key:HAWPXGHAZFHHAD-UHFFFAOYSA-N^N

N(what is this?) (verify)

Mechlorethamine also known as chlormethine, mustine and HN2 is a nitrogen mustard sold under the brand name Mustargen. It is the prototype of alkylating agents, a group of anticancer chemotherapeutic drug. It works by binding to DNA, crosslinking two strands and preventing cell duplication. It binds to the N7 nitrogen on the DNA base guanine. As the chemical is a blister agent, its use is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.

Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.^[1]^[2]

Contents

1 History

2 Uses

3 See also

4 References

5 External links

History

Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an nitrogen-based analogue of mustard gas (which is sulfur-based) and was derived from chemical warfare research. Secret clinical trials of the agent for Hodgkin's disease and several other lymphomas and leukemias in humans began in December 1942. Because of wartime secrecy restrictions, it was not until 1946 that the results of these trials were published openly.^[3]

Uses

It has been derivatized into the estrogen analogue estramustine, used to treat prostate cancer.

It can also be used in chemical warfare where it has the code-name HN2. This chemical is a form of nitrogen mustard gas and a powerful vesicant.

See also

Nitrogen mustards

HN1

HN3

References

^ Rappeneau S, Baeza-Squiban A, Jeulin C, Marano F (March 2000). "Protection from cytotoxic effects induced by the nitrogen mustard mechlorethamine on human bronchial epithelial cells in vitro". Toxicol. Sci. 54 (1): 212–21. doi:10.1093/toxsci/54.1.212. PMID 10746948. http://toxsci.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=10746948.

^ Takimoto CH, Calvo E. "Principles of Oncologic Pharmacotherapy" in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer Management: A Multidisciplinary Approach. 11 ed. 2008.

^ Gilman A. (1963). "The initial clinical trial of nitrogen mustard". Am J Surg. 105 (5): 574–578. doi:10.1016/0002-9610(63)90232-0. PMID 13947966.

External links

British Columbia Cancer Agency profile

v · d · eIntracellular chemotherapeutic agents/antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly

Vinca alkaloids (Vinblastine, Vincristine, Vinflunine, Vindesine, Vinorelbine)

Block microtubule disassembly

Taxanes (Cabazitaxel, Docetaxel, Larotaxel, Ortataxel, Paclitaxel, Tesetaxel) • Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid

dihydrofolate reductase inhibitor (Aminopterin, Methotrexate, Pemetrexed, Pralatrexate) • thymidylate synthase inhibitor (Raltitrexed, Pemetrexed)

Purine

adenosine deaminase inhibitor (Pentostatin)

halogenated/ribonucleotide reductase inhibitors (Cladribine, Clofarabine, Fludarabine)
thiopurine (Thioguanine, Mercaptopurine)

Pyrimidine

thymidylate synthase inhibitor (Fluorouracil, Capecitabine, Tegafur, Carmofur, Floxuridine)

DNA polymerase inhibitor (Cytarabine)

ribonucleotide reductase inhibitor (Gemcitabine)
hypomethylating agent (Azacitidine, Decitabine)

Deoxyribonucleotide

ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I

Camptotheca (Camptothecin, Topotecan, Irinotecan, Rubitecan, Belotecan)

II

Podophyllum (Etoposide, Teniposide)

II+Intercalation

Anthracyclines (Aclarubicin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Amrubicin, Pirarubicin, Valrubicin, Zorubicin) • Anthracenediones (Mitoxantrone, Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating

Nitrogen mustards: Mechlorethamine • Cyclophosphamide (Ifosfamide, Trofosfamide) • Chlorambucil (Melphalan, Prednimustine) • Bendamustine • Uramustine • Estramustine

Nitrosoureas: Carmustine • Lomustine (Semustine) • Fotemustine • Nimustine • Ranimustine • Streptozocin

Alkyl sulfonates: Busulfan (Mannosulfan, Treosulfan)
Aziridines: Carboquone • ThioTEPA • Triaziquone • Triethylenemelamine

Alkylating-like

Platinum (Carboplatin, Cisplatin, Nedaplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin)

Nonclassical

Hydrazines (Procarbazine) • Triazenes (Dacarbazine, Temozolomide) • Altretamine • Mitobronitol

Intercalation

Streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin)

Photosensitizers/PDT
Aminolevulinic acid/Methyl aminolevulinate • Efaproxiral • Porphyrin derivatives (Porfimer sodium, Talaporfin, Temoporfin, Verteporfin)

Other

Enzyme inhibitors

FI (Tipifarnib) • CDK inhibitors (Alvocidib, Seliciclib) • PrI (Bortezomib) • PhI (Anagrelide) • IMPDI (Tiazofurine) • LI (Masoprocol) • PARP inhibitor (Olaparib) • HDAC (Vorinostat, Romidepsin)

Receptor antagonists

ERA (Atrasentan) • retinoid X receptor (Bexarotene) • sex steroid (Testolactone)

Other/ungrouped

Amsacrine • Trabectedin • retinoids (Alitretinoin, Tretinoin) • Arsenic trioxide • asparagine depleters (Asparaginase/Pegaspargase) • Celecoxib • Demecolcine • Elesclomol • Elsamitrucin • Etoglucid • Lonidamine • HAMLET (human alpha-lactalbumin made lethal to tumor cells) • Lucanthone • Mitoguazone • Mitotane • Oblimersen • Omacetaxine mepesuccinate • mTOR inhibitors (Everolimus, Temsirolimus)

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

Categories:
Amines
Organochlorides
Alkylating antineoplastic agents
Nitrogen mustards

Mechlorethamine

Systematic (IUPAC) name
2-chloro-N-(2-chloroethyl)-N-methyl-ethanamine
Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682223
Pregnancy cat.	D (US)
Legal status	℞ Prescription only
Routes	IV, intracavitary, intrapericardially, topical
Pharmacokinetic data
Bioavailability	?
Metabolism	Rapid hydrolysis and demethylation, possibly in plasma
Half-life	< 1 minute
Excretion	Urine (50% as metabolites, <0.01% as unchanged drug)
Identifiers
CAS number	51-75-2^Y
ATC code	L01AA05
PubChem	CID 4033
DrugBank	APRD00249
ChemSpider	3893^Y
UNII	50D9XSG0VR^Y
ChEBI	CHEBI:28925^N
ChEMBL	CHEMBL427^N
Chemical data
Formula	C₅H₁₁Cl₂N
Mol. mass	156.055 g mol⁻¹
SMILES	eMolecules & PubChem
InChI InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3^N Key:HAWPXGHAZFHHAD-UHFFFAOYSA-N^N
N(what is this?) (verify)

Игры ⚽ Нужна курсовая?

Look at other dictionaries:

mechlorethamine — A drug used to treat some types of cancer and some precancerous skin conditions. It causes cancer cells to die by attaching to the DNA in the cells. Mechlorethamine is a type of alkylating agent. Also called mustine, mechlorethamine hydrochloride … English dictionary of cancer terms
mechlorethamine hydrochloride — A drug used to treat some types of cancer and some precancerous skin conditions. It causes cancer cells to die by attaching to the DNA in the cells. Mechlorethamine hydrochloride is a type of alkylating agent. Also called mustine, mechlorethamine … English dictionary of cancer terms
mechlorethamine — /me klawr eth euh meen , klohr /, n. Pharm. a nitrogen mustard, C5H11Cl2N, used in combination with other drugs in the treatment of Hodgkin s disease and certain other cancers. [ME(THYL) + CHLOR 2 + ETH(YL) + AMINE] * * * … Universalium
mechlorethamine — noun A particular drug used in chemotherapy … Wiktionary
mechlorethamine — mech·lor·eth·amine .mek .lōr eth ə .mēn, .lȯr n a nitrogen mustard administered by injection in the form of its hydrochloride C5H11Cl2N·HCl in the palliative treatment of neoplastic diseases (as Hodgkin s disease and leukemia) … Medical dictionary
mechlorethamine — mech·lor·eth·amine … English syllables
mechlorethamine — ˌmeˌklōrˈethəˌmēn, lȯr , mə̇n noun Etymology: methyl + chloroethyl + amine : a nitrogen mustard C5H11Cl2N used in the form of its hydrochloride in the palliative treatment of some neoplastic diseases * * * /me klawr eth euh meen , klohr /, n.… … Useful english dictionary
mechlorethamine hydrochloride — It is cytotoxic for all cells, but with a special affinity for bone marrow, lymphatic tissues, and rapidly proliferating cells of certain neoplasms. Used for the palliative treatment of Hodgkin disease, lymphosarcoma, and certain chronic… … Medical dictionary
MOPP — • mechlorethamine, Oncovin, pro carbazine, prednisone; • mission oriented protective posture [clothing] … Dictionary of medical acronyms & abbreviations
MOPP — Acronym for mechlorethamine, oncovin (vincristine), procarbazine, and prednisone, a chemotherapy regimen used in the treatment of Hodgkin disease. * * * mechlorethamine, Oncovin, pro carbazine, prednisone; mission oriented protective posture… … Medical dictionary

Academic Dictionaries and Encyclopedias

Mechlorethamine

Contents

History

Uses

See also

References

External links

Look at other dictionaries:

Share the article and excerpts

Academic Dictionaries and Encyclopedias

Wikipedia

Mechlorethamine

Contents

History

Uses

See also

References

External links

Look at other dictionaries:

Share the article and excerpts

Direct link