Normustine - Biblioteka.sk

Normustine
Clinical data

Other names	Bis(2-chloroethyl)carbamic acid
Identifiers
IUPAC name Bis(2-chloroethyl)carbamic acid
CAS Number	78619-95-1
PubChem CID	18377863
UNII	Q2KPX8TH4K
Chemical and physical data
Formula	C₅H₉Cl₂NO₂
Molar mass	186.03 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C(CCl)N(CCCl)C(=O)O
InChI InChI=1S/C5H9Cl2NO2/c6-1-3-8(4-2-7)5(9)10/h1-4H2,(H,9,10) Key:TTYAKTJQJVVKED-UHFFFAOYSA-N

Normustine, also known as bis(2-chloroethyl)carbamic acid, is a nitrogen mustard and alkylating antineoplastic agent (i.e., chemotherapy agent).^[1]^[2]^[3] It is a metabolite of a number of antineoplastic agents that have been developed for the treatment of tumors, including estramustine phosphate, alestramustine, cytestrol acetate, and ICI-85966 (stilbostat), but only the former of which has actually been marketed.^[1]^[2]^[3]

References

^ ^a ^b Brunton L, Chabner B, Knollman B (14 January 2011). Goodman and Gilman's The Pharmacological Basis of Therapeutics, Twelfth Edition. McGraw Hill Professional. p. 1709. ISBN 978-0-07-176939-6.
^ ^a ^b Fox BW, Fox M (6 December 2012). Antitumor Drug Resistance. Springer Science & Business Media. pp. 199–. ISBN 978-3-642-69490-5.
^ ^a ^b Decker M (5 April 2017). Design of Hybrid Molecules for Drug Development. Elsevier Science. pp. 201–. ISBN 978-0-08-101118-8.

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vindesine Vinflunine^§ Vinorelbine^#)
Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine^# Tioguanine^#)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine^# Carmofur Doxifluridine Floxuridine Fluorouracil^# Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine^# +daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine^#) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide^#)

I	Camptotheca (Belotecan Camptothecin Cositecan^† Etirinotecan pegol^† Exatecan Gimatecan Irinotecan^# Lurtotecan^‡ Rubitecan^‡ Silatecan^§ Topotecan)
II	Podophyllum (Etoposide^# Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin^† Daunorubicin^# (+cytarabine) Doxorubicin^# Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Losoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril^§

Alkylating	Nitrogen mustards: Bendamustine^# Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas: Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# Mitomycins Plicamycin)

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Abemaciclib Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Fuzuloparib) Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib Duvelisib Idelalisib Umbralisib^‡)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Elesclomol^§ Elsamitrucin Enasidenib Epacadostat Eribulin Estramustine phosphate Glasdegib Idecabtagene vicleucel Ivosidenib Lifileucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Plitidepsin Retinoids (Alitretinoin Tretinoin^#) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin

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