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Saving copy of the {{chembox}} taken from revid 486945798 of page Carmustine for the Chem/Drugbox validation project (updated: 'KEGG').
 
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{{cs1 config|name-list-style=vanc|display-authors=6}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Carmustine|oldid=486945798}} 486945798] of page [[Carmustine]] with values updated to verified values.}}
{{Chembox
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 487305398
| ImageFile = Carmustine.svg
| ImageFile = Carmustine.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 160
| ImageName = Skeletal formula of carmustine
| ImageName = Skeletal formula of carmustine
| ImageFile1 = Carmustine ball-and-stick.png
| PIN = ''N'',''N''’-Bis(2-chloroethyl)-''N''-nitroso-urea{{Citation needed|date=April 2012}}
| ImageName1 = Ball-and-stick model of carmustine molecule
| SystematicName = 1,3-Bis(2-chloroethyl)-1-nitrosourea<ref>{{Cite web|title=Carmustine - Compound Summary|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=2578#x291|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=11 April 2012|location=USA|date=25 March 2005|at=Identification and Related Records}}</ref>
| IUPACName = 1,3-Bis(2-chloroethyl)-1-nitrosourea<ref>{{PubChem|2578}}</ref>
| Section1 = {{Chembox Identifiers
| OtherNames = ''N'',''N'''-Bis(2-chloroethyl)-''N''-nitrosourea, bis-chloroethylnitrosourea, BCNU
| CASNo = 154-93-8
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 2578
| CASNo = 154-93-8
| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
| CASNo_Ref = {{cascite|correct|CAS}}
| ChemSpiderID = 2480
| PubChem = 2578
| ChemSpiderID = 2480
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = U68WG3173Y
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = U68WG3173Y
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 205-838-2
| EINECS = 205-838-2
| UNNumber = 2811
| UNNumber = 2811
| DrugBank = DB00262
| DrugBank = DB00262
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = <!-- blanked - oldvalue: D00254 -->
| KEGG = D00254
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Carmustine
| MeSHName = Carmustine
| ChEBI = 3423
| ChEBI = 3423
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 513
| ChEMBL = 513
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = YS2625000
| RTECS = YS2625000
| SMILES = C(CCl)NC(=O)N(CCCl)N=O
| ATCCode_prefix = L01
| StdInChI = 1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
| ATCCode_suffix = AD01
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| SMILES = ClCCNC(=O)N(CCCl)N=O
| StdInChIKey = DLGOEMSEDOSKAD-UHFFFAOYSA-N
| StdInChI = 1S/C5H9Cl2N3O2/c6-1-3-8-5(11)10(9-12)4-2-7/h1-4H2,(H,8,11)
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| StdInChIKey = DLGOEMSEDOSKAD-UHFFFAOYSA-N
|Section2={{Chembox Properties
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| C=5 | H=9 | Cl=2 | N=3 | O=2
}}
| Appearance = Orange crystals
| Section2 = {{Chembox Properties
| C = 5
| Odor = Odourless
| H = 9
| MeltingPtC = 30
| Cl = 2
| LogP = 1.375
| N = 3
| pKa = 10.194
| O = 2
| pKb = 3.803
}}
| ExactMass = 213.007181961 g mol<sup>−1</sup>
|Section6={{Chembox Pharmacology
| Appearance = Orange crystals
| ATCCode_prefix = L01
| Odor = Odourless
| MeltingPtC = 30
| ATCCode_suffix = AD01
| ATC_Supplemental =
| LogP = 1.375
| pKa = 10.194
| ATCvet =
| pKb = 3.803
| Licence_EU = yes
| INN =
}}
| INN_EMA =
| Section3 = {{Chembox Pharmacology
| Bioavail = 5–28%
| Licence_US =
| Legal_status =
| AdminRoutes = {{Unbulleted list|Intravenous|Intralesional}}
| Metabolism = Hepatic
| Legal_AU = S4
| Legal_AU_comment =
| HalfLife = 15–30 min
| ProteinBound = 80%
| Legal_CA =
| Legal_CA_comment =
| Excretion = {{Unbulleted list|Renal|Respiratory}}
| Legal_status = Rx
| Legal_NZ =
| PregCat_US = D
| Legal_NZ_comment =
| Legal_UK = POM
}}
| Legal_UK_comment = <ref>{{cite web | title=Carmustine 100mg Powder and solvent for Solution for Infusion - Summary of Product Characteristics (SmPC) | website=(emc) | date=24 March 2020 | url=https://www.medicines.org.uk/emc/product/11176/smpc }}</ref><ref>{{cite web | title=Gliadel 7.7mg Implant - Summary of Product Characteristics (SmPC) | website=(emc) | date=15 June 2020 | url=https://www.medicines.org.uk/emc/product/36/smpc }}</ref>
| Section4 = {{Chembox Hazards
| Legal_US = Rx-only
| GHSPictograms = {{GHS skull and crossbones}} {{GHS health hazard}}
| Legal_US_comment = <ref>{{cite web | title=Bicnu- carmustine kit | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6cbb63c-e0b1-43ee-ad6f-408da0772079 | access-date=27 February 2021}}</ref><ref>{{cite web | title=Gliadel- carmustine wafer | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=38962a55-a514-4c48-bea5-f99a8da4beec | access-date=27 February 2021}}</ref>
| GHSSignalWord = '''DANGER'''
| Legal_EU = Rx-only
| HPhrases = {{H-phrases|300|350|360}}
| Legal_EU_comment =
| PPhrases = {{P-phrases|301+310|308+313}}
| Legal_UN =
| EUClass = {{Hazchem T+}}
| Legal_UN_comment =
| RPhrases = {{R45}}, {{R46}}, {{R60}}, {{R61}}, {{R28}}
| Pregnancy_category =
| SPhrases = {{S22}}, {{S36/37/39}}, {{S45}}
| Pregnancy_AU = D
| LD50 = 20 mg kg<sup>−1</sup> <small>(oral, rat)</small>
| Pregnancy_AU_comment =
}}
| Dependence_liability =
| Section5 = {{Chembox Related
| Function = ureas
| AdminRoutes =
| Bioavail =
| OtherFunctn = [[Dimethylurea]]
| ProteinBound =
| OtherCpds = {{Unbulleted list|[[Noxytiolin]]|[[1,1,3,3-Tetramethylguanidine]]|[[Metformin]]|[[Buformin]]}}
| Metabolism =
| Metabolites =
| OnsetOfAction =
| HalfLife =
| DurationOfAction =
| Excretion =
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{gHS skull and crossbones}} {{gHS health hazard}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{h-phrases|300|350|360}}
| PPhrases = {{p-phrases|301+310|308+313}}
| LD50 = 20 mg kg<sup>−1</sup> <small>(oral, rat)</small>
}}
|Section8={{Chembox Related
| OtherFunction_label = ureas
| OtherFunction = [[Dimethylurea]]
| OtherCompounds = {{unbulleted list|[[Noxytiolin]]|[[1,1,3,3-Tetramethylguanidine]]|[[Metformin]]|[[Allantoic acid]]|[[Buformin]]}}
}}
}}
}}
{{Infobox drug
| drug_name =
| INN =
| type = <!-- empty -->
| image =
| width =
| alt =
| caption =

<!-- Clinical data -->
| pronounce =
| tradename = BiCNU, Gliadel
| Drugs.com = {{drugs.com|monograph|carmustine}}
| MedlinePlus = a682060
| licence_EU = <!-- EMA uses INN (or special INN_EMA) -->
| DailyMedID = Carmustine
| licence_US = <!-- FDA may use generic or brand name (generic name preferred) -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment =
| pregnancy_category=
| dependency_liability =
| addiction_liability =
| routes_of_administration =
| class = Antineoplastic agents
| ATCvet =
| ATC_prefix = <!-- 'none' if uncategorised -->
| ATC_suffix =
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US_comment =
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action =
| excretion =

<!-- Identifiers -->
| CAS_number_Ref =
| CAS_number =
| CAS_supplemental =
| PubChem =
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
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| ChEBI_Ref =
| ChEBI =
| ChEMBL_Ref =
| ChEMBL =
| NIAID_ChemDB =
| PDB_ligand =
| synonyms =

<!-- Chemical and physical data -->
| IUPAC_name =
| chemical_formula_ref =
| chemical_formula =
| C= | H= | Ag= | Al= | As= | Au= | B= | Bi= | Br= | Ca= | Cl= | Co= | F= | Fe= | Gd= | I=
| K= | Li= | Mg= | Mn= | N= | Na= | O= | P= | Pt= | S= | Sb= | Se= | Sr= | Tc= | Zn= | charge=
| molecular_weight =
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}}
}}

'''Carmustine''', sold under the brand name '''BiCNU''' among others, is a [[medication]] used mainly for [[chemotherapy]]. It is a [[nitrogen mustard]] β-chloro-[[nitrosourea compounds|nitrosourea compound]] used as an [[alkylating antineoplastic agent|alkylating agent]].<ref>{{cite book | vauthors = Silverman RB, Holladay MW | chapter = Chapter 6 - DNA-Interactive Agents |date= January 2014 | title = The Organic Chemistry of Drug Design and Drug Action | edition = Third |pages=275–331 | veditors = Silverman RB, Holladay MW |place=Boston |publisher=Academic Press |language=en |doi=10.1016/b978-0-12-382030-3.00006-4 |isbn=978-0-12-382030-3 }}</ref>

==Description==
Carmustine is an orange-yellow solid [[pharmaceutical drug|medication]] used mainly for [[chemotherapy]]. It is a [[nitrogen mustard]] β-chloro-[[nitrosourea compounds|nitrosourea compound]].<ref>{{cite book | vauthors = Rider BJ | chapter = Carmustine |date= January 2007 | veditors = Enna SJ, Bylund DB | title = xPharm: The Comprehensive Pharmacology Reference |pages=1–4 |place=New York |publisher=Elsevier |language=en |doi=10.1016/b978-008055232-3.61389-3 |isbn=978-0-08-055232-3 }}</ref>

==Mechanism of action==
As an [[Alkylation|alkylating agent]], carmustine can form interstrand crosslinks in [[DNA]], which prevents DNA replication and DNA transcription.<ref>{{Citation |title=NLM PubChem CID Index |work=Vitamin D Handbook |year=2007 |pages=239–244 |place=Hoboken, NJ, USA |publisher=John Wiley & Sons, Inc. |doi=10.1002/9780470238165.indsp1 |isbn=9780470238165 |doi-access=free }}</ref>

==Uses==
Carmustine is used as an [[alkylating antineoplastic agent|alkylating agent]] to treat several types of [[brain cancer]] including [[glioma]], [[glioblastoma multiforme]], [[medulloblastoma]] and [[astrocytoma]], [[multiple myeloma]], and [[lymphoma]] ([[Hodgkin's lymphoma|Hodgkin's]] and [[Non-Hodgkin lymphoma|non-Hodgkin]]).

Carmustine is sometimes used in conjunction with alkyl guanine transferase (AGT) inhibitors, such as [[O6-Benzylguanine|''O''<sup>6</sup>-benzylguanine]]. The AGT-inhibitors increase the efficacy of carmustine by inhibiting the [[DNA repair#Direct reversal|direct reversal pathway]] of DNA repair, which will prevent formation of the [[Crosslinking of DNA|interstrand crosslink]] between the N<sup>1</sup> of [[guanine]] and the N<sup>3</sup> of [[cytosine]].

It is also used as part of a chemotherapeutic protocol in preparation for hematological [[stem cell transplantation]], a type of [[bone marrow transplant]], in order to reduce the white blood cell count in the recipient.<ref>{{cite journal | vauthors = Damaj G, Cornillon J, Bouabdallah K, Gressin R, Vigouroux S, Gastinne T, Ranchon F, Ghésquières H, Salles G, Yakoub-Agha I, Gyan E | title = Carmustine replacement in intensive chemotherapy preceding reinjection of autologous HSCs in Hodgkin and non-Hodgkin lymphoma: a review | journal = Bone Marrow Transplantation | volume = 52 | issue = 7 | pages = 941–949 | date = July 2017 | pmid = 28112752 | doi = 10.1038/bmt.2016.340 | doi-access = free }}</ref> Use under this protocol, usually with [[fludarabine]] and [[melphalan]], was developed by oncologists at the [[University of Texas MD Anderson Cancer Center]].{{citation needed|date=February 2018}}

==Implants==
In the treatment of [[brain tumour]]s, the U.S. [[Food and Drug Administration]] (FDA) approved [[biodegradable]] discs infused with carmustine ([[Gliadel]]).<ref name="pmid17575228">{{cite journal | vauthors = Ewend MG, Brem S, Gilbert M, Goodkin R, Penar PL, Varia M, Cush S, Carey LA | title = Treatment of single brain metastasis with resection, intracavity carmustine polymer wafers, and radiation therapy is safe and provides excellent local control | journal = Clinical Cancer Research | volume = 13 | issue = 12 | pages = 3637–3641 | date = June 2007 | pmid = 17575228 | doi = 10.1158/1078-0432.CCR-06-2095 | doi-access = | s2cid = 14016432 }}</ref> They are implanted under the skull during a surgery called a [[craniotomy]]. The disc allows for controlled release of carmustine in the extracellular fluid of the brain, thus eliminating the need for the encapsulated drug to cross the blood-brain barrier.<ref>{{cite web|url=http://www.hopkinsmedicine.org/hmn/W05/feature3.cfm|title=Hopkins Medicine Magazine - In Spite of All Odds|access-date=2014-07-08|archive-url=https://web.archive.org/web/20141120001145/http://www.hopkinsmedicine.org/hmn/W05/feature3.cfm|archive-date=2014-11-20|url-status=dead}}</ref>

==Production==
Carmustine for injection was marketed under the name BiCNU by Bristol-Myers Squibb<ref>{{cite web|url=https://www.bms.com/life-and-science.html |title=Company Statement on BiCNU® (carmustine for injection) | publisher = Bristol-Myers Squibb Company |access-date=2015-01-31 |url-status=dead |archive-url=https://web.archive.org/web/20140711101801/https://www.bms.com/life-and-science.html |archive-date=2014-07-11 }}</ref> and now{{when|date=December 2017}} by [[Emcure Pharmaceuticals]].<ref>{{Cite web |url=http://www.emcure.co.in/news/docs/BiCNU%20Emcure%20press%20release.pdf |title=Emcure Press release |access-date=2015-01-31 |archive-url=https://web.archive.org/web/20140702050137/http://emcure.co.in/news/docs/BiCNU%20Emcure%20press%20release.pdf |archive-date=2014-07-02 |url-status=dead }}</ref> In India it is sold under various brand names, including Consium.{{citation needed|date=December 2017}}. The product is available as a generic version with other manufacturers offering the product licensed in the US and EU markets.{{citation needed|date=February 2021}}

== See also ==
*[[Bendamustine]]
*[[Lomustine]]
*[[Semustine]]

== References ==
{{reflist}}

== External links ==
* {{cite web | title=Carmustine Implant | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a611045.html }}

{{Chemotherapeutic agents}}
{{Portal bar | Medicine}}

[[Category:Orphan drugs]]
[[Category:Ureas]]
[[Category:Nitrosoureas]]
[[Category:Alkylating antineoplastic agents]]
[[Category:IARC Group 2A carcinogens]]
[[Category:Organochlorides]]
[[Category:Cancer treatments]]
[[Category:Chloroethyl compounds]]
[[Category:Multiple Chemboxes|X]]
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